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Last Thursday afternoon, I dropped my daughter at her cooking class and sat on a bench in the sun to wait the 45 minutes until pick-up. I looked up, and there on the front of Spike Lee’s Brooklyn offices was a freshly painted tribute to the Knicks. People gathered in clusters, snapping photographs and exchanging high-fives. This was the day before the Knicks, chasing their first championship in more than half a century, beat the Spurs by a single point in San Antonio and moved closer to a title.

They play a third game tonight—at Madison Square Gardens.

I know very little about basketball, but I know this feeling that it has unlocked here, and it’s contagious. It’s a promise that something that hasn’t seemed possible in my lifetime might now work out, an invitation to get excited, to hope, to be emotional in public. It’s eye contact in every direction you look. It’s permission to talk to strangers, and a topic on which to connect: Go Knicks!

This experience is electric. I love everything about it. I love it so much I just ordered a Knicks hat so I can participate. I’m high-fiving you through this screen.

The feeling of it reminds me a lot of the “6-7” meme that infiltrated our household last fall. I watched my first grader burst onto the playground, armed with the confidence enabled by a new tool that worked reliably every time he used it. The year before, he’d had just one buddy to whom he was devoted. But the fall brought a hand gesture and a quick “6-7.” Suddenly, he had something to say to everyone, and everyone answered back. “6-7.”

Adults said we didn’t understand the meme’s significance. There were so many think pieces! I always knew what it meant just by watching Jude. It was shorthand for belonging.

⁶🤷⁷ 6-7! 🗽🏀 Go Knicks!

It all adds up to the same thing: we’re looking for ways to invite each other in. And if we’re taking it to an extreme….if we’re painting the subway station bannisters orange and blue…or checking out that live map shared of all of NYC’s watch parties…maybe it’s because it’s exactly what we need right now. It all feels more urgent because we’re while living through a moment where we’re mostly shutting each other out.

Consider new research from the enterprise software company Workday that shows that AI may be easing the burden of some work tasks, but it is eroding our sense of connection to each other. This is in line with Stanford Professor ’s call for systems that preserve connection in the face of what he calls out as real relational risk. It’s all layered atop intense political disruption that has been worsened by our current leaders.

And, it mirrors what I feel day-to-day. I think of a close friend who texted last week to say that her pottery studio—where she goes to sculpt and create art—was embroiled in disagreement. The tensions began almost two years ago, she said. Here’s our conversation, verbatim:

Her: “i’ve already felt fracturing around me. and an erosion of the sense of belonging.”

Me: “Yes. That sense of belonging is creeping out of the places where we once sought it. I feel this at my office and in my kids’ school, every minor disagreement becomes a fracture. We have lost the ability to repair. We try to judge the whole of a person and by extension an institution via a slice of identity: are you with me or against me? Eventually, we are alone.”

Her: “any thoughts on how to preserve a sense of belonging in a community without prohibiting freedom of expression?”

I’ve been thinking about this question since she asked it. I’ve been making things more complicated than they are, trying to find answers to ideas that are better understood as a paradox. And then along come the Knicks, pulling off something that didn’t seem possible.

Getting me to talk to my neighbors, to feel totally bought in to a shared identity. Showing me that I belong here, with you, right now. Let’s hold our breath together for a win tonight!

🤓 Hello, Monday!

Joanna Stern was upstairs working when her wife texted: come downstairs and help make lunch for the kids. Apple Intelligence suggested a reply: "Sorry, I have other plans."

This was in the middle of her grand experiment to let AI manage all of her communication for her, so she sent it... and then booked it down the stairs to make the kids' lunches.

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Joanna Stern’s new book is called I Am Not a Robot. We get into it on this week’s episode of Hello Monday.

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A lot of the conversation around AI focuses on what the technology can do. Joanna spent an entire year testing that question, letting AI into nearly every corner of her life. She used it to communicate, organize information, analyze medical records, build a business, and even attempt to fold her family’s laundry.

What emerged was a story about where we want technology involved—and where we don’t. Three takeaways:

• AI is already most valuable in places where it removes administrative drag. Joanna used it to launch pieces of a new business that otherwise would have required hiring specialists or learning entirely new skills.

• The incentives matter. In healthcare, she found examples where AI appears to improve outcomes and examples where it may simply create more opportunities to sell services. The technology isn’t the whole story.

• We may need to think harder about the role of friction. If AI increasingly builds things for us, how do we make sure people still learn how things work, how to fix them when they break, and how to create alongside other humans?

🤓 Worth it….

Too Much Is Happening Too Fast (Charlie Warzel/The Atlantic)

“When people feel unprotected, they turn inward. Abandoned by our institutions, Americans left them in return.” on wellness libertarianism.

What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. My mission is to close the gap between the people building the future—and those of us living it.

Here’s his latest idea: As we navigate change, good self-care (paying attention to our own lifequakes) is not enough. We need group care. We need rituals.

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This week, Bruce Feiler joins Hello Monday to share what he learned about rituals from traveling the world to partake in them.

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We need rituals

That idea landed hard for me when Bruce came into the Hello Monday studio to talk about his new book, A Time to Gather. Bruce argues that ritual is not some outdated religious artifact. It’s one of humanity’s oldest technologies for helping groups survive change.

Right now, we are living through enormous change. You know what I’m talking about: AI is reshaping work. Institutions feel shakier than they once did. Loneliness is widespread. Many of the places we once found belonging — churches, civic organizations, even social media — no longer hold us in the same way.

Bruce’s insight is that humans have always responded to instability with ritual. A ritual, as he defines it, is an intentional act that tells us: this matters. You matter. We belong to each other.

This feels right in line with my instincts about the downsides of efficiency. We’ve spent years optimizing for efficiency. Often, we’ve optimized the humanity right out of everything, even ourselves. Ritual is, by definition, inefficient. It’s unnecessary. You don’t need to light a candle before dinner, or say a blessing in order to eat. You don’t need to gather colleagues into a circle before a podcast recording. (True story. We did it.) You don’t need to pause and mark a transition. But those are often the moments when we actually feel connected.

Bruce led a small ritual with a few members of our team before we started recording. It took about ten minutes. He pulled in the camera guy, the editorial assistant who had started that week, our producer who’d just returned from medical leave. We used the studio, squeezing in beneath the lights. And it felt kind of hokey while we were getting started. It involved lighting faux candles, writing our hopes on rocks, sharing things with each other that we usually keep for ourselves. Afterward, everyone felt different. More grounded. I still have my rock….

Bruce’s new book feels important to me right now. However the future emerges, it will be shaped by the moments we choose to create together. This is a quick primer on exactly how we create those moments in any environment:

🤓 Worth it….

Too Much Is Happening Too Fast (Charlie Warzel/The Atlantic)

The AI boom has created a frenetic online discourse where evangelists constantly hype each new development as revolutionary, creating narratives that change so rapidly that even AI insiders joke about being nostalgic for the “simpler” times of just two years ago. As Charlie writes, “One of AI’s enduring cultural impacts is to make people feel like they’re losing their mind.”

Also of note:

AI is super duper very unpopular among everyone except the people who really super love it.

And: People are speaking to each other less. ( /LinkedIn)

🤓 Double Worth it….

The Era of AI Malaise (Mat Honan/MIT Technology Review)

There are no words for what AI is doing, yet somehow has found the words. The exact right words. Read this. You will feel seen. You will feel better. You will feel certain that an LLM did not write it. Well, almost certain. As one example: “It’s…embarrassing to admit you’ve used an AI to do what it was designed to do. Sort of like being on a GLP-1. No one wants to admit it, but why is everyone suddenly so skinny and so smart?”

What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. I’m on staff as a senior editor at large at LinkedIn. My mission is to close the gap between the people building the future—and those of us living it.

It took Manoush Zomorodi to remind me: “You are a meat bag that is holding your brain inside of it.”

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Manoush Zomorodi is host of NPR’s TED Radio Hour and author of a new book, Body Electric: The Hidden Health Costs of the Digital Age and New Science to Reclaim Your Well-Being

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Your body has its own intelligence

Yeah, that physical body. I know it. And I take care of it! I really do. I exercise several times a week. I take my magnesium at night. And do you know how many steps I get in every morning? All so that I can arrive at the office and sit down at my computer…and sit, and sit….and sit. In the last few years, even going to meetings has involved sitting. Rather than shuffle to another room, I hit the button in my calendar invite and transport myself to a virtual room.

It was early in the pandemic that Manoush realized this approach to work was bumming her out and making her generally both less healthy and less productive…and it was probably doing that for everyone else, too. So, because Manoush is a journalist and because she’d already spent a decade building a body of work around attention, technology, creativity, and the human nervous system, she started to investigate.

Here’s what Manoush spent three years researching: the average American adult interacts with media for over 12 hours a day. We sit for nine or ten hours at a stretch. This is not good for us! Type 2 diabetes in young people has doubled over the past 20 years, to name just one terrible outcome of a sedentary lifestyle. Three out of four American adults have at least one chronic illness — many of them preventable.

So she teamed up with physiologist Keith Diaz at Columbia University Medical Center and invited 23,000 people to try an experiment: five minutes of gentle movement every thirty minutes.

One solution, it turns out, is almost insultingly simple: five minutes of gentle movement every thirty minutes largely offsets the harms of a sedentary lifestyle. She’s not telling us to go to the gym here, or to start a rigorous training course (though she’s obviously a big fan of her pilates class). Manoush suggests that by moving around a bit on such a regular cadence, we can go a long way toward addressing the harms that knowledge work has introduced.

That’s great for our physical health, and also helps us accomplish more. Our thinking is fresher when we move, our ability to solve problems becomes snappier. Maybe best of all, we’re all in better moods.

If we want to win the adult version of Olympics of the Mind, we’d do well to think of ourselves as information athletes.

“Google Sheets is my tool,” she told me, “and I need to use my body and maximize its ability just to be able to manage all the things I have to do.”

Office Hours is back!

Office Hours is our monthly gathering for people who listen to Hello Monday and want to go deeper — into the ideas, the questions, and the connections that emerge from the show. It’s a space to reflect together on work and life, ask the questions you might not ask anywhere else, find support through transitions, and celebrate each other’s wins. Whether you’re a longtime listener or brand new to the community, you’re welcome here. Join us May 13 at 3pm EST for what producer Sarah Storm lovingly calls “the kindest place on the internet.” RSVP right here!

Following up on last week’s letter, a few reads…

AI isn’t coming for your job. It’s coming for your mind. (by Tom Slater/Ballie Gifford)

“Verification without prior mastery risks becoming a superficial check rather than a genuine evaluation. Just as literacy gave us something new by repurposing something old, AI is reshaping the brain’s allocation of cognitive resources. The trade may be worth making. But right now, most people are making it without realising there is a trade at all.”

