I often talk with junior folks who are very concerned that if they somehow miss one rung on their career ladder, or they climb too slowly, they’ll fall to their professional death and never recover. While I understand where this fear comes from, my path has been anything but structured. I’ve wound my way through several industries before becoming the co-founder and CEO of Ethena, a Series A startup that’s reinventing compliance training.
A non-traditional path is an asset because your career progression isn’t a ladder, it’s a jungle gym. If you’re taking the generalist path, progress won’t be linear. That can feel stressful because you can feel “behind” your more specialized peers, or that you’re lost wandering in the woods.
But a generalist path can make you a great leader because you’ll know how to operate outside of your comfort zone and thrive in ambiguity. These skills are in high demand, especially in tech, where roles require people to grow really quickly. One day, you’re an individual contributor and weeks later, you have a team of 5.
Even if you’re on a more specialized path, flexing new muscles is incredibly important. It keeps you agile and dusts away mental cobwebs. Here are some of the things I took from each stop on my windy career path:
From the military: Leadership
I spent 7 years in the U.S. army, first as an engineer officer where I deployed to Afghanistan, and then in Civil Affairs, where I led training of foreign militaries in Cambodia and Mongolia.
I learned a lot in those years, but what I draw from most frequently is leadership 101. One of my favorite officers once told me that great leaders really just care (he said, “give a sh*t” but you get the idea). Great leaders care about those they have the privilege of leading. They think a lot about what their followers need, and they work hard to give them that. That’s not the same as wanting to be liked – being a great leader is more like being a great parent. It’s caring enough to say the hard thing or watch someone fail.
In doing something physically scary like jumping out of a plane or deploying to war, I also got to physically observe great leaders. The best ones projected calm especially when things got scary. Flailing your arms or raising your voice rarely help the situation. But a funny joke when things seem dark can really help keep everyone’s spirits up.
From a failed startup: start by starting
Toward the end of my time in the military, I found myself frustrated by bureaucracy. I wanted to work at a faster pace and with more autonomy. I also got really fixated on solving a problem I was facing – eating healthy with limited time. Together with a grad school friend of mine, we started a startup, Supper Meals, which aimed to connect local chefs with people looking for healthy, ready-to-eat meals. We bootstrapped the company and I learned what it takes to start a company from nothing.
I learned a lot in the year and a half that we worked on Supper, but I’ll skip ahead to the “failure” part because that taught me the most. My co-founder and I decided to wind down Supper and sell to a local company for a modest exit. But we gave our company a home and perhaps most important for me, I saw the lifecycle of starting a company and then winding it down. I realized that failure, while not ideal, isn’t actually death. It’s motivation to take what I learned, apply it, and win the next round.
I once heard an instructor in military survival school say that getting hit in the face is really helpful because you realize it’s not as painful as you think it’ll be. That’s what failing at my first startup felt like – I got hit in the face, and while I didn’t like it, it also wasn’t the end of the world.
From consulting: structure is helpful
After winding down Supper, I didn’t know what to do, so I talked with a bunch of smart people. They told me I should either join an early stage startup where my generalist skills would be useful or I should go into consulting and gain more private sector experience, until I figure out what I’m actually interested in.
I couldn’t find a startup I was passionate about so I did the default thing for “I don’t know what I want to do with my life” and became a consultant. I joined McKinsey where I stayed for a year. I’ll be honest– I did not love it. But I did learn.
But I am glad I did it for a few reasons:
- I broadened my network – this ended up being super helpful when I raised my first round of fundraising for Ethena. Previously, my network was mostly folks in the military and government, but at McKinsey, I met people who eventually became early angel investors.
- I got some of the business best practices juice in my system – it’s really helpful to know how large organizations work, even if, like me, you want to build a startup because the goal is eventually to scale it. At McKinsey, I learned a lot of management basics that I still draw on, things like how to structure meetings and how to use decks to tell stories. It’s not the sexiest stuff, but it’s incredibly helpful, especially as Ethena grows.
At Ethena: it’s all useful!
I’m now the CEO of a 50+ person company. We’ve raised over $20M in venture capital and we count companies like Netflix, Zendesk, Zoom and Carta as customers.
To be clear, none of my previous experiences “prepared” me for this. Everyday is different and my role is scaling as fast as the company is. But because I’ve had to grow and adapt in all of the different roles I’ve held, I’m pretty good at the act of figuring things out, which is basically what I do all day.
I’ve developed the skill set of figuring out what a role needs, figuring out what skills I currently have and which ones I need, and then figuring out how to get those skills.