What followed was not what any of us expected. The three of us didn’t tell polished love stories. We told convoluted tales of adversity and near misses. Stories about first impressions that turned out to be completely wrong. Stories about how we almost didn’t say yes to that date, and how close we each came to walking away before things even started.

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This brings me to the yellow tie.

I met my husband David at church my first weekend as a freshman at Duke. He was a senior at UNC, a couple of years older than me, wearing a pinstripe suit and a bright yellow tie. My first impression: he looked ridiculous, jokey, and unserious.

Over the following months, we moved in the same church community. He had a strange sense of humor, the kind that felt overly familiar. I told a friend at the time that he was borderline rude. What I didn’t know was that he thought his jokes were a way to be warm and inclusive, even disarming. I was a shy girl who didn’t appreciate it, and I avoided him whenever I could.

A year after we met, we ended up carpooling to a church retreat eight hours away. He offered to drive my friend and me. I agreed, mostly because my dad wanted a guy in the car for the road trip. At the retreat, he asked me out. I was so caught off guard that I asked him about a mutual friend I thought he was dating. He said, “What about her? She’s in China.” I genuinely believed he was asking me out while his girlfriend was abroad. A spectacular misunderstanding on both sides. I turned him down, and we went our separate ways.

Later that summer, we drove separate cars full of people to another retreat in Wilmington from Chapel Hill. During that retreat, he asked me out again. I decided to give him a chance. He had just graduated and was heading to law school, so we had only a couple of weeks anyway.

He told me to meet him at the Ben and Jerry’s on Franklin Street in Chapel Hill. I dropped everyone off, then drove straight there. This was before cell phones. I waited. Fifteen minutes. Thirty. Forty-five. No David. I gave up and started walking back to my car, certain I’d been stood up. That’s when I heard honking and someone shouting my name from a passing car. It was him.

I reluctantly stayed for the date, mediocre as it was. I went home unconvinced. We parted ways when he left for law school in Boston. A few months of back and forth followed, and we ultimately decided against long distance. Then, on December 22nd, after a year and a half of misunderstandings, avoidance, and a disastrous first date, we officially decided to be together. And nearly three decades later, here we are.

The other two at that dinner table had their own versions of this story. One described a husband who pursued her for months while she remained uninterested. The other talked about a first date so awkward that he didn’t call her back. It was only by chance that he picked up when she called him. Three happy marriages that might never have happened in the internet age.

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The History of Dating and Connections

I’ve been thinking about how people met their spouses across time. For most of human history, proximity was the algorithm. A sociologist named James Bossard analyzed 5,000 marriage licenses in Philadelphia in 1931 and found that one-third of couples had lived within five blocks of each other before marrying. The probability of marriage fell steadily with increasing distance (Bossard, 1931). A follow-up study in Duluth found the same pattern. You married people who lived extremely close to you, sometimes in the same building.

That started to change after World War II. Friends overtook proximity as the primary matchmaker, rising from about 20 percent of couples in 1940 to a peak of 40 percent by 1990. For more than six decades, your friends were essentially curating your dating life. They knew you and they knew the other person. When you connect two people, what do you share? Not a photo of them or some quote. You share what you have in common, and why they connected you. Any introduction carried implicit information: this person has been seen, and someone who cares about you thinks it’s worth your time.

Then the internet arrived, and that vetting disappeared. Meeting through friends peaked around 1995 and has been declining ever since. By 2013, online dating eclipsed friends as the most common way couples in America meet, according to Stanford sociologist Michael Rosenfeld’s landmark study. By 2024, roughly 60 percent of new couples report meeting online (Rosenfeld, et. al).

This is more than a shift in technology. It is a collapse of context.

When a neighbor introduced you to someone, that neighbor had already witnessed them living their life. When a friend set you up, they knew your quirks and hobbies . The introduction was knowledge transfer. That has been replaced by a profile made up of a few photos and a handful of pithy sentences, a format that rewards the first impression above everything else because there are a thousand more profiles behind this one, and you can always keep scrolling.

We have trained ourselves to decide who someone is in three seconds and move on if they don’t immediately impress us. There’s a strange irony in all of this. We live in a culture that celebrates the slow burn. Romance novels are built entirely around the distance between the meet-cute and the happily ever after. The adversity is the story. Pride and Prejudice without Darcy’s insufferable first impression is just two people who got along fine from the start. Enemies-to-lovers, second-chance romance, opposites-attract reluctant partners: these narrative arcs aren’t about a swipe and a match. They’re about the journey of a relationship.

Relationships thrive in friction and grow through adversity. Yet we have built a dating culture that eliminates every one of those conditions, handing all the power to the first impression and assuming something better is one swipe away.

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The Danger of the First Impression

The first impression is almost always incomplete. And sometimes, as I learned, just wrong.

My mother knew that someone I dated before David wasn’t right for me. She never said a word. When I finally ended it and asked her why she had stayed quiet, she said, “I was afraid that if I objected, it would push you closer to him. I needed you to come to that conclusion yourself.” She was wise enough to know that some conclusions had to be made by myself.

The man in the yellow tie went from someone I found off-putting to someone I built a life with. Our relationship didn’t change overnight, but he kept showing up time and time again. Whenever my kids ask about how much I disliked their father when we first met, I tell them: “Your dad is a fun-gi. He grows on you.” They think it’s hilarious.

Think about the relationships that matter most to you right now. How many of them started exactly the way you expected? How many required patience, a second chance, a willingness to look past the thing that almost made you walk away?

Technology allows us to judge people on very little data. We can write them off because of a photo or a few words. Think about how much less rich our lives are because we judge too fast or cut off too soon.

And then harken back to a world where we see each other as fully. That is what we miss if we judge too soon.

A few weeks ago, I sat down to dinner with a group of executives, founders, and investors in San Francisco, hosted by my friends at MediaMint. It was the kind of dinner that feels completely ordinary here and utterly surreal everywhere else.

We went around the table to introduce ourselves and share how we were using AI. Someone was building an agent to manage their household. Another person was running three agents in parallel before leaving the house, so there would be results waiting when they got home. One executive was using NotebookLM to generate custom podcasts about AI news so she could stay current during her commute. Someone else was using AI to summarize long documents that, as it turned out, may have been written largely by AI in the first place.

There was real excitement in that room. But underneath it, something else was running quietly, like a current.

Fear.

Not fear that AI was coming. Everyone at that table knew it was already here. It was the fear of falling behind. The fear that every moment you weren’t building, automating, testing, or optimizing was a moment wasted. Walking down the street and noticing the trees had somehow become an opportunity cost.

At some point, I looked around and said what I was thinking: “This is very normal for San Francisco. But this is not normal for the rest of the world.”

One investor called it AI psychosis. It’s a dramatic phrase, but I understood exactly what he meant. It’s that feeling that every minute not spent learning, building, or automating is a minute permanently lost. And the strange part is that the people most affected are often the ones who are furthest ahead. Everyone in that room was likely in the top fraction of a percent in their understanding of AI, and yet no one felt calm. No one felt like they had enough time.

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The candy store problem

My friend George Lee, who has spent years working inside some of the fastest-moving companies in tech, described it perfectly. He said working at a cutting-edge tech company is like being a kid in a candy store. Everything looks exciting, new, and delicious. The danger isn’t that you try something. The danger is that you overdo it.

I found myself doing exactly that.

I subscribed to a dozen AI newsletters. I checked LinkedIn and Threads constantly to see what was happening. I tried to follow every new trend and learn every new technique. I told myself I was staying current. I told myself this was what staying relevant looked like.

But I didn’t feel smarter. I felt more behind than ever. As if knowing more had somehow made me more aware of how much I didn’t know. The ocean kept getting bigger the further I swam into it.

That’s the paradox no one talks about. The more you consume, the more there is to consume. The faster the field moves, the faster you have to run just to stay in place.

More efficient, more busy

Someone told me recently that AI had made them significantly more efficient, but also significantly more busy. It was almost as if being able to do more created more to do.

I haven’t stopped thinking about that.

Because it might be the central tension of this moment. AI can help you do more. But doing more doesn’t automatically mean doing it better. When you clear the pile in front of you, you often discover a longer pile hiding behind it. When you remove the friction of starting something, you also remove the natural stopping points that used to make you ask whether it was worth doing at all.

Before AI, if a task took ten hours, you had to make a decision. Is this worth ten hours of my life?

Now, if it takes ten minutes, you just do it. And then you do ten more things like it.

I think about it like a treadmill. You keep adding speed because you can. But a faster treadmill isn’t taking you somewhere different. It’s taking you to the same place, only more breathlessly.

We tell ourselves we’re saving time. But sometimes we’re just filling the saved time with more motion.

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The world is not your LinkedIn feed

Here’s something worth remembering: most people are not doing any of this.

Most people are not spending their evenings setting up their Mac Minis to run OpenClaw. Most people are not using AI to generate podcasts about AI so they can discuss AI at the next event about AI. Most people are not kicking off multiple agents to run tasks while they walk their dog.

Most people are working their jobs, raising kids, caring for aging parents, paying bills, managing a household, and occasionally trying to figure out what everyone keeps talking about. For them, AI is something they’ve heard is important but don’t know where to start. It’s a technology that feels both magical and completely alien.

ChatGPT launched in November 2022. That’s less than three years ago.

Three years after the consumer internet started breaking into broader awareness, it was 1998. Google had just been founded. Amazon was still mostly selling books. Facebook didn’t exist. YouTube didn’t exist. The iPhone didn’t exist. The behaviors and companies that now define our digital lives hadn’t taken shape yet.

We were right that the internet would change everything. We were often very wrong about how, when, and who would lead it.

That’s where we are with AI. We are not at the end of this story. We are in the first chapter. And most of the world hasn’t started reading yet.

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What AI can and can’t do

I believe deeply in what AI can do. I spend my days thinking about how it can transform how we work, remove the drudgery from our jobs, and help people do things that used to feel out of reach.

But I also know what I don’t want.

I don’t want my life to be about hyper-optimization. I don’t want to measure my days by how many agents I ran or how many things I’ve successfully automated away. I don’t want every walk to become a learning session and every quiet moment to become a productivity problem to solve.

I want time to think, to consider, and to strategize. I want scarcity to drive prioritization and prioritization to drive decision-making. I want to sit with a hard question long enough that a real answer emerges, not just the first one.

That is what makes us human. And it is what AI cannot replace.

The most important decisions and epiphanies of my career were not made faster with better tools. They were made in the margins — on a long flight, during a quiet walk, in a conversation I almost skipped, while reading something on a whim. Those moments don’t show up in any workflow. But they are the ones that have mattered most.

The permission you didn’t know you needed

There’s a difference between staying curious and staying frantic. You can engage seriously with AI without being consumed by it. You can be thoughtful about what’s coming without making it the organizing principle of your entire life.

So here’s what I want to offer you, because I needed someone to say it to me.

It’s okay to let some things go. You don’t have to have an opinion on every model release or try every tool. The important developments will find you. It’s okay to protect the pauses, because not every idle moment is wasted — some of your best thinking happens in the gaps. It’s okay to go deep on fewer things, because one tool that actually changes how you work is worth more than ten you sampled and abandoned. And it’s okay to ignore the bubble. San Francisco is not the world. LinkedIn is not reality. Measure yourself against your own goals, not someone else’s performance.

The stillness isn’t a bug in your productivity. It’s a feature.

The real question

AI will make us better at many things. It will reduce repetitive, tedious work. It will change jobs and create new ones. It will help some people do things that used to require an entire team.

But the question was never whether AI can help us do more. It can. The question is what we choose to do with the space it creates.

Will we use every gain in efficiency to add one more thing to the treadmill? Or will we use it to unleash what humans are uniquely suited for — thinking carefully, connecting meaningfully, and spending our time on the things that actually matter?

AI should not make you feel like you’re always behind. Sometimes the most powerful thing you can do is stop running for a minute. Creativity and ingenuity have never come from doing more. They come from making space to think, daydream, and wonder.

That is something AI can’t take away.

Not my face. Not what I was wearing. The cross.

I have worn it for thirty years. My then-boyfriend, now my husband of more than two decades, gave it to me when I was twenty years old, about six months into our relationship. I put it on and have rarely taken it off. I did not choose it as a signal or sign to others. I was not thinking about what I wanted to communicate to the world. I was a college student who received a gift from someone she was dating. Yet for thirty years, it has been one of the most prominent things people notice about me.

Seeing that photo in a classroom full of students stopped me cold, because I had been invited to talk about personal branding, a topic I have always found a little awkward. It can sound like performance, like you are packaging yourself into something slick and marketable. But looking at that photo, I realized something I had never quite put into words before. The most visible part of how people experience me was something I never chose. It was just true.

That is the thing about personal brands that no one tells you clearly enough. You already have one. It is already speaking. The question is not whether people are forming associations about you, because they are. The question is whether those associations reflect the truth of who you are.

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What we broadcast without knowing it

Over the years, that cross has opened more conversations than I can count. People have asked me about my faith, what I believe, and how those beliefs shape my decisions at work and at home. Some who share my faith have told me their own stories. Others who have been hurt by organized religion have opened up about that too. People asked questions and shared experiences. A small piece of jewelry became, without any intention on my part, a doorway into more honest conversations than almost anything I have consciously crafted.

That is not unique to me. We are all broadcasting things we did not deliberately choose. It may be our accent, the way we dress, or the questions we ask. We are being judged whether we remember people’s names or details about them. Some of what people associate with us, we chose intentionally. Most of it accumulated over years of simply being ourselves in the presence of other people.

The point is not to manufacture something that you want to present that is compelling but inauthentic. The point is to pay attention to what is already being received and ask yourself whether it reflects who you actually are.

Jeff Bezos famously said, “Your brand is what people say about you when you’re not in the room.” Most people hear that as a challenge: go make sure your brand is positive. But actually, you need to first understand what is already being said.

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The story underneath the signal

During the class, students worked on short personal brand statements, then Professor Flynn called on them to share. Most of the first attempts sounded polished but distant. Good but somewhat generic statements. But they could have stood for anyone, and I asked them, “Make your statement, an N of 1.” Read aloud to your classmates, they should know it is you.

One student shared he wanted to work in consumer packaged goods and help brands tell better stories. That sounded reasonable, but I did not understand why it mattered to him. I asked him to tell me the story behind it.

He explained that many products do not work well for Black men, and he wanted to help companies build and tell stories about products that actually served his community, people who had been overlooked for too long.

The room shifted. What had been a general statement about brand storytelling became something specific, personal, and real. It was about belonging and representation.

Another student said he wanted to work in transportation, maybe the airline industry. Again I asked why.

He told us that when he was young, he moved far away from his extended family, and flying was what kept him connected to the people and places that made him feel rooted. Travel was how he stayed connected to those he loved.

Transportation was not about logistics. It was about the ache of distance and the joy of return, and a child who learned that movement could be a bridge to those he loved.

Both times, I asked the room whether they felt more connected after hearing their why. Both times, almost every hand went up.

Here is what I kept thinking about as I watched this unfold. Neither student had built a brand strategy. They had simply told the truth about their “Why?” and suddenly their brand meant something deeper and more real.

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What this means for you

I have been wearing that cross for thirty years and only recently started to understand what it has been saying on my behalf all this time. It has been telling people about my faith, my marriage, my sense of where I come from, and what I hold onto. I did not plan any of that, but it is just as much my brand as anything else about who I am.

