Last month I resigned.

There were three main reasons I chose to move on:

• I accomplished what I was brought on to do. I stood up a world-class OKR program, formulated a new company values system, built a new financial model, refactored the team, and enabled a major growth acceleration (6x growth in new ARR in one quarter). Not bad for 5 months of work.

• The next phase did not align with my priorities. The upcoming months would require my commuting to the city 3x/week or more (60-90 min each way), staying late, and traveling overseas. This doesn’t fit my priorities with health, family, or community. Layered on top of some misalignment on strategy and culture, I decided it was time to go.

• Timeless Leader needed my attention. While at CRED I made incremental progress on the infrastructure build and continued running Basecamp, but I could not ignore the opportunity to respond to deep needs with clear solutions. We’re building a Democratic Ownership Society, and I needed to spend more of my time advancing this mission, not less.

I’m proud of the work I did at CRED and grateful for the learning and new relationships I formed.

(In this fast moving age of AI, it’s really possible to work with a company for a few months and experience and enable serious transformation.)

Since finishing at CRED, I’ve been busy.

Let me fill you in on some highlights.

A New Timeless Leader Foundation

Late last year I explained that we needed new infrastructure. I’m excited to share just how much progress we’ve made here.

✅ Timeless Leader LLC is officially formed. EIN acquired. Bank account open. It’s a real company now.

✅ I built the first digital product! I completed The Democracy Investment Guide: Senate Edition a couple of weeks ago, and started selling within 24 hours of personal outreach. I’ll share more below—including how you can get your hands on it!

✅ I built my first sales funnel. Landing page > checkout page (with bump offer) > thank you page. Purchases trigger automated follow-up. This is the beginning of a business that scales.

✅ A full overhaul of timelessleader.com. I refreshed the brand colors, dumped most of the stock imagery, and focused the messaging around what I’m actually working on and how I can help. It’s cleaner, sharper, and up to date on what Timeless Leader is, who we serve, and the impact we can have.

There’s more I’m building that I’m not ready to announce yet — in particular what’s on the horizon for this Substack. Stay tuned!

Introducing: The DIG

DIG stands for Democracy Investment Guide. It’s a research-backed, principled system for building a portfolio of leaders and organizations that, as a group, offers the best chance of protecting and expanding American democracy.

This is a guide for commitment curation. It teaches how to exercise your rights and duties as a citizen. When most of us aren’t, and never will be, professional politicians or political operatives, we can’t spend all day analyzing the political landscape, not to mention volunteering to aid worthy causes and candidates.

Building on 22 years of experience taking my role as citizen seriously, teaching history and civics, making over $51K of donations to political causes, doing impact investing at Stanford and independently, and running corporate and financial investing strategy for multi-million dollar budgets, I’ve designed a strategy for investing unlike anything else out there.

❌ This is not donating to candidates based on vibes or partisanship.

❌ This is not piling chips based on which horse-race seems like the biggest nail-biter.

❌ This is not optimizing for proving you’re smart by winning the most races.

📊 This is investing with diversification and intention for long-term impact.

How it works

First we screen candidates on two non-negotiable red lines:

• The Responsibility Screen: do they take a soft position on accountability for the criminality, violence, and corruption of the Trump regime, or do they stand firmly for the Rule of Law, no matter how powerful its violators may be?

• The Humanity Screen: can they call Gaza what it is, or do they hedge? Worse still, do they give unconditional support for a genocidal campaign that has killed 70K+ people, hundreds of journalists and aid workers, destroyed >90% of infrastructure, and made life unlivable for an entire population?

The first screen knocked out every Republican running for Congress. The second screen knocked out a significant number of Democrats—including many prominent names, contenders in swing elections, and leaders who otherwise champion progressive values.

Those who remain are then scored on a two-axis, six-point evaluation:

Axis 1: Candidate Quality. How well does this person lead themselves, lead organizations, and lead movements? The more their life and career is defined by courage, independence, grit, good judgment, and actual results, the higher they score.

Axis 2: Investment Quality. Is this candidate likely to win? Will investing in this candidate advance the goals of democracy? Is investing in this race a good use of your marginal dollar?

Working with Claude as a research assistant, I’ve evaluated 500+ candidates, races, and organizations. The Senate edition is built and ready to purchase.

The full National Bundle (Senate + House, PACs, Party orgs, Non-profits, and the complete All-Scores Database) ships starting on April 3rd.

It’s also available now for pre-order. ⤵️

Your Early Access and Special Discount

Because you subscribe to this newsletter, I want to offer you a chance to get the DIG at a special price.

I have 20 coupon codes for this list. Each one is 50% off your purchase.

Just use the code “Substack” at checkout.

This means you can get the Senate guide for just $3.50, or the full National Bundle for $23.50 instead of $47.

If you’re thinking about investing in any political races or democracy-focused non-profits this year, getting these guides is a no-brainer.

If you’re giving in the hundreds or thousands of dollars, you want to be sure these sizeable investments will make a real difference.

And if you’re considering making your first $25 donation — of this cycle, or ever — this is a chance to be more strategic than most donors who have years of experience.

First come, first served. Just enter the code “Substack” at checkout.

Get The DIG now

I’ve only issued 20 of this code. Once they’re gone, they’re gone.

But don’t take action now just because of a discount.

Act now because the stakes for the future of our country and the world couldn’t be higher.

More soon,

— Joe “Digging into the real work” Ballou

Share

Leave a comment

P.S. The “Substack” coupon codes are real and finite. If you’ve been thinking about doing more for our democracy, this could be the perfect way to support valuable research while getting the info you need to act. Take a look.

PPS. I’m now open to work! Think: Chief of Staff, COO, or VP of Growth; project-based or full-time. It might seem at odds with everything above, but running multiple tracks simultaneously isn't a bug in my strategy, it's a key feature. Timeless Leader is my life-long mission, and I won’t force it to meet my near-term revenue goals. Working with others also makes me stronger: for example, CRED was an AI-native company, and my practice there with Claude made building the DIG in a month possible. What can I do for organizations? I build OKR systems, growth programs and GTM plays, product strategies, and high-performing teams. Critically, I help with both prioritization and execution. I also screen hard with who I work with: democratic values, serious transformational potential, and in need of my exact skill set. If your organization needs that kind of operator, let’s talk!

Read time: 9 minutes

What do a man recording his final words, a kids’ movie villain, and the Epstein files have in common?

They all reinforce that a sense of moral superiority, unchecked, is a pathway to evil.

Stomping on your ego is how you don't become evil yourself.

Building systems that make ego a liability, not an asset, is how we create a virtuous, Democratic Ownership Society that serves all people.

A Dying Man’s Advice

Eric Dane — best known as McSteamy on Grey’s Anatomy — died last week from ALS. The day after he passed, Netflix released his episode of Famous Last Words, an interview series recorded under the agreement that it only airs after the subject’s death.1

Dane was thoughtful and funny and remarkably at peace throughout. Despite noticeable physical impairments, his mind was sharp, his insights fully formed, and amidst many powerful reflections one line especially jumped out to me:

I would make a gentle suggestion…

every opportunity…

every SINGLE opportunity you have to stomp on your ego…

take it.”2

Dane knew his ego would disappear with his death. He got ready to part with it by stomping on it early. But he also talked about living on “in the memories of others” — in the people he’d loved, mentored, showed up for. He appears to blend these ideas to make peace with his losses and imminent departure.

It’s a lesson in short supply in the film I watched the very next day.

The Animated Bad Guys

A day after watching the Dane interview, I watched the 2022 DreamWorks movie Bad Guys with my kids.3

Fair warning: I’m about to extract a serious moral argument from a movie where a piranha can stink up an entire building with his noxious farts and a tarantula is a wizard computer hacker. Stay with me (also, spoilers ahead).

In Bad Guys, a crew of animal criminals get caught and are offered a shot at redemption under the mentorship of Professor Marmalade — an adorable guinea pig with a British accent who just won the film’s equivalent of the Nobel Peace Prize. If you’re already suspicious of the guinea pig, congratulations, you’re smarter than every character in the movie.

Eventually you find out that Marmalade is the true villain, and his outer image as humanity’s savior was just a ruse so he could steal from his charities and pin the theft on the traditional “bad guys” he had promised to reform.

The film’s writers offer a nugget of foreshadowing of this twist early on, when Marmalade compares himself favorably to Mother Teresa. Mother Teresa. If you know anything about her, this was the nun who spent her entire life serving the poor, sick, and destitute, not as a side-project or tax-write off, but for the work itself.

That’s the tell. While the main story arc was the transformation of the nominal bad guys from hardened criminals to our favorite anti-heroes, the less appreciated message of the movie is that elevated self-worth is one of the hardest flaws to overcome. It can even give rise to true evil.

I love that a DreamWorks comedy can teach complex lessons about good and evil — if you're paying attention. A whole industry of children’s media tries to do the hard work of setting up future generations (and their parents) to understand these things.

Unfortunately, these lessons don’t reach everyone, and even the craziest fictional plots hardly capture the depravity of what some people do in real life.

The Real Bad Guys

Millions of Epstein files have become public since the start of the year, and the scandal is so damning it’s tempting to tune it out entirely. If even Noam Chomsky4 had a relationship with this guy, if countless institutions, from Ivy League schools to JP Morgan somehow maintained contact with him, could he have been so bad? And if so, and the rot is so deep, what can one average person even do with this information?

Yes, it’s critical to pay attention, but not to memorize every detail.

We have to understand the dynamics that gave rise to this nefarious network, so we can call for accountability for the individual actors AND prevent such evil from repeating in the future.

Epstein could traffic, rape, and torture for so long and at such a large scale because functionally, he was a power broker. He connected influential people. He moved money around. And as part of his system of manipulation he lured those seeking more power into his system of abuse, trapping them in a conspiracy of silence and complicity.

We don’t live in a DreamWorks movie where a clean victory is guaranteed in 90 minutes. While shimmers of accountability are shining through in parts of Europe, the same people and practices that allowed this criminal abomination to fester are now infecting the core apparatus of truth and justice.

We need a reckoning, and we need to prevent such crimes from ever happening again.

There’s no hope in the files themselves. Only in what we choose to build in response — the structures, the accountability, the alternative. That’s where HOPE comes in.

So What Do We Build?

