10 things I wish I knew about careers when I started
I wrote this for all your college-age or new grad buddies...
👋Hi! I'm Molly. This is where I share the lessons I’ve learned from building fast-moving, messy, ambitious companies. For more from me, you can also find me on the WorkLife Podcast, on LinkedIn, and in Glue Club, a community for leaders who care about building great companies.
I have never been one of those people who knew what I wanted to do for work. You know those people? The ones who have known they wanted to be a doctor since they were 14? In college, my best friend knew she wanted to become a paper conservationist — someone who restores and maintains old documents. And that’s what she is today.
Cut to me, who majored in African History in college but ended up in tech. And my first job out of school was leading wilderness trips in Patagonia and Alaska. My parents were… unsure that that was a real job.
There’s some cultural programming and family programming telling you that as a 20-year-old you should know what you want to do. I know I felt that way and I see it in my younger friends as they head off to college.
But over my 20 years since college, I’ve become a big believer in the winding path as a powerful way to figure out the highest and best value you can bring to the world. I want to make the case that not knowing is not only OK, but that it can actually be a strength if you’re willing to lean into it and use the first part of your career to learn about yourself. It’s a different (and, I think, better!) way to do your twenties: “figure it out mode.” Eventually, you want to find the jobs and situations where it’s full of the stuff you are great at, you love what you’re doing, AND the world also highly values what you have to offer. To start that winding path, you have to use your 20s to collect data about yourself. That means you get to those bigger answers by 30 or 35 — not 25.
To be honest, I’m a general believer that some amount of exploration is good for anyone — even those of you who are like my college best friend and feel sure of what you want to do. I’m thinking of the friends who made it all the way through medical school and got to residency, only to realize they didn’t want to be doctors.
I’d argue everyone’s a little bit wrong about what they want to do at the beginning and your twenties are a great time to dig into that. You know you want to be a doctor? OK, what kind? A surgeon — why? One of my friends who started in medical school ended up leaving but then eventually led part of the business at One Medical. Embrace an open mindset and you never know where you will end up.
If you don’t know what you want to do or if you’re unsure, don’t race to put a stake in the ground, and don’t fall into the trap of pretending you know or feeling like you have to.
I also spent a lot of my early career rushing to the top of a ladder. If I could go back and give my 20-year-old self some advice, it would be to stop obsessing about leveling up and focus more on learning about myself and the world. A powerful foundation for a great career is a clear and deep sense of what you’re exceptional at (which is built from experiences) and a strong, deep network full of people who love working with you.
Sidenote: I went to college, but I think a lot of this advice is true even if you didn’t. I’ve become a big fan of less expensive options for school and getting training for jobs that leaves you debt-free instead of saddling yourself with debt that can make it hard to do things like take risks. If you didn’t graduate from college the most important thing is to not let that hold you back. Some of my most successful friends started by dropping out or not going, and they let the winding, exploratory path lead them to incredibly valuable skills.
And for any of you heading into college who aren’t sure what to major in, the same winding path idea applies. If you know you want to be an engineer — a career that is highly valuable these days — then definitely major in engineering. But stay open to the idea that you might want to be a product manager or a technical designer. And if you don’t know what you want to do, I would say that a great approach to college is to realize that learning about yourself — what you love, what you hate, what you’re great at, what you’re bad at — is more important than picking a major.
Alrighty so here are 10 things I wish someone had told me at the beginning of my 20s:
1. Once you get on the treadmill it’s hard to get off
One of the best things you can do right out of college is go do something different than whatever is a “traditional” path for you. (If you have the opportunity and can figure it out financially.) If you want to end up in tech or finance, then instead of going directly into Facebook or Morgan Stanley, go be an intern for companies in another country, or work on a farm, or go work on a Rhino preserve. Before you hop on the corporate treadmill, doing something that is truly different can help you grow in immeasurable ways.
Going off the beaten path can teach you an enormous amount about yourself and how other people live. I spent a year and a half leading trips for the National Outdoor Leadership School (NOLS) and it was the best management training I’ve had. I spent 30 straight days in pouring rain in Patagonia trying to help my students learn to be independent leaders. It made me grow up, and it also made me learn a lot about what I was good at.
[Side note to advocate for studying abroad in college if your school will give you credit: spending a semester in Cameroon with the School for International Training was among the best things I have done in my life.]
Once you get into the white collar corporate world, it’s hard to pause and do other things. This is something you only learn after you get on the treadmill… I always thought I’d go back to NOLS and continue being an instructor, but I never did.
