Roads less traveled: the non-linear career path

I cringe when people ask me about my career path. I don't know how to answer because it's a story that doesn't hold together particularly well. I did one thing, and then I did something else, and then something completely different. It wasn't strategic. I've never had a five-year plan.

There are some jobs I lament staying in for too long, and some experiences I lament not sticking to longer (e.g., my small business). There are times I should have taken a leap and didn't. There are times I took the leap.

I will probably never be one of those people who can say I've worked in a particular field for 20 years, and I worry about that sometimes. How does it sound when I talk about the jobs I've had? How do I compare to someone else going for a role I want?

I've led teams to create billion dollar proposals for government projects. I've owned my own storefront business. I've been a therapist in training. I've run countywide programs for a nonprofit. I've dropped out of film school. I've built people programs and processes for startups from the ground up. I've worked for major infrastructure firms, financial tech, HR tech, mental health service providers, and a research institute, among others.

To some people that might seem like an interesting background. To others, it probably sounds scattered and confused. Maybe I'm agnostic to industry and role, and live for the challenge. Or maybe I just have a particular set of skills and interests that go beyond what following one career path would give me?

I would like to think that recruiters would hear all this and think of me as a scrappy person who isn’t afraid to jump into the deep end. I would also like to think the people who are at the beginning of their careers asking me how I got to where I am understand there is nothing wrong with traveling a non-linear career path. There is also nothing wrong with not being intensely passionate about only one thing.

So when people ask me about my career path, I talk about what I’ve learned (a lot about people’s behaviors, storytelling, operational efficiency and project management), what has challenged me at times (change management and leadership buy-in), and what projects I am proud of (Culture Amp’s onboarding processes and Wellbeing Guide).

I don’t try to create a linear story or make it seem like this was all part of my master plan. If two proverbial roads diverged in the wood, and I needed to get on one for whatever reason, I got on it.

And that has made all the difference.