I’ve talked for a long time about the vision for Timeless Leadership: we’re trying to build a Democratic Ownership Society. What does that society look like? What are the specific changes to work toward?

I brought these questions into February’s Basecamp discussion — not as an open-ended prompt, but as a proposal.

HOPE is a framework for identifying what we need to change in our relationship with the earth, with our systems, with each other, and with ourselves — to build a society we’d want to live in and be proud to pass on.

Here’s how it works.

The opening line grounds us:

On this living earth, we forge a Democratic Ownership Society…

This isn’t a metaphor. It’s a scope statement. Everything that follows happens here — on this planet, among all living things. Not on a distant planet or drifting space craft.

Here.

We then develop the foundational layer that determines everything else: our Home. Earth. Unless we end wanton waste and exploitation, and replace it with stewardship of our only home, we’re screwed.5 Nothing else really matters.

Once you’re grounded, we have three pillars, with concrete, measurable changes to strive for:

• Opportunity — End childhood poverty. Create free enterprise for all.

• Peace — End gun violence. Empower peaceful citizenship.

• Education — End extremist ideologies. Foster a culture of learning.

There’s a lot of shit out there to keep us depressed, distracted, and apathetic. What gets us off our asses is being able to focus on unambiguous things we want to end, and the concrete replacement we’re building to replace them.

This is not a utopian vision or a pipe-dream. It’s a specific program for how to direct our work and resources to build a positive, lasting shared legacy.

But building that legacy starts with honesty. There are no "good guys." Just people who do good things, and sometimes screw up.

I've been striving to do good things for a long time, and I haven't always succeeded.

Maybe you feel that way too.

What matters is that we learn from it, strive to do better, and never believe we're better than anyone else — lest we prove the polar opposite.

HOPE can help with portfolio planning, it can help with life design, it can help with organizational and movement strategy.

It can help us separate from our egos, and worry less about who’s a good vs bad guy. It can help us focus on whether we’re building the systems that promote more of the good, and less of the bad.

In future posts I’ll share more about why I chose these specific pillars, how they interact, why certain things are left out, and what to do with all of it.

In the meantime I hope (😉) you’ll share:

What’s one way we can build systems for good that not a lot of people think about?

Leave a comment (references to cartoons and Netflix documentaries welcome!)

Leave a comment

PS. A Note about Basecamp

In April Basecamp turns one year old! Next week we hold our 12th monthly session. That means it’s nearly a full year of showing up, going deep, and building the practice of Timeless Leadership together.

If you’ve been reading along and thinking I want to be in that (Zoom) room — now is a good time to join. It’s still just $97/year for monthly group conversations that regularly go places I never planned for them to go, but we’re all richer for it.

All you need to do is upgrade with the button below and you’ll be added to the call invite (first Thursday of every month at 9:30am Pacific).

Hope to see you there!

-Joe “Stomping on my ego” Ballou

Subscribe now

And I’m thinking a lot about freedom.

What freedom do we have? What freedom have we lost?

How is freedom distributed, and what freedom are we still seeking?

Sometimes history rhymes with the present, and these three vignettes from my life—10 years ago, 20 years ago, and last week—remind me of how connected we are, and how the leaders who came before us still have unfinished work for us to continue.

Ten years ago | San Francisco

Nimmi and I sat in our parked rental car, staring at the fog pouring over the Golden Gate Bridge.

We were visiting the Bay Area to weigh a decision that would change our lives—whether to move 3,000 miles from home so I could attend Stanford. We felt the winds of the Pacific and the cool rain of a Bay Area winter. A dream we had discussed for a long time started to feel like a real possibility.

The radio was playing MLK’s “I Have a Dream” speech. Then I noticed a line I’d never really heard before: “Let freedom ring from the curvaceous slopes of California.”

I had just driven up and down these slopes. I imagined freedom ringing over these hills and mountains. I wondered if MLK knew this landscape personally or only imagined it.

And I felt a connection to the early settlers to the state of California who sought freedom. Attending Stanford felt like our own migration for freedom.

A few months later we made the move.

As I later learned, Stanford’s unofficial motto, adopted by the first president: “Die Luft der Freiheit weht”—means “the winds of freedom blow”.1

Ten years on, I question how much Stanford or Silicon Valley actually stand for freedom—and if those of us who came here for that reason can make that promise real.

Twenty years ago | Venezuela

In my senior year at Haverford, I spent six weeks in Venezuela and wrote a 92-page thesis on the Bolivarian Revolution. Hugo Chavez was at the height of his power, the Iraq War was raging, and I viewed my career through the lens of the role the US might play in 21st century affairs.

Since the start of this year, the US government has made bold attempts to revive blatant imperialist projects reminiscent of the 19th century.

I don’t think this will work out well. At all.

Not only because two world wars taught us that imperialism leads inevitably to great conflict. Not only because humanity and the planet alike have no interest in risking our future on the arrogant projects of a narrow group of ill-educated “leaders.”

Not only because Russia is cheering for the collapse of NATO.

Not only because Venezuela is deeply anti-colonial.

But mainly, most of all, because in the US, WE THE PEOPLE are anti-colonial.

Our greatest successes and failures as a nation all trace back to whether we were expanding or contracting freedom and democracy. This time will be no different.

Last weekend | Redwood City

I stood on El Camino Real with 700+ neighbors at an ICE protest, following the armed invasion of Minnesota and cold-blooded murder of Renee Good.

A high schooler near me held a sign with a powerful quote, attributed to Dante.

The quote was one of JFK’s favorites, though Dante never actually wrote it. What Dante wrote is sharper. In the Inferno, those who stayed neutral in times of moral crisis don’t even make it into Hell—they’re too insignificant. They are forever locked just outside Hell’s gates, doomed to chase a blank banner while being stung by insects. Dante calls them “these wretched ones, who never were alive.”

I don’t believe in a literal Hell that awaits evil people in the afterlife. But I do believe being fully alive means living for something. Living for something larger than ourselves—our country, justice, freedom—solidifies a legacy of honor and inspiration, even if we can’t count on history remembering our own personal contributions.

Freedom isn’t something you exercise once. It’s something you defend, again and again.

It’s something that grows when you give it, and collapses when you hoard it.

From the Bay Area to the far reaches of American influence and beyond, may winds of freedom blow stronger.

Happy MLK Day.

-Joe

P.S. Most of my days lately have been busy as Chief of Staff at CRED. Work on Timeless Leadership also continues: a new digital product is in the works, and we kicked off 2026 Basecamp with distributed leadership—one of the members facilitated instead of me! Outside of work, I’ve got my hands full parenting, life is good even when challenging, and I’m grateful for all of you!

Leave a comment

Subscribe now

Share

I set this checkpoint before I even started.1

I knew I’d need it, and I was right.

I’m Back in Operator Mode

Some of you know this reality too well.

Operator Mode is when you’re almost inseparable from the machine of the organization you run or help run. Your body clock syncs to the corporate clock. You’re 100% alert to Slack, email, task deadlines and calendar appointments from at least 9-5. There’s no real shutdown after hours because the business keeps humming and you need to check and adjust the dials.

When you carve out time for something not work-related, you feel like you need to make up for it late at night, or early morning, or on the weekend.

There are always goals just out of reach. You track 15 urgent fires and 150 backlog items and lose sleep over broken systems and fantasize about your nice-to-haves. You accept commitments you wish you didn’t have to because it has to get done and there’s nobody else to do it. To be an operator you have to over-commit, then find a way to close the gap. People are counting on you. Profit is counting on you.

You can’t shut down. The machine needs you.

You are the operator.

I learned this at Box when I was the senior manager responsible for strategy and growth programs for a business unit. Box Consulting (BC) enacted the actual transformation for customers like Apple, Broadcom, and State Street. We were the tip of the spear to get traction with our most advanced technology, win bigger deals, and demonstrate unmatched impact at scale. We weren’t selling software seats - we were delivering fundamental change in how organizations functioned.

And our performance got mentioned on earnings calls and affected the stock price. Investors were watching and executives were watching. My VP and peers were counting on me. My wealth and career tied to those numbers, even if I only had so much influence on them, and even if a pandemic or an activist investor radically altered our operating conditions.

When things went well or poorly, I felt that weight.

When pressure, incentives, visibility, measurability, competition all demand you give it your all, Operator Mode feels essential.

At CRED I feel it again. I presented to the board a few days ago. I’m hiring multiple key roles, transitioning out folks, and managing a team. I run our OKR process, set company targets, and approve the budget. My CEO travels often and when he’s out, I’m the leader in charge.

This is an operator job and I’ve turned on Operator Mode.

But unlike a few years ago, I now have concrete practices to protect what matters outside of the day job.

It’s not easy. It can feel like holding a position against a riptide.

Staying Tethered to the Shore

Operator mode took over pretty quickly at CRED. The external accountability, role-based commitments, and material incentives commands the calendar and clock.

The other gravitational pull is health and home. Family has immediate needs - well-being, learning, logistics, and connection. When these are cut back, it has serious and immediate consequences.

Movement work? That’s where responsibility is diffuse, timelines are long, and deadlines are always negotiable, even when ultimately the stakes are still really high.

It takes discipline to keep making investments in a movement when there’s limited gravity compared to what family and job demand. But it is possible, and that discipline actually becomes its own kind of gravity that anchors you to values and building the legacy you want. It’s what keeps you from getting swept to sea.

The hardest part can be knowing what that discipline needs to look like.

Infrastructure Progress & 2026

Six weeks ago I announced I was shifting from publishing to infrastructure building.2 That was both a real strategic priority and a move for public accountability.

Since that announcement, I’ve taken three steps3 to advance the infrastructure:

1. I renewed my GHL subscription to power my CRM and marketing automation

2. I reengaged the developer I worked with last year to build the Timeless Leader website so we can make some long-overdue updates.

3. I’ve built the segmentation strategy for attracting and engaging with different kinds of people with different needs.

I also hosted December Basecamp and signed up a new paid member. Growth is still all word-of-mouth, and it’s nice that this is doing well without too much effort.

The next steps from here are the following:

• Q1 - Finish Infrastructure Shift: launch at least 3 different landing pages and onboarding flows, and shift my emails off Substack and to GHL.

