Hey Reader,

Happy Saturday!

Whether you’re already a founder, might be a founder one day, or simply want to learn about the founder path for the sake of learning, thank you for reading my work. I’m grateful for you.

I’m running a little experiment this week by putting the mini essay first. Let me know what you think.

Let’s get to it.

A short essay sparked by my work with founders

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There’s this niche problem I’ve become fascinated with, which is: what happens when a founder or exec enters a career transition sparked by a theoretically positive event. This is the transition that comes after you sell your company, hire a CEO to replace you, get bought out by your partners, or step down from your executive role with enough cash in the bank to take a pause.

If you’ve been around a while, you’ll know this is partially selfish. I faced this myself and wrote about it here and here. But the more closely I’ve worked with founders 1:1 and the more founders I meet as peers, the more I see this as a serious challenge that pops up. A “champagne problem,” as a former colleague put it, but a problem nonetheless.

I’ve worked with founders going through a sale of their company. I’ve worked with execs leading up to and following a departure… But not many people talk about it publicly, because it feels insensitive. “I made all this money and now I feel lost” doesn’t land super well when most people are just hoping to have a secure job and provide for their families.

The societal expectation is that a positive ending should be an incredible moment of celebration. Congrats, you did it! Now be humble and enjoy it. You either have some money (perhaps a lot of money), some reputation, or both to show for it. This should be an easy transition… especially compared to being fired or laid off, or your company failing.

I think it’s important to talk about this stuff because it’s the reality some of you might face in the future and there are probably a few of you going through it right now. Here’s what I’ve seen that’s actually true: transitions are hard no matter the circumstances. But the circumstances dictate what’s hard about your specific situation.

When your company fails, or you’re fired or laid off, there’s no time to lollygag. You need income and you need to take care of your family. You have to hustle to close that gap asap. The existential questions can wait for later. The loss of identity and internal doubts about your ability as a leader can be dealt with another time. The hard part is finding a job or raising money for a new company and doing it fast.

But when you’re coming off a success, there’s not the same rush. You have money to give yourself some time off. Sometimes you have enough money that you never have to work again. Yet most people do end up working on something again, regardless of the money in the bank. And I’m here to tell you that the existential questions rage after a “success” that includes moving on from your company and your role.

The freedom created by the money and reputation also creates the challenge. Combined with the loss of one of the organizing principles of your life — your former role as the founder or key leader at your company — this can create a deep psychological hole.

You have time. You have money. You have reputation. You could do anything! And you have absolutely no idea what to do in the face of that.

Nothing is more threatening than having every option available. Where do you start?

And of course the next thing better be great because that’s what people will expect coming off a successful run… or you might feel like you still have something to prove because it didn’t turn out as well as you had hoped.

Oh, and wait, who even am I? Without that job and company I identified so strongly with, who am I outside of that? What do I want? What do I enjoy? What matters enough to spend my working hours away from my family?

It’s easy for the whole thing to tailspin into a story that you’ll never do anything worthwhile again or that you'll become irrelevant. Some people respond by anxiously jumping into something too soon. Some people descend into depression. Some people “retire” and spend time on hobbies and with family.

The people who come back better are the people who take time to sit with themselves and answer that question: Who am I? And who do I want to become through whatever I do next?

It takes patience. It takes courage. And it takes support from the people around you.

If you're in it right now, I see you. And if you've been through it before, I'd love to hear from you. How did you decide what to do next? What did you learn in the process?

Next week I’ll share the paths I’ve seen work well for founders to make the transition and get back to work.

A quote to make you think from a book worth reading
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“Telling or asking closed questions saves people from having to think. Asking open questions causes them to think for themselves.”

- Sir John Whitmore, Coaching for Performance​

In the transition from founder to CEO, your work often shifts from a focus on your product and customer base to a focus on your team and resource allocation. The job of a CEO is to maximize the potential of the team so that you get leverage for more and more impact as the team grows. Ideally that increase in impact also leads to increase in revenue.

Coaching can be a valuable core skillset for helping your team grow into what they’re capable of, and Coaching for Performance is a great starting point for building the skill.

Three links to encourage deep thought and breakthrough growth​
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1 Are you serious? By Visakan Veerasamy | Read time: 19min
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“[…]seriousness is something that really you can’t tell from an utterance. You can mainly only tell from watching how someone conducts themselves over an extended period of time. Over decades.”
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I’ve been accused of being too “serious” more than once in my life. In response, I’ve often been frustrated by how hard it is to find other serious people. Visakan’s essay on seriousness is the perfect encapsulation of that feeling.

You can be both serious AND goofy. But it’s hard to be both serious (as defined in this essay) AND cynical. Over the years I’ve had to learn how to take life seriously without always taking myself too seriously. I’m still working on that, to be honest. But I’d rather work on not taking myself too seriously than work on not taking life seriously.

Question to consider as you read: What are you serious about? Who are the other serious people in your life? How do you know? What actions would you need to take over the next 20 years to back up your desire to be serious with a track record of making it true?
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2 La Tête et les Jambes by Robert Wuebker | Read time: 11min
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“While it is extremely important to me that what I produce is impactful and appreciated by my community, it is just as important to me that the process of doing the work transforms me. This is my personal guide to project selection. Not what will happen if I get the intended outcome, but who I will become in the process of attempting to generate the outcome.”
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Work is an incredible tool for creating change in the world. If we choose our work well, it also changes us. This essay is a great reminder that the work we choose to do is not just about salary, or safety, but also about who we want to become.

Question to consider as you read: What type of person will you become if you do this work for the next decade? How is your work pushing you to change right now? What change is your work (or your team) asking of you, but you’re currently resisting?

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3 Finding Your Purpose and Living a Meaningful Life by Hunter S. Thompson (published by Shane Parrish) | Read time: 8min

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“Every man is the sum total of his reactions to experience. As your experiences differ and multiply, you become a different man, and hence your perspective changes. This goes on and on. Every reaction is a learning process; every significant experience alters your perspective.”
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I found this read particularly good in the context of the mini essay I included this week. Transitions are hard. Choosing what’s next is, ironically, sometimes harder coming off of a success. This is sage advice for how to think about what might come next.

Question to consider as you read: What abilities of yours do you most want to exercise next? How do you want to change or grow as a person? How do you want to live going forward? What project or company could you tackle next to enable that life?

Much love and respect,

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