This post builds on my summary of Jim Collins’s book, What to Make of a Life, so go read that post first. As I was writing that summary, I started to reflect on how his framework applied to my own life, but realized that I had too many thoughts, so I spun it off into this post.

Part of why the book resonated with me is that the idea of encodings mapped well to my experience, especially the experience of what Collins calls being “out of frame”, where you’re doing things that aren’t aligned with your encodings. Early in my life, I made the mistake of choosing paths based on what I thought I was supposed to do or that I was initially good at. This happened in physics (where I eventually dropped out of a PhD program) and in coding (where I lasted several years before switching careers). Neither of those lit me up, and my results reflected that – I never got great because I never got the flywheel going where I loved doing them, making me want to study or practice them more, so I would improve faster, which would make me love it even more. Even though I had natural talent in both disciplines (enough to get by for several years), I was eventually outpaced by the people that loved doing them because they kept investing in their growth, and I didn’t.

Another notable example of being “out of frame” is when I burned myself out. I had taken that particular finance job because I had consistently been given feedback that I needed to improve at process and operations, and I figured I would get the necessary practice if my whole job were process and operations. As I like to joke, I did improve…from absolutely terrible to below average. And to perform even at a below average level, I was working 100 hour weeks and feeling miserable, which is what led to burning out.

Meanwhile, the moments that lit me up were when I discovered a new way of seeing the world, a new framework, something that connected the dots and helped to make sense of experiences in a new way. I started this Unrepentant Generalist blog in part to share those moments and insights. On nights and weekends, when my colleagues were studying physics or writing code, I was reading books and listening to lectures in sociology, psychology, business and history to learn about different mental models and improve my skills at interdisciplinary translation, etc.

In this post from December 2006, I describe how I used this skill of connecting different ideas in a class for my master’s program: “In one class, we were having small group discussions, and towards the end, we were trying to summarize the group’s opinions about our reading, and I was able to string the discussion ideas together into a coherent pattern to present to the class on behalf of the group. In my other class, we had to do a group presentation and I ended up answering the questions at the end, because I quickly saw ways to reassemble our group ideas into a new pattern that tangentially related to the question.”

I just didn’t trust my experience enough to realize that was the path I could be following.

Fortunately, after I burned out, I found the Chief of Staff role that turned out to be the first job where I was operating “in frame”, where my broad set of interests and ability to communicate effectively across functions set me up for success in the job. It still took time to shape the job to really fit me, though, because I had to let go of the idea that something was good for me just because it was hard (the mindset that led to burning out). But once I found others to do the process and operations work that I found draining (and wasn’t good at!), I could concentrate on the big picture thinking and connecting the dots skills that came so easily to me that I felt like they weren’t work at all. Being “in frame” felt like cheating, because I had thought work was supposed to be hard.

Coaching has been a great fit for me because it lets me concentrate on what I do best (sharing different perspectives to help people get unstuck) with little of the process and operations work that I find draining. My wife sometimes jokes that I’m retired even though I’m working as a coach, because I spend my days mostly doing what I want (I love coaching), which is what being retired is supposed to feel like.

In that way, coaching is what Collins calls a “personal hedgehog”, where I “feel so compelled by what you are doing that you are willing to pay a lot of Stress and Drudgery Tax to be able to do it.” I don’t need “superhuman endurance, endless self-inflicted suffering, awe-inspiring work ethic, or even self- discipline” for coaching, because I feel “intrinsically compelled”. Collins calls this “flipping the arrow of money”: “Instead of work being a means to money, money became a means to work. … their true “work” could best be defined as pursuit of excellence in a hedgehog.” I could make a lot more money if I took other jobs in technology, but I choose to coach instead and aim to make enough money to cover my costs so I can keep coaching.

Collins’s description of cliffs and fog also matched up well with my life experience. The experience of burning out was a cliff that led me to start experimenting with new possibilities in life: I moved to the Chief of Staff role at work, I started riding bikes (which led to the peak experience of Leadville), I started dating again (which led to getting married and becoming a parent). But the difference was that I didn’t pre-commit to spending years on those paths (as I once had with physics) – I tried one step, and took more steps if they felt good (as Collins outlined in his description of how to get out of a fog). There wasn’t one single path for me to find – I just had to continue down paths that worked for me.