• Q2 - Multi-media marketing and teaching: The Q1 stretch goal is to kick-off a multi-media content project and start a fresh posting cadence across LinkedIn, Substack, and Youtube. If this pushes to Q2 or even Q3, that’s ok.

• Ongoing: Continue the Basecamp, and recruit more members to the Summit program.

Let’s talk about the lessons you can take from this for your own movement work.

Four Strategies for Your Own Movement Work

The lesson here isn’t “do exactly what Joe does.” It’s that leading a for-profit business and advancing movement work at the same time requires a specific discipline:

1. Limit work in progress. I’m alternating between building infrastructure and recruiting members. Not doing both at once. Right now it’s infrastructure season.

2. Maintain and nurture your audience. Even if marketing isn’t the key focus, I know some periodic updates and nuggets of value matter. This keeps forward momentum, even if it's slow going.

3. Set public checkpoints for accountability. I made a promise last month, and this is my follow-up. I’m not just making an agreement with myself, I’m committing to you. Without public stakes, it’s too easy to procrastinate and move the goal posts.

4. Get help. I can’t build TL infrastructure by myself while running CRED. So I pay for tools and project support. I’m also looking for more volunteers - to write, to host Basecamp calls, to spread the word. You can’t do movement work entirely solo, ESPECIALLY while in operator mode with a day job. It’s a shared effort.

These techniques are the bare minimum, but they work. I may not have the same level of pressure to make progress with TL as I do in my job or my family, but I can create conditions where I don’t lose touch with the legacy I’m committed to building.

What has no deadline in your life?

Your book, your business your movement….the legacy work that’s too easy to put off until “someday”… are you making the progress you’ve hoped for?

We’re approaching the end of the year, and it’s a great time to turn the dream of your legacy into a commitment to do the work.

If the commitment is already made but you’re juggling too much, focus on the few things that actually fit your capacity and move the needle.

Limit your WIP. Maintain your connections. Work out loud. Get help.

If you tie it to building a Democratic Ownership Society4, together we’ll make real progress in the year ahead.

Sending you warm wishes for the holidays,

-Joe

Leave a comment

Subscribe now

Share

PS. If your movement work IS your day job, your Operator Mode has the tailwind of passion and purpose. That said, the same techniques can help you be more effective, and might be useful to apply to your other side projects - for income or for impact.

Now it’s time to break the weekly rhythm in order to focus on better systems.

You read for different reasons

Different readers want different things from Timeless Leadership.

Some of you want organizational leadership insights from my work with startups. Others want business growth tactics.

Some of you want quick philosophical reflections, some of you love my long form essays, and there’s a wide range of reactions when we broach power, politics, and social commentary.

Importantly many of you read mainly because I directly invited you to read at some point, and you're interested in my journey, what I'm learning, where I'm headed.

This doesn’t even get into the range of interest you have in following along vs taking action with what you read.

All of this matters, but right now it’s very hard to tailor the experience so you get the most value from being on my list and spending time with me.

We need better infrastructure

Right now, if you want to go deeper with Timeless Leadership—join a community, work on something together, access advanced resources or training, or get more involved—the only option I can extend you is an upgraded subscription and access to Basecamp.

On the other hand, if you mainly want to read posts and occassional updates, it’s hard to avoid getting every announcement, offer, and call-to-action.

Everyone gets the same broadcast. Nobody gets exactly what they need.

I've tested what Substack offers for personalization. Their "Sections" feature requires you to manage your own settings in the app or browser (hard to find, not worth the effort). The paid tiers max out at three levels. This is all fine for a simple newsletter, but it's insufficient for building a real business, let alone a movement.

Substack is best understood today as a social media site. It’s a valuable channel like LinkedIn, Youtube, or Instagram and I’ll continue to use it, but I can’t depend on it solely for achieving what I envision with this project:

To build tailored experiences, create some separation between personal, business, and movement communications and resources, and be able to scale my audience, I need real infrastructure: CRM, marketing automation, differentiated landing pages, course builders and more.

If you want to participate actively you can find your best way in.

If you just want to follow along, you can do that without noise.

Going into building mode

I'm working full-time as a Chief of Staff, so this is happening in the margins—early mornings, late evenings, weekends when I can.

For the next 1-2 months, I use the limited time I have to work on Timeless Leader(ship) to stand up better infrastructure instead of creating more content.

That means no weekly posts while I build.

Once I’ve got some better systems in place, the content will come back but with a much better method to get the right communication to the right people at the right time.

What you can expect

• By early December I’ll send an update on progress

• When this infrastructure is in place, you'll have more control and options for how to stay engaged

• The content returns, with a great 2026 roadmap

• The community will start growing faster than ever, because we can turn on marketing and support new joiners with customized onboarding experiences

I'm excited about what this will unlock.

Whether you’ve been reading for two days or two years, thanks for being here.

Stay tuned for more updates, coming soon!

-Joe

P.S. Thursday’s Basecamp call was 🔥. 8 people showed up for a deep conversation on infrastructure (personal, business, and movement). This is exactly the kind of engaged community I’ve been hoping to build, and it’s working. Next month we’ll talk about annual planning—sign up now if you’d like to join, or reach out if you have questions!

Leave a comment

If you’re new here or getting caught up, we recently finished “Season 2” of this newsletter, and are in an extended interlude before Season 3 launches next fall.

Part of what we’re doing right now is looking back on what we’ve already explored. How much ground have we covered already? What should we double down on? What new things should we try?

All of this boils down to a vision to build a Democratic Ownership Society. We do this by building a movement of Timeless Leaders - everyday people committed to leaving a positive, lasting legacy despite a recognition that long term we won’t get personal credit for our contributions.

In our recent survey, you told me your favorite post from a list I provided was “Making Others the Heroes of Their Stories.”

What made this one resonate so much?

When we discussed this at our last Basecamp*, a few things stood out:

• Great hook: “Last week, I fucked up a sales call.”

• I talked about a newsworthy world development in a unique and valuable way

• I shared relevant personal stories - enhanced with great pictures

If you never saw this one or care to revisit, see for yourself.

Is this one of your favorites too? Hit reply and let me know.

Have a great weekend,

Joe

*Our November Basecamp is on Thursday. Want to join? Upgrade your subscription and get access to monthly group coaching calls with other Timeless Leaders. At just $97/year it’s the biggest ROI leadership development experience on the market.

Subscribe now

Leave a comment

As the Chief of Staff to the CEO, it’s my job to elevate his leadership and drive strategic execution across the business.

CRED is a Seed stage, VC-backed company.

The company is building a data platform to drive predictive analytics and automated workflows for sales and marketing teams.

Think about it as a solution for businesses who want to more efficiently figure out who to sell to, what to sell them, and how to sell to them.

It’s a hot space right now.

I interviewed for the role in August and accepted the offer to join the team in early September.

Now I’m in the role, practicing Timeless Leadership inside of an organization full time once again, and applying the same principles to keeping the other key things in my life (family, health, citizenship, and this movement) on track.

The STARS Portfolio

Starting a new role is a good time to revisit the classic The First 90 Days by Michael Watkins.

One of my favorite frameworks from this book which is essential for onboarding but also valuable at any time is STARS:

• Start-Up

• Turnaround

• Accelerated growth

• Realignment

• Sustaining success

These five situations represent different challenges and opportunities leaders face. Watkins explains:

Start-ups, turnarounds, and accelerated-growth situations involve much resource-intensive construction work; there isn’t much existing infrastructure and capacity for you to build on. To a significant degree, you get to start fresh or, in the case of accelerated growth, to build on a strong foundation. In realignments and sustaining success situations, in contrast, you enter organizations that have significant strengths but also serious constraints on what you can and cannot do. Fortunately, in these two situations you typically have some time before you need to make major calls.

Obviously by joining a startup, there’s a lot about my role that fits the “Start-up” situation in this model.

However, it’s not quite so simple.

As Watkins says, “as soon as you drill down, you will almost certainly discover that you’re managing a portfolio—of products, projects, processes, plants, or people—that represent a mix of STARS situations.”

Even though CRED is a startup company, it’s been around for a couple of years. We have multiple teams, products, and customer segments with different maturity levels and needs.

This means I have to practice different leadership styles throughout my day to make progress.

Heroes and Stewards

Watkins explains that for different kinds of situations, different styles of leadership are more valued.

For example in turnarounds:

…leaders are often dealing with people who are hungry for hope, vision, and direction, and that necessitates a heroic style of leadership—charging against the enemy, sword in hand. People line up behind the hero in times of trouble and follow commands… You need to act quickly and decisively, often on the basis of incomplete information.

In contrast, realignments:

demand from leaders something more akin to stewardship or servant leadership—a more diplomatic and less ego-driven approach that entails building consensus for the need for change. More subtle influence skills come into play; skilled stewards have deep understanding of the culture and politics of their organizations.

In my role as Chief of Staff, I’m more naturally positioned as a “steward” but given the organization is primarily defined by start-up and accelerating growth dynamics I also need to step into the hero role routinely.

It’s fun, it's complicated, and it’s real, but rewarding, work.

Our stewards are unsung heroes

One thing I especially appreciate about Watkin’s chapter on the STARS model is the survey results he shared from asking leaders about what kind of situations they most prefer. A whopping 47.1% of respondents chose the start-up situation, while the two lowest were 12.7% who chose realignment and just 7.4% for sustaining success.

At the same time, these same respondents rated the realignment and sustaining success as the two most challenging of the five situations.

He discusses why that is, and what it means, and concludes that we’re often operating in a world where certain kind of leadership situations (those that call for heroics) are disproportionately rewarded.

Meanwhile the ones that are actually harder have less visible and measurable results.

Is the lack of measurability and visibility part of what makes stewardship hard?

Or is it more the lack of recognition itself?

I think it’s probably both.

And it’s a good reminder that quiet leadership is at least as important as the loud kind.

As Watkins asks: “does the fact that companies reward turnarounds (and do not know how to reward realignments) make it more likely that businesses will end in crisis?”

What do you think?

-Joe “STARSy-eyed” Ballou

Share

Subscribe now

Leave a comment

PS(A). To all the Survey Raffle Winners - If you filled out the survey a few weeks ago and participated in the raffle, you should have already received your Substack gift subscriptions (make sure you check for them). If you won a different prize this will be delivered soon (provided I have your mailing address - otherwise you need to tell me it). Feel free to respond to my email titled “Raffle Results” with any questions!

