A Portfolio of Play
I still don't know what I want to be when I grow up.
Throughout my life, I've leaned in to activities that I found interesting or I felt like were teaching me things:
I learned how to play Magic: the Gathering from my friend's brother when I was five (It’s probably the thing that I’ve been doing the longest in my life besides riding a bicycle).
I picked up and stopped playing team sports like hockey, soccer, and rugby.
I played drums in an emo band throughout high school and got to share the stage with Portugal. The Man in college.
I'm not on a sports team. My drum set is long gone. But nurturing that curiosity shaped who I am today.
As I’ve gotten older, I realized that the key to my happiness has been turning life into a portfolio of play, something I've taken from how James Carse describes an infinite game:
“Because infinite players prepare themselves to be surprised by the future, they play in complete openness. It is not an openness as in candor, but an openness as in vulnerability. It is not a matter of exposing one’s unchanging identity, the true self that has always been, but a way of exposing one’s ceaseless growth, the dynamic self that has yet to be. The infinite player does not expect only to be amused by surprise, but to be transformed by it, for surprise does not alter some abstract past, but one’s own personal past." (Source)
This kind of openness and willingness to be transformed is what I mean by play. I run towards the things that excite me and do my best to not just choose, but invite, specific "stresses" into my life. This was an explicit approach I took with Yet Another Studio, refusing to sku-ify myself (package myself into neat service offerings) and instead embrace different activities and ways of being as a solo consultant/advisor/me-as-a-service.
The reality is that we are all managing a portfolio of our time (personally and professionally). We spend/invest it in different ways, and will concentrate and diversify those positions throughout our lives.
Given this, you'd think the goal would be optimization, but I've watched a lot of friends try to "optimize" their lives (which usually means remove friction) to failed ends. This is because not all friction is bad. Some friction is meaningful.
I've found that mess is often a feature not a bug. When things are too smooth, you don't engage and you don't think about them. You just keep moving along a path, not asking yourself whether you want to continue down it.**
Thanks to recent reads like Why Greatness Cannot be Planned and The Uncertainty Mindset, I've embraced the idea that goals should be about behaviors or processes, not outcomes. The questions*** I regularly ask myself are not "did I achieve x?" but instead look more like:
Am I spending time in ways that nurture me?
Did today bring me closer to the future I want for tomorrow?
What about me showed up today that I want to see more of?
Doing this has made me realize that asking what you want to be when you grow up is like asking where you want to end up. This isn't a useful question for me, because I'm much more interested in how I want to be as I'm growing up:
How do I want to be with myself?
How do I want to be with those I love?
How do I want to be at work?
How do I want to be in the world?
These are the inputs that I can control, and the things that have a much larger influence on how I spend my time than any destination I could think of.
So, I still don't know what I want to be when I grow up. But I'm learning that not knowing (and embracing that not knowing) is itself an answer. It's a choice to be open and keep playing. The question isn't what will I be, but who am I becoming?
That question, unlike the first one, I can actually answer.
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[1] This riff inspired by Nabeel's post.
[2] To quote one of my favorite bands, "The journey is more important than the end or the start."
[3] Here are some questions I sat with as 2025 wound down (X, as an app).