AI systems are about to start building themselves (by /Import AI)

It seems appropriate to pair the above reading with a recent newsletter by Anthropic cofounder , who writes there’s a likelihood that very soon, AI will begin to build itself. In other words, AI will operate its own R&D department. “If that happens, we will cross a Rubicon into a nearly-impossible-to-forecast future. More on this later.”

What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. I’m on staff as a senior editor at large at LinkedIn. My mission is to close the gap between the people building the future—and those of us living it.

But here I am, early on a Sunday morning in May, sitting at my computer, trying to work out the details of a thought that will not leave my mind. I’m doing this because it’s my real work, in a broader sense of the word.

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This hour will have a transformational impact on my productivity. It’ll shape my approach to both my shows, my thoughts for you, my ideas for my colleagues. And honestly, this is the hour that defines my sense of purpose.

But just to be very clear: no one is paying me for this hour. Technically, this Substack newsletter may be my work, but it is not my job.

When Job = work

Probably much like you, I’ve been raised to equate my work and my job. Our culture values work in accordance with its economic output: how much money do you make? Sure, there are plenty of jobs that don’t derive their prestige from the size of the paychecks they produce: professors, for example, or pastors. And since the fall of 1994, when I first cracked open Arlie Hochschild’s The Second Shift, I have understood that many forms of domestic work remain invisible and unpaid.

The industrial economy transformed “the job” into the primary unit through which human labor is organized, valued, and compensated. Paid employment became the primary way we measure human contribution.

The emerging problem here is that a lot of jobs just aren’t very good right now.

As AI re-organizes our professional lives into buckets of tasks, many of which can be done more effectively through automation, some of the jobs I was conditioned to respect are growing lousy. They don’t lead to a recognizable career ladder. They don’t offer stability. They often require that you learn and deploy new skills at such a rapid rate that traditional universities can’t move fast enough to equip you. And a lot of people think most jobs are going away. This recent Quinnipiac poll found that 70 percent of Americans think AI will lead to fewer job opportunities, up from 56 percent a year ago.

The discourse has converged on a single instruction: panic. But I've spent 25 years on the frontlines of tech's evolution, and I'd argue we're panicking about the wrong thing. The question isn't whether jobs are going away. It's whether we've ever been clear about what work is actually for.

It’s time to decouple our jobs from our work.

That Sunday morning hour I described is unpaid and uncounted and it shapes everything else I do. That is what I want to fight for—not just for myself, but for all of us.

The obvious responses to the JOBACALYPSE don’t quite get there. Reskilling programs assume the problem is a mismatch between workers and available jobs; if we just learn to prompt engineer or read a data dashboard, we’ll be fine. Regulation might slow the pace of displacement, but it won’t address the deeper question of what we lose when work becomes purely transactional. And while conversations about universal basic income gesture toward the right problem (we need to pay our rents and mortgages), they tend to treat the loss of work as inevitable and then ask how we compensate people for it, rather than asking what kind of work we actually want to build.

None of these responses address the real crisis: not that jobs are going away, but that we’re giving up on work.

That’s whyI keep returning to a movement that started in a piazza in Rome, with a journalist who looked at a McDonald’s and decided that efficiency was not, in fact, the point.

We need a slow food movement for work.

In the late 1980s, Carlo Petrini introduced a manifesto that declared that food should be good, clean and fair. The food we eat should taste good. It should be produced in a way that doesn’t harm the environment, animal welfare or our health. Those who produce it should be fairly compensated for their work.

The Slow Food Movement pushed back against this idea born of industrialization that speed, uniformity and efficiency should govern how we eat. It led to the larger farm-to-table movement. Early proponents of the movement noted that everything got better for everyone when we focused on being deliberate about every component of our food system. As the famous chef Alice Waters said in a 2015 interview: “When you eat fast food, you not only eat the food that is unhealthy for you, but you digest the values that come with that food.”

Those values? Says Waters: “fast, cheap and easy.”

So what would a Slow Food Movement for Work look like?

We need to reconceptualize work not as a source of economic output, but as the meaning-making machine of our lives, and to understand it as craft rather than throughput. We need to acknowledge that the texture of our working days matters. The relationship between a person and her work matters. We need a manifesto. Here’s a start, how can we improve it?

Office Hours is back!

Office Hours is our monthly gathering for people who listen to Hello Monday and want to go deeper — into the ideas, the questions, and the connections that emerge from the show. It’s a space to reflect together on work and life, ask the questions you might not ask anywhere else, find support through transitions, and celebrate each other’s wins. Whether you’re a longtime listener or brand new to the community, you’re welcome here. Join us May 13 at 3pm EST for what producer lovingly calls “the kindest place on the internet.” RSVP right here!

RSVP right here!

Getting started on your life’s work…

This essay found its seed in my conversation with Kantor upon reading her book for new grads, How to Start. In particular, this paragraph captured my imagination:

“Work is one of the legs that keeps the table of life standing up. Family, friendship, marriage, faith, rewarding work—take as many of these as you can get, because they operate in tandem. Relationships falter. People get sick. Jobs come and go. The combination keeps us upright, especially when one of the legs goes wobbly. But our stake in work is also collective. Despite everything, work is our engine of progress. Cancer therapies, new commercial aircraft, winning political campaigns, and every television show you’ve ever enjoyed were all made by groups of former strangers who labored together in shared discovery, discipline, and purpose. To declare defeat on work is to surrender possibility itself—for yourself, for everyone.” – Jodi Kantor, How to Start

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What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. My mission is to close the gap between the people building the future—and those of us living it.

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There’s a moment in almost every conversation I have about AI and work where the person I’m talking to gets this look. It’s not quite right to call this fear. It’s more like vertigo. The ground is shifting and nobody can quite see where it’s moving to.

I had that moment recently in the Hello Monday studio with Lee Eisenberg and Nick Hatton, the creators of Jury Duty and its new sequel, Company Retreat. It’s an elaborate joke of a show in which mock documentarians chronicle a company retreat in which almost all of the characters are actors.

Our main character, Anthony, is not…and he doesn’t find out that his new job is a TV show until the penultimate episode.If you haven’t seen it yet, do yourself a favor and at least watch the trailer:

This particular company that Anthony has joined is in the midst of a leadership transition as the founder prepares to step down. I won’t ruin the show for you, but I will say that a set of important characters are the three private equity employees who show up with the intent to purchase Anthony’s employer, Rockin’ Grandma’s Hot Sauce.

Lee and Nick have astute observations about workplace culture, many of which they reveal in this show. That’s what I was most curious about, so I pushed them to think about the identity people find from their work, the relationships that form inside companies, the violence of losing all of that overnight — when Nick landed on this idea that resonated. One the show, and in life, he said he worries most about dignity. “Work is a huge part of our purpose and our reason to get up and go and to do things.”

Here’s what I mean.

The “job” — as we understand it today — is not a natural feature of human life. It’s an invention, and in the long arc of history, it’s relatively recent.

Before the Industrial Revolution, most people worked, but they didn’t have jobs in the modern sense. They farmed or crafted or traded or built things. Work was woven into the fabric of daily life, inseparable from family and community and season. It wasn’t a discrete unit of economic activity performed for a set number of hours in exchange for a wage.

The job — the clocked shift, the employment contract, the org chart — was engineered to meet the needs of factories. You showed up. You performed a defined function. You were compensated. You went home.

For most of the 20th century, that bargain held. But we can all see that that bargain is now breaking down. AI gets the blame, but it shouldn’t: it’s accelerating a trend that was already underway.

Work is not the same as a job.

A job is an economic arrangement. Work is much more significant. It’s how we humans make meaning, contribute to community, develop mastery, and locate ourselves in the world.

When we conflate the two, we make a category error with serious consequences. We assume that the only legitimate form of contribution is one that comes with a W-2. We assume that dignity is something you earn through employment rather than something you arrive with. This is the idea Nick was getting at.

I want to propose something different. What happens if we think about work as a human right? We all have the right to contribute meaningfully. We have the right to be needed by someone, to build something, to leave something behind.

So what would it mean to organize our economy, our institutions, and our culture around that idea rather than around the job?

What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. My mission is to close the gap between the people building the future—and those of us living it.

At the time, this was hard to explain to others. It didn’t feel like I was starting over. I was able to draw from the crafts I’d honed, listening and writing. But nothing about this new gig felt anything like the jobs I’d had up until that point. What’s more, I was stepping off of a career ladder that was identifiable to others.

In conversation recently with Arthur Brooks, I learned this seemingly rash decision embodies a defined approach to navigating a career, one of four paths. Brooks drew from organizational psychology to offer it a name: “The Spiral.”

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Harvard professor Arthur Brooks joined me to discuss his newest book, The Meaning of Your Life: Finding Purpose in an Age of Emptiness.

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I’ve had Arthur into the studio four times now, and I’ve come to love speaking to him. Our conversations rarely stay tethered to the topic on which we’ve agreed. Instead, we address the areas of his research that feel most immediate.

Case in point: this week, we set out to explore the human approach to meaning, and how we’ve disrupted it in recent times. This is, no doubt, a critical question, but exploring it deepened my historical understanding of careers path.

The Four Career Concepts

There is a framework in organizational psychology that describes four distinct types of careers. It was first developed by researchers Michael Driver and Kenneth Brousseau at USC in the 1970s, who posited that there wasn’t one “right” way to do a career. In fact, they suggested, there are four approaches people tend to take.

Most of us have heard of exactly one of them, because it’s the only one our institutions (and often our parents) recognize and reward. That’s the linear career. You move up that proverbial career ladder, motivated by the power and status that each rung affords. This is what MBA programs implicitly teach as the goal.

There’s also the expert career. Experts are motivated by mastery of a craft in addition to status. Think of the surgeon here, or the tenured professor. A career path usually includes climbing up a few steps of a ladder, and then embracing a deepening line of specialization. These professionals are respected, though sometimes undervalued.

Third is the transitory career. People following this approach to managing a career make frequent changes; they’re motivated by variety and independence. Work is not the point; life is. This one gets judged most harshly in professional settings, though the freelance economy has begun to rehabilitate it.

And then there is the fourth type, the spiral career. While research may identify it, almost no institution prepares you for it. A spiral career is defined by periodic, deliberate reinvention roughly every seven to ten years. You take the knowledge, relationships, and skills from one chapter and fold them into something new.

The spiral type is motivated by personal growth and creativity. According to the research, we tend to thrive in exactly the kind of environment that the economy of 2026 is producing: flatter organizations, project-based work, AI-disrupted industries where the ladder has been shortened or removed entirely.

The Meaning of Your Life

I’ve been thinking about this framework ever since I sat down with Arthur, whose new book is The Meaning of Your Life. Arthur connects the spiral to something deeper than career strategy. More than just an efficient way to navigate a changing economy, Arthur argues that it’s actually a more honest way to live. A linear career requires you to build your entire identity around a trajectory. When that trajectory ends, as it always does, there is nothing to fall to.

