Hey Reader,

Happy Saturday!

I spent the latter half of this week in Chicago at an event called Tastemaker, the premiere industry conference for food creators.

My past work has led me to a fascinating intersection — one where I find myself working with both startup founders and some of the most popular creators in their industries. This always seems paradoxical when I share it with new friends, but I’ve come to embrace the fact that it’s a reflection of both who I am and the work I've done.

On Thursday I gave an hour-long talk on making the shift from creator to CEO (which could easily be the shift from founder to CEO) and what it takes to become the leader your team deserves. On Friday, I hosted a workshop in which I did three mini coaching sessions with talented food creators to help them continue to grow their impact.
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(Brief side note to say that I do a small number of speaking gigs a year and would prefer to do them at events run by people who read my work. Please reach out if I can fill a need on your conference agenda.)

I had a blast and it was a good reminder of why I have always and will continue to love the creator economy.

As always, I’m grateful you choose to spend your Saturday morning with me.

Let’s get to it.

A short essay sparked by my work with founders

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Last week I talked about the emotional holes founders can fall into after a successful exit of the thing they built. Whether that’s selling a company, hiring a new CEO, or a departure with a good financial return as an exec — I see a common trend that people struggle to find a new sense of identity. Sometimes, often even, that requires a trip down a path of anxiety and/or depression that includes attempting to answer existential questions.

This week I promised I’d share how I’ve seen folks dig out of that hole. I’ll admit that I have about five other things I feel compelled to write about this week (lesson learned), but I want to deliver on last week’s promise.

Here’s what I’ve seen:

1. Solve an existential problem - when you make enough money that you can retire, it often raises the question of “well what matters enough to spend my time on more than my family/hobbies/peace?” One way of answering that is to pick a problem that’s an existential threat to humanity. Climate change. Disease. Energy. Aligned AI. Becoming multi-planetary. Food production. These folks justify the return to the pain of entrepreneurship by picking a problem that has unequivocal value to society.
2. Take a big swing on the hot new thing — when you’ve built one thing successfully, that often means you’re in a position to capitalize on the next wave of exciting action. The prior waves went something like: creator economy, crypto, AI, manufacturing and hardware (happening right now). When you’re sitting around wondering what to do next, with the hard earned knowledge of a founder, an exciting new wave can get you out of your seat.
3. Do it again, but better — sometimes you can’t let go of what could’ve been. You know you did well, but you also know it could’ve been so much better if you had made a few different decisions. Founders that take this path copy what they did before, but with answers for all of the mistakes they made previously. They might build a similar product for a new industry, a new product for the same industry, or they might do almost the same product for the same industry (this sounds like it couldn’t possibly be true but it happens all the time!)
4. Settle into a lifestyle with new priorities - this is basically retiring. There’s nothing wrong with it. You might see founders that take this path hang their own shingle as a fractional executive, consultant, speaker, or essayist. But the bulk of their time shifts to other priorities — family, community, perhaps getting engaged in local politics, or engaging deeply in hobbies as “work.”
5. Step back and empower other founders - sometimes you know too much to do it again, but you want to stay close to the game. Rather than be a repeat founder, you decide to support founders in some way. This might mean raising a fund, becoming a coach (like me!), starting an accelerator in your hometown, or any of a myriad array of options to encourage founders to start and keep going.

Knowing the options doesn’t solve for the indecision that comes when many options are available to you. And, to be honest, I’m not sure I know what changes when people in the dark hole go from lost to having direction. But I do know that eventually everyone emerges.

What I think might be true is that there comes a day when the pain of having no direction is worse than the pain of picking an imperfect direction. And on that day, I believe the decision that happens is: “Maybe there isn’t a best path. So I’ll pick the best one from where I sit right now.” And then they get going and adjust from there.

So my hope in sharing these different paths is that if you find yourself in that deep dark hole after achieving the thing you once hoped to achieve — that maybe you can come back to this email, look at your options and decide “today is the day that I’m going to start again, imperfectly, but with purpose.”

A quote to make you think from a book worth reading
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“How we approach our sorrows profoundly affects what comes to us in return. We often hold grief at a distance, hoping to avoid our entanglement with this challenging emotion. This leads to our feeling detached, disconnected, and cold. At other times, there is no space between us and the grief we are feeling. We are then swept up in the tidal surge of sorrow and often feel as though we are drowning. An approach of reverence offers us the chance to learn a more skillful pattern of relating with grief. […] Learning we can be with our grief, holding it softly and warmly, is the first task in our apprenticeship.”

- Francis Weller, The Wild Edge of Sorrow​

This is the book I find myself most often recommending to founders and friends. We have no rituals or practices for properly relating to grief in the west. Rather than processing it, we carry it around as repressed emotion that often lives deep in our bodies.

I’ve come to believe that the cost of joy is grief. In all the years that I repressed sadness, fear, and grief, I wasn’t really able to experience joy and hope. And the reason is that if we have hope… if we allow ourselves to feel pure and unadulterated joy… then we are at risk of losing the people, experiences, and circumstances that made us feel the hope and joy to begin with.

But if we know, with certainty, that we can survive loss, then we can open ourselves to the hope and joy that life offers. If we know that when the time comes we will be able to grieve, in whatever way is required, then we can settle into the joy of life.

Whether that grief comes from the loss of a friendship, the loss of a loved one, or the loss of a business — the principles in this book apply.

Three links to encourage deep thought and breakthrough growth​
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I don’t have three links for you this week. I’m writing to you from a plane from Minneapolis to Portland as I return home from the event I mentioned in the intro.

Rather than pushing beyond the energy I have available to give you three reads, I’m going to accept that the quote and the mini essay are enough this week. I'll be watching the new Hunger Games film instead of offering you less than enthusiastic reading recommendations. I'm human that way.
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I wish for you that you’ll know when you’ve done enough on a given day or week as well.

Much love and respect,

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If you enjoyed this newsletter, forward it to a founder friend. You can also recommend me to a founder or creator as a coach.