Finding your path (plus another plug for my upcoming webinar and class)
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Cedric Chin wrote a post last week called The Idea Maze is a Useless Idea, where he observed that instead of a well-defined method for a company to find product-market fit, the only pattern he could find was to keep experimenting until you get lucky.
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In the comment thread, somebody asked how they could find a direction to orient their own lives. I wanted to share my response here as I think my readers would appreciate this perspective:
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I’m not sure I have a better answer to finding a direction than the essay. Because I think what you are effectively asking is “How do I find personal product-market fit (PMF)?” If you cultivate an obsession that has no value to others, then it may make a nice hobby but it can not be the basis of projects and pursuits that drive one's career.
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Experiment. A lot. See what gains traction. Don’t make any bets you can’t afford to lose. Stay in the game until something you want to do connects with the market.
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One corollary to the essay is that the way to accelerate through the Idea Maze is to develop the capability to experiment faster and at lower cost. My friend Seppo Helava is convinced this is the key skill to finding PMF - the team that can experiment faster is more likely to win, as he explains in this post and this one. I think the same applies to finding a personal direction - run low-cost experiments constantly to learn more about what energizes you and brings you joy.
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That being said, I think there are often clues in your history as to your long-term obsession. People have likely been telling you what it is in your professional feedback. The projects at work that you are most proud of, the times at work you were energized and excited to come to work, those are your clues if you can connect the dots.
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15 years ago, the team I was on got a new manager, who observed the team in action for a couple weeks to understand the dynamics. He came to me and said “Eric, you’re the guy that everybody goes to when they get stuck and don’t know what to do - you’re my new #2”. At the time, I was delighted and thought that meant I was on track to be a good manager. But what I figured out (ten years later) is that my actual obsession is with coaching others, and helping them figure out their own path when stuck. Once I leaned into that five years ago, things unfolded much more rapidly than they did for the first 20 years of my career, because I was personally aligned with my job in a way I hadn’t been before.
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To continue the theme of test faster, once I identified coaching as a possible job, I didn’t just quit my Google job and become a coach. I ran a set of experiments to reduce risk and test PMF.
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- I coached friends and acquaintances for free to see if I liked doing it.
- I interviewed several professional coaches to get their advice on the road ahead and next steps.
- I took a year long coaching training program to get professionally certified (and confirm that I’d still like it if I was immersed in it).
- I started a coaching side business to see if people would pay me to do it.
- Even when I quit Google, I had a couple years of savings in the bank and gave myself a deadline of making enough to cover my costs in a year and a half or I’d have to go get a job.
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Each experiment derisked the path and increased my confidence it was a good fit. But it started with small tests I could do in an hour a week. So start running those low-cost experiments to learn more about your own path, and if you need ideas, read my book!
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One last call to attend my 30-minute free webinar this Friday, Sept. 6th, where I share some of what may be holding you back in your career and How to Unlock Your Executive Potential. Sign up even if you can't attend live so you can get the recording.
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As a reminder, all of these appearances are to promote the group coaching offering I'm launching in late September, on How to Become a More Effective Executive. Please check it out and forward it to anybody who is struggling with that transition, so they can learn from my years working with top Google execs as the Search Ads Chief of Staff and my past five years coaching executives to greater success.
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And now for the normal personal development content…
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LinkedIn: These are ideas that have helped my clients (or myself), and that I share via LinkedIn to help a wider audience, and archive here.
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- Action follows commitment. The biggest blocker to change is the stories we tell ourselves about our identity. "I could never..." or "that's not who I am". It's not...until you decide it is. When you make a commitment to a change, you will figure out the next steps to become the person who embodies that change.
- What separates executives from people early in their careers. Another post promoting my webinar above, but has some insights about what's different about being an executive.
- What do you do when working harder isn't working? Once you realize you can't do it all by working harder, then you have to become more thoughtful about what you choose to do with your time and energy. It becomes less about you, and more about prioritization and delegation, working through others to get results.
- Are you undervaluing building connection and relationships in your job? I had conversations with an early-career individual, and an experienced executive, and surprisingly ended telling them both the same thing: to invest more in building relationships and connection as a way to advance their career.
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- Henrik Karlsson shared the design process he used to create a more satisfying life, which is similar to what I recommend above. "I paid attention to things I liked to do, and found ways to do more of that. ... I kept iterating—paying attention to the context, removing things that frustrated me, and expanding things that made me feel alive."
- I also loved another post of his: A blog post is a very long and complex search query to find fascinating people and make them route interesting stuff to your inbox which is very much part of the reason I write on the Internet.
- Cate Hall wrote a post on How to be More Agentic, which I love as somebody who wrote a book to remind people that You Have A Choice. She shares advice like "Court rejection", "Seek real feedback", "Increase your surface area for luck" (another theme of this newsletter!), "Assume everything is learnable", and most importantly, "Learn to love the moat of low status" (if that's a challenge for you, read chapters 2 and 3 of my book).
- Cedric also linked to a post from her fiance, Sasha Chapin, about Things you learn dating Cate Hall which is pretty amusing as a counterpart, but still insightful: "I think the crucial difference with Cate is that she has really, really internalized the idea that everyone is winging it, which, luckily, means that you can wing it at everything, too. ... This mentality enables her to approach potentially intimidating enterprises with eager open-mindedness; she is always willing to ask dumb questions, think from first principles, and look for ways to improve."
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Thanks for reading! See you in a couple weeks!
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My kids moved to a new school a couple miles away, and rather than spend an hour in the car each day, we invested in an Urban Arrow Family Cargo e-bike last week. I love getting some exercise during the school dropoff/pickup, the kids love being able to see the world around them, and it's better for the environment. It's expensive but we use it every day as a car replacement, plus it's fun!
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This is the Too Many Trees newsletter, where I share what I’ve been writing and reading in the realm of leadership and personal development. My executive coaching practice is centered around the idea that we are more effective in moving towards our goals when we become more conscious and intentional in focusing our time and attention, and learn how our unconscious patterns are holding us back. If you know somebody that could benefit from my perspective, please forward this to them or let them know they can set up a free intro chat with me.
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