10 things I wish I knew about careers when I started

I wrote this for all your college-age or new grad buddies...

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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. 

2. Use your 20s to collect experiences and learn about your strengths, NOT climb the ladder

If you’re overly fixated on “being right” about your career path early on, or finding the perfect first job, then you’re going to miss all the learning that comes with being wrong. Self-knowledge is one of the most valuable things you can get out of your twenties. That means it’s perfectly okay to pick the wrong job a few times, or take on a really risky project and fail. 

After every experience – project or job– pay attention to what you loved, what you hated, what you were good at, and what you were bad at. Write those things down. I really believe that the most powerful thing you can do in your 20s is get an in-depth and robust sense of these four lists: 

The way you fill out these lists is by collecting experiences. Just trying things. What job should you take after college? Try something! Figure out the job version of your favorite hobby and try it. There are so many different ways to make money (what a job is)... sometimes the most important thing is just to start rather than feel paralyzed by finding the perfect thing. I can almost guarantee you that your first job won’t be your forever job, but you’ll learn a ton in 2 years and then you can move on. 

Your goal is not to find the perfect role; it is to learn. Learning means that every job and every chapter should give you more data to put on your lists. It is fine to look at your manager and the people more senior than you and think that you don’t want their jobs — that’s good data!

Eventually what you’re looking for is the overlap between your lists — particularly the overlap between what you love doing and what you’re exceptional at. That overlap is what will lead you to roles that make you successful and (most importantly) happy. That’s the key to finding your unique superpowers. Every signal that you get about what you love doing and are exceptional at is a signal about what job you should take next or, said better, what experiment you should try next. 

That’s ultimately the theory of strengths-based management – that if people’s work is aligned to their strengths they tend to be higher performers – and I think spending your 20s trying to deeply understand your individual, unique strengths will take you much farther than rushing to an “answer” about what you should do in life or racing to the top of a ladder at your first job. Sadly one thing you learn over time is that it’s relatively easy to be successful and unhappy. Seeking success and happiness together requires a journey of self-knowledge and not just blindly climbing a ladder. 

If you rush through this meaningful phase of getting to know yourself, you can hit a plateau in your thirties and forties. You can ask these questions in your forties if you want to and many people do, but it’s so powerful if you use your 20s to ask them and use the answers to help craft your path. 

There are many chapters to a career. When you’re young, it feels like you have to “get there” as fast as possible, but it is truly better to play the long game. You end up happier, more fulfilled, and likely more successful. 

3. Take risks

A good way to gather lots of data for your lists is to seek what I call J-Curve jobs. J-Curve jobs are risky career moves that could potentially have a big payoff and upskill you extremely quickly. But they feel really uncomfortable because you’re stepping into shoes that are way too big for you to fill, and because failure is a real possibility. 

I fell in love with J-Curve jobs when I was asked to help build a phone at Facebook. I knew nothing about mobile and had to decide whether to leave my comfortable job on Facebook’s People team. A friend asked me, “Why don’t you go see how actually good you are?” I took the leap and eventually, I came out the other side as a completely different person. Because I chose to take that risk, I had a completely different understanding of what I was good at and a totally different set of career opportunities than I had at the beginning. Each J-Curve job I’ve taken since has been the same.

Now is the time to take big risks. Put on your learner hat and get comfortable with being uncomfortable. Classic financial investment advice for people in their twenties is to have high-risk portfolios that take advantage of compounding growth – simply put, you have many years ahead of you, now is the time to take bigger bets that might pay off. Similarly, the first 10 years of your career is the perfect time to take leaps that help you figure out the boundaries of what you’re good at.

4. It is more important to learn than to know

I think there’s a fear when you’re early in your career that you’re supposed to know things. The first time I was given a management job, I was like, shit, am I supposed to know how to do this?