PPS. There are a few CREDs out there. Our website is credplatform.com

Week 42 of 2025. Still showing up, even when the week fights back. Here’s what’s happening.

First - a few recent events with Timeless Leadership relevance:

• Jane Goodall passed away at 90. She spoke at my college graduation ceremony. She gave voice to the truly voiceless and helped us expand our view of humanity and nature. I just found out Netflix has a recent special on her called “Famous Last Words.” I plan to watch.

• Venezuelan opposition leader María Corina Machado won the 2025 Nobel Peace Prize. I spent six weeks in Venezuela 20 years ago and wrote my senior thesis on the Chavez government. Conditions have been on a steady slide since then, and the Nobel Committee’s decision here represents a bold statement about the importance of democracy and civic leadership for peace and prosperity.

• The US government shutdown enters its third week, layering risks of system-level instability, corruption, and conflict, and demanding civic action. On that note…

OPPORTUNITY FOR ACTION TOMORROW:

Across the US, another “No Kings!” rally is happening tomorrow. Timeless Leadership is deeply democratic, and opposed to the ideas of concentrated and arbitrary, unchecked power. This is not a partisan gathering, it’s an American gathering - and one that freedom loving people around the world can stand for. Show up, and bring a friend!

Timeless Leader newsletter updates:

✅ Survey complete: In the end we collected 38 responses and exceptional data that validates what we’re building and helps plan the future direction. Thank you for the responses!

✅ Raffle complete: Winners notified, and prizes are being distributed.

🗓️ Publication timing insight: 57.1% of respondents have no preference on when you receive these updates, and another 20% prefer weekends. My take-away? I’ll test different sending times moving forward, while keeping the weekly cadence.

Coming soon: I’ll share a bit about the Chief of Staff position I recently stepped into and what it’s teaching me about organizational leadership in real-time.

For the rest of 2025: I’m planning to continue weekly posts that share quick updates, resurface the best content from two years of writing, and point to helpful resources in your leadership journey.

Looking ahead to 2026: You asked for it, and I plan to deliver - multi-media interviews! Business Growth mini-series on go-to-market strategy and/or hiring and org design! And later in the year - Season 3!

Thanks for being here through this evolution.

-Joe

I only know because my brother randomly Googled him.

My friend and I lost touch - not dramatically, just the slow drift of busy lives. The last time we connected was a “Happy Birthday” message I sent him a few years ago. He thanked me for it. That was it.

Nobody from our old community reached out to tell me he’d died. I’d drifted that far away.

He was 40. The obituary didn’t say how. Just that it was sudden. Wife, two kids, a dog, a job, hobbies. From what I could piece together online, he seemed happy.

But I’ll never really know.

Death keeps showing up lately.

My parents’ neighbors just lost their 22-year-old son after a brutal fight with cancer. He was the first person my daughter ever trick-or-treated from. My parents knew him since he was a toddler.

My dad’s cousin died in her own battle with cancer, only months after her mom died.

Political violence seems only to increase, and twenty thousand children have been killed in Gaza as we now enter the third year of an endless, senseless genocide.

Life is fragile. Time is short.

And it makes me question: What am I building? Does it matter?

In this newsletter, I could focus all my energy on helping people succeed in conventional terms - climbing ladders, building impressive resumes, making good money.

But if that’s all we do - if we help people climb ladders without asking where those ladders lead - what’s the point?

Meanwhile, our institutions are cracking. The federal government isn’t even open. The military is turned on its own people. As Yeats said, “the center cannot hold.”

When the center fails, we’ve been led to believe we have only two choices: retreat into private life, or sacrifice everything trying to save the world.

Timeless Leadership offers a third way.

Focus your limited time on what you can actually influence. Build systems that outlast your energy. Teach others so the work doesn’t depend on you alone.

Save Time. Make Time. Escape Time.

That means pursuing only as much power and money as you need to achieve your mission - and nothing more.

It means measuring success by how far you help a movement progress.

It means dedicating more time to teaching others than doing everything yourself.

The next phase of this project will really double down on helping us all do this in practice.

But I need you to weigh in on how that might apply to you, in your life, right now.

The survey closes tomorrow night (Wednesday, Oct 8 at midnight PT).

Please take the survey now.

Help me make our time count,

-Joe

The best leaders I’ve worked with have a superpower: they bring fun to their followers.

Contests. Prizes. Awards. Playful approaches to serious work. Team building that doesn’t feel forced. Art and music woven into culture. They understand that joy isn’t frivolous – it’s fuel. It creates energy, builds connection, and makes people actually want to participate.

So here’s my question: Can a newsletter do this?

Can asking for feedback actually feel rewarding instead of extracting? Can a survey be something you want to participate in, not something you begrudgingly complete?

We’re about to find out.

By now you know I’m running a feedback survey to shape the future of this Substack. Unlike most survey asks, I’m not just asking for your time—I’m making it genuinely rewarding. 38 39! prizes worth over $1,350 – and the way I’ve structured the raffle, your odds of winning something real are surprisingly good.

Of course, the main reason to participate is that your response gives me data I genuinely need to make better decisions about future content. The more complete the dataset, the smarter I can be about what to build, what to write, and how to serve you better.

The raffle makes this a genuine win-win, and it grows in value proportionally to how valuable the data is. The more people participate, the more prizes unlock, the more fun this gets for everyone.

Let’s take a look at what’s up for grabs.

Ready to start? Survey is here.

Here’s What’s in the Mix

Every prize is intentionally chosen to support your journey as a Timeless Leader – these aren’t random giveaways, they’re tools that reinforce what we’ve been building together.

Already unlocked and ready to raffle:

🎁 21 one-month subscriptions to premium Substacks – These aren’t random blogs. I’m talking about writers with 50K-100K subscribers, published authors, A-list interviews, people genuinely respected in their fields. Politics, markets, investigative journalism, culture criticism. Part of being a Timeless Leader is curating your information diet – consuming fewer, better sources instead of drowning in noise. I’m a paying subscriber to these publications because they’re that good, and I’ve got gift subscriptions to share. Win a month, discover a voice that changes how you see the world.

📚 Books that shaped Season 2 – Saving Time by Jenny Odell (already unlocked – this is the book that gave us the moss story and powerfully affirms just how poorly we understand time in general), Mainstreet Millionaire by Codie Sanchez (NEWLY ADDED to the raffle – the subject of my July 8th post that can help you support your community and build portfolio income), The Portfolio Life by Christina Wallace (featured on August 20th, full of tools, and unlocks at 20 responses - we’re almost there!), 4,000 Weeks by Oliver Burkeman (unlocks at 40 responses– using mortality as motivation to choose what matters), plus a Bookshop.org gift card and additional titles at higher milestones. These are some of the texts that shaped how I think about leadership, time, and legacy.

High value prizes that unlock at 50 responses:

💼 Leadership consultation (one hour with me) – We could run the “Time Telescope” exercise from the Season 2 finale, where you evaluate a movement or opportunity through the Virtue Star framework to decide if it deserves your biggest time commitment. Or we could do a simulated Chief of Staff session like I run with executives every day – we’d work through your actual organizational challenge in real-time, designing systems, clarifying priorities, or building your strategic roadmap. Your choice, your challenge, one hour of focused problem-solving. ($400 value)

🏕️ Three Basecamp memberships – Full year of monthly coaching calls and community access. Basecamp is where Timeless Leaders practice together – the community that helps you implement Save Time, Make Time, and Escape Time in your actual life, not just theory. ($97 each)

How the raffle works

Everyone who responds gets 1 ticket. Early responders get bonus tickets. The first 10 slots with super bonuses are claimed, but if you snag one of the remaining first 25 slots you’ve got 3-4 tickets competing for 21+ prizes already unlocked.

Your odds are genuinely good.

You can do this in <3 minutes

Probably closer to 2 if you move quickly.

Most questions are optional. I’m really just trying to gauge:

• What’s your reading experience like right now?

• What do you want to see next?

• Would you check out multi-media content?

Whether you signed up yesterday or two years ago, you’re a close friend or someone I’ve never met - if you’re getting this email, I want to hear from you.

🎟️ Take the Survey Now 🎁

We’re a pay-it-forward kind of community

Don’t want a prize? Give it to someone else. The Substack subscriptions make perfect gifts. The books are great for colleagues or mentees. Even the leadership consultation – you could give that hour to someone you’re investing in.

This isn’t about me giving you stuff. It’s about us helping each other out, collaboratively shaping a movement that creates lasting impact, and having some fun and being generous along the way.

3 minutes. Real influence on future direction. Solid odds of winning something valuable for yourself or someone you care about.

Let’s do this.

-Joe

P.S. We’re closing this Wednesday night (Oct 8) at midnight PT. Can we hit 50 responses? Your 3 minutes might unlock hundreds of dollars in value for the whole community.

I didn’t attend the volunteer organizing meeting when my whole family got COVID.

In the past few years, I’ve run into multiple obstacles to giving heroic effort. I “didn’t have time” so many times, and if I checked the news or simply thought about the scale of certain problems, I could find myself paralyzed with guilt or overwhelm.

It’s taken a long time for me to learn that I don’t need to be the one to do everything - I just need to do the RIGHT THINGS at the right times.

I realized this very publicly about ten years ago when I was running for class president at Stanford GSB.

I initially got into the race because only one classmate had announced his intention to run, and it looked like he might go unopposed.

I thought our class deserved a competitive election.

Once I threw my hat in and another classmate did too, things heated up! By the time we were giving our final speeches, I could see clearly that both of my opponents had tremendous leadership strengths and were more than capable of performing in the role. At the same time, I felt worried that by stepping into this role myself, I’d end up neglecting other areas that only I could do - like my coursework and launching the “Hell Yes Club” I really cared about starting.

So I ripped up my speech and dropped out of the race in real time, instead explaining that my vision for “servant leadership” (my campaign slogan) was not something I felt I needed to be president to fulfill.

From Billions to Bake Sales

A year later at Box, I experienced how leaders-follower exchanges were central to billion-dollar outcomes.

The company had brilliant leaders who elevated their strategists, advisors, operators, and program managers to bring their vision to life.

In turn, staff elevated leaders.

