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This newsletter explores investing, career transitions, parenting, and other topics that engage me. You'll receive a shiny new edition in your inbox every two weeks.

None of my writing should be considered advice, investment or otherwise. I learn best through the writing process and conversations with others. In that spirit, I'd love to hear your thoughts.

I was touched to receive so many kind responses to my last essay, Running with Doug. Thank you. This edition features a more practical topic. But one that's been a source of tremendous growth.

The Think Tank

In late May, I wrote an article on LinkedIn, What I learned Jumping off a Cliff, that shared what I learned in making a mid-career pivot from finance (30 years) to a rent payment startup.

In the article, I made several suggestions like having a plan, distilling your goals, engaging in conversation, and finding a coach. I stand behind everything I wrote with one glaring act of omission.

It’s time to fix that.

For over five years, I’ve joined two friends, both former colleagues, on a weekly call that has become a foundational practice for my personal and professional growth. As a neat side benefit, the process has fortified our relationships. Also, it feels great to help friends work through significant challenges in their lives.

Not a Mastermind Group

Our calls are loosely inspired by what’s traditionally called a mastermind group. But that sounded too pretentious. Still, we wanted a name that set a tone. Also, a name for scheduling is easier than referring to “that meeting.”

So we leaned into our self-deprecating natures and dubbed this hour-long session “The Think Tank.” The work we do is serious, but we don’t expect to influence any national policy debates. Humor is an acceptable part of the process.

Our group works for some of the same reasons people hire coaches, work with therapists, seek spiritual guidance, or write in journals. Nothing beats working through challenges in a safe environment. We predominantly focus on the professional sphere, but life rarely segments itself cleanly, so we also stray into personal finance, health, and other areas.

Here’s one example.

Around year-end, we review our annual goals supported by specific projects and habits. This can be a transformational exercise, and it has been for me.

While I’ve intended to do this for years, it never happened until I introduced external accountability.

This year, we allocated an hour dedicated to each of us, which allowed plenty of time for exploration and discussion. Of course, this was the crescendo of a process that reflected many hours of preparation, planning, and reflection.

Sure, you can conduct an annual review by yourself. But when you introduce others you trust into the conversation, it’s magic. Every year, my partners in the process spot inconsistencies between my stated goals and my priorities. They see right through the well-constructed traps laid by my ego. With each bit of thoughtful feedback, the thinking evolves, and the plan of attack improves.

How we do it

The Think Tank’s structure continues to evolve with our needs. The best sessions have a moderator and an agenda set in advance to dig into a specific issue.

We’ve found a weekly cadence to work well. Fortunately, not every week requires a deep dive, but we’ve found the regularity helpful to stay current, and it’s fun to catch up. These less intense round-robin sessions offer an opportunity to share updates on the major topics in our lives.

Why it works

This process works because we trust each other, and we’re therefore willing to externalize our ideas.

Trust is essential. Full stop. That’s what creates a safe environment that invites open discussion and risk-taking. In our case, it helps that we’ve known each other for more than a decade and that we’re all interested in personal growth.

But even though we’re friends, and laugh a fair bit, the work is not easy. On the contrary, because we trust each other, we welcome honest feedback that can often be difficult to hear. We also play devil’s advocate with impunity. The process is rooted in our collective self-interest. We care deeply about helping each other, and we hold each other to a high standard. Think tough love.

We know that thinking often improves when shared with others. The Think Tank is an ideal space to test ideas and get feedback. Like in writing, insights often reveal themselves in the outer world, once they’ve been freed from the inner critic. Also, fresh perspectives enrich the thinking process.

The Basics

You’ll find lots of resources around mastermind structures online, but be careful. Nothing is more important than finding the right people. Without an existing foundation of trust, it’ll be difficult to make much progress. In my experience, I’ve found it helpful to work with friends who know me well in a professional context. Former colleagues might be excellent people to approach.

In terms of size, three feels about right. Ideally, you’ll want more than one perspective. But the bigger the crowd, the more challenging the logistics, and the less air time you’ll get. Remember, you don’t want to hide.

Also, like any other practice, consistency matters. While It’s ok if you miss sessions, try to honor your commitment and stick with it. Respect for the process translates into respect for each other.

Conclusion

I don’t know why The Think Tank didn’t appear in the original article, but I've tried to set the record straight. I’m grateful to my partners for their insights and unwavering support.

I hope you'll try something similar. Reach out if I can help.

Other stuff

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Founders Podcast: #275 The Essays of Paul Graham I've finally discovered why others rave about David Senra's Founders Podcast. There are actually three episodes dedicated to Graham, co-founder of startup accelerator Y Combinator. Start with this one. In this podcast, Senra shares his thoughtful takes from a handful of Graham's essays. One highlight was a review of Why to Start a Startup in a Bad Economy, written in 2008, but feels particularly timely again. If you don't want to read his extensive writing first-hand, Senra offers an efficient way to extract Graham's gold.

​Listen to the Podcast (1 hr 23 mins)

The Beauty of Hardship This short essay by Lawrence Yeo reflects on the role of hardship and what it can tell us. I often find myself nodding along as I read his work. If you're unfamiliar with Lawrence, I encourage you to explore some of his longer essays at More to That. Start with Money is the Megaphone of Identity and The Many Worlds of Enough. You can thank me later.

​Read the essay​ (5 mins)

Why Success Doesn’t Lead to Satisfaction You've probably noticed the dopamine hits from our wins fade faster and faster. But there's hope! In this Harvard Business Review article, Ron Carucci suggests ways to reexamine your relationships with 1) money, 2) achievement, and 3) recognition and status. He also offers some ways to recalibrate our measurement tools. Thanks to Khe Hy for surfacing this article. Khe has explored this topic before, most notably in Escaping the "When-Then" Trap.

​Read the HBR article (9 mins)

And a Farewell Photo...

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