“Your career will not keep you warm at night,” he told me. “Your career will not be by your bedside as you’re taking your dying breath.”

What the spiral protects you from, Arthur suggests, is what he calls the arrival fallacy — the devastating discovery that achieving what you wanted doesn’t feel the way you thought it would. If your identity is a single thing, losing it is catastrophic. If your identity is a practice of becoming, you are never finished — and never truly lost.

This week on Hello Monday, Arthur and I talk about the spiral, the meaning gap, and why the highest achievers so often feel the emptiest. We also get into his 80/20 rule for evaluating any opportunity — 80% excitement, 20% fear, 0% deadness — which helps shape how we decide when to make a leap, and what to move toward.

You can find the episode right here:

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What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. My mission is to close the gap between the people building the future—and those of us living it.

Two years ago, that conversation focused mostly on the smartphone impacted kids. Today, however, that conversation has evolved. We’re waking up to the impact its had on everyone.

As Jon told me in the studio: “We adults, we are overwhelmed. We become scattered and fragmented. We lose our ability to focus."

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The separate forces pulling at our attention

Jon and I dissected the forces that keep us reaching for our phones. It’s not as simple as one would think. There are two separate forces pulling at our attention, and we tend to conflate them.

The first is what he calls “quick dopamine.” It’s the variable-ratio reward systems baked into social media and games that function like slot machines in our pockets. Personally I attempt to fight this one by turning my notifications off, and switching my screen to grayscale. (And if you were to pick up my phone right now, you’d discover I’ve undone both of these hacks; they never seem to last.)

The second is something I hadn’t really considered: workaholic compulsion. Knowledge work today requires constant responsiveness—even if managers suggest the opposite. Dominant company culture that requires you to reply to texts within 15 minutes, which creates, as Jon puts it, is “a company designed to never let anyone think.”

Real productivity, and here I’m talking about the birth of new ideas, requires a kind of friction that I’ve written a lot about this year, robust downtime and a process for introspection. It’s much easier to just check Instagram 17 times an hour and fritter our time away.

In this week’s conversation, we get into all of this, and I run an idea of my own by Jon. Check it out:

What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. My mission is to close the gap between the people building the future—and those of us living it.

Professor Richter was interested in the question of hope. So, he repeated the experiment. This time, he watched the rats swim until the moment they began to struggle. Then, he pulled them out, let them rest….and put them back in. (See? VERY CRUEL.)

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This group of rats swam longer—much longer. They swam for 60 hours, around 240 times as long as the first crew. The only variable here was their mindset: these rats believed that their was a possibility their persistence might be worth it. They had hope!

Our beliefs are programmed. This is a core conviction that I’ve explored throughout my work. It was the animating idea of my memoir, Family Outing, which traced the evolution of my family members’ beliefs as we each made our way out of a closet. It’s the reason why our annual Dream Job Exercise works well and consistently for those of us who embrace it. It’s why I was excited to drop into conversation with Nir Eyal about his new book, Beyond Belief: The Science-Backed Way to Stop Limiting Yourself and Achieve Extraordinary Results, which unsurprisingly became an instant bestseller.

Nir invites us to think of our beliefs as tools. When we investigate them, we can reprogram them—or at least, understand how they are driving our behavior. He posits that most self-help books draw a line between our behavior and our benefit. An example: “If you want to have enough money to purchase a home, save a bunch each month.”

Inevitably, especially for our big goals, our motivation flags. Nir says this is because we’re not attending to the role that our beliefs play in fueling the motivation. He actually draws a triangle, which I’ve tried to replicate here:

His point is that you can have a clear goal (buying a house!) and a path to the goal (saving up!), but if the belief isn’t there ((“I don’t really think I’ll ever get there because I’ve failed in the past.”), it all falls apart.

There’s so much nuance to this, of course. Just because we want to shift a belief, for example, doesn’t mean we can. And, often in moments of conflict in our lives, we would do well to look for the underlying beliefs that are driving the conflict. (Deep gratitude to my incredibly good-natured wife, here, who simply shrugged and smiled when I told her that I’d dissected a recent moment of our own conflict in this episode.)

It’s a good moment to be paying close attention to our beliefs. Our larger culture is perpetuating so many beliefs about our future that are dark. These beliefs are contagious, and I’m the first to tell you that it’s much easier to feel bleak about our future, than to do the rigorous analysis of our own belief system and then sit in the uncertainty and allow for the possibility of hope. But if we do that work, I’m certain we’ll uncover our own reasons to swim.

And the swimming, be it 15 minutes or 60 hours, is actually the point.

I’m bringing back Office Hours!

Many of you will remember that when we ended Office Hours in December, I planned to stand up a book club. The tech solution for that has been slow to emerge, but it’s coming. In the meantime, I’ve missed a consistent connection point with the listeners who make Hello Monday into a community. So, I’m going to stand up and Office Hours next Wednesday. We’ll see how it goes, and consider bringing it back if folks are into it. If you’ve never been, let this be your invitation! We’ll check in with each other, talk about the ideas in Nir’s book, and make some plans for the future. Can’t wait!

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What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. My mission is to close the gap between the people building the future—and those of us living it.

I spent my time reporting on the rise of various technologies. Youthful founders promised me their well-funded inventions would change the way we lived.

As a futurist, Amy had an informed perspective on what would actually stick.

Ever since, I’ve looked to Amy as a guide for how our current inventions collide with emerging trends to inform the future. This past weekend, she gave her annual SXSW talk, an event that routinely sells out despite its early Saturday morning time slot. Shortly before that, I invited her into the studio to help me discern what this chaotic moment means for our immediate future.

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Check out the episode here!

We’ve living through creative destruction

Amy’s framework for this moment is called creative destruction. It’s a term she borrowed from the Austrian economist Joseph Schumpeter, who wrote about it in the aftermath of World War II. The idea is this: there are moments in history when external forces — technological, geopolitical, social — compound and collide in ways that make the old ways of doing things obsolete.

We are in one of those moments now.

What makes this one different from previous cycles like the Industrial Revolution, the post-war boom, or even the early commercial internet is the sheer number of convergences happening simultaneously. This is not just another AI conversation. Amy is talking about how AI and robotics and biotechnology and energy infrastructure and geopolitical competition all smash into each other at once, creating structural changes that most organizations will recognize too late.

As she put it at this year’s SXSW talk, a convergence tells you what’s going to become inevitable.

Here’s what happens to work when our jobs start to go away

Amy says that the white collar jobs being eliminated right now are probably not coming back. This is where years of experience advising executives in leadership positions comes into play. She says what we all kind of know, that it’s not like the tech is so much better than the people its replacing. But adding headcount back would require leaders to admit they made a mistake, and they’re not going to do that.

It’s actually going to make a lot of things shittier for awhile. The quality of our cognitive output is going to decline. And we are going accept that as the cost of efficiency.

I found this both clarifying and devastating. Clarifying because it names something I’ve been feeling but couldn’t articulate. Take my original profession; does anyone think that the quality of journalism can be maintained if we’re not training people to do excellent work? How did we think this was going to end up?

Devastating because it suggests that the bargain we’re making isn’t just economic. Collectively, we’re willing to let go of this excellence across every domain in the name of a balance sheet.

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Which brings me back to efficiency, the wrong value for our time

You know I’m obsessed with efficiency and how thoroughly it has colonized our understanding of what work is for. In an earlier piece I wrote for this newsletter, I traced that value back to Frederick Winslow Taylor and his 1909 principles of scientific management, and argued that we’ve built artificial intelligence as its apotheosis: the most efficient processes, made more efficient still.

Amy’s framework supports this idea. She suggests that creative destruction cycles have a shape. They begin with convergence, move through disruption and fear, and arrive somewhere new. Our radical focus on the values of the last era (industrialization) will lead it through the disruption, and will force the destruction more quickly. It often feels like the future is happening at us. But by paying attention to the way these trends are converging, we have the opportunity to engineer our own future.

Amy pulls up the driving-on-ice analogy here, and it feels apt after the winter we’ve had in Brooklyn. When you hit a patch of ice, the instinct is to slam on the brakes. That’s the reaction. The correct response is counterintuitive, and it will save your life every time. You steer into the slide. You keep your eyes on where you want to go, and take your foot off the gas. You have to let the car find its footing.

The future isn’t foretold. It gets created by the decisions we make in the present. Every decision we make influences a future that hasn’t arrived yet. The question is whether we are making those decisions deliberately, with information, or whether we are reacting out of fear and FOMO while the ice carries us somewhere we didn’t choose to go.

What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. My mission is to close the gap between the people building the future—and those of us living it.

Then the industrial era arrived, and we needed a different kind of smart. We needed people who could memorize, analyze, sort, and execute at scale. So we invented IQ as a way to measure and rank cognitive horsepower. We built entire systems around it. Our schools screened for it. Our hiring pipelines rewarded it. By the time I came along in 1975, we held up IQ as the scorecard that mattered above all others.

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This week’s guest on Hello Monday is Liz Tran, author of AQ: A New Kind of Intelligence for a World That’s Always Changing.

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At some point in the late 1990s, the business world embraced emotional intelligence — EQ. This was the ability to read a room, build trust, navigate relationships. This Harvard Business Review article, first published in 1998, suggested it was more critical to success than IQ. We updated the scorecard.

As we enter a new era that will be defined by AI and its adoption, it’s new time for another update. Enter your agility quotient—AQ.

This week on Hello Monday, I spoke with executive coach , who makes this argument in her new book, AQ: A New Kind of Intelligence for a World That’s Always Changing. The intelligence that matters most right now, evaluates your capacity to handle change, disappointment, and uncertainty without losing your footing.

And unlike IQ, which is essentially fixed, or EQ, which has a ceiling, AQ is fully in your control. You can raise it.

Liz has a great way of thinking about it that I found helpful personally. She has developed a framework of four archetypes that describe your natural style of navigating change. Each has real strengths — and real blind spots.

The novelist plans, researches, and drives toward a clear end goal. They (we!) make timelines, love agendas, and find deep empowerment in having a map. Their core motivation is freedom — specifically, the freedom to chart their own course. The risk: when life goes off-script, they can be knocked sideways.

The firefighter thrives in real-time chaos. They’re the person you call in a crisis, a natural problem-solver who operates best when everything is on fire. The risk: they can resist planning altogether, assuming things will change anyway.

The astronaut moves fast, innovates instinctively, and leads from the front. Motivated by passion, they’re often the first to see what’s coming next. The risk: they can leave everyone else behind, changing direction so quickly that their team loses the thread.