That is the question. Not “what do I want my personal brand to be?” but “what is already true about me that I have not yet put into words?”

Ask people you trust what they associate with you and what stories they tell about you when you are not there. Some of what they say will feel exactly right. Some of it will not, and that gap is worth understanding.

Then ask yourself what you wish they knew. Not what sounds impressive. What is actually true about why you care about the work you do.

The student who wanted to build better products for Black men did not need a brand strategy. He needed someone to ask him one question. The student who wanted to connect families through travel did not need a tagline. He needed to say the true thing out loud.

Most of us already know the true thing. We just have not said it yet.

I did not choose that cross as a signal. I chose it because it meant something to me. And it turns out that is exactly why it resonates with others. The things we carry because they are true are almost always the things that land.

Deb’s Note: From time to time, I bring in guest authors to Perspectives to share their point of view and bring a different take on a topic I want to learn more about. When I first read this piece from Molly, I found myself going back through my own life, thinking about the clubs I am in, the ones I never announced, the ones I carried quietly for a long time before finding someone else who was in them too. There is real generosity in writing something this honest, and I think you will feel that as you read it. I hope it gives you the same thing it gave me: the relief of feeling a little less alone in something you thought only you were carrying.

Life is full of clubs you don’t know exist until you’re in one.

I first discovered this when I had my first miscarriage. It’s one of those binary life moments: either you’ve had a miscarriage, and you know what that experience is like, or you don’t. When I met someone who was in the miscarriage club, I didn’t have to explain why it was hard. They already knew.

That’s what clubs are. When you meet someone who’s in yours, you feel immediately understood. You skip the part where you have to justify yourself. You just... know that they know.

There are so many of these clubs. In work and in life.

The “I got laid off” club
The “children of first-generation immigrants” club
The divorce club
The IPO club
The IVF club
The harassment club
The “I got acquired and had to run the integration” club
The “I had to shut my company down” club
The cancer club
The “I’ve lost a child” clubThe list is actually endless.

It goes without saying that being a member of different clubs varies wildly in terms of both what it feels like and how important it is to your identity. Some of those you’d choose again in a heartbeat. Others you’d give anything to not be in. But either way — once you’re in, you’re in. You keep the membership card forever.

Some clubs carry shame

Some clubs make you want to actively hide that you’re in them.

Getting laid off or fired can feel like a mark you’ll carry forever. I’ve watched a lot of friends go through it — especially at the CEO and C-suite level, where, honestly, it happens a lot. The more senior you get, the more likely you are to get fired at some point. It’s just the nature of a bigger, more public role. Every single time, the person feels like: “this defines me now. No one will ever be able to look at my resume or hear my story without the headline being ‘they got fired.’” UNTIL they meet someone else in the “I got fired” club, particularly someone whose career they admire. Finding other people who have been through it and come out the other side makes such a difference to the level of shame and isolation you feel.

I’ll tell you a story about a club I’m in. A while ago, I took a C-level job at a company that needed to be turned around. It didn’t work. I have carried shame and embarrassment about that role and my feelings of failure ever since — on almost every level. If only I hadn’t taken the job. If only I had gone in with a much stronger, clearer plan. If only I had done a layoff sooner. If only I had asked for X or Y. If only, if only, if only. That kind of failure has a way of becoming a story you tell yourself over and over, and the story is rarely generous.

Recently, though, I was talking to a friend who’d been through something similar — a turnaround that failed. As he walked me through it, I found myself listening differently than I listen to my own story. I could see clearly all the external factors working against him – the bad board, the structural problems that existed long before he arrived. What I saw was that he did some of the best work of his career in an impossible situation. And I thought: there was genuinely no way for him to win.

And then, quietly, my brain said: why is it so easy for me to see that for him and so hard to see it for myself?

Shame clubs make you think you’re the only one in them — and that you deserve to be. The “I failed” club, the “my company didn’t make it” club, the “I was pushed out of something I built” club. These aren’t clubs people announce at dinner parties. And because nobody announces them, you can go a long time thinking you’re the only one in them, when in reality there are people all around you carrying the same thing quietly and judging themselves just as harshly.

The “I’m struggling with my mental health” club. The “my marriage is falling apart” club. The “I burned a relationship I really valued” club. The “I’m drowning financially” club. These aren’t clubs people want to announce.

One of the most powerful things about finding your club — especially the ones with shame attached — is that naming it out loud is often what creates it. The club doesn’t exist until someone is willing to say “me too” first. When you share that you’re in it, you give other people permission to find you.

And once you’re a veteran — once you have some distance from the initial shock and some perspective — you have something valuable to offer newer members. The thing that helped you most when you were in it: someone who already had the words, who didn’t need it explained, who could say “I know exactly what you mean” and actually mean it. Someone who could also help you see the future. I’ve had people do that for me, and I’ve been able to do that for others.

Clubs give you more than comfort; they give you language

The best thing about finding your club isn’t just that it makes you feel less alone. It’s that it gives you language for something you couldn’t previously explain.

People talk about this a lot when it comes to losing someone close to them — a spouse, a parent, a child. That if they’re talking to people who haven’t been through that kind of loss, it can feel like a battle, but when you find someone who has, you immediately feel at ease.

It works the same way at work. The first time I had to do a layoff, I felt like I was carrying something I couldn’t put down and couldn’t describe. I felt shame, anger, guilt. When I finally talked to someone who’d been through one, I didn’t have to describe it at all. They already knew what it felt like. That conversation didn’t give me advice; it gave me words. And the words made it easier.

When you’re in something hard and you can’t find the words, it’s exhausting. Finding someone in your club ends that. You stop struggling to explain. They already have the words, and sometimes, in hearing their words, you understand your own experience better.

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Sub-clubs

Clubs have sub-clubs. And sometimes, connecting with someone in the club but not your sub-club can actually make you feel worse, not better.

A friend of mine was diagnosed with a serious, scary, late-stage form of breast cancer. She found that talking to people who’d had early-stage diagnoses was actually disheartening because her experience was so different. It’s not that the broader breast cancer club doesn’t matter. It does. But the closer someone’s experience was to hers, the more she actually felt understood.

Someone gave me similar advice after I delivered my first child. There’s a club of people who have carried and delivered babies, but there are sub-clubs within that. My friend told me to find people whose delivery was closest to mine, because that specificity matters enormously when you’re trying to understand your own recovery and what comes next.

A relevant work example is acquisitions. There are so many different types of acquisitions, and finding people who have been through one with the same power dynamics or similar deal structure as yours can make a big difference to how relevant the advice is.

The instinct when you’re in the middle of something is to find anyone who’s been through it. And that can be a good start. But it’s worth going further — to find the people whose version most closely mirrors yours. It makes a difference to whether you leave feeling seen or more confused.

Go find your people — the specific ones

Once you understand the idea that there are all these clubs that people are in, you start to see them more easily, even the ones you’re not in.

A few months ago I was at dinner with a close friend. It was the one-year anniversary of her mom’s death — I hadn’t even realized it when we made the plan — and at some point during the meal it came up. She started talking about what the last year had been like, what losing her mom had actually felt like, and I found myself listening in a particular way, carefully, like I was being let into something. I feel lucky that both my parents are alive and healthy, but I know it’s a club I’ll be in someday. One of the ones I’m scared to join.

Recognizing the clubs you’re not in can teach you a lot. What do your friends who are in the “I’ve lost a parent club” wish they had known? If you watch a friend in the “chronic back pain” club it will make you both grateful for your lack of pain and want to do a lot of core strengthening.

Most of the clubs that have mattered most to me are ones I never asked to join. You don’t sign up for the miscarriage club, or the “really extremely fast acquisition” club, or the “taking care of your friend who is dying” club. You just wake up one day, and you’re in it. For a long time, I tried to muscle through those moments alone, like finding other people who’d been through it was somehow an admission that I couldn’t handle it myself. It wasn’t. It was the smartest thing I could have done.

When you find yourself in a club, the most useful thing you can do is go find the other members. Not just anyone who’s been through something similar. The members of your sub-club – the specific people whose experience most closely mirrors yours. Finding them will help you stop hiding or trying to muscle through it. It will give you perspective, tools, and immediate relief.

They’re out there. And somewhere, someone is hoping you’ll find them first — that you’ll be the one who says “me too” and gives them permission to stop carrying it alone.

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Molly Graham - company builder. Lover of weird metaphors. Current work: Host, TED’s WorkLife Podcast. Founder, Glue Club & The Guild. Previous work: Facebook, Google, Quip, Chan Zuckerberg Initiative.

People would yell at my family to “go back where you came from” while we walked down the street. I brought steamed buns (bao) to school, handmade with my mother, and my classmates questioned why I would eat something so weird. Every difference felt magnified. The food we ate was strange. The heavy accent my parents had made them stand out. The shape of our eyes was unlike that of others. No matter where I went, I felt like a walking billboard for someone who didn’t belong.

So I spent much of my childhood trying not to be seen.

Never fitting in

I tried to be smaller, quieter, and much less noticeable. I figured if nobody paid attention to me, maybe they would stop commenting on how different I was. But not a week went by without some joke, slur, or casual remark reminding me that I was the “other.” Sometimes people meant it maliciously. Other times they treated it like harmless humor. Either way, it made me want to shrink within myself and be invisible.

When I told my parents, they would usually say the same thing: ignore it. They are just ignorant. My parents understood something I didn’t yet fully appreciate. Survival often meant not making waves. When the local Southern Baptist Church didn’t accept our family as members, we left, and suddenly, we became Presbyterian which they remained until their passing. There we found a community and connection. They never let things get to them and moved on without much fuss even though I know it hurt to be rejected.

They had immigrated from Hong Kong to America for college with almost nothing. They built a life here through grit, sacrifice, and stubborn optimism. In our home, we spoke Chinese. We celebrated Chinese traditions. My parents created community wherever they could find it, helping start Chinese school, Bible study groups, and friendships with far-flung Chinese families they found. They joined the Chinese restaurant community.

They were unapologetically themselves in a place that rarely reflected them back. At the time, I didn’t understand their confidence. I couldn’t understand why they thought living in this town was their American Dream. I desperately wanted to blend in and be like everyone else.

Every few years, after saving for a long time, my parents would take us back to Hong Kong. Going from a small Southern town to one of the busiest cities in the world felt like stepping onto another planet. Six million people on an island was a shock to the system for a child who grew up in a town with fewer than 14,000 people. The skyscrapers, billboards, and unending lights felt like another world, but I didn’t fully belong there either.

My relatives told me I dressed too American. I was too tan, too tall, and too fat. The shopkeepers who saw us thought we didn’t understand them when they insulted my sister and me in Chinese because we looked like foreigners. Our Cantonese sounded old-fashioned, frozen in time from the version my parents had brought with them decades earlier. Cantonese, it turns out, evolves. My parents had unknowingly passed down a linguistic time capsule.

In South Carolina, I was too Asian. In Asia, I was too American. For a long time, I thought that tension meant something was wrong with me. Now I understand it differently.

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What it means to be Asian American

Being Asian American often means living between worlds and seeking belonging where you can. We learn to translate your culture, expectations, and identity. You learn when to code-switch. You spend a lot of time lost in translation. But you also learn resilience.

I recently listened to comedian Aziz Ansari talk about growing up in a small town in South Carolina. His family, like ours, found community where they lived, even though they were really different. That resonated deeply with me because so many immigrant families built islands of belonging in places where they otherwise felt alone.

My daughter Bethany interviewed her grandmother before she passed away. During that conversation, my mother-in-law spoke about how grateful she was for America and the life she was able to build here. That stayed with me.

My parents and in-laws all came here for college and ended up spending the next sixty years in America. They were forever foreigners in the eyes of some people. Their accents never fully disappeared. Their traditions remained different. But they loved this country fiercely and devotedly.

They believed in America even when America did not always fully embrace them back. As a child, I thought strength meant blending in. Today, I think strength means something else entirely.

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What it means for the next generation

My kids don’t think that much about Asian Americans. They have all been in Chinese class since they were toddlers, but they resist speaking it unless required to. They love Asian food, but live in a place where it is abundant and accessible.

The other day, one of my kids attended an event, and afterward, she said, “That was the first time in my life I felt like I didn’t belong.” I was confused, and then I realized she had grown up in a community where 40% of her high school looks like her. Never had she felt a sense of alienation and otherness that had marked most of my childhood. And to experience that for the first time as a teen was surprising to me.

It is funny how chinamaxxing became a thing recently. I am bemused at the fact that things that were once considered weird are now sought after. Ube, lychee, and tapioca are things I grew up with, and now they have become mainstream in our culture. The bao that was once weird is now accepted. The dumplings we made at home because we lived too far from an Asian grocery store can now be bought at any supermarket. Now kids all over drink boba and eat eggball waffles.

Progress is a strange thing. It does not erase what came before. The fact that my children can grow up eating bao without shame does not undo the little girl who sat in the cafeteria wishing her lunch looked like everyone else’s. The fact that Asian food, music, books, films, and stories are now more visible does not mean belonging is automatic. It means the aperture has widened to include more ways to belong.

That is what Asian American History Month means to me now.

It is not just a celebration of culture, food, or achievement. It is a remembrance of the people who came before us, who crossed oceans, accepted indignities, and created belonging out of almost nothing. It is honoring those who embraced life in a country that did not always love them back. It is recognizing the quiet courage of parents who told us to brush it off because they were trying to survive, even as we teach our children that they do not have to disappear to belong.

When I was growing up, there was a pushback on being a “hyphenated American”. When people asked me where I was from, I would say “New York.” They would then ask, “No really, where are you from?” I would answer again, “New York.” They would ask, “What are you?” And I would say, “American,” because I refused to give in and use the hyphen.

For much of my life, I thought being Asian American meant living in the hyphen, never fully one thing or the other. Too Asian here. Too American there. Never being good enough to fit in anyplace.

Now I see that hyphen differently. It is the place where my parents’ sacrifices meet my children’s acceptance of who they are. It is where the steamed buns my classmates once mocked become the bao my kids can pick up on the way home from school without thinking twice.

I used to think belonging meant becoming smaller. My father used to proudly tell everyone, “The highest I could aspire to is to be in Congress, but my children? They can be president.” Maybe my parents had it right after all.

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Last week, I had three conversations with people who had each been laid off. Though the circumstances were very different, the emotional experience was almost identical. They were grieving the loss, and each of them began to turn that experience inward.

These were people who, just days earlier, had been operating at a high level. They were leading teams, making decisions, and talking to customers. They went from full calendars, clear purpose, and key goals to silence. The rhythm to their days suspended in mid-air, held in a kind of stasis as everything around them seemed to move on without them. They went from knowing where they fit in that symphony and now inexplicably playing to an empty room.

When I asked each of them what story they were telling themselves about what had happened, the answers were strikingly similar, even though the situations themselves were not. They weren’t talking about strategy shifts or leadership changes or broader market dynamics. They were talking about themselves, about what they must have missed, what they should have done differently, how they could have prevented it.

It was as if they were trying to take something inherently uncertain and make it feel explainable by turning it into a personal failure.

There is something comforting, in a strange way, about believing that if something went wrong, it must have been within your control. Because if it was within your control, then maybe next time, you can avoid it or fix it.

But that isn’t always what’s true.

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How the story affects our actions

Years ago, while I was working with my coach Katia, there was one question she asked me over and over again, often at moments when I was most certain I understood what had happened.