Another big cliff was when I broke my neck in a bike crash in 2016. That near-death experience naturally led to questions of purpose and meaning: if I had died, would I feel that I had lived a good life? Being a Google Chief of Staff was great, but it was no longer a purpose I believed in. So that kicked off the step-by-step process of exploring what would become my next career of coaching.

I also liked Collins’s descriptions of NATILIE (Not All Time In Life Is Equal) moments. I’ve had some amazing experiences that came out of leaning in when I had an exciting opportunity:

• The Chief of Staff job is a notable one, as helping Google leaders navigate a tricky business transition taught me a lot about how to lead through times of uncertainty, and I draw on that experience as an executive coach. I was fortunate that I was single and could lean into my career at the time, so I could really seize that opportunity when it fell into my lap.
• My time singing with the San Francisco Symphony Chorus is another such experience. I was singing in a community chorus in Oakland after college, and the director happened to be an associate conductor with the Symphony Chorus and encouraged me to try out, which I would never have imagined was a possibility for me. But I was accepted, and that led to being part of Grammy- and Emmy-award winning performances, as well as singing at Carnegie Hall.
• Another NATILIE experience was exploring a new relationship in 2017. I had never been in a long-term relationship, but felt I was ready after sorting out some issues through a few years of therapy. Rather than tentatively easing in as had previously been my habit, we traveled to the Philippines for a 10-day trip together in our third month of dating, and within the first year, I had traveled to her home country of Bulgaria (and stayed with her parents), and we moved in together. We decided it was better to stress test our relationship quickly rather than waste each other’s time. Happily, we are still together almost ten years later, and have three kids.

I was initially skeptical of Collins’s book, because I don’t think his research methodology maps well to people, and because there’s no scientific evidence for encodings or luck or any of the other just-so stories he tells in the book. He’s pattern matching across a biased set and coming to his own conclusions. And yet his patterns match my experiences.

I have had the fortune of trying many things in life, and when I didn’t pay attention to what felt aligned (what Collins would call my encodings), it didn’t turn out well: physics and software and my burnout experience as described above, or playing violin for 13 years as a kid but never getting particularly good. When I did what was fun and enjoyable for me, my efforts resulted in fast improvement: coaching, choral singing, volleyball, ultimate frisbee, skiing, biking, and now weight lifting.

As a side note, I improved fastest when I did those activities with people who were better than me. I have a competitive nature, so I would push myself harder to improve. And watching others meant I could pattern myself off their templates of what better looked like. Once I hit the point where I was mostly caught up to those around me, I rarely kept pushing myself into the realm of true excellence – the toil of gradual improvements never compelled me.

Similarly, that cycle of improvement only kicks in on activities where I want to commit to that effort: I never got fluent in another language, I am laughably bad at drawing or visual design, and have zero interest in crafts like gardening or woodworking. Does that mean I don’t have encodings for those activities? Or just that I’m not interested in practicing enough to improve at them? I don’t think it really matters as the advice from Collins (and in my book) remains the same: pay attention to what energizes you, and use that as your compass to navigate life.

That being said, there are times when it’s worth pushing through things that feel hard and effortful. As recent books I read advocated, it’s good for our health to stretch the mind and body, and excellence requires pushing beyond what others will do. Being a parent is very challenging for me, and yet not being able to walk away has led me to deal with long-held trauma. Socializing is more challenging than scrolling on a phone or watching TV, both in terms of scheduling and in dealing with the complexities of other humans, but a necessary investment to avoid the debilitating effects of loneliness.

And as Collins describes in his chapter on Choosing Responsibilities, we get to choose the purpose and meaning of our lives. Who or what are we willing to sacrifice for? What impact do we aim to create with our encodings and skills? I have been consistently devoted to helping people develop more of their potential capabilities (Collins might call this finding and activating their encodings), and coaching is a great way to do that for others (and personal development helps me do that for myself and my kids). As people increase their capabilities (and claim their own agency), they can create greater impact and hopefully change the world. In my book, I write: “changing the world starts with choosing your actions to consciously live in the world you wish to bring into existence”, and coaching enables people to do that more effectively.

Do I think Collins has the one true method to make the most of your life? No. But the patterns he identifies of encodings and “personal hedgehogs” and cliffs and fogs match my experience, so I think this book offers a useful framework of possible moves people can make to increase their life satisfaction and meaning and purpose.