The neurosurgeon won’t move until they’re ready — and their version of ready is exceptional. They hold an impossibly high bar, excel at complex projects with a lot of moving pieces, and bring a precision to their work that no one else can match. The risk: the perfect can become the enemy of the good, and speed sometimes matters.

I’m a novelist, unmistakably.

Understanding that has helped me make sense of decisions I’ve made throughout my career — including some I’m navigating right now. Like, I’m ruled by my need for autonomy, above all else. It’s irrational the degree to which it drives me.

If you’re curious where you sit in this framework, Liz has a quick quiz here that is remarkably reliable for the two minutes it will take you.

Our technical skills have a five-year half-life.

One more thing I haven’t stopped thinking about from our conversation. Liz mentioned research out of Harvard’s Digital Reskilling Lab, so I went back and looked it up. It was conducted in collaboration with Boston Consulting Group and published in a 2023 Harvard Business Review piece called “Reskilling in the Age of AI,” and it revealed that our technical skills have a five-year half-life. In some industries, its shorter. In tech, for example, it’s two and a half years. The researchers found that this erosion is accelerating — driven by AI, automation, and the pace at which entire job categories are being restructured.

What the research also surfaces is where organizations are failing to respond. Most companies are still investing in technical reskilling — teaching people new tools, new platforms, new hard skills — when the evidence suggests that’s a losing game. The skills you retrain people on today will be half as valuable in five years. What holds its value, the researchers argue, are the durable human capacities underneath the technical ones: the ability to learn, to adapt, to navigate ambiguity, to work across difference. These are the things that no software update can replicate.

Reframing “reskilling” from tool acquisition to human development feels like the most important career insight hiding in plain sight right now.

Check out the episode!

What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. My mission is to close the gap between the people building the future—and those of us living it.

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I’ve interviewed Melinda many times over the last decade. We’ve done thoughtful sit-downs for Wired and she joined the very first season of Hello Monday. I interviewed her on the final stop of her 2019 Moment of Lift tour in front of 2,500 people at Seattle’s McCaw Hall. It felt like a hometown celebration. President Obama beamed in to congratulate her. The whole thing was big and polished and electric!

But the interview that has stayed with me happened earlier, at Stanford.

In 2017, Stanford Women in Business invited Melinda to chat with alumni and a group of students that included her older daughter, Jennifer. Melinda was relaxed, bold, and deeply herself in this setting. She spoke with the young women in the audience, rather than to them. She implored them to use whatever privilege they had as leverage to lift someone else, and to believe in themselves especially when things got uncomfortable.

“We know that women, even in the workplace, have more doubt than men,” She said. “And society gives them all of these messages along the way that ‘maybe you can’t do this, and we’re not sure of you.’ You have to keep your confidence up.” (I pulled this from the campus paper reporting on the event.)

You could see the through line between the values Melinda was describing and the choices she had made in her own life. Despite being underestimated by a high school guidance counselor, she had figured out very early how to hold on to her ambition; she finished Duke University in 1986 with a double major in computer science and economics…and then went to business school. Melinda told the audience about her own evolution in the early days of Microsoft, which had only about 1,000 employees when she started. She had to trip into her own style of leadership through experimentation, and only then did sought-after developers line up to work with her. In an environment full of people who didn’t look and sound like her, she had to figure out how to trust herself.

I’ve thought about that exchange often in the years since, especially as the public narrative around Melinda’s life has shifted. She could have disappeared from the public eye when her marriage ended. She could have chosen privacy, comfort, distance. No one would have begrudged her that choice. Instead, she has used any attention that comes her way to continue to step into public conversations about women’s health, about philanthropy, and about power, even as those conversations intersect with scrutiny directed at her former husband.

Melinda embodies a feminine approach to leadership that is finally, fully rising. She doesn’t posture as someone who has all the answers. What she models instead is a kind of leadership that acknowledges complexity and emotion without being swallowed by either. She names what she’s learning and she owns what she feels. In that way, she moves us all forward.

I don’t know that we talk enough about this style of leadership, but I see it everyone around me. It’s in Jen Hatmaker’s full acknowledgement in her recent memoir that she is no one’s leader; she’s trying to figure things out alongside everyone else. It’s in Caroline Wanga’s assurance that we won’t find the answers to our career questions in a book; we will need to look within ourselves. This emerging style is relational rather than domineering, invitational rather than directive. It doesn’t insist that power means control. It suggests that power can mean amplification.

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I hope you’ll join me and Melinda on Wednesday, and when you do, I hope you’ll pay attention not only to what Melinda says but to how she says it. Watch the pauses. Watch the way she considers a question before answering. Notice how often she redirects attention toward the women and girls whose work she is funding and elevating. She uses her platform deliberately to expand the circle of who gets heard.

That’s what I saw at Stanford, when she spoke to her daughter and her daughter’s friends. That’s what I’ve seen in the larger venues, too — even and especially when the lights are brighter and the stakes are higher.

There is something that we all can embody in this approach, especially right now. There is so little clarity to be had around anything right now, but people who promise clarity, certainty and answers are not being honest. Leadership is about being willing to show up in the mess, to use the resources and credibility you have, and to extend an invitation for others to step forward alongside you.

It’s worth watching closely.

Hello Monday: This week’s episode is on menopause

This week, I sat down with , founder of Midi Health, to talk about menopause, perimenopause, and the quiet way midlife women are being pushed to the margins of their careers because we misunderstand what’s happening in their bodies. We dig into hormone therapy, misdiagnoses, ageism, and the research showing how untreated symptoms can erode authority at work. This is a conversation about power. If we get it right, it could unlock a generation of women at exactly the moment they’re poised to lead….

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What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. I’m on staff as a senior editor at large at LinkedIn. My mission is to close the gap between the people building the future—and those of us living it.

❄️❄️❄️ (Scroll to the bottom for a blizzard pic)❄️❄️❄️

In the winter of my senior year of college, I took a trip to New York City with friends. We were on the cusp of of our adulthood, flush with the confidence that comes from four years of study, freedom, and exploration. We were certain we finally knew who we were.

To mark this moment of emerging, we got piercings: nipple (Heather), tongue (Paul), eyebrow (me).

Three months later, I graduated and moved to a small town in Haiti to volunteer at a hospital. I lived with and worked for an 86-year-old matriarch named Gwen Grant Mellon who had started the hospital with her husband decades earlier. She had deep, beautiful leathery wrinkles and wore the same headband every day, holding back her long white hair. “Oh, you’re going to want to take that out,” she told me, nodding to the small silver ring that had only just healed. “You want people here to trust you.”

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Nearly 30 years later, I remember standing in front of that mirror in my bathroom, nervous about my new environment and my new boss, unscrewing the fastener and and slipping the ring from its spot. I felt like I was putting down a piece of myself that I knew I would not pick back up. I felt angry at her.

Madame Mellon had already learned the lesson she was trying to teach me: Context is everything.

I thought of Madame Mellon a lot this week as I listened to the edit of our episode with Tomas Chamorro-Premuzic, author of Don’t Be Yourself. His argument isn’t anti-authenticity exactly. Rather he embraces Madame Mellon’s pragmatic point of view that we need to understand that how we perform our identity will contribute to how successful we will be.

We’ve turned “just be yourself” into moral advice. Tomas argues it’s strategic advice — and incomplete.

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Three ideas from our conversation have stayed with me:

1. Authenticity is easier when you already belong.

If you’re part of the in-group, your “true self” often aligns with what’s expected. If you’re not, deviation carries a cost. The price of nonconformity isn’t evenly distributed.

2. What matters isn’t whether you feel authentic — it’s whether others experience you as authentic.

That can sound cynical, but it is not meant to be. Trust is relational. Influence is relational. There is always some degree of calibration in leadership. Performance isn’t the opposite of sincerity; sometimes it’s the vehicle for it.

3. There’s a difference between self-expression and effectiveness.

We already understand this in our closest relationships. We don’t bring our whole selves to our partners or our children. We bring a version of ourselves that is shaped by care, responsibility, and purpose.

So why think about this now? In a workplace reshaped by AI, “be yourself” is too blunt an instrument. The more useful question might be: Who do I need to be in this context to do the work well — without losing myself entirely?

I’m still very close with both Heather and Paul. If memory serves, Paul removed the tongue piercing after the tiny metal ball chipped one too many teeth. Heather’s piercing also didn’t hold. Arguably we are all more fully ourselves than we were in those earlier years, seasoned by decades of life and the pattern recognition that has developed by middle age. We’re growing better and better at learning which version of ourselves to be in any given moment.

PS: We’re in the midst of a blizzard!

Here in New York City, the roads are closed and the snow is falling. Last night, the dog announced he needed to go out, waking me at 12:30am. I slipped into the warmest coat I have and followed him into our front yard where the snow fell so fast I couldn’t see far in front of me. There was no one out at all, no foot traffic and no cars…

As I write, daylight hasn’t yet arrived, but it has been snowing all night and the snow is predicted to fall most of the day. The children will shortly wake and the day will be lost to indoor forts, wet gloves, snow angels, cabin fever, and too much TV. If you’ve got a good recommendation for a vintage 90s family movie, hit me up…

And one more full view….

What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. I’m on staff as a senior editor at large at LinkedIn. My mission is to close the gap between the people building the future—and those of us living it.

Toward the end of the episode, Dr. Al-Hashimi suggests she try generative AI to stay atop her records. Dr. Santos hesitates, then gives in. “I’m usually here at least a couple hours after every shift trying to catch up, so…” she trails off.

As viewers, we’re with her. We want her to take the help.

And then Dr. Robby, our seasoned, cynical wizard of a hero, cuts in and shuts it down. “Sure AI will make doctors more efficient, but hospitals will expect us to treat more patients without any extra pay, of course,” he quips, “all the while eliminating staff positions for attendings and residents…”

Efficiency becomes the justification for extraction.

This is the story that has played out across business throughout history. New technologies promise to save us time. They’ll allow us to meet the demands of jobs that always feel like too much, while returning our time to us. My father, a lawyer, believed this when he brought home an Apple IIc in 1985. (Instead, he just started spending evening hours on the computer.) I believed it the first time my job sprung for a Blackberry for me in 2007. (Instead, my own line between leisure time and work dissolved.)

Inevitably, we work harder and longer, or worse, we lose the opportunity to work at all. The business leaders making these decisions tend to point to technology in their reasoning.

And wow is that true this year! As big companies cut thousands of roles, executives point to automation and “AI transformation.” Amazon is trimming more than 2,000 jobs in Washington after a much larger restructuring last year that the company framed as AI-era realignment. Pinterest recently blamed its workforce reductions on a pivot toward AI work. In the broader economy, January saw the highest job loss figures for the start of a year in nearly two decades, and while AI wasn’t the sole cause, it was listed as a factor in many staffing decisions.

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Technologist Rumman Chowdhury joined me this week to talk about power, participation, and responsibility in a moment when technology is moving faster than our institutions.