“What is the story you’re telling yourself?”

At the time, it felt almost too simple, like it couldn’t possibly get at the complexity of what I was dealing with. But over time, I realized that the question wasn’t about simplifying the situation. It was about separating what actually happened from the guilt and regret I had layered on top of it.

Those two things are not the same. In moments like this, the meaning we assign can be far more powerful than the event itself. The narrative stood between me and the objective reality, and it colored every reaction and respond I had.

Fighting the wrong war

Someone I trusted introduced me to a product manager they described as “exceptional”. This PM had thrived in their previous role, had strong recommendations, and seemed like exactly the kind of person we would want to bring into the company. I had her brought in for an interview with a team that was focused on her space.

After reading the negative feedback, I requested to interview this person myself. And the interaction was so different from what I expected, so much so that it was almost disorienting. She was guarded, defensive, even at times combative. The conversation felt less like an exchange of ideas than someone who was trying to figure out if I was going to accidentally screw her.

I couldn’t reconcile it with everything I had heard from her reference. Afterward, I followed up with the referrer to understand what I was missing. It turns out that she had just exited a difficult situation with their previous manager. Her trust was shaken and she was trying to avoid being in the same situation again. While that is understandable, her approach to the interviews was a response to the story she was telling herself.

What was protective in one context became limiting in another. She was telling herself that she needed to protect herself, which ended up costing her an incredible opportunity. By fighting the last war, she could not move forward.

How stories become walls and walls become barriers

When something difficult happens, whether it’s a layoff, a broken relationship with a manager, or a moment where things didn’t go the way we expected, we don’t just move on from the event itself. We build a story around it, one that helps us make sense of what happened, and then we carry that story forward into everything that comes next.

It then becomes the reality of what happened. We start showing up based on that reality. Others start reacting to that behavior which then reinforces the story we told. Gradually over time, the story becomes the truth.

There is a difference between learning from an experience and letting it dominate your point of view. Seeing the blind spots for what they are and rewriting the story allows us to break free.

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Rewrite the narrative

For those who recently were laid off, they were living in bewilderment and confusion. For a long time, their careers in tech felt relatively predictable. If you perform well, you grow your career. You advanced and got promoted. There was an implicit belief that things would continue to move forward in a way that was, if not guaranteed, at least directionally consistent. There was stability. That assumption is breaking down.

To make sense of what happened, they each looked inward. They were plagued with “If onlys…” but I asked them to rewrite the story. What if there was nothing they could have done? What if it happened that they were unlucky to be on the project that was cut?

I asked them each to tell me, “What is the story you’re telling yourself?” And each wondered if they could have tried harder or done more. They consider whether they have failed in some way. Perhaps, but perhaps it was truly out of their control, but approaching the path forward with disappointment and anxiety would not make their journey easier.

I asked them to accept what happened as a stumbling block, but to leverage it as a stepping stone to the future. By reframing, it gave them a new way of retelling the story so that they could look forward not back, and would prevent them from fighting the last war.

I wanted them to show up to the next interview without a sense of desperation and fear, but with confidence and assurance of their value. In small and subtle ways, the way they show up would reflect the story they were telling.

If you are stuck, learn to rewrite the story.

1. Write down the story you are telling yourself. Explain what happened both good and bad in a single sitting. Don’t edit or try to optimize. Just get the words out. Tell the story of what happened, including what you did or others did. Consider the actors and what they mean. If possible, consider describing to someone in a video or transcript so it comes more naturally.

2. Read or listen to what you wrote. What was the crux of the story? What feelings did it evoke? Most people notice patterns when they do this. The story is not neutral. It has a point of view, judgement, and conclusions. Right or wrong, it is real.

3. Rewrite it without judgement. What if you shifted the ending to focus away from blame and on learning? What would the story tell you?

The story you tell yourself doesn’t just describe what happened. It determines what you do next and how others perceive you.

You may not be able to change what happened, but you can change the story you carry forward and the actions you take from there. And sometimes, that’s the one thing you need to free you to move forward.

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I recently met Martin Yan, the man behind the long-running, pioneering show Yan Can Cook.

We were at a dinner hosted by Hyphen Capital, brought together by Dave Lu, who has a gift for convening Asian American leaders. It was one of those rare gatherings where every seat held someone with an interesting story, and yet somehow the room still felt intimate, almost like a table full of friends.

I was seated across from Jean, a partner at Cooley who had flown in from New York for the event. Beside her sat Martin Yan. As the dishes from the Chinese banquet began to arrive, I noticed something that caught me off guard. Martin was quietly serving Jean, and then the others at the table, moving from person to person without drawing any attention to himself. There was no announcement, no sense of performance, just a simple act of care from the most recognizable person in the room, surrounded by C-suite executives, artists, and community leaders.

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I leaned over to Jean and joked, “This might be the only time you’ll ever be served Chinese food by Martin Yan himself.” I asked if I could take a photo, and he laughed, playing along, holding a dish mid-air as he posed. He was warm and gracious, completely present in a way that made the moment feel both light and memorable.

3,500 Episodes of Showing Up

As the meal went on, he began sharing stories about his life. He talked about his show, his cookbooks, and his love of travel. At one point, he turned to the table and asked us to guess how many episodes of Yan Can Cook he had filmed.

I thought back to being a kid, standing in our kitchen, watching him on a small television while my mom cooked dinner. She loved watching him because he showcased the dishes she grew up with, even as we lived in a small town in South Carolina where few people looked like us. His show felt like a bridge between worlds, something familiar in a place that often felt foreign.

I knew he had been around for decades, so I guessed maybe a few hundred episodes. Others at the table offered their guesses. He smiled and then said, almost casually, “Over 3,500.”

Three thousand five hundred.

The number was hard to process. If he had filmed every day, that would have been nearly ten straight years of shows. He talked about the pace, filming back to back, traveling for weeks at a time, making it all work in conditions that were far from perfect. When someone asked him how he managed it, he didn’t offer a grand answer or a carefully crafted philosophy. He simply said, “You just have to show up and do it.”

That line stayed with me.

Most People Stop Before They Start

Because not long before that dinner, I had come across a statistic that surprised me. Only 8% of podcasts make it past ten episodes. People start with excitement. They plan, script, record, and launch. They share it with friends, celebrate the beginning, and then, somewhere along the way, they stop.

Not because they failed, but because they stopped showing up.

Persistence sounds simple when you say it out loud, but it is much harder to live. Showing up, day after day, especially when the work feels repetitive or the results are uncertain, requires a kind of discipline that most people underestimate. It is easy to start something. It is much harder to continue when no one is watching, when the payoff is unclear, when the work becomes routine.

And yet that is exactly what Martin Yan did, 3,500 times over.

At a time when Asian Americans were barely visible in mainstream media, he brought Chinese cuisine into homes across the country. For many people, his show was their first and only exposure to a culture they did not grow up with. He made it accessible, joyful, and human, not something distant or exotic, but something that could be understood and appreciated.

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The Woman Who Never Stopped Either

That idea of showing up stayed with me as I thought about another experience I had recently.

I visited Cameron House in Chinatown, a place with a long and powerful history. The building is named after Donaldina Cameron, a woman who, in the late 1800s, dedicated her life to rescuing young girls from trafficking and forced labor. She showed up every day to do work that was difficult, dangerous, and often unseen. When the 1906 earthquake destroyed the building, the work did not stop. It moved and continued, carried forward by those who believed in the mission she had started.

Over 150 years later, that work still continues.

Donaldina Cameron did not know what her legacy would become. She was not building toward recognition or historical significance. She simply did the work in front of her, one day at a time, saving over a thousand girls, hiding them when danger came, and helping them find safety and a new life.

The scale of what she accomplished is extraordinary, but what stands out even more is the consistency behind it.

The same kind of consistency that Martin Yan described so simply at dinner.

You show up. You do the work.

The Phone Call I Never Forgot

I think about this often in my own life. I have done over a thousand coaching calls, including two just last week. People reach out during moments of uncertainty, when they are trying to make a decision or navigate something difficult, and I try to be there for them. There are times when I wonder if those conversations matter in any lasting way.

Then I remember being on the other side of one of those moments.

When I was a freshman at Duke, I once called a law professor, intending to leave a message. Instead, Amy Chua picked up the phone. She didn’t know me, and she had no reason to stay on the line, but she did. She asked questions, listened, and gave her time to someone who was, in every sense, a stranger.

That conversation stayed with me.

Years later, I saw her at a party and almost didn’t go up to her. It felt awkward to remind her of something she likely wouldn’t remember. But I did it anyway, and I thanked her. She didn’t recall the conversation, but she was kind and gracious in that moment too.

It made me realize something simple but important.

You never really know which moments will matter.

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Presence Is the Point

Most conversations fade. Most interactions pass without leaving much of a trace. But every once in a while, something sticks, and it shapes how someone sees themselves or what they believe is possible.

Those moments are rarely planned. They happen because someone chose to show up.

That is what stayed with me most about Martin Yan that evening. It wasn’t just the number of episodes or the longevity of his career. It was the way he carried himself at the table, serving others without hesitation, as if that was the most natural thing in the world.

He showed up for his audience for decades. He showed up for the culture he represented. And in that moment, he showed up for the people sitting around him, one plate at a time.

What Lasts

We often think impact comes from big, visible moments, but more often it is built quietly, through consistency, through presence, through the willingness to keep going when it would be easier to stop.

So much of life comes down to that simple idea.

Showing up, again and again, even when it feels small, even when it feels unnoticed, even when it feels like it might not matter.

Because over time, that is what creates something meaningful.

And that is what lasts.

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When I wrote my first post for Deb's blog, I told you I was the behind-the-scenes one. The sister who didn't need the spotlight. The one who shows up quietly and makes things work. What I didn't tell you was how I got there.

It wasn’t temperament. It wasn’t some zen-like comfort with invisibility I was born with (do I look bossy in that photo above?). It was a skill. Hard-won, sometimes painful, learned-the-hard-way skill that took me from a middle school snack table to a chemical plant in West Texas to a startup Slack channel where I was apparently deploying insufficient emojis.

I have always been the person who sees what could run better and cannot help herself from fixing it. Growing up, that instinct had a name. Not a kind one. Deb was the driven one, the one who aimed for 100, the one who made everyone feel her presence when she walked into a room. I was the oldest, but she was the one people noticed first.

And I was bossy.

That was the word for me. For a long time, I thought it meant something was wrong with me. It took me three very different rooms and about forty years to understand what it actually meant.

Bossy is a skill. And like any skill, it takes a long time to learn how to use it well. Women are twice as likely to be called bossy at work, even though they aren’t more likely to act that way.

Bossy Without Allies Is Just Exposure

“Caroline, you are so bossy.”

I was in 7th grade. He was in 8th. We were at an after-school art club, running a snack sale, and Patrick (not his real name), who had appointed himself in charge through no process I recognized as legitimate, did not appreciate the way I was organizing the cash box and optimizing our revenue per transaction.

I froze. I had spent my entire young life being good. Straight A’s. Respectful. Quiet when quiet was called for. My parents told me to keep my head down and not make trouble. I had worked so hard to make myself small, to take up exactly the right amount of space (not too much, never too much) and still, somehow, I had ended up here: standing in front of a table of granola bars, chocolate chip cookies and rice crispy treats while a boy twice my size told me exactly what he thought of me.

The part that stung most wasn’t the word. It was the crime I’d committed to earn it. I had noticed something that could be done better. I had done it better. And apparently, that was enough to be a problem for Patrick.

Because boys who take charge are leaders. They’re decisive. They have vision. When Patrick positioned himself as the authority over a middle school bake sale with zero credentials and maximum confidence, nobody blinked. But when I, armed with actual math and a reasonable theory about snack pricing, stepped in and made things run better? That was threatening.

Bossy is the word they use when a girl does what a boy gets praised for. It’s the polite version. The grown-up packaging for an old message: you are too much, get back in your lane. Patrick was in 8th grade and said it without dressing it up. The men in conference rooms I walked into later had learned to be more careful. But the message was identical.

I got that message loud and clear at age eleven. And for a long time, I slid back into the shadows.

What I understand now: Bossy without allies is just exposure. The instinct was right. The execution was isolated. Patrick had the room. I had the cash box and nobody was watching my back. That’s not a bossy problem. That’s a coalition problem. The skill wasn’t wrong. I just hadn’t learned how to use it yet.

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Bossy With Strategy Is Power

About a dozen years later, I was a brand new engineer at a chemical plant in West Texas, handed a problem with no obvious solution. We had an anaerobic concrete reactor in the waste treatment unit that needed an internal inspection, but couldn’t be taken offline. It had to keep running while we figured out whether the walls inside were holding up.

So I did what I do. I researched. I cold-called professors who specialized in ultrasonic testing technology, read their papers, tracked down companies working on the problem, and built a case. Then I walked into a room full of Reliability Engineers and proposed a solution.

The response was immediate.

“Caroline, you’re a brand new engineer. We’re not interested in your Star Wars technology.”

The technology worked. It was real, it was tested, and it was exactly the right tool for the job. But I was twenty-something, I was new, and I was in a room full of engineers who were engineers before I was out of diapers. They had been solving problems their way for a very long time.

I’d made the same mistake as the snack table without realizing it. I’d walked in and been right out loud, in front of everyone, all at once. Bossy with no runway. That’s a fast way to lose before you’ve started.

So I adjusted. I found the one engineer who hadn’t crossed his arms, the one who’d asked a question instead of throwing a dismissal. I went back to him one-on-one, without an audience, without anyone’s ego on the line. He got it and once he got it, he became my ally.

Then I brought in an outside expert. Someone with credentials the room couldn’t dismiss, who could say the same thing I’d been saying and be heard differently because of the letters after his name. Was it frustrating? A little. Was it effective? Completely.

The technology was adopted. The reactor got its inspection.

What I understand now: Bossy with strategy is power. This wasn’t less bossy than the snack table. It was bossy at a higher level. I stopped leading with the idea and started building the conditions for the idea to land. The meeting before the meeting is the real meeting. Find your allies before you need them. Brief them privately. Let them arrive already converted. The goal was never to be the hero. The goal was to get the reactor inspected.

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Bossy Is Not a Fixed Setting

I spent the next twenty years applying that lesson. Work the room before the meeting. Find your ally. Let the idea travel on someone else’s credibility when it needs to. I got good at it. Good enough that I built it into an identity. The behind-the-scenes one. The woman who makes things run without needing anyone to notice.

I thought I had finally cracked it. Don’t be too loud. Don’t be too much. Make things run and let others take the bow.

And then a startup made a note about my emoji usage and I had to start all over again.

In 2022, after fifteen years of running our family business, I pivoted into helping startups find their footing. What I hadn’t prepared for was this: for the first time in fifteen years, I was not the one in charge.

I walked into organizations built by people half my age, fluent in tools I’d barely heard of. Slack. HubSpot. AI workflows. A communication culture where tone was conveyed not just in words but in punctuation choices and the strategic deployment of emojis.

I didn’t want to get it wrong. So I did the thing I’d spent years learning not to do. I made myself small. I watched. I said little. I was careful in a way that felt deeply unnatural after a decade and a half of being the person everyone looked to for answers.

And then I got feedback that I needed to soften my tone.

With emojis.🫠

I had spent my career learning to project authority in rooms full of skeptics, and now I was being told that a well-placed 🙌 would do more for my credibility than anything I’d learned in fifteen years of running a company.

