Finding the Right Ladder
It’s one of those mornings when it’s hazy and gloomy outside, and I’m struggling to find the inspiration to work. I left my job at Semgrep recently and have been working on something new in Singapore. More on that later.
Historically, I’ve struggled to accept a slow morning. Today, though, I decided to get an artisanal espresso, put on some mellow music, and stare at a wall for a bit. Somewhere along the way, my mind wandered back to college, when I was trying to figure out what I wanted for myself.
I remember feeling overwhelmed by all the choices in front of me. Big tech or a startup? What kind of engineering did I want to do? What about promotions, titles, and the different paths I could take? I felt like I had to get these decisions right, as if each one could set the course for my career. Looking back, things were rarely that black and white.
Over the years, I’ve also found myself talking to people who had taken different paths (startups, big tech, getting into farming, etc.) to see what I could learn from their experiences. Of course, hearing about an experience is no substitute for living it yourself. There’s only so much you can learn secondhand, but it’s a good place to start.
For all the uncertainty, the one thing I was sure about was starting my own company someday. Looking back, I just didn’t know how to get there (and still don’t). The more people I spoke to, the clearer it became that I couldn’t collect enough opinions to find the answer. Some emphasized the value of a big company, while others swore by the ownership and pace of an early-stage startup. Some valued breadth, while others pushed for depth. They weren’t necessarily contradicting one another. They were making choices based on what mattered to them.
I could keep collecting opinions, but at some point, I had to figure out what mattered to me.
That left me with a more personal question: what did I actually want out of my own life? I’ve talked about this at length with friends, and we often come back to a simple version of that question: what gets you excited to wake up in the morning? I’ve come to think of this as finding your “grounding factor”.
I think the answer matters a lot when it comes to your career. Maybe it’s:
the freedom to work on hard problems, the satisfaction of building something from scratch, or the people you get to spend your days with.
Maybe work is a means to build a comfortable life outside the office. Or maybe it’s a big part of what makes life exciting in the first place. It’s easy to look at someone else’s career and want the same title, company, or accomplishments for yourself. But we rarely see the trade-offs behind them, or whether we’d actually want the life that comes with them.
Having your own grounding factor gives you something to return to when making decisions, especially during temporary setbacks. A bad manager, a disappointing quarter, or a missed promotion can make you question whether to stay or leave. What makes sense depends on what you want from your career in the first place.
Of course, what matters to you can change over time, too. You don’t need to have everything figured out before making your next move. Sometimes, you only discover what you want by trying something and seeing how it feels.
Once you have some sense of what matters to you, it changes how you think about the steps you take to get there. Yet I think we often do the opposite. We focus on the next promotion, title, or milestone before asking ourselves why we want it in the first place.
I’ve started to think that the more interesting question is what kind of life we want to build, and what role work plays in it. Maybe it’s starting a company, becoming a great engineer, or leading a team. Maybe it’s having the time and freedom to spend with your family, or doing work that leaves you with enough energy to enjoy everything outside it. There isn’t a hierarchy to these things. They matter differently to different people.
I knew I wanted to start a company someday, but figuring out how to get there was never going to be as simple as following someone else’s path. Looking back, the experiences that helped me most weren’t necessarily the ones that looked best on paper. They were the ones that taught me something about the kind of work I enjoy, the people I want to learn from, and the life I want to build. Each experience gave me a little more clarity, even when I couldn’t see exactly where it was leading at the time.
I still don’t have all the answers. I’m figuring things out as I go, just as I was in college. But I’m more comfortable with the uncertainty now. I don’t need to know exactly where a path will lead before taking the first few steps, and I don’t need someone else’s path to tell me whether I’m moving in the right direction.
Maybe finding the right ladder is less about knowing exactly where you’ll end up, and more about having a sense of what makes the journey worth taking.