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When we blame the AI, we’re letting our broken systems off the hook. Perhaps even more critical, we’re missing the places in these systems where we have agency.

That’s why I recruited Rumman Chowdhury to the Hello Monday studio earlier this year. She’s a seasoned technologist, an MIT-trained data scientist who has built a career working in responsible AI. Rumman spent years at Accenture. She worked at [the company formerly known as] Twitter until Elon Musk took over. She’s advised governments including our own. Her message is clear-sighted and hopeful: we must assume our own agency.

This stuff isn’t happening to us. The AI is being built, deployed, and justified by choices. Decisions about staffing, restructuring, investment priorities, product design are human decisions. These decisions reflect incentives, economics, power dynamics.

This moment in the ER? This is just one example of a decision playing out. Who is right? If we, like exhausted Dr. Santos, give in and let the new AI app assist us with our charting so that we can get home by dinner, what’s next?

Dr. Robby doesn’t have to be right about the future. There is another version, one in which the technology allows us to spend time in more human-centered ways. Getting to this future will require us to make peace with AI tools, and more important, it will demand we rethink the incentives that underly our profit-driven systems.

Companies lay off people because leaders decide to reorganize or because investors want efficiency stories. They are responding to boards that want cost savings. All of this is choice, not destiny.

Our job, in this context, is to figure out how we engage with the decisions being made around AI. What do we understand about how these tools work? How do we recognize incentives? How do we decide what kinds of work and systems we’re willing to support?

The more we talk about the why behind these shifts, the more we begin to see that we’re not just spectators in this transformation. That’s why it’s worth listening to this week’s episode, which you can find right here:

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My Theory of Media in 2026: IRL For-eva

Last week, I sent around a lengthy framework for what I see happening to social media this year. To wit: social is giving way to offline interactions as the most urgent form of media. I’m not the only one who thinks this, of course, but I tried to explain why it’s happening…and mentioned three examples of a future medium that excites me…synchronous IRL:

HUGE: January saw the official launch of In the Room Live, our interactive live conversation with notable figures. I’m one of the hosts who bring conversations with figures like Brené Brown, Malcolm Gladwell, and Mark Cuban.

MEDIUM: I’m launching a book club for Hello Monday listeners. We’ll convene virtually, with intention, screens on, to talk about ideas. To get on the list to learn more, email HelloMonday@LinkedIn.com

TINY: I’ve started hosting breakfasts, filling the table with a half-dozen folks who don’t know each other and figuring out how to start and build conversations that aren’t scripted.

These tiny breakfasts fill me up. On Friday, one of the six attendees was an artist who makes things just to make things. It’s a refreshingly simple idea. She’s a design principal at SYPartners where she wrote this very smart piece on the conflict inherent between creativity and productivity. At breakfast, she had on a great sweatshirt. “Where did you get that?” I asked. “Oh, I made it,” she said. I’m not the only person who asked, so she put it up on Shopify for friends who wanted one. She’s selling it at cost because the point was never to profit. The point was to make a thing that mattered. If it matters to you, you can get one, too.

Book Recommendation: Founder Unfriendly

A month before my wife gave birth for the first time, we moved into a ground floor apartment on Seventh Avenue in Park Slope. It was a loud but lovely, and very overwhelming moment in life. Out of nowhere, a box of ice creams arrived with no return address. Only later did I learn that had sent them. He noticed via Insagram that my new home was near his, so he dropped off a housewarming gift. I’ve since moved, and I never see the guy enough, but I always read his “heartbeat” emails because they’re the most human emails in VC-land. You can read about funding and also what it’s like to watch your daughter take an active dislike to your passions (baseball). Now he’s got a book that will surely deliver on his unique brand of charisma-meets-intellect to tell you the things others won’t about how to get funded, and also about how to operate generally in business. Pre-orders are out: Don’t sleep on it.

What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. My mission is to close the gap between the people building the future—and those of us living it.

I thought of this yesterday afternoon as I strolled our dog around the block in the midday sun. There was no wind, so single digit temperatures didn’t feel so terrible. It’s still too cold in Brooklyn for snowmelt, so nothing is wet and drippy. The powdery white dust of snow squeaked beneath my boots. As I stopped to let the dog sniff, this colorful child’s mitten sprung into view with a colorful wave.

Who could be sad about losing this mitten? It’s so joyful! Maybe it wasn’t lost at all. Maybe it was left as a gift, a child’s wave for everyone braving the elements for a walk.

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Perspectives are contagious

That’s a long way to say that I’ve been thinking a good deal about perspective these days. Our perspectives are so contagious. They’re often shaped by broader forces like the news out of Minneapolis, the terror in Iran, the closing of the Kennedy Center. UGH. It all seems so bad, and the bad feels bad, and we’re stuck in bad. Our perspectives feel fixed.

But they don’t have to be so rigidly set. They can be flexible. I’m not trying to make you embrace your inner Polyanna here. That’s not helpful. But loosening up on our certainty that we know how to feel about any set of events allows us flexibility. The path to accessing that flexibility is paying deep attention to what we often fail to notice in ourselves and others.

It’s listening.

This is the throughline that surfaces in nearly all of my interviews these days. People join me in the studio to talk about sales or discuss management strategies. This week’s guest, the author Jonathan Smith, brought us a new book on negotiation. It’s called Fight Less Win More: How Master Negotiators Influence Hearts, Minds and Deals.

I love specific instructions on how to be better at bringing others around to my wishes. I talk a big talk about negotiating, and struggle with the skills in practice! And Jonathan works with Chris Voss, who has talked hostage-takers out of banks. So I was excited to see what his brand of magic was.

A few minutes into the conversation, I realize we were once again reviewing very specific details on how to listen. Jonathan sees every conversation as a negotiation to be won, and you win by creating enough space for another person to feel seen. He has processes; he talks about labels and mirrors, about silence that stretches just long enough to feel uncomfortable. He describes restraint, and invites us to set aside the urge to assert or explain ourselves. But really wants he’s saying is just listen!

Jonathan will tell you that listening, like any other muscle, atrophies when we stop using it. We have to practice. And I’ll just tell you that as he pushed me to think about low-stakes opportunities to practice, I realized I’d heard something like this before in therapy years ago. What stayed with me most was his insistence that the goal of negotiation is the relationship you build through it Progress, in this framing, and “winning” is moving the relationship to a healthier place, even if that movement is slow.

Which brings me back to the mitten. The easy interpretation of a mitten on a fence post in winter is loss. But listen. If you take the time to focus on this minute, you may hear the vibrant colors of our humanity persisting. As 2026 serves up a stream of broader events and sends chilly temperatures and snow dumps that make everything feel emotionally and physically harder, it’s worth asking ourselves what stories we’re assuming without listening.

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What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. I’m on staff as a senior editor at large at LinkedIn. My mission is to close the gap between the people building the future—and those of us living it.

Waiiiiitttttt a minnnnute, this is the AI right? The AI has assisted you? Or maybe it has even written this for you?

I’m not convinced this is terrible. I’ve had the experience of vomiting a string of thoughts into a LLM and reading the coherent output and thinking: YEAH, that’s what I was trying to say.

But when I perceive others to be relying on these tools, I have an immediate emotional reaction. (And by the way, this recent academic research surveying 27,000 participants suggests other people do, too.)

I feel alienated, cheated on, like I got to the proverbial party of ideas too late and everyone has left and now it’s just me and a machine.

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I feel like someone has devalued my time, has in fact spent seconds on text that demands I spend minutes in order to decode it. It doesn’t feel fair somehow.

I wonder if the author understands I can see through this and is comfortable with the compromise, or if she actually feels I’ll believe her work is original to her. I wonder what it would even mean for the work to be original to her.

I feel lonely.

This is how social media ends.

As 2026 gets underway, we’ve hit a tipping point. No one wants to hang out on the internet anymore. Signs of this are everywhere. My year began with ’s newsletter telling me How to be less online in 2026. Gen Z is buying devices like The Brick that will block the most addictive apps on your phone. My hairdresser told me she’d begun observing Shabbat. “Mostly, I want a formal reason to get off my phone and rest,” she told me.

Some of this is happening because we’ve woken up to just how harmful attention fragmentation can be, how impactful it can be on our mental health. Activist academics like Jonathan Haidt (who is coming into the Hello Monday studio next week) have been educating us on social media’s impact on our ability to pay attention. That work has led to school districts banning phones. In the fall, the entire country of Australia banned social media for kids under 16. At the same time, jury selection began this week for the first in a series of trials that will be meaningful for social media companies; in each, parents are suing platforms for their impact on their children’s mental health.

So yes, we’re collectively acknowledging that maybe this tortured way in which our nervous systems are continually activated as we scroll through social media is bad for us, especially for those of us who are not yet adults.

But that’s not why we’re spending less time on Facebook and taking Instagram off our phones. We’re leaving social media because it’s boring and bad and it makes us feel gross.

To wit: social networking began as a way to connect us to each other. Back in the early aughts as broadband became pervasive, we launched our Friendster and MySpace profiles with curiosity and hope. Yes, these sites magnified many of our worst qualities but we also found meaning through these connections. More than two decades later, social media has become a solo experience, an algorithmic reflection of oneself. What do you like to hear? What do you believe is true? Social media serves up more and more and more of that.

Here’s My Theory of Media in 2026:

At its core, media is the infrastructure that allows meaning to move between people. It is not the content, though I came into the field aspiring to craft beautiful stories out of my ideas. It is not the technology, though technology has determined how those stories and ideas get distributed. Media is felt reciprocity, the promise that when you deliver ideas, someone receives them. A medium only works when we believe that most of the time, when we speak, someone is listening and our words have the potential to matter.

To say it another way: Everything is community, and community is the feeling that when you talk, someone else listens, that your words have the power to shift their thoughts and actions.

Social software design has co-opted that word over the past two decades, along with words like “friend.” Right from the start, companies focused on engagement rather than designing for human needs. They focused on scale, finding ways to incentive us to build MORE connections, rather than deepen our connections.

The first time I spoke to Mark Zuckerberg in the fall of 2005, when he was still living and working from a “hack house” in Palo Alto and he didn’t yet have a head of communications to help craft a message of any sort, he described a vision for a next-gen phonebook. I still have the transcript, “It’s a pretty strong resource of information indexed by people’s names and who they know,” he told me. “It’s a good utility.” Of course most utilities behave like monopolies in order to function well. Think electric company. Phone company. That’s why they’re heavily regulated. Mark stopped using this language in interviews early on.

Remember the Dunbar number?

Somewhere around 2010, most of the founders I spoke with would talk about the ”Dunbar number,” the result of research introduced by the British anthropologist Robin Dunbar. He said humans can meaningfully maintain social relationships with about 150 people.