I laughed. 😂And then I got to work.

I learned the channels: public, private, and threaded replies. I learned that a message without a single emoji could read as cold to someone who’d grown up communicating this way. I learned that being the least digitally fluent person in the room wasn’t a threat to my identity. It was just a new room to figure out.

What I understand now: Bossy is not a fixed setting. It’s a read-the-room skill. The emoji note wasn’t telling me to stop being bossy. It was telling me the room needed me to show up differently. Bossy in a startup looks like warmth, presence, and engagement. I hadn’t lost the instinct. I’d just forgotten to translate it.

Here’s where I’ve landed, forty-something years after a 7th grader tried to put me in my place over a snack table:

Bossy was never the problem. Bossy without self-awareness is the problem. Every room needs someone who sees what’s broken and can’t look away. The skill is learning how that person shows up.

Alone, bossy is vulnerable. With strategy, bossy is powerful. Translated for the room, bossy is influence.

Most women spend their whole lives being told one of two things: you’re too much, or you’re not enough. It took me three very different rooms to understand that the answer to both is the same. Know your room. Build your coalition. Never apologize for seeing what needs to be fixed. And never confuse the strategy with the instinct.

The instinct is almost always right.

I’m still organizing the cash box. I’m still the person who notices what could run better and can’t quite help herself from saying so. The difference is I’ve stopped treating that as a flaw to manage and started treating it as a skill to deploy. I still work quietly in the background but I now know how to read the room, build coalitions, and how to make things happen.

The world doesn’t need fewer bossy women. It needs more of us who have learned to be bossy well.

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I was six years old when we moved from Queens to a small town outside Charleston, South Carolina.

My parents had spent their entire lives in New York City. Everything we owned was packed into cardboard boxes and loaded onto a truck heading south. My mother asked us to draw lines on the tape so we would know if someone tampered with the boxes. When we arrived at our new house, there was an unused recreation room in the very back of the house where most of the boxes went. Slowly, over months and then years, my parents found what they needed to build their new life in South Carolina. But many stayed sealed.

As we grew up, that back room was always a mess. There were stacks and stacks of unopened boxes that created a fun playground for two mischievous little girls who went to play Hide and Seek and King of the Hill among those boxes.

A few years later, we moved again; this time to a nearby small town with better schools. The mountain of boxes moved with us. This time, they went into the garage. My dad lovingly bought and assembled metal shelves to hold the boxes. I remember the walls lined with them, with dust settling on top. This time, we stayed for 10 years in that house, and many of the boxes remained unopened.

We are what we carry along

When I was seventeen, the naval shipyard where my dad worked was closing, so he was reassigned to another town. This time in Georgia. My mom stayed behind with me so I could finish high school, and I helped prep boxes for the move. One afternoon I noticed a box still sealed with the same moving tags from more than a decade earlier.

I was curious. What could possibly be so important that it survived multiple moves but was never needed?

When my dad came home for the weekend, I suggested we throw it away. If he had not needed it in over a dozen, surely he did not need it now.

He hesitated. What if it were something valuable? So he took a box cutter and opened it. Inside were coils of old telephone wire and equipment, all surplus from when he had worked for the phone company in New York. He had not thought about it in years, and he had never opened the box.

Yet after we looked at it, he carefully taped it shut again and brought it with him to his next home in Georgia.

Clutter is often just delayed decision-making.

When my father passed away fourteen years ago, that same box was still there, but this time their Georgia home. And this time, we discarded the contents that we could not give away. I ended up donating two dozen hats he had collected, at least thirty pairs of barely worn shoes, and all of the trophies from my high school days that I had begged him not to move to Georgia after I graduated.

It is strange how our belongings travel with us. They move from city to city, from house to house. Sometimes they outlast the seasons of our lives that created them.

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Coming full circle

Recently, I have been sorting through our own boxes. We moved last year, but we only took our furniture and three loads of laundry with us. And over weeks and then months, we carefully and gradually only went back to take the things we needed. We kept everything else in the garage as we rented out our home on Airbnb. We decided this year to move it to a long-term rental, so the day finally came when we had to move everything out of the garage.

It has been surprisingly painful. We have all of the things I have avoided sorting through sitting on my patio waiting on me to make the hard decisions. Most of what we own is evidence of a life we are no longer living or had inherited from both my parents and in-laws.

I also found a decorative shell plaque that used to hang in my parents’ bedroom. They bought it on a trip from Asia before they had kids, and now I am not sure what to do with it. I am debating finding a home for it, but I don’t want it to be in a bin forty years from now waiting for my kids to make a decision I couldn’t.

What do we keep? What do we let go of? That is the question.

When my mother-in-law passed away, it happened so quickly. One day she was fine. Within two weeks, she was gone.

Her laundry was still in the washer. Dishes were still in the sink. It was as if her life had paused mid-sentence. The house simply waited for her to return. We packed up her dresses. Her shoes that she had worn only once or twice. The quiet evidence of a life that had been moving forward right until it stopped.

Standing in the middle of all this stuff, I keep asking myself the same question.

How much do we really need?

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How to edit your things and your life

Decluttering is not just about cleaning out a garage. It is about changing how we live.

1. Dedupe
Start by gathering like with like. When we moved, I discovered at least a dozen pairs of scissors scattered throughout the house. I put them all in one place. Standing there looking at the pile, I realized something simple. A household does not need this many scissors.

We often buy duplicates because we cannot find what we already have. The first step to decluttering is sometimes just taking inventory and figuring out what you have.

2. Add, don’t subtract
Decluttering can feel overwhelming because we assume we have to go through everything we own and decide what to remove. That is exhausting. Every object becomes a decision, and every decision carries emotion.

There is an easier way. Instead of starting with subtraction, start with addition.

Find a separate space. It could be a closet, drawer, or shelf. Then begin choosing only the things you truly love and actually use. The items you reach for get put into circulation, and everything else is discarded or donated at the end of 90 days. Clarity often comes not from forcing ourselves to let go, but from intentionally choosing what to keep.

3. Be intentional
Every object takes up more than physical space. It occupies mental space. Before keeping something, ask whether it serves the life you are living today. Not the life you once had. Not the life you imagine you might have someday.

I gave up my ravioli trays because I realized that, as cool as that dream was, I was never going to make ravioli at home. And that’s okay. I gave up my painting supplies and canvases in the same way. Accept that you are changing and your needs are too.

4. Force hard decisions
What I found is that everyone has the “room that shall not be named” where things accumulate, hidden from view. Mine was in our garage, and moving forced it out into the open. Once we had to face sorting through 100 boxes of randomly packed things, we found things we never imagined we even had. There were three crates of brand new baby clothes much of which we passed on to new mothers in need in the neighborhood. I found appliances that were never used (soymilk maker, I am looking at you) and decorative trays and mismatched silverware that just took up space. I found the candle from my husband’s fourth birthday and the baby hats our kids came home with from the hospital. We had just pushed these off to the future us, and now we are facing that decision headon.

5. Keep the memory, not always the object
I have memories from my parents of things they loved, trips they took, and events they attended. But I don’t have space or home for half sets of silverware and platters from long ago. I decided to scan every photo and video tape we had, keeping things that no longer served. Then we sent the items to new homes where they could be loved.

Our parents grew up in a world of scarcity. They saved everything. Our generation lives in a world of abundance. We are surrounded by disposable clothing, online purchases, and abundant possessions.

Our children will inherit not only what we build, but also what we accumulate. We keep objects because they mean something to us, but sometimes they also weigh us down.

Letting go is not disrespect, but rather making space.

Before you go to bed tonight, open one drawer. Choose three things you no longer need. Let them go. Then move forward without the box you never opened.

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In early 2023, a few weeks after ChatGPT launched, I ran an experiment I haven’t been able to stop thinking about.

I fed the model a set of questions from a podcast I’d recently recorded — real questions, the kind that require judgment about leadership, disruption, and organizational change. I told it to answer as if it were me: Charlene Li. Then I had people rate the responses blind, on a scale of 1 to 10, without knowing which answers were mine and which were the AI’s.

The results shook me. On some questions, the AI scored higher than I did. It was more concise, better structured. I outperformed it on the genuinely creative answers such as the unexpected angles, the questions nobody had thought to ask yet. But averaged across the whole set, AI performed at roughly 80% of my level.

I felt like chopped liver. Like my time was already running out.

The anxiety that followed was specific and unsettling. It felt like a new version of “publish or perish,” a race between me and my AI doppelgänger, where every new model release would close the gap a little further. Future fatigue set in. I couldn’t see how to stay ahead of something that was already so close behind.

And then I did something that changed how I saw the whole thing. I looked very carefully at that 20% difference.

What I found wasn’t a list of skills or topics. It was something harder to name. My stronger answers had a different quality — I was reading the emotional timber of the question, digging below the surface to the question that lay underneath it, connecting it to a conversation or idea I’d encountered recently that wasn’t in any AI training set. I wasn’t just answering. I was bringing myself to the answer in a way the model couldn’t replicate, because I was the only one who had lived my specific combination of experiences, relationships, and half-formed thoughts.

That’s when I stopped asking the wrong question.

The wrong question is: Can AI replace me?

The right question is: Who does this force me to become?

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When your foundation dissolves

For most of our careers, professional identity has been built on what we know. For thirty years, mine looked like this: I ran a research and advisory firm, Altimeter Group, with a full team — researchers, editors, a controller, and sales. We produced reports slowly and deliberately. I wrote, spoke, and advised in a traditional manner. That work, and the expertise it represented, was my identity.

Maybe your career looks different. But the foundation is the same: we got promoted for knowing things and built authority on competence.

AI doesn’t just threaten that foundation. It dissolves it. I can now do everything Altimeter did — research, synthesis, content creation — at a pace and scale that would have been unimaginable then. The team I once needed? Agents. And when the foundation goes, so does the identity built on top of it.

I’ve spent thirty years studying how technology disrupts organizations and the people in them — sitting inside the transformation as it happened, not just analyzing it afterward. At Adobe, I watched leaders navigate one of the most wrenching pivots in Silicon Valley history: abandoning the packaged software model that had made them great and betting everything on the cloud. Customers signed petitions. Employees raged internally. People would pull me aside and say, in the same breath, “You won’t believe the amazing things we’re doing and the insane things we’re doing.” But the leaders never wavered. They saw the fear, understood the anxiety, and held the line anyway. That steadiness — while staying deeply human — is what separates leaders who create transformation from those who just survive it.

My central conviction has never wavered: it’s never really about the technology. It’s always about the people. That’s what Dr. Katia Walsh and I found after two years interviewing over fifty executives for Winning with AI: The 90-Day Blueprint for Success, published earlier this week. The leaders who are winning aren’t the most technically fluent. They’re the most human.

I am probably not the first person you would expect to write a book on AI. I’m not a technologist. For most of my career, AI was inaccessible to me: too technical, too opaque, requiring skills I didn’t have. ChatGPT was the first AI tool I could actually use. And even then, it took time. That early version made plenty of mistakes; you couldn’t fully trust it. So when it turned out it could do a pretty decent job of imitating me, my head was spinning. I felt pressure as someone who advises leaders on disruption, I was supposed to have answers. Instead, I had vertigo.

What I’ve come to realize is that this is exactly why I was the right person to write a book on AI. Not despite being a non-technologist, but because of it. If I could find my footing in AI, understand it deeply enough to advise the world’s largest organizations, and build an entirely new way of working with it, so can you.

That’s when I stopped trying to outrun the feeling and started asking what it was telling me. What I heard was this: I had a lot to learn. And so did everyone else. The muscle I needed wasn’t AI expertise I didn’t have. It was adaptability. The ability to learn something new, feel lost, and keep going anyway. I’d been building that muscle for thirty years without knowing it had a name.

I still feel it. In 2025, I tried vibe coding by building a group scheduling app almost entirely through AI prompts. I barely know how to use Terminal on my MacBook. I went in circles for weeks, stuck on things any real developer would have solved in an afternoon. I eventually handed it off to my son, an AI product engineer, who sorted it out in a fraction of the time. It would have been easy to read that as failure. But I’d pushed myself into unfamiliar territory, stayed there longer than was comfortable, and understood the architecture of what I’d built in a way no tutorial could have taught me. The frustration was the curriculum.

I still get imposter syndrome about AI. I probably always will. But I’ve stopped thinking that disqualifies me. If anything, it means I’m still in the game.

If you’ve felt that disorientation, you’re not having a breakdown. You’re having an awakening. The disorientation is the signal.

What leaders actually do

Here’s the distinction that changes everything: managers maintain the status quo. Leaders create change. They step into voids. In every era of technological disruption — the printing press, electricity, the internet — the defining question was never whether things would change. It was who would show up to shape what the change became.

This is that moment.

I know a truck driver, now in his mid-forties, who understood this instinctively. A few years ago, he could see autonomous vehicles on the horizon, not tomorrow, but coming. So he got licensed to transport hazardous materials. His reasoning was clear-eyed: that’s where automation will go last. The regulatory complexity, the liability, the edge cases, it would take decades. He knew that. So he invested in extending the years he could do the job he loves, not by resisting change but by reading it clearly and moving to where it would reach him last.

He’s driving with that license now, though not every run requires it. The full transition is still probably a decade away, he figures. But as someone who genuinely loves his work, he didn’t wait for disruption to arrive at his door. He led himself first.

That’s the sequence that matters right now. Lead yourself first. Then lead others. Then lead your organization. It’s not easy to disrupt yourself, especially when you can see the change coming, which goes against every instinct to protect what you’ve built. But there’s a difference between being swept along by disruption and steering into it. My truck driver friend didn’t wait to find out which one he’d be. He decided.

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Lead it, or it leads you

As AI grows more powerful, the fears grow louder, and they’re not wrong. Nearly two-thirds of workers expect AI to make the workplace feel less human this year. When something feels that large and threatening, the temptation is to step back and let others sort it out.

I understand that impulse. But I’ve come to believe it runs exactly the other way.

AI is being built right now by companies, governments, and individuals with wildly different values and intentions. The leaders who will shape how this goes need to be people who care about how it goes. Here’s the data point that stops me: according to BCG’s AI at Work 2025 report, employee positivity about AI rises from 15% to 55% with strong leadership support. Your presence in this conversation is not a neutral choice.

You can only push back on something you understand. You can only advocate for responsible, ethical use of AI if you’ve actually engaged with it. Avoidance isn’t neutrality. It’s ceding the room to whoever shows up.

What the 20% actually contains

Back to my experiment. What AI couldn’t replicate was the 20% that came from a unique perspective: the unexpected angle, the creative leap, the question that only emerged from reading the emotional undercurrent of what was actually being asked.

That 20% is not a consolation prize. It’s the whole game.

But here’s the risk: it’s easy to let that edge go dull. Not because AI takes it from you, but because you stop reaching for it. When a tool can synthesize, summarize, and structure on demand, the temptation is to stop asking the questions that only you can ask — the ones born from your specific combination of everything you’ve lived, built, and learned. That synthesis isn’t in any training set. It’s yours alone. And it only compounds if you keep investing in it.

What it actually looks like to start

There’s probably something you know you should be using AI for but have been putting off. Maybe you don’t have time. Maybe it feels hard. Maybe you feel like you need to know more before you try.