I was on both sides of this routinely, sometimes representing work to the whole company and other times prepping executives to run conversations I might not even be part of.

The partnership was where we drove impact, not individual heroics.

That dynamic later became the foundation for my Chief of Staff practice.

It happens outside of work too.

Last year when I was asked to run for PTO president at my daughter’s school, I had to make the same choice I’d made at Stanford. The role was important, but taking it would mean stretching myself too thin across evening meetings and weekend events when my capacity was already limited.

Instead, I joined strategic committees where I could contribute most effectively.

Three Questions for Role-Switching

This isn’t about doing less. It’s about knowing when to lead and when to follow.

I usually make this choice based on three questions:

• Do I need to do it as a duty or calling?

• Am I sure nobody else is equipped and willing to do this?

• Can I do it effectively, both now and for the duration of the commitment?

Ideally I lead when all three of these questions are a yes.

Otherwise, I look at how I can support others.

These scenarios can happen all the time, and conditions can change quickly.

Micro-moments like passing the mic in a meeting. Macro-decisions like changing roles or authority for a specific endeavor. It happens across your portfolio life - sometimes leading more at home, sometimes at work, sometimes in your community, all while letting others lead elsewhere.

But here’s what matters most: being a good follower isn’t just stepping back. It’s actively supporting.

Research shows that followers actually get the job done - they’re not passive recipients of leadership vision. Instead, leadership gets co-created between leaders and followers rather than imposed from the top down. This challenges what researchers call “the romance of leadership” - our cultural tendency to over-credit individual leaders while undervaluing collective effort.

From Individual to Movement

This dynamic - leaders willing to follow, followers willing to lead - is how one individual sharing an idea transforms into many people forming a movement.

Right now, I’m stepping into followership by asking you to help lead our direction.

The fall survey closing next week will help me prioritize what organizational leadership topics to cover, which business growth areas to focus on, whether to experiment with multi-media content and guest voices, and how to balance post frequency and length.

When you complete it, you’re helping shape what we build together.

Take the Survey

The survey closes October 8th. Your input determines everything we do next.

-Joe

Subscribe now

I’m writing from Playa del Carmen, Mexico.

Last week I joined a company in a full-time Chief of Staff role.

This week we have company wide off-site to develop strategy and culture.

I’m leading and facilitating 12+ hours of sessions.

I’ll tell you more about the role and company soon.

(There are lots of opportunity for me to apply Timeless Leadership here)

Hope you’re having a great week,

Joe

PS. The fall survey is live! Fill it out ASAP to shape the direction of this newsletter and win cool prizes. It will only take 5 minutes.

Before you head into your week and your inbox is flooded, I hope you’ll take five minutes and fill this out.

Ready to start? Here's the link!

Maybe you’re curious to know more about the survey before diving in?

What’s on the survey

Only the critical things I need to know to keep making this better week by week:

• 4 multiple-choice questions about your subscriber history, habits, and preferences

• 6 questions about the content over the past year (4 multiple choice, 2 short answer)

• 3 questions about what you hope to see in the coming year

• 6 simple questions about who you are and how to follow up

It shouldn’t take more than five minutes to fill this out.

Every question was thoughtfully crafted and the data will significantly inform my plans starting in October. Should we start a podcast? Should I write about leading in particular roles or industries? What business growth topic most intrigues you?

Real decisions.

I really appreciate your input and value your thoughts.

Take the Survey

Finally—this isn’t just a great survey that will inform how we move forward.

It’s also something fun with lots of immediate rewards for those who participate!

How the raffle works

Every respondent gets 1 raffle ticket. In addition, you can get additional tickets and bonuses based on when you respond:

• 1st Respondent: 10 bonus raffle tickets + 1 Year Free Basecamp (claimed)

• 2nd-9th Respondents: 9 bonus tickets (still some remaining)

• 10th Respondent: 9 bonus raffle tickets AND 1 hour free leadership consultation

• More special bonuses for the 11th-25th and 50th Respondent

Full List of Raffle Prizes listed on the first page of the survey itself.

FYI - I once founded and ran a game-based learning company. So the gamification here is not my first rodeo. 🐂 🎲

Fun right? Start Now

Don’t worry, I won’t email you every day about this.

(But maybe a few reminders ;))

Just want to get some good initial traction on the opening weekend.

Happy Sunday!

-Joe

Here's that link one more time

As we look forward to the next phase of what we do here at joeballou.substack.com, I want your feedback. So it’s survey time!

Start Now!

To make this extra fun, I’ve come up with 38 PRIZES that I’ll raffle off, including gift subscriptions to other Substacks that I love, several books that we discussed over the past year, up to SIX year long Basecamp memberships and two private 1 hour leadership consults, and even an exclusive Timeless Leadership training.

Some of the prizes I’ll give away no matter how many people fill this out, while others are only unlocked if we reach key milestones.

This is the Best Survey of 2025

The survey will be open through October 8th and the drawing will be on October 9th, BUT the sooner you fill it out, the more raffle tickets you get!

→ If you’re one of the first ten people to fill it out you’ll get TEN raffle drawings (and yes, you can win more than one prize).

→ If you’re the very first respondent, you automatically get a free year of Basecamp!

Ready to Start? Go Now!

I say this as often as I can but it’s always worth repeating - I plan to write about and enable Timeless Leadership for the rest of my life.

This is not a short term project.

We are just beginning.

I hope you’ve enjoyed some of what we’ve done here so far, but there’s always room to improve and your feedback is essential to make it better, faster.

Check out the survey and fill it out this weekend. More than 100 of you read these emails every week, and I’d love to get at least as many responses by the time the survey closes.

Take the Survey Now

I look forward to reading your thoughts!

-Joe

PS. This survey really will inform what we do next, in a significant way. The more of you that fill it out, the more weight this survey will have!

PPS. I’ve written hundreds of surveys in my career and I’m proud of this one. Check it out!

The Basecamp Labor Day Sale (10% off — so only $87.30 for the year) ends tomorrow.

Sign Up Here!

Every month we come together to workshop the biggest questions of self leadership—what to commit to, how to balance it all, and how to even be a leader in the first place.

Our members are entrepreneurs and operators, investors and board leaders, educators, coaches, and organizers, all committed to creating a more positive impact.

Here’s what they say about the experience so far:

The Timeless Leadership Basecamp is a reflective circle that brings both clarity and meaningful connection. Joe’s sharp and strategic frameworks make the experience deeply impactful and inspiring!

—Jing (Founding Partner, Investor)

Joe is an exceptional leader that has built an enriching space… In a few short months, I have already connected with so many insightful individuals who’ve helped empower me in my pursuits.

—Christian (Founder, Board Chair)

Joe’s monthly Timeless Leader calls have been a great grounding rod… They remind me to attach my work to even deeper level of meaning.

—Bryan (Co-founder, Partner)

One of the most insightful, generative hours I have every month.

—Arielle (Executive Coach, Board Chair)

Joe…creates space for professionals to think beyond next quarter’s earnings — into legacy, mission, and meaningful impact. We need more of this in today’s business world. I especially appreciate his gift for distilling complex ideas into simple, actionable insights… [it] brings clarity and momentum to my work.

—Amanda (Strategy Consultant, Research Analyst)

As you can see, in just one hour a month we're unlocking something that's sorely lacking for so many of us: a safe space to lead ourselves in an unpredictable and dangerous world.

This is the last sale I’ll run for the rest of 2025 (not even Black Friday), so you won’t see this $87.30 price again.

Ready to support this work and access the most affordable and impactful space for elevating your leadership?

Get a Full Year for <$90!

I’m excited to have you join us. Together we will build a positive, lasting legacy.

—Joe

PS. I’m also not sending any more reminders about this, or other stand alone promos of any sort for at least a few months (so please don’t unsubscribe 🙏). The next time you hear from me I’ll have a survey with some prizes attached, so make sure to look out for that!

Subscribe now

Labor Day Sale

It’s hard to believe that in the past few weeks we wrapped up TWO big marathons. ICYMI:

• The Email Mastery Mini-Series wrapped up on August 23rd, and I pulled together the final summary into a key lesson on Continuity and Closure.

• We ended the Saving Time season of Timeless Leadership with a three part finale, looking at the “Micro” time scales, medium time periods, and big, big picture time scales of self leadership.

If you followed along, I hope you felt the build up, and I also hope you experienced some satisfaction with the ending.

Next week, I’ll send out a short survey to gather some feedback on where we’ve been and where we’re going next.

Now, it’s time to regroup… at Basecamp!

Tomorrow’s Basecamp - and Special Sale!

September’s Basecamp is tomorrow, and we’ll get cosmic!

Our prompt will borrow from last week’s Moonshots to Stardust post. We’ll share and develop our long-term commitments, and explore how the Virtue Star can be used to prioritize and clarify those goals.

As always, we'll work through real examples from the community to help you clarify what deserves your precious time and energy.

Also, as last week’s post discussed the labor movement as one of the “moonshots” that made America more free, just, truthful, loving, and peaceful, I’m offering a special Labor Day Sale:

If you sign up in the next week, you’ll get 10% off for the next year (save $9.70).

Sign Up Here!

If you’ve been thinking of joining, now’s a good time!

We’d love to see you at our monthly gathering.

-Joe

PS. If you have any questions about Basecamp or Timeless Leadership more generally, please reach out!

Subscribe now

Read time: 11 (worthwhile) minutes

In this month's The Nation1, Elie Mystal shared a story from World War II that I hadn’t heard before:

A B-17 pilot's plane was shot up over Nazi Germany. The bomber was hit directly in the gas tank, not once but numerous times, but for some reason the tank did not explode. After an investigation, it was revealed that the shells that hit the gas tank had no explosive charge in them. Instead, inside one was a note, written in Czech. It read: "This is all we can do for you now."

Somewhere in occupied Czechoslovakia, a resistance worker faced a dire choice: participate in destruction or resist.2 They could follow orders, make the bombs work, and fuel the war machine. Or they could refuse to make the world worse, even at enormous personal risk.

That worker's name is lost to history, but in that moment, they embodied the hardest challenge of lasting leadership: will you act ethically, even if it comes with a personal cost and little or no reward?

We don’t live in a fairy tale, fighting simple battles between good vs evil. Instead, we face multiple dichotomies:

Love or hate?

Peace or violence?