That was back when social media worked. I’d even venture to say it was good. In those early days, you knew most of the people you interacted with. They knew you; you didn’t need Uber stars and Yelp reviews to establish your reputation. This IRL context traveled with your conversations. What’s more, the attention we afforded each other was both limited and mutual. The rules of the early social networks mirrored the rules of your offline community.

Rather than understand this size as a principle of our nature, Web 2.0’s founders set out to overcome it. For the most part, as they built the software we grew to love, they placed value on our attention rather than our relationships with each other. They measured “engagement” and “time spent” online, rather than examining how we spent that time. Their emerging advertisement-based business models demanded it. To unlock more engagement, seducing us to spend more time online, the dominant social media sites stopped organizing around people and started organizing around content. The rules for interacting no longer mirrored offline life.

(There are exceptions here. My favorite social network of this era is Meetup.com, a company that exists solely to help people get together in real life around common interests. I’ve also always thought that Mighty Networks founder really understands the mechanics of community, and her company prioritizes depth over scale.)

Mixed Signals

For many years, social media was a mess of mixed signals in which we could still find the connections that delivered on our desire to feel a sense of belonging, but we had to find them in between TikTok videos and our colleague’s vacation photos. Connection came from the comments in threads, the DMs we sent, in private groups and side channels.

Then things got worse. Around 2016, the year that has recently inspired so much nostalgia, companies began programming their algorithms to feed us material that performed well rather than prioritizing the people we knew. Suddenly everything got a lot faster, and people got meaner. Absent context and reputation, there were no consequences for our behavior, and outrage was the fastest path to attention. (This is why cancel culture took off in 2016, but that’s another essay.)

Still, we looked to social media to connect with each other, to participate in moments of both synchronous and asynchronous shared attention. Even as it has become harder to do, we have found each other through social software. I’ve seen this first hand as I’ve grown Hello Monday on LinkedIn over the last seven years. The show brings strong ideas and a point of view, but it exists because its community of real people tune in and talk to each other and to me about those ideas. Media is felt reciprocity.

For a long time, social media as a communications medium has been fading. As companies remain beholden through their business models to the economics of engagement and scale, people have lost patience with the process of sifting through the silt to find what they once treasured. A decade ago, the school’s PTA could start a Facebook group and communicate reliably on it because nearly all parents had an account, that’s no longer a given. Americans spent 20% less time on Facebook last year than they did five years ago, in 2017. On Instagram, engagement quality is weakening. Instagram head Adam Mosseri has said that people aren’t sharing in the feed as much, alleging instead that they prioritize direct messages. The twenty-somethings that I know don’t post; they opt for direct messages within private communities and group chats, largely composed of people they know.

Which brings me back to the ick I feel when I read that Substack newsletter or LinkedIn post that definitely got its assist from AI.

AI is the best thing to happen to social media

Most will agree that no one wants AI slop, the cheap and often bad AI content that turns up in our feeds. Far more nefarious is the “maybe AI” filter we’ve been conditioned to apply to posts and messages from people we know. We’re still looking for each other in our social media output, only now we have no proof that we are finding each other, or that we have been found. Media is felt reciprocity, and on today’s social platforms, no one feels met. So they’re starting to opt out…and look for something else by way of replacement.

This is how a new medium is born.

We need to make and share meaning. It’s the core of our humanity. This need to exchange meaning as a path to a shared belonging is why media exists. And we’re about to see things get a lot more interesting. Right now, most virtual paths to real identity and shared context are so misshapen that the only reliable way we have to find each other is to get together.

So in 2026, WE WILL GET TOGETHER!

This is a better world I’m talking about. But it’s not going to arrive because we opt into our best nature. It will arrive out of necessity when nothing that is mediated is real. What can we trust? Where can we find help? In our alienation and uncertainty, we will find each other.

We are entering a golden age for community events, a window of time in which we’ll be forced to put real innovation into figuring out how and when to be together.

A few examples that excite me:

TINY: I’ve started hosting breakfasts, filling the table with a half-dozen folks who don’t know each other and figuring out how to start and build conversations that aren’t scripted. I dream of building this into the breakfast series I piloted nearly a decade ago when I was at WIRED, a way to start the day with dialogue and creative energy.

MEDIUM: I’m launching a book club for Hello Monday listeners. We’ll convene virtually, with intention, screens on, to talk about ideas. We’ll cap each session at 30 participants, and everyone who shows up will be expected to contribute. (To get on the list to learn more, email HelloMonday@LinkedIn.com)

HUGE: January saw the official launch of In the Room Live, our interactive live conversation with notable figures. I’m one of the hosts who bring conversations with figures like Brené Brown, Malcolm Gladwell, and Mark Cuban. This program is distinguished by its live chat feature, enabling us to have a shared experience at scale. It’s for people who understand that the joy and meaning in a conversation comes from being part of it, from being together, in the same place, at the same time.

How we clarify what we value

AI brings us clarity about what we actually value. When we can no longer trust that what we’re reading came from a person who meant it, we are forced to seek out places where meaning is harder to fake. Media will survive, but only insofar as it remembers its job. It exists to move ideas between people who can feel each other on the other side. Media is felt reciprocity.

The future belongs to the spaces (online and off) where reciprocity is unmistakable, where it’s clear that someone else is really there.

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What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. Currently, I’m on staff at LinkedIn as a senior editor at large. My mission is to close the gap between the people building the future—and those of us living it.

Danny Fontaine, author of Pitch: How to Captivate and Convince any Audience on the Planet, joins me in the Hello Monday studio

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When I was a magazine journalist, my job was to descend into someone else’s life, sometimes for weeks. I’d sit at their kitchen tables, meet their children. I’d ask about their ambitions, plumb their dreams. I’d gently nudge the edges of their failures. I’d listen more than I talked.

At the end of the process, I would go home and write a story about them.

More often than not, they would walk away thinking: Jessi and I vibe. Jessi is my new friend.

Of course, they didn’t actually know very much about me at all. What they experienced was my attention. It was the rare feeling of being deeply listened to.

The thing I missed about selling

That lesson came back to me this week during a conversation on Hello Monday with Danny Fontaine. Danny writes and thinks about pitching for a living. I’d invited him into the studio because I wanted to think about selling.

Even after decades in business, I have this preconceived notion about what it means to be good at sales…and it’s way too narrow. I’ve thought of those who possess this skill as endless extroverts, willing to push ideas, products and services. The trouble with this perception is that it misses what it actually means to be good at it.

This is a moment where we all need to be better at sales. For one, many of us are moving into independent consulting work and we will need to win clients as part of this work, regardless of our specialties. But more than that, sales is about so much more than winning business. It’s about persuading someone to come around to your point of view, to back your idea. And isn’t that necessary in everything we do?

Pitching someone is what I was doing as a young journalist at Fortune when I showed up in Salt Lake City, say, and asked Josh James to show me around town. Or when I Div Turakhia, in the process of explaining how he turned his day’s loan into a billion-dollar business, handed me the keys to his Ferrari and invited me drive it through San Francisco’s South Beach neighbhorhood. Or when I convinced Sheryl Sandberg to have lunch with me just after she’d taken the big job at Facebook in 2008, and raced to get the first profile of this new executive in print.

The more I listened, centering my subject, the more likely I became to win the story, and for the story to be a winning story. The techniques, always, was to facilitate an authentic connection. Then I could ask for information.

That’s the idea from this conversation that stuck with me: emotion comes before information. It’s how humans decide what matters.

We like to believe that logic leads and feeling follows. In reality, it’s almost always the opposite. We feel first. Then we look for data to justify what we already sense to be true. But when we rush to the facts, we often trigger resistance instead of trust.

That’s why the most effective pitches don’t start with “Let me tell you why you should go with me.” They start with “I see you. I understand the problem you’re living with.”

It’s the same dynamic that made my reporting work. People don’t leave conversations thinking you’re brilliant because of what you said. They leave thinking you’re brilliant because of how interested you were.

🤓 Worth it: Minnesota is a harbinger of what is ahead. Where is tech’s outrage?

reports that tech’s workers are getting tired of reporting to tech CEOs who are silent on the subject of ICE. In a USA Today article, she chronicle an emerging petition signed so far by 300 employees of the types of companies that, a decade ago, defined their brands in part through their commitment to activism and to liberal, democratic values. (Remember Google’s motto? “Don’t be evil.”)

It’s worth pointing out that this piece came out last week, days before the murder of Alex Pretti. Here’s an emerging list of the companies that are speaking out against this shooting. It’s unsettling to see how little the tech sector is represented on this list.

Here it’s worth remembering that business as we’ve conditioned it to function in North America is not about activism; it’s about making money by any means necessary. And what’s true is that the scarcity mindset has come for tech’s leaders. Writing for the Wall Street Journal, Tim Higgins reports that a subset of the tech world believes the bridge is about to be raised for those chasing the American dream. And everyone is worried about being left on the wrong side.

What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. My mission is to close the gap between the people building the future—and those of us living it.

🎧 Check us out on LinkedIn, YouTube, Apple Podcasts or Spotify 🎧

This week executive coach Muriel Wilkins joins us to unpack the beliefs that quietly shape how we lead—and how they can start holding us back.

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But first let’s start with this….

Kyle is among my most talented friends, and one of my oldest, so I can recognize intimidation when I hear it in his voice. We’re lucky enough to work together, and last Monday, we were both in our home offices, so we met up for a brisk winter walk.

After a couple of years as an independent contributor at LinkedIn, Kyle has recently moved into a management role, inheriting a a large team spread across the globe. As we crossed the street into Fort Greene Park, he inhaled the crisp air, and began to tick through his hopes for the year ahead. His new team has the potential to have massive impact this year…but first, Kyle must learn how to nurture it, where to push and when to focus.

Where he once held himself to high expectations, he now must inspire others to deliver on these expectations. It sounds easy when I write it, but this is hard messy work, and Kyle is self-evolved enough to realize it.

“It just feels really clear to me,” he said. “What got me here is not going to get me there.”

Here’s Kyle racing my son. I’d bet on him, wouldn’t you?

What got me here is not going to get me there.

I clocked the phrase. This is the mantra for 2026: I can feel it everywhere.

It applies to politics. Here in NYC, as we watch a new Mayor set out with optimism to improve life for New Yorkers, I think about the fall’s election in which a massive cohort of voters said, we need to try something new.

It applies to business and our careers. As companies rush to adopt automation and AI, the promise was fewer tasks and more leverage. Instead, many people are working harder, longer, and faster. We are managing more systems, more information, and more change at once. Productivity tools multiplied and so did pressure, and the ground keeps shifting.

All around us, there is a collective recognition that the skills have proven most helpful to us may now be holding us back; we will need to learn to do things differently in order to keep up with the change unfolding around us.