You already have what you need. It’s called curiosity. Here are three places to start:

1. Use AI to learn how to use AI. Open a tool — ChatGPT, Claude, whatever you’ve been meaning to try and just ask it how to use it. Ask it to walk you through a task you do every day. You are one question away from starting.

2. Bring it into real work, not a test. Use AI on something that actually matters to you this week, a communication you’ve been struggling with, a document you’ve been avoiding. The stakes make the learning real.

3. Do it in public. Use AI visibly, with your team. Make a mistake in front of them. Say “I don’t know how this works yet, let’s figure it out together.”

And here’s what it will feel like when you start: uncertain. Messy. Like you’re missing something obvious.

Good. That feeling is called leading.

Your team isn’t watching for certainty. They’re watching for courage, for someone willing to move toward the unknown before it’s completely mapped. I didn’t have Terminal figured out when I tried vibe coding. I still don’t! But I showed up anyway, and that mattered more than the app I was trying to build.

The identity crisis AI is giving you isn’t a threat to who you are. It’s an invitation to become who you need to be.

So here’s the question I’ll leave you with: What’s the experiment you’ve been putting off and what would it mean for the people around you if you stopped waiting and just began?

Step into it.

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Charlene Li is the co-author of Winning with AI: The 90-Day Blueprint for Success (with Dr. Katia Walsh), available now. She is a New York Times bestselling author and one of the leading voices on leadership, disruption, and digital transformation.

For most of my career, we built companies like symphonies. There was a conductor. The music selection was impeccable. There was a written score. There were sections in which the strings, woodwinds, brass, and percussion each knew their part. Half a beat off, it became cacophony. But in sync, they created beautiful, complex music together. Sure, it was hard to get 70 to 100 musicians to play in concert, but the results were rich and breathtaking.

The same was true of tech companies. As products got more complex and coordination costs increased, there were more and more specialized functions. The atomic unit of success shifted from a PM and an engineer to two dozen people across eight different functions working together to get things done. Product, engineering, design, analytics, research, technical program management, content strategy, and product marketing all played their part.

We created complex roadmaps locked in advance. We managed handoffs and code reviews. We planned and replanned. If everyone played their part correctly, products shipped, and customers were serviced well. For years, that model worked and scaled.It ended up building some of the most iconic software companies of our generation.

But we are not in a symphony world anymore. We are moving into a jazz world.

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The Symphony World Is Changing

The symphony world is optimized for stability and predictability. It is designed for power, scale, and richness. Large teams operate with defined roles. Handoffs are structured. Specifications are detailed. There are rehearsals and careful preparation. If a violinist suddenly experiments mid-performance, the entire piece can fall apart.

This model made sense when:

• Software was expensive to build

• Iteration cycles were long

• Coordination costs were high

• Tools were relatively static

You needed orchestration because changing direction was costly. The score had to be right before you started playing.

It is important to acknowledge that symphonies are not rigid machines. Great orchestras interpret. They respond to the conductor. They shape phrasing and tempo together. Discipline and artistry coexist. In the same way, great companies have always balanced process with creativity. The difference today is not that orchestration disappears. It is that it is no longer enough.

The Jazz World is Upon Us

In jazz, a small group of musicians plays within a loose structure. There is still a key. There is still a tempo. There is still a shared understanding of the form. But within those guardrails, improvisation happens in real time. Musicians listen closely to one another. They adjust mid-phrase. One introduces a riff. Another builds on it. The music evolves as it is being played.

That is the world AI is pushing us into.

A prototype can be spun up in a single afternoon and shown to customers. Suddenly, the strict boundaries between roles begin to blur. PMs can prototype and run research. Designers can build experiences to test with users. Engineers can shape product direction. The sheet music becomes more of a suggestion than a rule.

One of the biggest shifts is not technological. It is cultural. In jazz, roles are fluid. The pianist may carry the melody for a while. Then the saxophone. Then the trumpet. Each musician remains a master of their instrument, but they are also deeply attuned to the group.

AI is lowering the cost of crossing boundaries and creating opportunities for cross-training. You no longer need to wait for another team to produce the first draft. Exploring, testing, and learning become everyone’s responsibility.

This does not eliminate specialization. In fact, jazz requires extraordinary discipline. Improvisation is only possible when mastery is already in place. The real skill is not freedom from structure. It is the ability to create within it.

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From Conductor to Bandmate

Leadership changes too.

In a symphony world, the conductor aligns dozens of people to a fixed plan. The goal is precision. Success is measured by how faithfully the score is executed.

In a jazz world, leaders create conditions. They set themes and guardrails. They build small, high-trust teams. They encourage experimentation while maintaining coherence. Feedback is continuous and dynamic. Instead of asking, “Did you follow the score?” they ask, “Did we create something better together?”

Listening becomes the defining leadership capability. Not just listening to customers, but listening across functions. Listening for signals. Listening for new ideas emerging from unexpected places.

Each individual now needs both depth and range. The ability to go deep in a craft still matters. But so does the ability to step into adjacent spaces and contribute.

The Risk of Staying Orchestrated

There is a danger in clinging to the symphony model too long. There was a time when big ate small and where rollups and integrations made sense. Then came a period when small ate big and disruptors arrived on the scene. Today we live in a world where fast eats slow.

Large organizations are comfortable with orchestration. Clear roles. Clear approvals. Clear hierarchy. These structures provide safety and predictability. They also create inertia.

Jazz requires discomfort. It requires:

• Letting go of perfect plans and rigid roadmaps

• Accepting iteration as the default

• Giving people more autonomy to make mistakes

• Trusting judgment over process

This is especially difficult for leaders who built their careers mastering orchestration. The instinct is to grip the conductor’s baton tightly because control feels safer.

But when tools evolve monthly, freezing the score becomes the greatest risk.

What This Means for You

Ask yourself:

• Are you optimizing for orchestration or adaptation?

• Are your teams small enough to respond quickly?

• Do people need permission to explore?

• Are roles rigid or fluid?

If you are a PM, are you waiting for engineering to build your ideas, or are you prototyping them yourself?

If you are a designer, are you waiting for research or analytics to give you feedback, or are you running quick experiments?

If you are a leader, are you rewarding predictability over learning?

The jazz world does not mean chaos. Jazz still has structure. There is still shared intent. The difference is that creation happens together, in motion, rather than in sequence. The companies that thrive in the next decade will not be the ones with the most detailed roadmaps. They will be the ones who can listen, adapt, and build in real time.

In a symphony, perfection is harmony and synchronicity. In jazz, perfection is dynamism and energy. The music of work is already changing. The question is whether we are still rehearsing the old score or learning how to improvise.

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In my first few weeks at Stanford Graduate School of Business, one of my professors gave the class an assignment: “Write your obituary.”

We were in our mid to late-20s, in the prime of our lives. We were young people who had just made it into one of the most competitive MBA programs in the world. We were healthy, ambitious, and ready for adventure. We were at the starting line of what we assumed would be long, impressive careers.

Our stories were just beginning, yet he was asking us to write the ending.

Everyone went home and did the assignment. We wrote about the impact we hoped to have. We shared about the families we wanted to build and the kind of leaders we imagined becoming. We wrote the pre-mortem for our lives when we had just started living them.

In a later class, the professor returned with a summary. Across the obituaries written by overachievers, the themes were strikingly similar. We talked about family, meaning, and impact. We confidently asserted that we would all die first, except for one student who wrote that he would hold hands with his wife and die together. We were thoughtful, earnest, and destined to live until we were close to 100.

Fast forward fifteen years to our class reunion. Two of our classmates had passed by that event. Their obituaries were no longer hypothetical. Their stories were complete.

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Letting the Future You Want Help You Determine Today

I have thought about that class often over the years. I graduated from business school more than two decades ago, and that obituary assignment is something I still revisit from time to time.

As the years passed, I would occasionally wonder whether I was making progress against those words I had written long ago. I built the family I wanted. I built a strong resume. I accumulated titles, responsibilities, and measurable success.

But at its essence, was I living the life that the 22-year-old version of me envisioned?

When you are young, life feels infinite. There is much more ahead of you than behind you. The next thing is always right around the corner. You focus on finals, landing the internship, the job offer, or graduation. You chase the next promotion, title, and milestone. Motion feels like progress.

But writing your obituary forces you to measure differently. You ask yourself, ‘What remains when the motion stops?’ That question unsettles us because so much of modern achievement is built on motion, but motion does not always result in meaning.

I studied engineering at Duke. I went to Boston Consulting Group, then Stanford. Then had a career in tech. Each step made sense and moved me forward toward some goal. For long stretches of my life, I was not asking what kind of story I was writing. I was asking what the next step should be.

Those are very different questions and will get you different answers. The story question optimizes for meaning. Your days are notes which make up the symphony, not just isolated and disconnected moments in time. When you look at things in isolation, prestige is seductive because it is measurable. Your LinkedIn looks better, and you show you are someone. But seeking meaning is quieter and hard to quantify. It doesn’t come with applause or praise.

I have written about the six years I spent having children, and how it set back my career. Regardless of whether it slowed me down or even ended my career, I would make that choice again. That part of my obituary is non-negotiable.

Each time I took a risk, I thought about my obituary, and it guided me in a new direction. It led me to pursue something that felt riskier and less certain because it aligned more closely with the impact I wanted to have. Letting go of the clearly defined path and stepping into ambiguity is hard, but through the obituary lens you gain clarity. It forces you to zoom out beyond this quarter, this promotion cycle, and this LinkedIn post. What life do you want to lead? What really matters in the dash between those two dates?

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How to Write Your Own Obituary

Writing your obituary is a powerful self-reflection tool that can surface misalignment in your life and open your eyes to possibilities you may have overlooked. Here’s a guide to get you started.

• Start with a blank page. Sit with it for at least an hour. Imagine the beats of your obituary. In the highlight reel of your life, what is included? What is left out? Who matters?

• Start writing bullet points. Map out your lifeline and highlight the key moments. What would you be most proud of? What are the turning points? Pretend a stranger is reading it; what would you want their takeaways about you to be?

• Create your narrative. Write your story. What are the themes? What did you value? How would you be remembered? Aim for 500 to 1000 words.

• Reflect on your story. Read it and set it aside. Come back a week or two later and reread it.

• Decide what you want to change.

  • If I continue living exactly the way I am today, is this obituary what I would choose?

  • What would need to change to achieve the narrative I seek?

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I go back and speak at Duke and Stanford a few times a year. I look out at the eager young students, and I see myself from over two decades ago. I think back to when I sat down in those same seats after turning in my obituary. It seemed so easy to follow the path set before me.

But life is not just a list of job titles and promotions. You can build a life that looks extraordinary from the outside, one that others admire, one that looks good on paper and in photos, yet still feel like something is missing because you never fully chose it. Autonomy over choice and ending is the creative license of the author.

So why do we write our resumes before we even think about our obituaries?

One serves as a record of where you have been. The other reveals who you were.

In my book Take Back Your Power, I opened the final chapter talking about this exercise and how it changed my way of seeing the world. Writing your obituary forces you to reflect on your choices from the end of the story, giving you a chance to reverse-engineer the outcome you want.

Write your obituary before you write your resume.

I used to hate birthdays when I was a kid. No matter what I was doing or how old I was, it always felt like it was such a disappointment. My parents were immigrants without a lot of money. I grew up in a town where I never felt accepted, and birthdays were just a reminder of those things.

I remember one year when my mom was away from home for my birthday, so I baked my own cake. My dad took me shooting with his BB guns in the backyard. It was pretty depressing, actually, and I remember thinking, “Birthdays suck.” I was 9 or 10.

As I grew older, birthdays seemed like something to be tolerated, just another day in the year. But I wanted my children to have a very different experience with birthdays. I wanted to make each birthday special in some way. Except a funny thing happened. They also treat birthdays super casually. I ask them every year if they want to have a party, and almost every time, they say no. Instead we just go out to eat and have a small celebration.

A few years ago, my friend’s husband died. Prior to his passing, she dreaded birthdays, but now sees every single birthday as something to be cherished. So on this, my 50th birthday, I want to commemorate the occasion by sharing what I have learned over the years.

I have been writing this blog for over five years and in that time have posted over 250 articles. Many of these lessons I learned the hard way. Looking across everything, these are the 50 lessons that mattered most.

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Identity and Direction

1. Define success before the world defines it for you.

If you do not articulate your own mission, you will optimize for someone else’s metrics. Writing a personal mission statement forces clarity and alignment.

2. The company you keep quietly shapes who you are.

Who you surround yourself with can influence your habits, mindset, and decisions, in more ways than you realize. Choose your circle carefully.

3. Treat life like a beta test; each day is a prototype.

We fear letting go or changing course, but sometimes pivots aren’t detours; they are the path.

4. Scarcity buries possibilities. An abundance mindset creates them.

Scarcity teaches us to view the world through a zero-sum lens, obscuring solutions and shrinking our world. But an abundance mindset allows you to discover win-wins you never considered.

5. Choose the story you tell about yourself.

If we do not take initiative in the narrative of our lives, it takes control of us. Change the story, change your life.

Career Foundations

6. Product manage your career like you PM your product.

Product managers build roadmaps. Few people build them for their own careers. Treat your life with the same consideration.

7. Learning to work with anyone is a secret superpower that unlocks new opportunities.

You will not always be able to choose who you work with. Inevitably, you are going clash with someone, or someone is going to clash with you. Knowing how to diffuse conflict and find common ground is a crucial skill.

8. Making friends at work can yield unlimited dividends.

Conventional wisdom says to clock in and out without getting too attached. But your colleagues can be powerful allies not just at work, but in life.

9. Build your career beyond your job and keep your eye on your broader learning.

As your competency increases in a role, your execution gets better, but your learning suffers. Your current role is just one chapter in your overall journey. Map accordingly.

10. Networking is not a dirty word but rather an opportunity for connection.

Change the way you look at networking, from transactional to connection.

11. When you enter a new role, preparation is key to landing well.

There are many pitfalls and challenges when it comes to starting a new job, whether it be a move within your existing org or a new one. Set yourself up for success.

12. Change is inevitable, but we can choose what comes next.

Many things in life happen that we don’t prefer, and even when the change is something long-awaited, navigating it can still be challenging. There is no roadmap for handling life’s transitions, but the good part is that we get to choose how we respond.

13. Having children may alter your career timeline, but you can stay true to the trajectory.

Maternity leave taught me that roles change who we are, not just what we do.

14. If you aren’t thriving, maybe it’s time to plant yourself in new soil.

Find a place where you are in the right conditions to thrive, and see who you can become without the constraints of where you have been.

15. There are no shortcuts. Sometimes the only way out is through.

Avoidance doesn’t make the change go away. The next steps may not be easy, but neither is staying where you are.

Leadership

16. Management is a learned craft, not just a stepping stone up the ladder.

Being good at your job doesn’t mean you’ll automatically be a great manager. Management is its own skill, and if you want to manage people, you need to learn it.

17. Learn how to solicit feedback to grow faster and gain more than you imagined.

No leader is perfect. At every level of your career, there will be room for improvement, yet at higher-level positions, it is harder to come by. Learn to ask for feedback so you can keep growing.

18. Think like a founder (even if you aren’t one) to unlock both skills and opportunities.

Great founders have a lot to teach us about leadership, courage, and creativity. The mindset of a founder takes your work from ordinary to remarkable.

19. Extreme clarity is the ultimate gift for yourself and your team.

Better a clear “no” than a messy “yes”. Misalignment stalls progress and creates rifts among teams. Drive extreme clarity to give everyone the best path forward.

