Depth Chart

Joining a great startup can be intimidating. Everyone around you is incredibly smart, fast, and unnervingly fluent in their own esoteric domain. You’re pushed hard to keep up. Until one day things start to click, and suddenly you’re genuinely enjoying the work, feeling like you somehow got an invite to join an exclusive club.

For many ambitious and talented people, that pressure is part of the appeal. But over time, that experience changes. Your first manager is promoted to a director and has less time for you. The gifted peer who mentored you moves on to a different company. Departments of one become real teams. And you yourself might be asked to fill in one of these new gaps in the org chart.

You’re probably excited for your new role initially, but after a few months it’s easy to feel like the company has lost its magic. All those incredibly talented colleagues you used to work with are doing their own thing, and you aren’t being pushed to learn at the same rate.

People sometimes describe this by saying “The company isn’t what it used to be”. But often it doesn’t mean the company has lost its way, but that you’ve lost track of your role in the company. Now you’re expected to be the incredible colleague pushing others and pulling them up to your level.

I view it like a depth chart in team sports. I remember the first day of soccer tryouts freshman year when I was standing next to seniors who had a foot, two vocal registers, and half an inch of facial hair more than me. From my spot (deep) on the bench, these people felt superhuman. But a couple years later I was keeping up. Then I was the senior intimidating (and being admired by) the next batch of freshmen, whether I was ready for it or not.

Startups work the same way, just without a chart posted on the wall. If you’re good and you want it, one day you’ll look around and realize you’re the person others are looking to for advice. Or if you don’t realize it, you’ll sit around waiting to get pushed— career at a standstill— while everyone else expects you to pull.

It can be an uncomfortable transition. Being pushed is straightforward— it’s obvious what you need to do to keep up, where you’re falling behind, and what good looks like. Leading and pulling others up to your level isn’t. It means your decisions have second-order effects. You’re giving advice without being sure it’s right. You’re shaping work you won’t personally do. You’re working with people who are expecting you to push them, not the reverse.

I remember being confused the first time I got asked for career advice. What did I, a 26 year old engineer, have to say that’s valuable to someone else in their career? Quite likely nothing. But it was still a clear sign that my role was changing. I could either lean into it, or shy away and hope that someone else would show up to take over. It’s all too easy to choose the latter without realizing that you’re choosing at all.

This dynamic doesn’t disappear as you get more senior, the timelines just compress. Even senior executives start their first day expecting to be pushed, needing a firehose of context about their new company’s specific norms, culture, and business before they can make effective decisions. The difference is that they’ve risen through the ranks by successfully navigating these push-to-pull transitions before. They’ve recognized the pattern and how to act on it so that they can move from being pushed to pulling others in weeks or months, not years. That’s how they get to their level.

I view pushing and pulling as complementary skills, where I want to do a mix of both. If I’m only ever being pushed, I’m capping my ability to lead and compound impact. If I’m only ever pulling others up, I’m not directly advancing my skills and losing touch with the work that earned me credibility in the first place.

It’s more like a portfolio than a ladder. Any given role will bias one way or the other, so the real work is being intentional about which mode I’m in, and where I want to be next. Sometimes that means staying put. Sometimes it means leaving and looking to others for guidance again. The failure mode isn’t picking wrong, it’s drifting between modes aimlessly or not reflecting honestly about what mode you’re in and where you want to be.

Like a portfolio, I try to check in ~quarterly: Who did I learn from? How did I compound my impact? What type of work do I want to gravitate toward next? The magic of a startup isn’t that it’ll push you forever, it’s that it gives you the freedom to choose for yourself when to stop waiting and start leading.