In the year to come, we’ll need to evolve. That evolution cannot begin externally with things we do. It starts internally, as we reconsider who we are, what we value, and how we show up for ourselves and others. These are January’s questions.

Please meet Muriel Wilkins

In hindsight, I couldn’t have anticipated how perfectly timed this conversation with Muriel Wilkins would feel. Muriel has a coaching practice and advises c-suite executives. She’s been helping people get unstuck, getting deep into their most gnarly problems with them, for years. Listening to her podcast is a bit like watching that Showtime series Couples Therapy; you can see at every turn how problems that seem intractable and structural at the outset boil down to belief systems. Her new book, Leadership Unblocked: Break Through the Beliefs That Limit Your Potential, was published by Harvard Business Review Press in October 2025

The reality is that while we can change our mindsets, this is hard work, and not many of us will. Muriel’s book explores seven hidden beliefs that regularly thwart the people she has coached. Many of those beliefs felt familiar to me, and we got into several of them at length in this week’s episode. (One example: “If I can do it, so can you.”)

She then offers a three-step framework for how to work with a blocking belief. It’s designed to slow us down and have us spend time in the challenge before we attempt to skip to the solution. We’ll explore and apply the steps in our conversation, but here’s the takeaway that will apply to your career, sure, and also to every other way in which you try make your way forward this year: Leadership is an iterative process.

Our goal isn’t to change who we are, or even what has worked so well to get us to this point. Rather, it is to expand our range, allowing us to access news paths to who we are becoming.

🤓 Worth it: the big questions

How do we talk to each other?

A friend, , recommended this series of interviews called The Enemies Project. Professional mediator Larry Rosen is the creator and host. Rather than pundit-style debate, the show pairs two people with deeply opposing worldviews and helps them actually listen and find humanity in each other. It’s a very compelling listen/watch.

What do we believe?

The information war will be fought through Chatbots, write and Damon Beres in The Atlantic. The people who control these products have a greater ability than ever before to manipulate the narratives we absorb.

How do we survive?

Y’all, in case you missed it, The Corporation for Public Broadcasting has elected to shut down. It seems a safer, more socially responsibly alternative than going dormant.

What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. My mission is to close the gap between the people building the future—and those of us living it.

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Once I could dream it up, that job became much easier to find.

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Once again, I launch the year with the Dream Job Exercise, a powerful visioning tool to lend us agency as we move into the future. This has been the most important tool in my own professional life, and I’ve shared it with everyone from my sister (hi Katje!) to my BFF to colleagues.

For those who would rather read than listen, I bring you the episode’s full transcript. And if you just want the directions, scroll all the way down to: Dream Job Exercise!

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From the news team at LinkedIn. I’m Jessi Hempel, and this is Hello Monday. It’s our show about the changing nature of work and how that work is changing all of us.

And here we are again, a new year. It’s that strange little pause where everything feels possible. Right? Nothing at all feels certain yet.

Happy new year. I really mean that. I hope this one brings you some steadiness, and maybe even some clarity. Because if you’re listening today, I know that you are feeling the shift under your feet. I am too. I’m starting this year with more questions than I have had about my own job or my own career in a very long time.

Here’s what I know, but I just can’t really unsee anymore. Work is changing, but not in that “future of work” panel discussion kind of way. No. In some more real way, right now. Everyone I know is feeling it. I’m feeling it. I mean, look at me. I have this job I really love. Hello Monday is only part of it. I also host live conversations for our premium members here at LinkedIn. I get to help shape media strategy for the company broadly. My colleagues are smart, kind people. They care as much as I do about this mission that we have. We get to help shape how tens of millions of people understand and advance their careers.

I’m just going to say this is the kind of meaningful work I was going for when I got started in the workforce and still. I can see it. I can see the writing on the wall.

It’s as if my own career has primed me to recognize my job’s demise. After all, I spent two decades reporting on business for BusinessWeek and Fortune and Wired. I’ve spent seven years now exploring what’s happening to careers every Monday morning with you. And that’s why I can tell you with some certainty that this job I have today is going to go away.

Two years from now, I will be doing something entirely different. Maybe here at LinkedIn, maybe somewhere else entirely. I don’t know.

I’m guessing that even if you’re a person who loves your job, you might be noticing this about your own situation. AI is coming for so many of the parts of my own work that I’ve loved.

Companies are trying to keep up with this new pace of change, and in the process they are investing differently. Projects get cut. Layoffs are a constant. This is the new reality of professional life.

I’m here living inside this very uncertainty, this uncertainty that I’ve covered for so long, and I’m going to tell you it is uncomfortable. This year, I don’t have all the answers. I’m sitting here in this studio asking the same questions that you are:

How do we enjoy the work we have now when the ground keeps moving?

How do we prepare for what’s next when we don’t know what will really matter?

How do we build a life that we can trust?

These, these are the questions that will drive our show this year, the questions that will drive me. And I want to bring up two big ideas as we ask them.

First, I want to ask you to hold hope as your centerpiece.

You know me, I am a techno optimist at heart. I believe in people and I believe that we have the ability to put technology to use in service of our better selves. Now, it doesn’t mean that we’re always on the right track, but we have the capacity to be.

Second, I want you to hold front and center this idea of agency.

We are not solely reacting to the change happening everywhere around us. We are actually agents of that change. Now, we don’t have to predict the future to shape it either. We don’t even have to see the whole path. We just need one clear signal, what we actually want.

That’s why every year we come back to this ritual together, the dream job exercise. Now, its significance is that it wakes up that part of us that still knows how to imagine. If I had to name one skill for 2026 that will carry us through, it is that.

It is imagination.

This is the quintessential skill that will help us create a future that is better than the future that we are all scared of. The future that newspapers and politics and society would have us believe is in front of us. Folks, if we want better, we first have to see better.

Where did the dream job exercise come from?

I do this exercise every January. And back when I started in 2018, I really wasn’t even sure why I was doing it. Back then I was in this particularly miserable job. I’d hired this career coach and she’d asked me to write my job description. I wasn’t fully bought in on her yet. I’ll tell you that. And I also thought my prospects were pretty bleak. I was pretty unhappy in the job I had.

I knew what I wanted.

I mean, I wanted an interesting, meaningful gig. I didn’t want it to take up all my time. I wanted to take time off to write a book, paid time off, where I could keep my healthcare benefits and everything because, hey, my wife had just found out she was pregnant and all. And by the way, I wanted a significant paid parental leave.

I mean, when I wrote that all down, and even when I think about it now, I have to ask, “Isn’t this just too much to want? Too much to ask for?” So this coach of mine, she urged me to put my notions of what was possible to the side and to pretend my way to the perfect world for me. And I did it.

I sent her a draft and she sent it back. She asked me to think even bigger and to get really specific. And yes, folks, this is where I just got really annoyed with her, but I did it anyways.

She wanted to know what my office looked like, how much money I made, and then she asked, “Was I certain about that? What was I responsible for achieving? Why did it matter to me?” The end result was a one-sheeter for a job that I really thought could not possibly exist, but I knew that if I got it, I’d feel great about it. I knew it really would be the perfect job for me. I printed it out, I folded it up, I slipped it in my wallet and I did not think about it again. Today, I have a version of that job. Every last thing that I wrote in that description, well, it came to pass. And it wasn’t that I magically summoned it. It was that a few months later, when LinkedIn approached me about a job, I knew what I was looking for. When we needed to figure out together what that job would look like, I’d already written it down.

Now, if you’d asked me then, I would have told you that it all came out of the blue, but that is not actually what I think. I’ve had so many career experts on Hello Monday, and you’ve heard me say it on this show. I have come to believe that we can only achieve what we can imagine. You know, often we limit our imaginations before we even know what we want. Drafting my dream job, well, it broke me out of the limits, the constraints of how I thought about what I could do. Once I could dream it up, that job became much easier to find. That’s what I’m trying to say. And here’s the thing. I believe that it can do the same thing for you.

Like I said, we do this exercise every January, and I always invite you to email me your finished product.

Over the last couple of years, hundreds of you have done this exercise, and so many of you have sent along those dream job descriptions. So many that I’ve started to collect some sense of what we want from our professional lives. And I’m going to tell you, it’s beautiful. In a phrase, we want to contribute, to live well. Okay, so here we go.

THE DREAM JOB EXERCISE

I want you to take a moment now to gather your tools. You’re going to grab a pencil and a paper, or if you’d prefer to do it on a laptop, that works too. That’s how I do it. You’re going to need a minimum of about 15 minutes for your first pass, not more. Choose a quiet spot. A place you know that the kids aren’t going to bust in just when you’re hitting your stride. I often pull my laptop right into my lap on the sofa. We have this great corner underneath this window that looks out into a beautiful tree.

What’s important here is that you approach this exercise with a clear mind and that you allow that mind to wander. So put your phone or laptop on airplane mode, silence those notifications. Make sure you can’t access the internet. I mean that because if you can, my guess is that you will.

Oh, and one more thing. If you don’t have moments in the next 15 minutes where you feel bored or uncomfortable or wonder if you’re doing this right, if you don’t dislike it just a little bit, you’re probably not doing it right.

Okay. At the top of the paper, write dream job description for January 2036.

Yeah, that’s right. 2036. That is 10 years away. Now, if you’ve been with us for a while, you’ll note this part’s new. We have looked five years out in the past. The problem with five years is that it’s just too close. We edit ourselves. We spend a lot of time trying to think about how we’re going to get where we’re going to get instead of wondering about what it is that we want to feel when we get there. We get stuck in the question of whether we know practically how we’re going to achieve this goal that we’re dreaming up, and this is not the point. When Debbie Millman first brought her version of this exercise to us years ago, she held up 10 years as a sweet spot. She said it was far enough out in the horizon that we really can believe that anything and everything can be different.

We can stop planning and start dreaming.

So first, I want you to imagine who you are. Take notes here. It’s all part of the job description. If you don’t know the answers to the questions that I’m asking, well, that’s okay. Just make something up. You can always go back and change it. Do you live alone or do you live with a partner? Do you have kids? Pets? Are you a city dweller? Do you live in a place where you can take a hike every day? What are you wearing?

Really, specifically, what are you wearing? And remember as you’re taking these notes, don’t write down things that might be possible. Really imagine what you would most love. And as you write down the things that you know that your heart wants to happen, just be there in the idea of that, in the reality of it. Okay?

So give your job a title. And again, make it up. That’s fine. My job title back in 2018 was Head of Technology and Humanity at The Atlantic. Now, I never worked at the Atlantic, but when I landed at LinkedIn, I recognized that the brand was just as important to me as the Atlantic. I’d landed it. I’ll tell you that.

Now write down everything about this job. What’s the work? How does it get done? What is its underlying purpose? And why is that meaningful to you? Where do you do it? Do you go into an office? If so, how often? What’s your workspace look like? What are the tools that you use? Who do you talk to every day in your job? Who do you make sure you never have to talk to? What is everyone’s opinion of you? How flexible is your schedule, really? Does that matter to you? Do you travel?