Truth or falsehood?

Justice or impunity?

Freedom or oppression?

These ethical dilemmas might be simple enough to decide on their own, but when they play out simultaneously we can get caught in the tension.

Truth without love still lets in hate.

Love without justice invites impunity.

Justice without peace promises violence.

Peace without freedom welcomes oppression.

We can feel the appeal of hate when we know the truth, or the tug of violence to serve justice. It’s how great movie villains build ethical codes that you can kind of understand, and real world dictators can rally millions behind their extremism and destruction.

But here’s the good news: we don’t have to be good all alone. In fact, when we join movements that defend multiple virtues, it’s easier to do the right thing. That gives space and momentum to the effort to advance these virtues as systems in society.

We don’t all have to be movement leaders. Small sacrifices and contributions add up, and over decades, lifetimes, even centuries, we leave a positive, lasting legacy.

Today, in our final installment of Season 2: Saving Time, we finally address how to lead ourselves over these vast time scales… starting with a framework I started crafting as a teacher in the Bronx.

A Star to Guide Timeless Leaders

Fifteen years ago, my high school students faced choices that seemed uniquely modern: prepping for SATs and state exams, avoiding gang entanglements, and sifting through misinformation on Youtube.

But as we studied history together I observed how under the surface, their decisions mirrored ethical quandaries faced by leaders the world over.

The more I dug, the more I saw the same five battles between virtue and vice recurring over and over, from Ancient Egypt to the Arab Spring. They infused entire social movements and the fabric of society, and had predictable outcomes.

The movements that endured? They integrated all five virtues.

The civilizations that collapsed? They dropped the ball on one or more of them.

That's when I began developing the Virtue Star3: a framework that captured the interconnection of five virtues essential for sustainable, positive social change.

Since moving into organizational leadership and training leaders, I’ve resurfaced and refined this framework to help chart long-term leadership commitments. The Virtue Star offers a way to evaluate the quality of existing movements, and a guide for deciding how to help out.

We make ethical decisions all the time, but the most important ones come down to the commitments we make to multi-decade ethical endeavors.

3 Time Scales for Movement Commitments

When we think about our legacy, long-term commitments to movements are how our contributions are made to last. Today, we’ll briefly look at three different ways to think about long-term leadership commitment, and how they’ve shown up for leaders of various social movements:

1. The moonshot takes a decade or more to achieve a critical breakthroughs

2. The obituary takes a lifetime, but can shift entire nations

3. The history book takes centuries, but reshapes civilization itself

The point isn’t that the movements we’ll look at (Child Labor, Civil Rights, Women’s Rights) have different durations, or that there aren’t other worthy and important movements. Rather, the movements I chose to write about here offer useful case studies for different types of long-term leadership commitments and how they reverberate across time.

The Moonshot: Commitments to breakthroughs

The term 'moonshot' comes from John F. Kennedy's commitment to land Americans on the moon within a decade. But moonshots aren't limited to technological advances. Every social movement pushes against strong gravitational forces that require sustained effort to overcome.

The drive to end child labor demonstrates how movements achieve breakthroughs through campaigns that last a decade or longer. In 1904, reformers established the National Child Labor Committee with a clear goal: federal legislation prohibiting child labor in mines, fields, and factories.4

NCLC hired Lewis Hine to document the realities of child labor around the country, and launched public education campaigns to rally support for change. Their messaging emphasized the moral importance of sparing children from grueling and dangerous work. In 1916 they finally achieved a major breakthrough with the Keating-Owen Act, which restricted interstate commerce for goods that involved child labor.

Victory seemed complete - until the Supreme Court struck it down in 1918 as unconstitutional.

Rather than abandoning their cause, reformers launched a second moonshot. For twenty more years, they lobbied and organized, and finally, in 1938, the Fair Labor Standards Act set new Constitutionally durable rights for both child and adult workers.

The movement to end child labor succeeded across three decades because they never wavered from their moral vision, while maintain moral discipline in their tactics: they chose truth-telling about child welfare over industry pressure and peaceful organizing over violent confrontation.

Many committed leaders in this movement nevertheless weren’t completely defined by it. For example, NCLC board member Jane Addams contributed to the moonshot effort while staying involved in multiple reform efforts over the course of her life.

But there’s another approach to long-term leadership commitment that you might recognize: life-long commitment.

The Obituary: Commitments That Define a Life

When legal systems excluded women from full citizenship, it created a challenge requiring sustained commitment across entire lifetimes.

Alice Paul exemplified this pattern.

In her early 20s, Paul became invested in the movement for women’s suffrage while studying in England, even going to prison and enduring force-feedings for her activism. After returning to the US and leading the successful campaign to pass and ratify the 19th Amendment, she easily could have declared victory and moved on.

She did the opposite: she committed to achieving full constitutional equality for women.

Three days after the 19th Amendment was ratified, Paul announced a moonshot that she’d spend the rest of her life fighting for: the Equal Rights Amendment. For the next 57 years—until her death in 1977—she pursued this single goal.

Paul never doubted the moral clarity, comprehensiveness, or importance of winning full equal rights for women. She also stayed determined to pursue this goal without making compromises that might fundamentally jeopardize the ultimate outcome.

The ERA passed Congress in 1972 but failed state ratification by the 1982 deadline. Paul died knowing her life's work remained unfinished, but the achievements along the way (including over 300 laws that her National Women’s Party helped draft) and her inspiration of countless followers make her contributions to women’s rights among the most significant of any leader in 20th century.

Her 1977 obituary5 framed her entire life as a crusade for true, unwavering, Constitutionally protected equal rights. A central figure of the movement, Paul left others to carry the torch for women’s rights.

Shifting to another movement, we’ll now look at how a commitment to distributed leadership contributes to the multi-century continuity of movements that’s usually only visible when you zoom really far out.

The History Textbook: Commitments that Shape Civilization

The earliest civilizations introduced sophisticated systems for fairness, like Hammurabi’s Code and Athenian democracy.

These societies also had slaves.

A uniquely evil human invention, slavery continued through the Post-Classical period and crashed into the Early Modern Period when it arrived in the American colonies in 1619. From there, it entrenched itself into the foundations of the nation and together with the genocide of native people, became one of America’s two original sins.

Slaveholders and slave traders completely stripped the humanity from the enslaved, robbing them of all five of the virtues on our star.

It took slave rebellions and an abolitionist movement, a Civil War and a botched Reconstruction, an Industrial Revolution and a Great Migration to bring America to the dawn of the Civil Rights movement, when generations of injustice, oppression, violence, falsehood, and hatred had still not given way to a more virtuous era.

The people were ready to rise.

We might talk about the Civil Rights movement as a struggle for integrated schools and water fountains, access to bus seats and the ballot box.

But the truth is, like the other movements we’ve discussed here, it was about fundamental human dignity. Black Americans wanted all the rights that America could afford any of its people, and to get that they understood the importance of pursuing virtue in a virtuous way. Despite countless temptations and set-backs, the Civil Rights movement succeeded because they refused to mirror their opponents' methods. They found discipline in faith and wisdom. They wouldn't respond to hate with hate, lies with lies, or violence with violence. When attacked with fire hoses and police dogs, they chose discipline over retaliation.

And they did it by the millions.

Because the movement had people like Septima Clark.

Clark is our textbook leader today, because in her long-term commitment to the Civil Rights movement she built citizenship schools to teach others how to extend and carry on the movement. Between 1957-1970, she trained some 10,000 leaders6.

Every movement that lasts depends on leaders not just like the charismatic MLK Jr, but also organizers and teachers like Septima Clark who brought people in, showed them what to do, and helped them do it on their own.

They make the movement move.

Clark retired from her role with the Southern Christian Leadership Conference (SCLC) in 1970, and dedicated her final years not just to Civil Rights but to other causes as well. Yet her legacy endures in the movement because she made a contribution of unmatched scale.

The change that teaching enables becomes the thematic anchor for centuries.

How You Can Use the Virtue Star

The Virtue Star is a practical navigation tool I've refined through fifteen years of research and real-world application.

Here's how to use it for the hardest decisions in leadership: which movements deserve your biggest time commitments, and how best to show up once you’re there.

I call this exercise the “Time Telescope.”

First, pick a movement and look at it through the telescope (from a distance, but with focus). See if you can find the Virtue Star. You’re looking to understand 2 things:

1. The Movement’s Goal: Does this movement seek to advance all 5 virtues, or does it leave some behind?

2. The Movement’s Method: Does the movement use the virtues as guides for how it pursues its goals, or does it succumb to hypocrisy?

Your view of the movement’s goals and methods will tell you if the movement is worthy of supporting in the first place. If it does sufficiently support and adhere to the five virtues (to your satisfaction), you need to look again, but this time, with you as part of the movement. Do the movement’s weaknesses match your skills, perspectives, or other resources? If so, will you:

1. Ignore the movement anyway, or contribute only minimally?

2. Sign up for a moonshot, helping work towards a big audacious goal?

3. Commit your life to the movement, allowing it to shape you as much as you hope it might shape the world?

4. Focus on sustainability of the movement, ensuring others can continue to lead the work long after you’re gone?

I’ve done this exercise to consider how I approach movement building with Timeless Leader and a Democratic Ownership Society, which encompass some of the other movements (like eliminating gun violence, childhood poverty, and extremist ideologies) that I’m willing to dedicate the rest of my life to.

I hope you’ll take the Virtue Star with you, look at it with a Telescope, and use it to help you curate your commitments on the longest time scale.

We Are All Stardust

Carl Sagan reminded us that we are literally made of stardust—atoms forged in the hearts of dying stars billions of years ago. When we really zoom out, we realize how insignificant our lives are on the scale of the universe.

But just because one day our legacy will be erased from the cosmos does not mean we shouldn’t care.

Instead, it should free us to go beyond ourselves, and tap into whatever bigger force for good needs our energy most.

The Czech munitions worker knew it when they made dud shells.

The NCLC knew it when they freed children from the factory floor.

Alice Paul knew it when she fought for women’s equality.

Septima Clark knew it when she trained the next generation of leaders.

There are so many causes and movements out there. They have the ability to change people’s lives, and even the trajectory of our country, the planet, and the rest of human history.

Pick up the telescope. Find the Virtue Star in a movement that needs you.

