Making Space for What’s Next

On leaving Substack and following curiosity

My last day running ops at Substack was a few weeks ago. And… I’ve been hiding in the shadows! 🥷🏿

I wanted to write something about the end of this chapter, but it took time to feel rested, ready, and eager to put words down.

When my wife Yoko left her UX design job after nine years, we joked about feeling like vacuum-sealed foam mattresses.

The queen-size IKEA mattress arrives in an impossibly small package. You grab the box cutter, slice open the thick plastic and… it slowly and creepily unfurls…

It takes time to decompress from a job that becomes your day-in, day-out for many years. Even a good and purposeful one. I wanted to feel unfurled before excavating what I did and what comes next.

The tour

I started at Substack in 2021. They’d been a client of People & Company, and after their Series B, Substack acquired our small team to join the 20-ish person company. Timing felt right. I was hungry for a new mission and more collaborators.

About six months in, I was asked to lead operations. It was a pivotal moment in my career.

What followed was a four-year tour of building the core operations that helped the business scale. I started functions, built teams, and fixed problems. Over time, my scope included overseeing Finance, Biz Ops, Legal, Support, Trust & Safety, HR, and more. I’m proud of the backbone we built. The team, business, and platform multiplied. I also made it through periods that were intensely hard. Being VP Ops was shapeshifting work—consuming, challenging, and altogether perfect.

*~ A tangent ~*
Looking back now, I’m struck by how much can change personally over 4–5 years. I spent a big chunk of my 30s, 50% of my waking hours, with those teammates in that environment. And life just… happens in and around that work. My farewell email mentioned that when I joined Substack, I had hair, wasn’t a runner, and didn’t have a cat or a baby. All of that is different now.

So much life swept through me and my reports. I sat with people through seasons that were deeply happy and deeply sad. It was a privilege to witness people through all of it.
*~ End tangent ~*

Three chaotic people who used to work at Substack.

Gut

By the four-and-a-half-year mark, I felt in my gut that it was time to move on. It didn’t smack me in one day. More like a familiar rising tide of certainty.

When curiosity dims—when I’m not showing up with the same presence, joy, and intensity—internal alarm bells ring. Since the start of my career, I’ve optimized for work that’s genuinely interesting to me. Curiosity has been my compass, and following it has served me well.

So when my gut says it’s time, it’s just time. I take the wheel and make a change. Even if what comes next is murky.

Coincidentally, I left my first job after four years and wrapped People & Company after a similar stint. Maybe I have a natural “work shelf life.” And so here we are: the end of a chapter as an ops leader at Substack and the start of something new.

Everything and nothing

There’s this lovely children’s book we’ve been reading to the kiddo: Let’s Do Everything and Nothing by Julia Kuo. The title has been ringing in my head as I think about what’s next. At this point in life, what do I want to make space for? Everything and nothing.

As of now, we’re in the middle of a few slow weeks without expectations. My wife watched the toddler for a few days while I went on a solo Iceland trip to reboot. It was stunning and wonderful. More adventures with family are brewing.

Yes, I have an appetite to eventually lead ops for another organization. And I’ve started taking on select ops advisory work that energizes me. But in this season, I feel a strong pull to focus on creative work of my own.

There are apps, art, and experiments on my mind. Some small and absurd, others more ambitious. They’ve been tugging at me. It feels like the creative technologist / artist in me has been on the bench for a few years (for good reason). The tools today, especially with AI, open up possibilities to build interactive projects that used to feel out of reach. And in my experience, even the strangest creative detours inform how I operate down the road.

So I’m deliberately making space to make—to grab hold of my curiosity. Years from now, I’d rather say I built ten weird and wonderful projects than squeeze a few more drops out of the same well.

Curiosity, for me, isn’t a spark. It’s a tool. You use it to dig. You follow it deeper into a space until you’ve excavated every corner. And when that ground stops giving as much, you don’t wait around. You pick up your lamp and look for the next pocket of possibility. And sometimes you return to old caves with fresh eyes!

I’m itching to see what I’ll uncover, which is exactly why I’ve got to go digging. The work’s shape is undetermined, but I’m confident it will take shape and that the journey will shape me too.

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