Now, spend some time here on benefits and compensation. Like really dig into it. What do you get paid? How and when does it change? When do you get time off and how flexible is it? What benefits are really important to you? Do you want a four day work week or do you want to leave in the middle of the day on Thursdays for two hours to coach field hockey for your daughter? What is your real path to advancement in this role? And is it the kind of advancement that moves you forward personally or are you ascribing to a larger collective goal?

Double your word count!

Okay. So once you have jotted down the answers to all these questions, I want you to drop that text into a doc in your computer and do a word count. Now back in 2018, my first draft was 225 words and that seemed kind of long to me. I really thought I’d gotten everything, but the first direction my coach gave me was double it. And that’s what I’m going to ask you to do. Whatever your number is, I want you to double it and make that your goal. Okay? So for your second 15 minute exercise, which you can do now or you can do later, I want you to tell me even more about that job. What it feels like to do it, where it happens, how it happens, why it’s the job for you.

You might feel compelled to use AI at this stage. That is okay. But listen, when you do, I want you to experiment with using it as a thought partner, not as a writer. Ask AI what you’re leaving on the table, what you might want to consider.

Here’s a prompt I love: Think of someone public who you really admire. I did it this year with Michelle Obama. Then ask your AI (I tried it with both Claude and with ChatGPT): What would Michelle Obama encourage me to think about?

Okay. So here sometimes accountability can be a helpful tool. If you’d like a reader for that job description, send it to me in the body of an email. Our show’s email address is hellomonday@linkedin.com.

Here’s my promise to you. First, that I will not share this beyond the Hello Monday team. You can consider it private with us. And two, that I will read every single email you send and I’ll reply.

Okay, now you need to give this the space that it needs to sink in. Put it down for a day or even up to a week. And when you pick it up again, make any final edits. Read it out loud once to yourself. If you can print it out and put it in a place where you can find it, do.

Again, I stuck mine in my wallet. I kept it there for a very long time.

What comes next:

Then your next job is just really to forget that it exists because your work is done. You’ll see for yourself the impact this exercise will have. It will become a filter for you as you make career related decisions in the year to come.

Okay folks, that is it for the dream job exercise. And I just wanted to take a moment here to tell you what a pleasure it has been to be on this journey of curiosity with you this past year.

You know, my son was born the year that we launched the show, right? And he is seven now. My daughter is four. They almost sleep through the night. Almost. Okay. Truly, we’re not really close on that one, but they’re learning to do other things. They’re learning to read. They’re discovering how to look after themselves in all the big and small ways. And we are changing too. In all the big and small ways we are growing together. You know, this next year brings an urgency to the questions that we’re asking. It brings more chaos and more uncertainty. And here I challenge you to see those things as gifts, to understand that in the midst of it all is opportunity if we only look for it.

Send me your questions, especially the ones that you can’t find answers to in other places. You can send them to hellomonday@linkedin.com.

Show ideas for 2026!

And if there’s anybody you really want to hear from, well, send that to us too. I can’t promise you I know how to get to them, but if I can get them into the studio, I will. I hope you have a really wonderful start to the new year. And I’ll be right back here in this studio next Monday with more from Hello Monday.

I am Jessi Hempel. It’s been great to be with you.

** A note of thanks to Robin

To Robin, and to all the job coaches out there who do the sturdy work of caretaking our egos and our ambition, of holding our hands through hard changes and pushing us to discover everything within us and to put it into practice. Thank you!

What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. My mission is to close the gap between the people building the future—and those of us living it.

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Next to the fire are two baskets, ivy and oak. At some point, I grab a sprig of each to toss on the fire. This is a ritual to mark our own survival, the idea that we’ve come through this darkness. As I tried to explain to my son last night, it’s a chance to name and let go of that which has gotten us here, but will no longer serve us as we move into the light.

“I don’t want to let go of anything,” he told me. He’s a literal guy. Also, an acquisitive guy. He likes getting things and holding on to things.

Me, too. It’s been a year of the kind of change I wouldn’t have imagined in earlier moments in my life. I’m talking about the political environment in which we find ourselves, the economic landscape. But also, my own job has changed this year as my team combined with another and I moved to a new manager. At home, parents are aging and so are the kids and their needs are changing. I find myself clawing at anything I can control, a response to fear. I don’t want to let go of anything either.

We stood there, me and Jude, leaves in our hands, for a very long time.

Sparks of the fire leapt up and danced in the air, jumping just out of its enclosure. A cousin stomped them out and we watched the flames for a bit longer. Finally, I was ready: “Jude, I’m giving up my need to know the future.”

This need to know what comes next has served me well. It’s helped me build a career and a life. But this year that need has become so heavy. It takes so much energy to keep gripping for certainty in a moment that refuses to offer it. I often run for bad answers just for the relief of knowing, of having an answer. Do you ever do that?

But I couldn’t explain all of this to Jude last night. He whispered something I didn’t hear. Then he threw his leaves in the fire and ran off into the woods to play more night tag.

How to fall in love with questions….

For our final new episode of Hello Monday this year, I wanted to sit with uncertainty instead of trying to outrun it.

My guest is Elizabeth Weingarten—journalist, behavioral scientist, and author of How to Fall in Love with Questions. Elizabeth offers a way to change the questions we ask when everything feels unstable.

In this conversation, you’ll learn why our tolerance for uncertainty has eroded in an age of infinite information—and why that matters. You’ll hear how asking the wrong questions can trap us in false, binary choices that keep us stuck. And you’ll learn a powerful framework for understanding different kinds of questions: the ones that resolve quickly, the ones that take years, the ones that stay with us for a lifetime. Also: the ones we’re better off letting go.

Elizabeth argues that better questions can act as an internal GPS, guiding us toward what we actually want instead of what we think we’re supposed to want.

This is how we truly let go of the things that don’t serve us.

Check out the show

What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. My mission is to close the gap between the people building the future—and those of us living it.

A few weeks ago, a friend wrote to say she had just been laid off. Her text was so focused on the specific details that it sounded almost clinical, so I hit her back: “You ok?”

🎧 Check us out on LinkedIn, YouTube, Apple Podcasts or Spotify 🎧

Victoria Foster is an executive coach and co-founder of FutureWomen. She joins Hello Monday to help listeners navigate layoffs, uncertainty, and career transitions by separating who we are from what we do.

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“Yeah,” she responded. A little scared because, you know, bills. But gosh, she texted, she was relieved. She’d spent so long bracing for the possibility of losing her job that she hadn’t fully registered how much she didn’t like it.

I’ve been hearing versions of this story with increasing frequency. Sometimes the job is gone. Sometimes it’s still there, technically intact, but hollowed out.

Like, last week, I hosted a small breakfast for a handful of creative professionals my age. Two of the three guests described nearly identical situations. They were still employed, still outwardly successful, but they were underused. Their roles required only part of what they could offer. Over time, that left them feeling flat, lonely, and quietly disengaged.

And yet, neither was rushing to make a change. There was this unsaid understanding: At least I have a job. And that got me thinking about something I’ve noticed this year…

A lot of jobs aren’t very good right now.

As companies restructure to meet the growing demands of shareholders who are anxious to harness new technology, even “safe” roles feel tenuous and vulnerable to lay-offs. What’s more, in trying to move quickly, companies are delayering their managers, shifting strategies and killing projects. It’s harder than it has ever been to figure out how to plug in.

And when a job disappears (or when it stops really asking much of us) the hardest part often isn’t the loss itself. It’s realizing how much energy we’d been spending propping up something that no longer fits, and how little space we’ve given ourselves to admit that.

That’s why I invited Victoria Foster to join me for an episode of Hello Monday.

Victoria works with senior people at moments of transition like layoffs or pivots. She’s quick to describe how tightly most of us tie our sense of self to our roles. We define ourselves by our work, particularly work that’s visible and rewarded. When it disappears, we get scared and that fear is paralyzing.

One idea from our conversation keeps resurfacing for me. She articulates the difference between what we’re excellent at and what we bring to the work. Underneath our titles are qualities that are harder to name but far more durable, things like curiosity, discernment, the ability to see patterns, to help others think, to create trust. These are the qualities that will travel with us.

Take me. Ask me what I’m good at, and I’ll tell you I’m an expert interviewer. It’s the thing I know about myself. But Victoria pushed me to think about what underlies that. I’m curious, empathetic. I love listening well. If interviewing went away, I’d still find lots to do.

We need each other

Layoffs and periods of underuse tend to push people into isolation. We replay decisions and second-guess ourselves. We try to solve everything privately and quickly, skipping right to the question of what’s next. That mental compression makes it harder to see what’s actually available to us.

Victoria talks about slowing our stories down enough to reclaim our agency within them, and in this conversation, she offers a framework and several practical tools for how to do that. Wherever you are in your career, I hope you’ll take something meaningful from it.

And if you’ve found yourself newly unemployed this holiday season, drop me a line. I’ve got a half-dozen free subs for LinkedIn Premium and I’d love to share one with you.

🤓 Worth it:

I’m going to try something a little different with this section. Instead of dropping one-off articles that make me think, I’m going to try to tie those article together as trends….here goes:

Creative careers are ending. makes a case for the end of the career author, and argues on behalf of the portfolio career, pointing out that throughout history most writers also do other things. goes deep on how experienced workers in creative fields are finding their skills obsolete, a phenomenon he calls the Gen X Career Meltdown. This inspired several rebuttals like this one by Erin Looney that made points along the lines of: it’s not over! and some of us are doing better than others!

Which brings me to the classic 1967 film The Graduate:

Mr. McGuire: “I just want to say one word to you.”
Ben: “Yes, sir.”
Mr. McGuire: “Plastics.”

Everyone’s consulting! joined Hello Monday this week to give us on a primer on how to do it well. I still believe that it can be more reliable than most corporate work, and that it’s the best career move for senior professionals in search of a new opportunity. As more people are finding that consulting feels more stable than rolling up to one corporate entity, they’re learning how to do it out loud. offers a public performance review of her first 18 months as a “fractional.”

We’re in the midst of an information crisis. The crisis is making it difficult for us to know anything at all, and that makes it really difficult for us to get along with each other well, and the information crisis part of this problem is not getting better. But we can get along better with ourselves and each other, and offers a quick primer on what we’ve learned from other historical information crises and how it applies to now.

🤓 Double Worth it:

AI is delivering according to the average of everything that humans have already thought and done, and it’s work is, as writes, “expected and probable.” The more improbable you make yourself the less likely your ideas can be replicated by AI. He suggests we aspire to “a delicate balance between highly improbable and warmly useful to others.”

What’s this newsletter about again?

I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. My mission is to close the gap between the people building the future—and those of us living it.