Make a big commitment, and maybe… just maybe…

Even stardust can leave a lasting legacy.

And that’s the end of Season 2! Thank you for joining this journey exploring so many dimensions of self-leadership, going all the way back to last fall! I hope you enjoyed it and found something valuable. Also, thanks for overlooking my typos and other flaws that happen without an editor.

What's Next: We’ll enter another interlude! I’m still deciding how exactly to approach the time between now and when we start Season 3, but I think it will rely heavily on conversations. It will also be fun. Also: we’ll still have the Basecamp!

Help Build a Virtuous Movement: If the Virtue Star framework resonates with you, share it with someone who's evaluating their long term commitments to social change. They might appreciate a look through the telescope.

Share

Refer a friend

Leave a comment

Subscribe now

Over the past seven weeks I wrote that email is the backbone of your business that requires CEO level commitment to maintain. I wrote that there are (at least) 8 different kinds of email, that there’s a useful 2x2 matrix you can use to guide your email strategy, that you need to segment your list (but not too much) and that email requires a level of infrastructure that might surprise you.

Then last week, I showed how I’ve used AI to accelerate intuition in my writing process, and publish 1-2 times per week, every week, all year long.

In this final installment of the summer 2025 Email Deep Dive Mini-Series, we’re going to show vs tell an important lesson in email: know when to bring closure.

We’re done!

We started on the email mini-series adventure because I thought documenting my own learnings on email (not ironically through email) might help you leverage email more effectively in your leadership practice.

I also wanted to kick-off the Business Growth section of my Substack as a place where everyday leaders can learn strategies and tactics for business and organizational leadership that are thoroughly researched, tested in the real world, and aligned to the goal of building a Democratic Ownership Society.

That said, I know that probably NONE OF YOU signed up for this list to get weekly emails about email. 🤪

So while I hope this has been helpful and useful for future readers, you and I can take a deep breath.

WE’RE DONE WITH EMAILS!

(Director’s Cut voiceover: this is me providing “Closure”)

My writing will continue on the core topic of Timeless Leadership every week, but I’m taking a pause on Business Growth writing… until it’s time for another mini-series.

(and that was “Continuity”)

But before you go - can you fill out this little poll question? It will help me think about what that mini-series might be.

Thanks for voting, and reading! If you missed some of the previous posts from the mini-series: I provide links below with a quick blurb about why I wrote each one of them.

See you next week for the finale of Season 2: Saving Time in my main “Timeless Leadership” newsletter!

-Joe

Week 1 - 8 Types of Emails

Here we catalog the range of emails that exist for different purposes and requirements, and solve different business and customer needs.

Week 2 - The Role of Email

This argument underpins everything else in the series (and helps explain why I was doing it in the first place).

Week 3 - Email Prioritization

Knowing that email is important and what different kinds of emails are isn’t enough: you need to know how to pick which emails need attention, right now.

Week 4 - Email as a Priority

Even though I argued in week 2 that email is a business’s “backbone”, it’s possible that it still gets under-resourced by CEO-level leadership. Try to avoid that misstep.

Week 5 - Email List Segmentation

Emails don’t happen without recipients! I didn’t write about building a list in this series (short answer: ads, web traffic, lead magnets, events, organic social, referrals, outbound, and constantly delivering value to existing subscribers), but this post addresses how to manage whatever list you do end up building.

Week 6 - Email Infrastructure

It took me a long time to learn and it’s surprisingly hard to find a good walk through of the entire range of tools and technologies needed to run a quality email program.

Week 7 - Email and AI

Finally we covered AI because (a) most people are curious about AI, (b) AI has a very clear application to marketing, but can be done very poorly, and (c) I have enough direct experience using AI for email that it seemed like the right way to share.

Before you go: Don’t forget to fill out the poll at the top of this post!

If you’d like to share more feedback, two questions I’d love to get answers to:

1. Did you have a favorite post from this series? If so, which one?

2. What’s one thing you learned, or one thing you think I missed?

Drop a comment or send an email, and I’ll be sure to reply! You can also book time with me here. I’ve love to meet more of you and learn more about what you’re working on and how I can help!

Subscribe now

Leave a comment

Read time: 6 minutes

Two and a half years ago, I left Box where I had dedicated myself to a foundation-setting phase of my life: I built skills, network, impact, and some financial security. Box provided the stability to start a family and take paternity leave. Box was where I learned how to build businesses at scale and also where I discovered my passion for leadership development.

What followed my departure has been the most intense period of exploration in my adult life—testing business models, applying my capabilities outside a large organization, and learning to balance my entrepreneurial ambition and passion for service with the reality of raising young children.

I call this my "scaffolding phase." I’ve expanded my sector and functional skill set and network. I’ve broadened the role I play at home and my service engagements. I’ve widened my view of the movement I want to build and the time scale to make it happen.

All of these new and farther reaching activities and experiences have built on my prior foundation to provide scaffolding for my next act.

As that scaffolding proves its strength, it’s time to move into a new phase.

It’s time to build.

This week, we’ll talk about these kinds of shifts that occur across quarters, years, and multi-year periods.

Whereas in Part 11 of the Saving Time finale we looked at curating commitments on a micro time scale, today we zoom out. When we move through seasons and write new chapters over years, every decision becomes a portfolio balancing decision.

We’ll break down today’s post into three sections: Quarters & Seasons, Annual Rhythms, and Multi-Year Phases.

For each section, we’ll examine two types of practices that can help you fine-tune, rebalance, and fully reconstitute your commitments.

Welcome to leadership over periods—where you're no longer just managing tasks, you're managing trade-offs.

Let’s dive in.

Fine-Tuning: Quarters & Seasons (3-12 months)

Within a year, the calendar divides into four net quarters. Three months is a great length of time for taking on serious projects, and creating check points on bigger commitments.

The year also features natural seasons that bring their own transitions in weather and ceremonies, and institutional seasons (tax season, soccer season, testing season) that introduce decision points, opportunities, and challenges.

During the year, effective self leadership requires integrating these overlapping check-points with your own goals, and making sure that you stay on track with your current vision and commitments. The focus is optimization: "Am I executing my current commitments well?"

Reflect: Personal Dashboard Check-ins

There are two kinds of personal dashboards you might consider checking at least quarterly, to monitor that your staying aligned to your existing commitments.

The first is contingent upon you having clarity on your commitments, which means they translate to personal OKRs or a similar framework where you have SMART goals with clear metrics. I’ve done this before, although I don’t do the personal ones consistently every quarter. When I do, it helps me not only set up my commitments intentionally, but also hold myself accountable to delivering on them.

The second kind of personal dashboard is one that doesn’t require advance planning—you can pull it up any time. These dashboards facilitate reflection on your energy, effort, and emotions over a recent time period, and make it possible to notice when a key area of your life is over or under resourced.

A simple dashboard from the book Designing Your Life by Bill Burnett and Dave Evans2 keeps it simple. Take 4 areas—Work, Play, Love, Health—and rate each from 0 (empty) to Full. After reviewing your responses, you can ask yourself: Where am I thriving? Where am I struggling? What needs attention this quarter?

Additional options include the classic Wheel of Life3, time audits (suggestions available in Christina Wallace's The Portfolio Life4), or reflecting on 4 burners theory5.

Plan: Prototyping and Sprints

Prototyping Your Seasons: Bill Burnett and Dave Evans advocate for small experiments that let you "try out some version of a potentially interesting future" rather than making massive life changes. These can be tiny, or can span 3-9 months to test new directions before major commitments.

To test prototypes you can simply try them out for a set period and review at the end, or you can aim to be more iterative. Try borrowing from Agile methodology. Keep tasks in backlogs and execute them in sprints (1-2 weeks at a time) to continuously evolve your prototype to see if you can get it to fit to your desired end goal. This also helps you balance testing something new with maintaining your existing commitments.

It's the same project, program, and portfolio management we use in business, but applied to life. It works surprisingly well for maintaining momentum on multiple fronts.

Additional suggestions you might consider include GANTT charts and project management tools, holding partnership alignment sessions with your spouse or life partner, and using your quarterly planning to inform your monthly and weekly rhythms we talked about in Part 1.

Rebalancing: Annual Rhythms (1-2 years)

Every year or two, you're faced with the choice of making more significant portfolio adjustments while keeping the same core priorities and values. You might change jobs or the kids change schools. You add or drop a volunteer commitment. You might change something key about your daily routine, environment, or friend group. With the longer type horizon and built in transition points, you ask: "Given what I've learned, how should I reallocate my time and energy?"

Reflect: Past Year Review

Rather than forward-looking resolutions, Tim Ferriss advocates6 for analyzing what actually generated positive and negative emotions over the past 12 months. Review your calendar week by week, noting peak positive and negative triggers. Identify the 20% that produced the most reliable peaks.

This exercise is enlightening and can be depressing. However the reflection offers a sober assessment of what activities most impact your life satisfaction, and give you a chance to change how much time you spent on things that made you miserable.

Portfolio pattern assessment using Wallace's moonlighter/zigzagger/multi-hyphenate categories can add another lens.

Plan: Portfolio Architecture

Schedule the Positive First: Based on your Past Year Review, get the activities that generated peak positive emotions on your calendar immediately. As Tim Ferriss puts it: "lest they get crowded out by the bullshit and noise that will otherwise fill your days."

Create Your NOT-TO-DO List: Write down the people and activities that reliably made you miserable. Post it somewhere visible. These are things you'll stop accepting out of obligation, guilt, or FOMO.

Rebalance Your Portfolio Pattern: Maybe you've been moonlighting but want to become a multi-hyphenate. Or you've been zigzagging and want to settle into one primary focus with side projects. Use your reflection to consciously choose your approach for the coming year.

Christina Wallace's four pillars (identity, optionality, diversification, flexibility) and calendar harmony principles can guide your rebalancing strategy.

Reconstituting: Multi-Year Phases (2-7 years)

Here's where portfolio thinking becomes truly strategic. At this timeframe, you can actually change your values, context, and the "big rocks" of your life. This is where you make the consequential decisions: Should you move to a new city? Start a new business? Run for office?

The multi-year phases add up quickly: soon (next week actually) we’ll be talking about decades and centuries, but it’s at this time scale that you are still making decisions with immediate, measurable impact and where you have the opportunity to reconstitute while you’re still in your prime working years.