20. Regardless of your title, executive presence is one of the most important skills in organizations.

Knowing how to appeal to those higher up on the ladder is a useful skill for any career stage.

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Influence and Communication

21. Connection, not words, is the key to influence.

It’s not about being right, it’s about finding common ground.

22. How you say it is just as important as what you say.

How you speak shapes what people think of you. There is power in using your voice.

23. Give the gift of feedback by showing, not telling.

Giving and receiving feedback is necessary, but often difficult. Delivery determines reception. Learn how to give feedback in a way that feels like a gift, not an attack.

24. Being impressive and making an impression are two different things.

The greatest leaders aren’t necessarily the smartest or loudest people in the room. They’re the ones who make others feel valued and understood.

Systems and Incentives

25. Execution fails because of systems, not effort. Find ways to change the system, not just the individuals.

It’s the little things that slow down productivity and create interpersonal strife. Instead of blaming people, examine the processes and systems in place.

26. Misaligned incentives distort entire systems, so find incentives that align teams.

From academia to tech, reward structures drive unintended outcomes.

27. Small efficiencies compound into big points of leverage.

Ten hours saved monthly becomes weeks annually. Focus on leverage to save time and multiply your impact.

28. Product strategy begins with empathy.

Vision without customer pain is theater.

Perspective

29. Data can change the way you look at the world. Leverage charts to change your perspective.

The charts that linger often challenge assumptions and make visible what was once invisible.

30. Solve for joy, and the rest will come.

Ambition without joy becomes brittle. Find what fills you up and build around it.

31. Regret holds you down. Live life moving forward, not looking back.

Regret is the act of looking backward. The more steps you take while looking back, the fewer steps you take while looking forward to where you could go.

32. Forward motion requires getting unstuck from something holding you back.

Clarity often follows action.

Mentors, Sponsors, and Coaches

33. A mentor advises. A sponsor opens doors. Find a sponsor to make a step function in your career.

Both are integral for not only advancing your career, but finding meaning and purpose along the way.

34. Credit is infinitely divisible. Generosity is a gift that pays forward.

Another mentor taught me to give more credit than necessary. Influence grows when ego shrinks.

35. Grow your coaching tree; pay the wisdom forward.

When someone pours into you, find people you can do the same for. You’ll be surprised by how much of an impact you can make in the lives of others.

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Life and Integration

36. Technology amplifies leverage, and AI will reward those who learn to harness the technology.

AI will not replace judgment; it will reward it.

37. Becoming a connector multiplies your impact.

Learn to see each relationship as a potential opportunity for creating a connection between two people who otherwise may not have met.

38. Rituals carry legacy. Honor the traditions that made you who you are.

Food, traditions, shared moments outlast titles. Create a legacy though understanding your family journey.

39. Openness accelerates growth. Give yourself the space to expand the aperture and see greater possibilities.

A Year of Yes broadens your horizons and carves paths you never saw before. Learn how to make space to explore.

40. Writing clarifies thinking. Create, don’t consume, to open your mind.

Consistency in writing sharpened my voice and convictions.

Enduring Truths

41. Ask what someone is optimizing for, and you learn what makes them tick.

Conflict often hides incentive misalignment. Alignment happens through mutual understanding.

42. Recognition and gratitude means more to others than you think.

Lift others up through praise and create more opportunity for connection.

43. Leading through others means enabling them to do their best work.

The higher you rise, the more your job is not to do but to lead through others and their success.

44. Adding instead of subtracting means you know what truly matters in your life.

The sunk cost fallacy and loss aversion can hold you back. Release your anchors and learn to let go.

45. Hard conversations and feedback are accelerants.

Avoidance prolongs dysfunction. Ask the hard questions to get to the truth.

46. Success may look different from what you were taught.

Many “rules” about career progression were built for a different era. Interrogate assumptions before you obey them.

47. Get rid of the maybes in your life. Let your yes be yes and no be no.

Prioritizing ruthlessly creates space for what actually matters. A fast no is better than a slow yes.

48. Don’t mistake motion for progress.

Busyness can be a disguise for stagnation. Separate the signal from the noise.

49. The long road is still the road that you can traverse with enough time and planning.

We often think our aspirations are out of reach, but with a clear plan and some discipline, nearly anything is possible.

50. You are still becoming, no matter what the age.

Every version of you was preparation for who you are today. The next version of you is being created every day.

Every year for the past 11 years, I have spoken in Professor Pfeffer’s class, Paths to Power, at Stanford. He has been instrumental in my career both as a mentor and as a friend. It is thanks to him that I ended up writing my book, Take Back Your Power. During that class, someone asked us, “What is the most important skill to have?” One of the other panelists said something that I absolutely agree with, and that’s what I’m writing about today.

Cooperation is an Option Until it Becomes a Necessity

One of the most important skills in a long career is learning how to work with anyone. Yet it is also one of the least talked about, perhaps because it feels so obvious on the surface, but so difficult in practice.

Early in your career, this skill does not feel particularly important. When you are an individual contributor, especially just out of school, you often have many options. You can join Team A instead of Team B, work on Product X rather than Product Y, or move between areas that interest you. Large organizations tend to offer many teams, many managers, and many paths forward, and if a particular dynamic or relationship does not work, there is usually a way to change it by just moving teams or assignments.

As you rise, those choices quietly begin to disappear. Once you become a manager, there may only be one or two roles at your level, and as you move further into senior leadership, you often take on responsibilities that are truly “an N of One” roles, with no parallel position and no obvious lateral move. At that point, the ability to make the role work becomes existential because if you cannot succeed there, there is nowhere else to go.

This is even more acute when you get to the top. You rarely get to choose your investors, boards, and your C-suite peers. The group of people you need to work with narrows, and your control over who you have to work with is nonexistent.

And yet, we spend surprisingly little time talking about how to actually work with people.

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The Unglamorous Reality of Cooperation

We talk endlessly about leadership, vision, influence, and executive presence, but we rarely talk about the day-to-day reality of working with people who think differently than we do, who operate with different incentives, or who may even seem to actively resist our ideas. I wrote recently about making friends at work, and while this topic is related, it is not the same thing. This is not about being social or universally liked. It is about learning how to work productively with almost anyone.

I am also not talking about truly destructive people. Narcissists, abusive managers, or people who intentionally undermine others do exist, but in more than twenty years of working across companies, boards, and leadership teams, I have encountered very few people who genuinely fall into that category. Most difficult situations are far more nuanced than that.

In most cases, people are rational actors responding to abitions, pressures, and fears that are not always visible from the outside. They have working styles that differ from ours, they are motivated by things that may not motivate us, and when we misread those dynamics, we often assume bad intent when the reality is simple misalignment.

As you become more senior, you also lose the ability to choose all of the parameters around you. When you join a board, the board already exists. When you join a management team, you do not get to choose your peers. When you are hired into a product area, you are often the last person to join (unless you started it yourself). At that point, the question is no longer whether you can choose who you work with, but whether you can learn how to work effectively with the people in front of you.

There are a handful of practices that have consistently helped me do exactly that.

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Practices to Work Well With Anyone

1. Begin with empathy

The first is to start by understanding what people value, which usually means starting with incentives rather than personalities. What are they trying to accomplish, how are they measured, and where do they want to go next? This sounds obvious, but it is surprisingly easy to skip, especially when collaboration feels strained. When things are not working, we tend to focus on what we need, what our team needs, and why the other person is being difficult, rather than pausing to ask what might be driving their behavior.

I once worked with someone who seemed actively hostile toward my team, and for a long time, I could not understand why. Meetings were tense, decisions dragged, and collaboration felt far harder than it needed to be. Eventually, I learned that this person had recently been passed over for promotion, in large part because their manager believed they had a poor working relationship with my team and that their success depended heavily on us. From their perspective, we were not peers or collaborators, but an obstacle standing between them and their next step.

Once I understood that, my approach changed completely. Instead of treating the situation as a conflict to be managed, I said, “Let’s get you there together,” and we had an honest conversation about what success would look like for both of us. The relationship shifted almost immediately, not because anyone had changed their personality, but because we had finally aligned on incentives. This was not a bad person. It was a frustrated one, and I had simply failed to see it.

2. Find commonality

Another powerful lever is finding common ground, which often matters more than we expect, even when it seems small or irrelevant to the work itself. Imagine walking into a room where someone is indifferent toward you or openly skeptical, and then discovering that you grew up in the same place, went to the same university, or worked at the same company earlier in your career. Or maybe you have kids of the same age or have the same hobby. Something subtle but meaningful shifts in that moment, because you move from being an abstract counterpart to being someone familiar standing on common ground.

This is not about forcing connection or manufacturing rapport. It is about being genuinely curious and paying attention to the details people share along the way. Those small moments are often the fastest path to trust, and when people feel even a sense of shared identity, conversations are richer, and collaboration becomes easier.

Equally important is taking the time to get to know the person, not just the role they play at work. We like to pretend that work is just work, but it never really is. People bring their full lives into the office, whether we acknowledge it or not. They carry ambitions, disappointments, joys, and losses that shape how they show up every day, even when those things have nothing to do with the job itself.

Making space for that does not mean oversharing or crossing boundaries. It can be as simple as asking about a weekend, celebrating a child getting into college, or showing up with empathy when someone is going through something hard. If work were only about executing tasks, AI could replace all of us tomorrow. What makes collaboration effective and meaningful is the relationship and the trust that comes from seeing each other as whole people.

3. Share the praise

Another lesson that took me longer than it should have to learn is the importance of making other people look good. This is one of the most powerful and underused leadership tools I know. I once read a line that said there is no upper limit to how much praise people can absorb, and while I laughed at the time, experience has shown me how true it is, when that praise is genuine and specific.

My team once hit a major milestone, and we did what many teams do. We celebrated internally, told the story of our success, and moved on. What we failed to do was thank the teams whose work made that success possible, particularly the platform and infrastructure teams whose contributions were essential but largely invisible. Unsurprisingly, they did not see our success as their success because we had never made that connection explicit.

The next time, we were intentional about doing it differently. We included those teams in the celebration, publicly acknowledged their contributions, and made it clear that without their work, none of what we had accomplished would have been possible. The difference in how they engaged with us afterward was immediate. Credit is infinitely divisible, praise costs nothing, and when people feel genuinely seen, they show up differently.

4. Take a team posture

Finally, I have learned that sometimes collaboration breaks down not because of disagreement, but because of posture. There is a physical metaphor I learned from Chris Cox that I return to often: When people sit across from each other, they naturally fall into debate mode. When they sit at an angle, they tend to have a conversation. When they sit on the same side, they are looking at the future together. The same dynamic exists emotionally. If people feel they are across from you, they prepare to defend. If they feel you are beside them, they begin to build.

Bringing people to your side does not mean avoiding hard conversations or pretending disagreements do not exist. It means framing challenges as shared problems and successes as shared wins, and making it clear through both words and actions that you want the people around you to succeed and that you are willing to stand with them when things get difficult.

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As your career progresses, technical excellence becomes table stakes. Strategy matters, and vision matters, but the ability to work with almost anyone quietly becomes one of the most decisive skills you can develop. You will not always get to choose your team, and you will not always get to change the context. But you can choose how you show up. You can choose curiosity over criticism, alignment over assumption, and generosity over scarcity.

Most people are not your enemy. They are navigating their own constraints, ambitions, and fears, just like you are. When you learn to see that clearly, you unlock a level of leadership that no title can give you.

If you found this helpful, you may like these Perspectives:

I grew up in South Carolina in the 1980s and early 1990s, during the great hollowing out of the state. I remember the feeling of living in a state in decline, something which was evident all around us.

Manufacturing was leaving the state. Textile mills shut down in favor of imports. Factories that had anchored entire communities for generations went dark. I traveled across the state for speech and debate tournaments, and I remember driving through towns where the largest building sat empty in the center, a hollow shell behind chain-linked fences. The work left, and with it the vitality of the town itself.

In South Carolina, manufacturing jobs dried up. One in four South Carolinian industrial workers specialized in textiles, yet textile and apparel-related jobs dropped from 120,000 in 1994 to 49,000 (a loss of over 50%). By 2004, 75% of textile jobs were erased due to factory closures, outsourced manufacturing processes, and roles made redundant by new technology left workers flapping in the wind (source). The jobs that did replace them were less stable and paid less. They also lacked advancement opportunities that fueled the middle-class growth of the state.

We did not call it displacement then. We did not talk about structural shifts or labor transitions. We just saw it happen before our eyes. We watched families move away, schools shrink, and main streets emptied.

In 1996, the government closed the doors to the Charleston Naval Shipyard, where my dad worked for over a decade. He was reassigned in 1993, the year before my high school graduation. Many of his colleagues took buyouts, but my dad was close enough to retirement that he accepted whatever assignment they offered. We moved across the state to a small town in Georgia. A few years later, that site had massive layoffs, and my dad was reassigned again, this time to a more remote posting at a base in Oklahoma.

Job displacement is not theoretical. It is a physical manifestation of the changes in our economy. It uproots families and reshapes communities. It lingers long after the economic models say things have adjusted.

I think about my time growing up in SC when people talk about AI automation today. Technology is incredible in so many ways. I have devoted my career to the field because of the positive impact it has on the world. But there are tradeoffs. Just like you can’t chase a metric blindly without guardrails, you also can’t rush headlong into the AI era without understanding the true impact it can have. There will be a lot of societal benefits, for sure. People who lacked access to education, health information, or insights will now be able to unlock it. But each technology leap forward (including globalization of supply chains) is concentrated with shareholders, while the consequences are borne elsewhere.

What follows are six observations about what is actually happening now.

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Work is Going to Change Due to AI Productivity Gains

In 2024, McKinsey’s report “A New Future of Work” estimates that 30 percent of current office work hours could be automated by 2030. That is a significant improvement in productivity, but also the loss of entry-level jobs where training happens.

This will be applied unevenly. In some sectors, this will reduce the need for incremental hiring, while in others, the result will be full job displacement. Companies will have a choice between taking the cost savings to the bottom line and reinvesting in incremental growth. The jury is out on where these productivity gains will manifest: the top line or the bottom line?

In 2025, global tech companies eliminated roughly 150,000 to 170,000 roles, according to Layoffs.fyi, marking another year of significant contraction across the sector. Several major firms publicly linked portions of those cuts to AI-driven efficiency gains. That is just one sector in one year. Forecasts from firms such as McKinsey suggest that the displacement risk is significant, impacting from 25% to 30% of jobs in key industries.

(Data: U.S. Bureau of Labor Statistics 1, 2)

This all makes sense. A large bank laid off most of the team that summarized the news from global markets for the US team. Why have a full team staffed when AI can automate 80% of the job with human oversight? AI is transformative, but in small and quiet ways. This will continue over time.

The Move from the Agrarian Society to an Industrial One is Analogous

The move from agrarian communities to an industrial one is illustrative of what happens in times of major change. We move from horses to cars, manual labor to tractors, and small farms to large corporate farms.

(Data: Census Bureau, USDA, Gilder Lehrman Institute)

We don’t try to keep employing horses or encourage young people to become farmers. Instead, we adapted, and society shifted around the displacement. We found new areas to invest our human ingenuity, and society advanced. We now produce way more food than we ever thought possible, and even go on to waste about 40% of it.