Reflect: Impact Dashboard and Compass Calibration

Multi-year decisions are the most consequential, so they deserve deeper reflection. Two complementary frameworks can help you see both the scope and the values at stake.

Value (Re)Setting: Your values underpin all your decisions, so having a clear view on what matters in your life really matters. Also, while values change over time, they tend to hold constant for at least 3 years. You can use Google or an AI to easily find a value exercise, but whatever structure you go with (here’s one7), make sure you:

• Balance the real and the aspirational.

• Settle on 2-6 values total. Not more, not less. (You can nest secondary values within your principal ones)

• Frame the values as nouns (you value “this thing/idea”) and use statements as principles that you follow to honor those values

• Think about how the values intersect, how you settle tie-breakers between them, and whether your values cover the key scenarios for which you need them to guide you through

• Make sure your personal values align with those held by your family, workplace, and community.

My personal values for this phase of my life are courage, compassion, and integrity.

Compass Calibration: In addition to the Designing Your Life book, there’s a class by the same name at the d.school that I took in 2017. In that class, we did an exercise from the book where we articulate our “Workview” and “Lifeview” as a way to help define the “compass” we can use to guide us on our long term journey.

In my own documents it’s clear that 8.5 years ago I had already defined a compass that still guides me today. In my Workview I wrote that "Good work is concerned with connecting the past to the future. It assures the outcome of effort is preserved, so that the work that occurs tomorrow will build on the work completed today." In my Lifeview I wrote that "Life is about experiencing change, and creating it. It's about the moment, and the legacy."

Your compass helps you envision how your values play out in the work.

A good multi-year dashboard can help you assess if you’re on the right track and how you might reconstitute your portfolio of commitments if you need a major adjustment.

Impact Dashboard Assessment: Nell Derick Debevoise, a speaker on leadership (who reads this Substack), developed the “Impact Dashboard” that she has used with her coaching clients. With this tool, you can map your activities across six Spheres of Impact (Self, Family, Job, Workplace, Community, and Money) and the Spectrum of Impact (Government, Non-for-profit, Social Enterprise, and Corporate) to deeply assess your investments and their alignment to your goals.

Her insight8: many high achievers burn out not because they're not having impact, but because they’re severely imbalanced across spheres.

When you have the data on how your impact plays out across different spheres and the spectrum of impact across several years, you can better plot the next multi-year phase of your life.

But before you commit, it might make sense to not only plan one multi-year vision, but multiple.

Plan: Odyssey Planning

Also from Designing Your Life (clearly I think this is a book worth reading), the Odyssey Planning exercise involves creating three very different alternative versions of the next ~five years. Each should include a timeline, a six-word headline, key questions you'll explore, and a dashboard rating resources, likability, confidence, and coherence.

This is scenario testing for the biggest bets of your life. If you have a life partner, do this together (Nimmi and I have). If you don’t, create these scenarios, and ask a few trusted advisors to help you think through it further.

Once you have a favorite plan, start moving towards it by using your quarterly and annual processes as the structure for implementation.

An Odyssey might be extreme way to put it, but I know from experience the right planning can turn a random phase into an intentional adventure, and can help put you on a path to building the legacy you most care about.

Which of these time scales do you have practices for?

Today we looked at leading yourself from seasons of a few months to phases that could last several years. Each of these time scales deserves intentional reflection and planning to effectively curate your commitments, manage your life “portfolio”, and stay true to your values and purpose.

If you’ve read this far I’d love to know: which of these practices have you used before? What did you learn? Which are you to going to try next? Do you have other practices that you swear by that you’d like others to know about?

As I move from scaffolding to building, I look forward to building more together,

-Joe

Share

Subscribe now

Leave a comment

PS. Next Week: Part 3 of the Season 2 finale will explore the longest view—how your major life commitments across decades create the platform for contributions that outlast your lifetime.

If today’s post clicked for you, give it a ❤️ and share it with someone navigating their own seasonal or phase transitions.

Read Time: 5.5 minutes

Happy Saturday, Timeless Leaders!

I'm working through revisions of this email while my daughter dances in ballet, and I'm struck by the irony of writing about machines, with machines, as I'm immersed in reminders of human growth, beauty, and fluidity.

Truthfully, if I had my way, nobody would be doing anything with AI right now. We have problems of human civilization that only humans can solve, and AI will not be a miracle panacea. Moreover, its presence is consuming massive resources and attention that make it harder to address poverty, ignorance, conflict, and environmental collapse.

Yet, AI is here, and its availability presents a choice: do you opt out, or do you learn to leverage its power for good? I’ve chosen the latter, and when it comes to writing, I’ve found that AI becomes genuinely useful not as a replacement for judgment or a robot who writes every word, but as a robust platform for strategic coherence and consistent execution, regardless of what else you have on your plate.

Email Consistency Is So Hard for Leaders

Every week of this series, we've uncovered the same underlying issue: email success requires sustained strategic thinking and constant execution, but leaders have many other balls in the air and only tend to look at email amidst rapid context-switching.

Yet whether you write emails yourself or direct a team, you need a way to:

• Show up much more often than feels humanly possible

• Maintain your strategic voice across dozens of touchpoints

• Ensure each email builds on your established positioning

• Keep editorial standards consistent when you're pulled in multiple directions

• Transfer your thinking effectively to team members who execute

This isn't just an email problem—it's a leadership consistency problem. How do you maintain strategic coherence when time is scarce and your attention is constantly divided?

How Claude Accelerates Intuition

Of all the LLMs, I've settled on Claude from Anthropic as my go-to AI assistant (and the least problematic LLM from an ethical standpoint). More importantly, Claude has proven invaluable for maintaining strategic consistency across all the context-switching that leadership requires.

Instead of "artificial intelligence,” AI used well is better understood as "accelerated intuition." Its power rests in effective partnership with a human operator. For email specifically, tools like Claude can serve as memory (preserving your thinking between context switches), coach (pulling together disparate threads, and making new connections) and translator (helping team members understand and execute your approach).

Instead of using AI solely to write individual emails, use it as the engine for continuous evolution.

Build a Knowledge Base in Claude’s “Projects”:

1. Upload core context to the knowledge base (your bio and beliefs, details on your audience, your business goals and constraints, and samples of your writing)

2. Input text instructions on the type of role Claude can play (coach, copy-writer, editor), and provide explicit instruction on how it interacts with you (“Ask questions before dumping a wall of text”)

3. Initiate a dedicated conversation to codify your complete email strategy

4. When it looks good, copy-paste that refined strategy to your knowledge base

5. Launch new chats for specific groups of emails (like a sequence, campaign, or series)

Be honest and provide personal detail that can help Claude understand who it’s serving. I’ve shared how "My vision is to build a Democratic Ownership society through Save Time, Make Time, and Escape Time. The business is less than a year old, still building sustainable client growth while supporting a family." A page of additional detail follows. This allows Claude to understand not just what I do, but why I do it and what constraints I’m operating under.

Once you’re set up with a project, each chat becomes a workspace for rapid generation. The magic isn’t about nailing the perfect prompt with a ready-to-publish piece on the first go. It comes from investing the same time you’d take to hand write a first draft, and partnering with the AI to move through 20 drafts in the same time.

Prompting to Progress and Express Your Ideas

If you take a prompt engineering course, you’ll likely learn about “prompt chaining” as a “reinforcement learning” technique. There are some more best practices you can pick up from a course, but I’ve learned from practice that simply treating the LLM like a tireless sparring partner gets the job done.

Here are some prompts just from one of my lengthier chats that helped me develop break-through ideas and novel approaches to communicating them:

• On email types: "Are there any established frameworks out there for grouping these and showing relationships between them? A 2x2 or spectrum graphic? Who's covered this and did they do a good job? Where's the gap?"

• From the Main Street Millionaire work: "The line 'her framing misses the deeper stakes involved.' don't like this as the transition to the body of the piece. Prefer something that captures this idea as the limitation: 'she only covers the second half of the "democracy-ownership society" that we talk about'"

• On the CEO’s role with email: “"Title: 'Commit or Quit' isn't the right contrast. Is this even an email about a decision at all? It's more about the CEO role + recognizing the cost of treating email as an afterthought."

• A version of this used often, after debating and finally settling on an approach: “Generate a complete, updated draft of this piece that incorporates our new insights and perspective, and includes at least two strong examples from this chat to exemplify the lesson."

There are a lots of ways to get started in a chat to develop writing. You can upload a draft or an outline, or you can brain dump your thoughts, or you can ask a simple question “What should I write about this week?” The power doesn’t come from where you start, but from how you go back and forth, offer feedback and new context, take the reins yourself and fix the problem and then show the AI what good looks like, and finally… upload the final version and ask for a proof-read. ;)

AI for Email Isn’t Limited to Standard LLMs

There are many more ways you might look to incorporate AI into your email program. Specialized tools like oJoy from Frank Kern and Email Game Changers from Ian Stanley give you access to copywriting and email sequence techniques the experts use. Your ESP probably has AI built in as well.

Then there are tools like Clay which you can use to research the market, build target outreach lists, and generate personalized emails.

But whatever other tools you use, if you have a solid Claude Project for email you can use it to prep for those sessions, and you can test the outputs through Claude. Ask: Does this serve our larger goals? Does it fit our relationship-building approach? Does it maintain consistency with our established voice and positioning?

Working across tools (and for some of you perhaps agents) is one of the last, most essential techniques to get the most out of AI. It takes more orchestration and expertise, but it can completely change what’s possible.

For now, you can figure it out on your own, but Claude alone is able to help you do it faster, or do it 10 different ways, and ultimately, keep your emails sending while you attend to a million other things.

Where This Goes Next

The leaders building the strongest email programs aren't just using better tools…

They're maintaining strategic consistency at scale.

AI can accelerate your planning and content generation process, preserve your strategic thinking across context switches, and empower your team members. As a result, your email program reflects your leadership approach consistently, and can keep scaling, up-leveling your business across the board.

Are you using AI for email, or other types of writing?

What works? What do you want to try?

Send me an email, or leave a comment.

-Joe

P.S. Next week: you’ll get both Part 2 of the Season 2 finale, and the final post wrapping up this entire mini-series! It’s been a fun summer, and I appreciate you reading.

Subscribe now

Leave a comment