While some communities lost, the US as a whole thrived. The US population tripled, and nominal GDP grew roughly 20x. Horses were no longer economically viable, and farming is less than 2% of the workforce today.

Like the manufacturing loss of the 80s and 90s, the first half of the 20th century forced us to change the way we work.

The coordination layer in modern organizations faces a similar dynamic. Not because humans cannot coordinate, but because AI systems offer a lower cost structure at acceptable or perceived acceptable quality. These decisions are driven by economic optimization, not by careful consideration of what capabilities are being lost.

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Income Distribution Changed Along with the Workforce

Manufacturing automation from 1980 to 2010 provides a useful history lesson. U.S. manufacturing employment peaked at about 19.5 million jobs in 1979 and fell to roughly 11.5 million by 2010, dropping from roughly one-quarter of total employment to under 9 percent, even as the GDP doubled. But the benefits of this growth were not evenly distributed, as we saw a dramatic gap open between worker productivity and worker pay. Today, worker productivity is at a historical high (90.2%), yet workers’ hourly pay has only increased by 33% since the gap first appeared in 1979. (Source.)

The economy grew. Labor’s share of the growth shrank. In the late 1970s, the bottom 90 percent of earners captured roughly 60-65% of total income growth, and the top 1 percent captured about 10 percent. Today, the top 1 percent captures about 20 percent of national income, yet the bottom 90 percent captures only 40-45%. Simply put, Americans are producing more than ever, yet their share of the pie is getting smaller.

Income Inequality in the US

In an AI world, it is possible that workers will capture 30% of the gains, and infrastructure owners could capture 70%.

Impact Will Be Uneven and Uncertain

If entry-level employees disappear, what does that mean for leadership development? No one shows up to a law firm as a third-year associate or at a consumer company as a marketing expert. Someone has to do the training. In many apprenticeship fields such as tech, law, banking, and consulting, it is unclear what will happen when that changes.

I am a techno-optimist. I believe that we will unlock new ways of doing things and thus create more productivity, which will result in the growth of GDP. But we need to fix the way we employ human capital, and the transition will be hard.

(Data: SoCalGIS)

In 2014, truck driving was the most common job in the majority of US states, but times have changed. Today, fast food and retail workers are the top jobs in 25 states.

(Data: Voronoi)

These jobs are less stable, more temporary, and have less opportunity for growth.

Without a ladder where workers can get on the first rung, what does that mean for the future of innovation and technology?

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Changing the Social Contract

A company I know was able to replace 80% of a key analytics and modeling team with an AI tool they built in-house. The reality was that the AI output exceeded the quality of that from the team, and there were no other roles in the company that suited their skillset. They made sure to place each of these employees in new roles outside the company and helped them with the transition.

I mentioned the story to another tech leader, and he said, “Perhaps a better way would be to pay those whose intellectual capital was used to create the models a licensing fee for their contribution.” I am not sure how workable that is, but universal basic income or some way to allow families to have a stake in the productivity gains is vital as we go through this transition.

There is no easy answer. We have been through multiple work revolutions and come out the other side a stronger economy, but do we come out with stronger communities and societies? That is the key question we all need to wrestle with.

This article was co-authored by Lexi Reese, who is the founder of Lanai and former COO at Gusto (ex-Google). She is a leading expert on AI governance and regulation, Council on Foreign Relations member, and former Harvard Business School Fellow. Check out Lexi’s Substack here.

Special thanks to Tom Fishburne for allowing us to use his illustration for the cover photo of this article!

It has always made me sad to hear people say they don’t want to be friends with their coworkers. Some of my closest friends began as coworkers. And while “I’m here to do a job, not make friends,” sounds like the kind of traditional wisdom that creates a successful career, workplaces can be filled with abundant opportunities for the kind of community our lonely world desperately needs.

The Workplace as Community

Our local neighborhoods used to be our communities. There were civic organizations, churches, neighborhood groups, and shared rituals. As many of these spaces have faded, people are increasingly meeting people where they work.

I belong to a church community. I participate in Lean In groups. Those matter. But I also continue to find deep meaning in the coworkers who became friends along the way.

I write about this in my book, not as a career strategy, but as a life philosophy.

In my book, I talk about four types of allies: your manager, your mentor, your sponsor, and your team and circle. Mentors and sponsors are relatively well understood, and I have written extensively about both. I have also written about your circle, the people closest to you who help you make sense of the world.

What I have not written nearly enough about is your team.

Your team is the group of people you work with day to day to accomplish something together. They are the people you spend as much time with as your family, sometimes more. And yet I often hear people say, “I go to work. I’m not here to make friends.”

But that is where so many friendships begin. Some of my closest friends are people I worked with years ago. They are people I traversed a stretch of life with. Maybe only for a few years. But the impact was lasting.

The same is true of many friendships from my early days at PayPal. We started our careers together. We helped each other land jobs, navigate hard managers, recover from setbacks, and say yes to new opportunities. In some cases, we have worked together more than once.

That is a precious thing.

As we think about what we are trying to do with our lives, we should not forget how important this team is. These are the people laboring beside you every day to create something for the world, whatever that thing is.

They are your co-conspirators. Your partners. Your teammates.

At Ancestry, we used to say that you play for the name on the front of the jersey, not the back. When you are part of a team, you are part of something bigger than yourself. You show up differently when you believe that.

You will spend more than half your life at work. The people you meet and the experiences you share there matter. You each hold part of the other’s experience.

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We Are All Connected

I live where I live because a former coworker, Robyn, told me I had to buy the house a few houses down from hers. I discovered cancer early because of Mauria, someone I worked with and met at PayPal. I worked at Facebook because my former engineering partner, Guy, reached out and championed my candidacy.

I have written before about my friend Ha Nguyen. She was on the eBay side, and I was on the PayPal side during the eBay-PayPal integration in 2002. We have been friends, on and off, for more than twenty years. She introduced me to my cofounder. She is the Vice Chair of Women in Product. She supports me in a thousand small and big ways. She knows how to get into my house and can borrow anything at any time. In fact, I think she is working upstairs in my living room right now. She has shown up every single time I asked.

I have helped former coworkers find jobs, advised their startups, helped introduce them to investors, and hire others. I have recommended them for boards, invested in their funds, and had them speak at my conferences.

They have helped me immeasurably, and I have helped them in return. I have been to their weddings and baby showers. I have sat beside them at funerals. We have celebrated promotions, launches, and acquisitions. We have also carried each other through illness, loss, and moments of deep uncertainty.

The richness of these relationships cannot be underestimated. Work does not just have to be a place you punch in and out of. It can be a place to discover meaningful relationships, build belonging, and create true community.

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The Importance of the Lynchpin

Many years ago, my friend Alan started convening a group of us who had worked together in the early 2000s. It was a magical moment in time, roughly from 2000 to 2004. We went on to navigate life in Silicon Valley together. In this photo, there are two of my managers, several of my direct reports, and people who now work for and with each other again. We have continued to live life together well after we are no longer actively working together.

Recently, we attended the funeral of a friend who is missing from that picture. We had worked together nearly two decades ago, but he always made it a point to connect whenever possible. A lot of the people who came to celebrate his life were those he worked with and turned into friends over the years. They were his colleagues whose lives he had touched. They were teams he built. They were people who sat near his cube that stayed in his life.

He turned coworkers into friends. Every one of us in that room was better for it.

His smile had always been a reason for us to gather. Standing there, I decided that I did not want the next time we came together to be another funeral.

So, this week, I hosted two dozen former coworkers and friends from PayPal at my house for dinner.

Several people told me they had not seen each other in fifteen years. And yet, when they walked through the door, it felt easy. Like picking up a conversation that had simply been paused.

It was deeply gratifying to bring together a group of people who cared about each other, who had built something meaningful together, and who are still connected all these years later.

How to Make Friends at Work

That brings me to a question I get surprisingly often: how do you actually make friends at work?

I read once that friendship is not transactional, but rather reciprocal. I liked that statement.

Be generous without keeping score
Share information freely. Make introductions. Offer help. Advocate for people in rooms they are not in. Most work friendships grow over time. They begin with trust and blossom with nurturing.

Invest in the in-between moments
Coffee, lunch, walking meetings, a quick check-in after a hard meeting. Friendship is built in the spaces between the formal moments, not just in meetings or deliverables. Those small, repeated interactions are where people move from role to relationship.

Let yourself be human
You do not need to overshare, but you do need to be real. Mention your kids, your parents, your hobbies, or what is weighing on you. When you allow others to see you as a whole person, you give them permission to do the same. Vulnerability is often the invitation that turns a coworker into a friend.

Tend the relationship beyond the job
This is where many connections fade. Send the note after someone leaves. Celebrate the new role. Make the introduction. Check in a year later. Life is long, and the world is small. The relationships that last are the ones someone chooses to keep tending.

And finally: Be the person who convenes. Every group needs an Alan, someone who can be the reason to get together.

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Community does not happen by accident. Someone has to send the invite, host the dinner, organize the reunion, or say, “We should get together.” That someone can be you.

Make friends at work.

You may not realize it in the moment, but years from now, when you look around a room filled with people who once built something alongside you, you will be grateful you did.

I have always loved data. Charts allow us to visualize data, which in turn reveals perspectives we hadn’t considered. A chart can validate something you long suspected, or challenge a bias you didn’t even realize you had. I have a penchant for collecting interesting charts, and I have shared many of them here with you.

You can read the original posts here:

• Ten Charts I Can’t Stop Thinking About

• Ten More Charts I Can’t Stop Thinking About

• Ten Charts I Can’t Stop Thinking About - Part Three

• Ten More Charts I Can’t Stop Thinking About - Fourth Edition

Today, at a time when AI is moving faster than any technology before it, it can feel like a runaway train of progress. Data provides much-needed grounding, and charts can help us demystify the buzz and also offer clarity. I’ve collected these charts that illustrate the AI era and shared them below, along with my thoughts.

1. Gen AI Launched With A Bang, and Consumers Felt It

Image: https://www.globalxetfs.com/articles/generative-ai-explained

The ChatGPT adoption curve is a chart I always think about. ChatGPT 3.5 launched in November 2022, and within just two months, ChatGPT hit 100M users, faster than many modern tech tools.

Something that always seemed five years away (after decades of investments) arrived with an unmistakable impact, making a huge splash that everyone felt. AI went from abstract to real almost overnight. Consumers adopted it at an incredible rate of speed, and it wasn’t just a flash in the pan. Retention was 80%+ after one month (crazy high), and the curve up at the end (60%+) means people are coming back more. Whether it is for personal or professional use cases, users are clearly finding reasons to stick around past the hype.

2. AI Adoption is Faster Than the Internet and Cellphones

Image: Winbuzzer, Microsoft

This chart puts AI’s adoption in the context of other revolutionary technologies, not just internet products. Each of these technologies was the AI of its time. They changed so much of the world around it, yet still took years to take hold. Not so with AI.

Usually, there is an S-curve of adoption. A few early folks picked up the technology (I am looking at you Gordon Gekko), but it didn’t hit widespread adoption for years. AI was different because there wasn’t a long ramp. Usage began immediately, speaking to the clear value people felt from the start.

3. Cost to Compute Far Exceeds the Revenues

Image: A1a2research

This chart is a quiet but critical one.

Despite massive usage, the cost of training and running large models far exceeds the revenue they generate today. That tells us where we are in the cycle. We are still building the rails on which the whole system is built.

This is an investment phase, not a harvest phase. Just like early internet days, there was a lot of investment, but it takes time for business models to shake out. Pets.com, Webvan.com, and Kosmo.com fell by the wayside, but what emerged later was Chewy, Instacart, and DoorDash. We still need a lot of CPUs to do the training to extract value, and it looks like that phase will last for quite a while longer.

4. Capital is Highly Concentrated

Image: STATISTA

Image: SaaStr, Perspectives

This chart shows capital concentrating heavily in a small number of companies, models, and infrastructure providers. The power law is extreme. A handful of players control the foundational layers of AI, and that is where a lot of money is going. Beyond that, we are seeing the emergence of applications and businesses on those foundational layers, all built with AI. But that means other spaces are getting much less investment during this time.

5. AI is Changing Industries and How Things Are Done

Image: AXIOS

This chart is startling because of how quickly it became true.

In under two years, AI-generated content crossed the halfway mark. Entire industries changed almost overnight. The takeaway is not that AI content is inherently bad, but that in a short time, original content is now a minority of what is available. What happens when AI is training on AI writing? Do models improve or degrade? The jury is out.

6. Companies Are Struggling to Achieve ROI

Images: MIT

The MIT data showing that roughly 95% of embedded or task-specific AI pilots fail to reach production is sobering.

There was a rush of excitement about how AI was going to change everything, but it didn’t translate to tangible business results. AI experiments launched without changing workflows, incentives, or decision-making won’t succeed.

AI does not work if we don’t include the human factor. If people don’t trust the tools or they are unwilling to adopt them, these pilots will continue to fail. Companies need to take into account that just implementing AI is not enough. It requires integration of the work into what people are doing, and the work has to be redesigned to integrate both AI tasks and human input.

7. AI is More Beneficial for Executives Than Frontline Workers

Image: Wall Street Journal

This chart makes the unevenness visible.

Executives report larger time savings than frontline employees. That makes sense. Many AI tools are optimized for summarizing, synthesizing, and decision support, work that maps closely to executive responsibilities.

Further down in the organization, workers are stuck with antiquated processes, tools, and workflows. The interdependency makes it hard for any individual worker to effect change. Without intentional design and thoughtful adoption, AI will quietly widen internal value creation.

8. Women Use AI Much Less Than Men

Image: University Of Chicago

Even within the same roles and industries, women use AI tools at lower rates than men. Many women report feeling like AI is a shortcut or cheating, and thus they avoid it. I was speaking with a recruiter at a big Silicon Valley firm, and she said that without AI on the resume, candidates are at a significant disadvantage. Imagine you were applying for a job at a tech company in 2000, but didn’t use the internet. Or you were working in consumer tech in 2013, and you said you didn’t understand mobile.

Adoption gaps compound over time, especially in fast-moving technological shifts, and companies are looking for talent that is AI-ready and can demonstrate proficiency.

9. AI Is Changing the Employment Landscape

Image: Josh Bersin

The labor market shows that new college graduates are being hit first.

Many industries employ on-the-job training. Entry-level work is often structured and repetitive as you learn the ropes. But that is exactly the kind of work AI can replace. If no one starts as a copywriter, does anyone make it to editor? If there aren’t first-year associates at professional services firms, will there be partners?

This is something we need to wrestle with.

10. We Are Only Beginning to See What AI Can Do

Image: Our World In Data

The final chart is the most important because it is the most humbling.

When placed alongside past technological revolutions, AI adoption is still early. What feels experimental now may look obvious in hindsight. Technology is advancing at an incredible clip. If these patterns of improvement are a guide, expect more industries and workers to be disrupted.

We don’t know the ultimate destination, but AI is disrupting so much, so quickly, that things are changing by weeks, not years. We ignore the implications at our own peril. I hope as you ponder the role of AI in the world, you take a moment to think about how it is affecting what you do and what you need to do to future-proof yourself.

I once had an analyst on my team who was doing the job of an interim Product Manager day-to-day. He had earned the respect of the engineers and was trusted by cross-functional partners. He already was the PM in everything but title. But to make it official, he had to clear one last hurdle: the PM transfer interview.

All transfers into Product at Facebook had to pass the same bar. No exceptions. Even if you were already doing the work or your manager was championing you, you still had to clear that one last hurdle.

He failed. Though he clearly had the skills, judgement, and relationships, that one interview stood between him and the role he was already excelling in. We were both frustrated by this. So, later, when he got another shot, I prepped him by filming a mock interview and playing it back. Then I asked a simple question, “Would you hire him?” He paused, shook his head, and said, “No. He’s all over the place.”

That was the issue. He was too detailed, too many things to say, too quickly. He wasn’t providing clarity for the listener. Even though he was perfect for the role, the interviewer couldn’t determine that based on how he came across in the interview. With practice, he learned how to structure his answers, land his points, and communicate with intention. He passed the loop. He went on to have a successful PM career and is still in the role to this day.

I’ve seen this pattern over and over. The truth is, interviewing is a skill. And it is a different skill than doing the job.

The interview is often the real gate

Over the years, I’ve interviewed and hired over a thousand people. I led product recruiting at Meta for many years, and I watched incredibly strong candidates fail interviews. Not because they lacked skill or experience, but because they didn’t know how to articulate it.

You can be excellent at the job and still fail an interview. And you will not get to that job without the skills to get past the front door. Most interviews are not just testing whether you can do the job, but whether someone wants to work with you to do that job. That sounds subjective, and it is. But it is also reality.

Hiring managers are asking themselves things like:

• Can this person communicate clearly under pressure?

• Would I trust them in front of executives, clients, or the board?

• Do they have good judgment? Intuition? Self-awareness?

• Would I enjoy working with them?

You can give all the “right” answers and still lose the room if the interviewer cannot picture you as a partner. That is why interviews reward preparation and communication far more than raw competence.

I am not defending the current hiring system. We all know it has huge blind spots and is flawed in many ways. But this is the system we have today, so my goal is to show you how to navigate it.

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Interviewing is a skill, so treat it like one

I have seen too many candidates try to wing it. After all, they have a decade of experience in the job. They know the ins and outs of their skill set. The company would be lucky to have them. For years, I did interview prep, and clearly, interviewing is a skill that atrophies over time. You can be the best at what you do, but be unable to articulate it and thus unable to get the offer.

I urge candidates to practice. Then practice some more. You would not run a marathon without preparation, so why would you interview without it?

Learn to tell your story. Nail the narrative arc. Have your examples on hand. If you freeze in an interview, the interviewer is not thinking, “They are nervous.” They are thinking, “Will this person freeze in front of our board?”

While this may sound like an unfair leap, it is a real and common one. Practice protects you from misinterpretation.

Your stories matter as much as your resume

Interview questions feel different, but the underlying themes are remarkably similar across roles and industries:

• Tell me about a failure

• Tell me about conflict

• Tell me about a hard decision

• Tell me about something that did not go as planned

• Tell me about a time you had to perform under pressure

They’re not just asking about your ability to do the job. They’re trying to figure out how you, specifically, do the job and if it is in line with what they need. If you answer the question without understanding what the interviewer is actually listening for, you miss the opportunity. Always ask yourself: What are they really trying to learn about me?

You should have a small set of stories that you can adapt depending on the role and the organization. What changes is not the story, but what the company or team values. A startup may listen for speed and adaptability. A large organization may listen for judgment and stakeholder management. A client-facing role may listen for clarity and trust-building.

Know what they are looking for and show them proof you’re exactly that.

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Think about what lands, not just what you say

I can vividly remember my first meeting with Sheryl, when I had just been hired at Facebook. I pitched her the idea for Facebook Marketplace, and she replied, “First do the job you were hired for, then we’ll talk.” What seemed to me like sharing a great idea could have given her the signal that I was not serious about the job.

Don’t think about what you are saying; instead, focus on what your interviewer hears. Tailor your message to their concerns and aspirations. Find commonalities and points of interest that will connect you. Mimic their body and spoken language. Choose your stories carefully.

A quick guide to interview prep

If I were interviewing today, here’s what I would do:

1. Build a story bank: Have 6–8 core stories at the ready that cover failure, conflict, influence, ambiguity, leadership, and impact. Think through ways they can be adjusted and personalized to each organization you are interviewing with.

2. Practice out loud: Thinking is not enough. Interviews reward verbal fluency. Work with a friend, ask a mentor for a mock interview, or take advantage of AI tools (like Superinterviews by Sidebar) to help you prepare. Use every resource at your disposal to dial in your pitch.

3. Ask for a moment if needed: It is okay to say, “Let me take a second to think.” It is better to pause and ask for time than to ramble or leave long silences.

4. Tailor, do not spray and pray: Every company and hiring manager is listening for something slightly different. Know what that is and adjust your stories accordingly. If growth is their challenge, focus on your experience there. If they are experiencing growing pains, focus on that.

5. Connect then communicate: This is not a written exam or else they could just give you a list of questions to type out answers to. They are looking to connect and get a feel for you. At the end of the day, your interviewer wants to know that you are someone people will want to work with.

6. Help them imagine you in the role: Speak as if you already own the problem. Show judgment and reasoning, not just answers. Show you can do the job before you get the job, and you will leave the room with your interviewer feeling confident in their choice.

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A final thought

Hiring is a system that has evolved over many years. Interviewing is an imperfect process that tries to sift through to find the perfect person. But it often screens out good people, who otherwise could excel at the job.

The good news is that, just like any other skill, interviewing is something you can master. You can learn it and prepare for it. This will turn the odds in your favor.

If you already have the skills, the experience, the ideas, your job is to present them in a way that can be easily understood and appreciated by the person on the other side of that hiring desk.

Make them want to want you, and you will land that offer every time.

If this was helpful, consider sharing it with someone who is preparing for their next interview. And if you want to go deeper, you may find these Perspectives helpful:

• A Simple Guide to Nailing Your Interview

• Non-Obvious Tips for Landing the Job You Want

• 5 Steps to Take Back Power in Your Career

I have spent much of the past few years having to say no. Not out of desire, but being swamped with so much, I had to learn to prune to retain my sanity and focus on what mattered. That also meant I missed out on a lot.

From the moment I landed my first job out of business school, I have worked continuously. A week later, I started at PayPal. From there, I went from role to role, company to company, without a break in between. I would end one job on a Friday and start the next one on a Monday. I never took time off between chapters. I never left space between identities. I just put on a new badge and marched on.

Other than pausing to have kids, I barely gave myself the chance to breathe, much less take a break. Suddenly, I woke up and more than two decades had passed since I started in tech.

I put one foot in front of the other and continued my path upward and onward. I chased forward momentum and kept building and building. I never stopped long enough to sit still, and anyone who knows me knows that stillness is not something that is in my nature.

But this year changed all that. As I worked on my Year in Review (a practice Katia taught me), it looked totally different. This year broke the pattern. It was a year where I didn’t have a set path, and thus had the freedom to say “yes” to things that I could not have imagined.

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Embracing Yes

Early in the year, I stepped down as the CEO of Ancestry after 4 wonderful years at the company. My last day was set to be the same as my surgery for early-stage breast cancer. Simultaneously, my husband’s company was acquired, so we decided to take the year off together and explore our interests.

I told myself that this year, I would show up. I had missed countless events with friends and family: birthdays, anniversaries, and more. I had traveled nearly half the weeks last year, even when my mom was at home with us in hospice care. So, I wanted to be able to say yes to everyone and everything I could.

Some yeses, I did not get to choose.

I said yes to surgery. Yes to 20 rounds of radiation. Yes to being vulnerable in ways I had never practiced before. Yes to learning the limits of my body. Yes to five years of Tamoxifen, a drug with meaningful side effects, because it also cut my chances of recurrence in half.

Those yeses were necessary. They taught me that sometimes the freedom to choose means making space for things we didn’t anticipate or want, but saying yes meant embracing and running toward something rather than reluctantly accepting it.

In the middle of all of this, between diagnosis and surgery, we finally moved into a house we spent nearly four years building. The house was meant to be a place where our parents could all live together with us, but sadly, we never got to enjoy it with them. We moved in when it was still partly unfinished. I hired movers to just move our furniture and whatever laundry we had in the baskets, and then we spent the next few months slowly bringing what we needed over.

For years before that, my mom lived with us. She had Stage IV cancer for many years, and her health was fragile. We lived carefully during Covid and even after. We rarely had people over because we didn’t want to risk her increasingly fragile health. Our home became a place of protection from the outside world, rather than a place we could invite others in. When we moved into the new house, we made a conscious decision to change that.

David had told me before we married that he wanted a home that was open to everyone. We hosted weekly Bible studies and dinner parties for years, but after mom got sick, we stopped. He continued to admire our friends, Al and Ann Ko, who always had others over, even when it was messy, busy, or imperfect. Now, without our parents here with us, we said yes to inviting people in. We hosted three Women In Product events, invited the Duke DTech community over, and had our friends over for our 25th anniversary. We had monthly dinner parties for friends and strangers, and we invited friends to come and stay with us.

Yes to Connection

I opened up my calendar to connection. That led me to meet Sheila, who connected me with TEDx San Diego for a talk, where I met incredible people like Sarah Patcher and Emily Bouchard. I had planned to speak about the book I was working on, but pivoted to Let’s Make It Awkward instead. Sometimes “yes” means letting go of pre-planned notions and letting it take you where it will.

I started advising founders and helping entrepreneurs make their dreams come to life. I joined the board of Poshmark after being a seller and customer for many years. I consulted for a couple of large organizations that were looking for advice. I worked with Ha on recruiting for a startup.

I said yes to writing my next book, and I created the framework that will be the basis for it. I shared the framework with dozens of people who gave feedback and insight into their transitions.

I said yes to dinners with the kids. We played board games and sang karaoke and drove each other crazy. We binged Resident Alien, Matlock, Psych, and Ghosts together. I spent late-night sessions helping Bethany with her college applications and Danielle practicing her speech for competition.

I said yes to events I could never have made before. I was attending a milestone birthday party and ran into someone who had flown in from far away just to be there. He said, “Life is too short not to celebrate every moment we have together.” I went to back-to-back holiday parties and stayed late without feeling the need to rush home.

I said yes to learning AI and understanding where this revolutionary technology can take us. I took a vibe-coding class, which led me to become a founder myself.

Saying yes meant being open to things I never could have done before and filling it with friends, connection, and possibilities.

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What I Learned from a Year of Yes

1. Yes does not have to be perfect. You do not need to see the entire path to take the first step. Your house can be messy, and your first steps can be wobbly. My mantra is “people come for connection, not perfection.”

2. Showing up is often enough. Don’t wait until you are ready. Sign up and do it. Improvise and learn along the way.

3. Push yourself out of your comfort zone. Saying yes to things you find challenging stretches your muscles in new and unexpected ways. Like any muscle, it gets stronger the more you use it.

4. Take time to process. The temptation of go-go-go means sometimes you leave no time to reflect. In the midst of yes, learn to sit in silence and think about what you’re learning and what you want.

After a lifetime of momentum, I let go of my identity tied to a job and joined the “Blank Name Tag Club”. Rather than letting it feel like a loss, I created a sense of possibility. Anything and everything could fill that line, and that led me in new and unexpected directions.

I’m excited to see where the next set of yeses take me.

What are you saying “yes” to this year? Let me know in the comments.

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Related Perspectives:

Last year was a significant one for me, with exciting new opportunities, difficult lows, and big changes; but it was also a big year for Perspectives. Next week, I’ll share my learnings from 2025, but this week, I wanted to share some highlights from this incredible community we’re building together.

For starters, there are over 4,000 more of you than there were in 2024. Welcome! I never thought back in 2021 that Perspectives would grow (and continue to grow) as it has. This newsletter is a labor of love. Each week, I think I am out of things to say, and every week, I am inspired to write something because of all of you.

Across socials, Substack, email, and LinkedIn, Perspectives has reached hundreds of thousands readers, connecting people across industries and cultures through shared interests and values: family, parenthood, AI, heritage, health, career growth, and leadership. Late last year, we relaunched Dear Perspectives, a LinkedIn newsletter companion to Perspectives, where you can read answers to your questions. That newsletter quickly grew with over 2,000 new faces.

Together, we’ve swapped stories about everything from grief and decluttering to napkins and first jobs. We’ve discovered commonalities, learned how to make things awkward, bonded over being the “lecture” parent, and more. I started this blog as a way to untangle my thoughts and share what I felt may be helpful to others on their journey, even as I walked my own. Looking back at 2025, I can see that I am not working them out alone.

Top 5’s of 2025

Here’s our 2025 highlight reel. Catch up on anything you missed below.

Top 5 LinkedIn Posts:

These LinkedIn posts clearly resonated with so many of you, as they were my most popular posts on the platform last year.

1. My Ancestry exit announcement was a bittersweet moment.

2. My post about the 2025 Women in the Workplace report. The ambition gap is widening, and women need more support inside and outside of the office to recover that lost ground.

3. Bethany and I shared our tips for teaching kids about money; we also had the opportunity to share those tips at the JP Morgan Asian American Summit. Dave told me I’m not allowed to cut napkins in half anymore.

4. I shared guidance for building executive presence, a cheat sheet I wish I’d had as an introverted manager, but any professional can use to elevate their career.

5. About a week after my Ancestry exit, I shared what I was planning to do next. (Which, after two decades of nonstop work, was a healthy dose of nothing!)

Top 5 Substack Articles:

The Stacks readers loved most from 2025.

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My Top 5 Perspectives:

These are my personal favorites from 2025.

Featured Guest Writers

Last year, we had the opportunity to learn from guest contributors who introduced us to new perspectives and resonant stories. I would like to extend a special thank you to the friends and colleagues who joined us in 2025:

• Audrey Wisch, CEO and co-founder of Curious Cardinals, shared what parents need to know to prepare kids to thrive in an AI future.

• My surprise cousin, Kat Lieu, shared her story of trading in her white coat for an apron, and how food connects us all (to ourselves and each other). As a bonus, this guest article included a wonderful Taiwanese Snowflake Crisp recipe (Kat’s favorite).

• Former perfectionist and recovering overachiever Yue Zhao (ex-Instagram, Thumbtack) challenged us to view failure as a feature, not a bug, of success.

• My new friend Sheila Gujrathi, MD, talked about the power of mirrors in our lives; she shared the touching story of her incredible mother as her first mirror, and the journey she took to becoming her own.

• Marily Nika expounded on the dawn of the AI Product Builder and what it takes to succeed as a PM in the age of AI.

• My eldest daughter, Bethany, authored a retrospective essay, sharing what she’s learned from watching my example. (It wasn’t as bad as I thought it would be!)

• My sister, Caroline, peeled back the curtain to talk about her life behind the spotlight, and how success can be found in many ways beyond climbing the ladder.

The Art of Perspectives

Last year, I decided I wanted Perspectives to have a unique, signature look. When my youngest daughter heard I was using AI to create custom images for my Substack cover photos, she was having none of it. So, beginning in September, she insisted on hand-illustrating all of my cover images. Each Sunday, she illustrates an original image to match the theme of the article I’ve written for the coming week.

Here are my top 5 favorite illustrations she created for Perspectives this year:

Whether you are a casual reader of Perspectives or an every-newsletter devotee, thank you for being here. I’m excited to see what 2026 holds for us. We have some really great things planned for the year.

Is there anything you’d like to see me write about this year? Please let me know in the comments.

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