Stop worrying about that. Make learning a strength of yours, and embrace the identity of someone who doesn’t need to know everything. When I started at Facebook, Chris Cox was the head of HR, and he’d never run HR before. I remember watching him with people who would use big fancy words and acronyms and try to tell him how to do HR at Facebook, and Chris would just look at them with these big eyes and say, “I don’t know what you mean by that. Can you explain it to me?” It was so beautiful — and it took away none of his power. 

The best people in the world are confident enough in themselves to say, “I don’t know.” And the best leaders in the world are great learners. One thing a lot of people don’t recognize about Mark Zuckerberg is that he is the fastest learner you’ve ever met in your life. It’s a huge, standout strength of his. Most of the CEOs that started as founders (Bill Gates, Tobi Lutke, Jeff Bezos, Mark, etc.) have learning as a strength – they are voracious learners because they realize that to keep up with their company’s growth, and eventually with the growth and change happening in the world, they have to learn.

If you learn how to learn in the working world — like a different phase of school — it can become an automatic superpower that opens up all sorts of doors. Try saying, “explain that to me,” or “what do you mean by that?” or “I don’t know how to do this, can you help me?” Learning how to ask questions that feel stupid was one of the most important things that helped accelerate my growth and ultimately my career. I am now unafraid of things I don’t know or don’t understand because I know I can learn. I wish it was a skill I had figured out earlier. 

Truly, this advice is for any career stage — the world around us is evolving so fast that the “learners” will almost always win over the “knowers.”

5. Be useful

One of the most powerful things you can “be” in a job has nothing to do with your title. You want to be the person that everyone wants to work with. 

The absolute best way to be that person is to focus on being useful. Look around at the people you work with and ask how you can be useful to them — regardless of titles and job descriptions. How can you help them meet their goals? How can you make your boss’s job easier? How can you make someone else look good? You want to be the person that everyone trusts to make things happen, who makes others look good, and who everyone wants to work with again. 

THAT is what gets you invited to interesting J-Curve opportunities. Being useful – the person that everyone wants on their team – is a superpower that no one talks about. It gets you access to opportunities that you could never apply for. 

Focus on being useful. Just trust me. 

6. Don’t be a dick

If the whole point is that you want people to WANT to work with you again… don’t be a dick. There will be moments when you think you’re powerful and you think you can stomp all over people, but in five years, the person you were a dick to will have founded the next DoorDash or whatever. Don’t be a dick to the interns or the assistants just because you think you’re more powerful than them. 

The only regrets I have from my career are times when I didn’t treat people as well as they deserved. Nothing is worth it.

Also, don’t ruin it all when you leave. It’s not that you can’t leave, it’s just that you should leave well. You spent all this time building relationships with people at the company and they’ve invested in you. I don’t mean give 6 months’ notice, I mean don’t burn the house down when you leave or leave with no notice or steal clients or whatever. It’s pretty simple, but you’d be amazed at how many people screw everything up on their way out the door. 

The only thing you take with you when you leave a company, truly, is learning and relationships. Don’t f**k up the relationships on the way out.

7. Follow great people

Eric Schmidt famously told Sheryl Sandberg, “If you’re offered a seat on a rocket ship, don’t ask what seat. Just get on.” He said that careers take care of themselves at companies that are growing quickly. 

Here’s my take — it is much much harder than it used to be to spot the rocketships. My advice: screw the companies, follow great people. 

The best way to manage your career is to find those incredible people who will shape the next few steps of your journey. I followed my boss Elliot Schrage from Google to Facebook. Then from Facebook, I followed Bret Taylor to Quip, and after that I went back to work with Mark Zuckerberg and his wife Priscilla Chan at their philanthropy … every job I’ve ever had has been because of people I’ve worked with before.

When I look for who to follow, I look for brilliant managers, mentors, and even senior peers who I have loved learning from, who make me better, and who are invested in me in some way. They push me to be better. 

And this ties back to my point about being useful — I was useful to these people, and they took me with them on their adventures.

8. Build a network by making friends at work

One of the most powerful things you can have as you exit your twenties is a group of people scattered across interesting companies who would do anything for you, and vice versa.

The best way to build that network is by staying in touch with people you’ve loved working with in the past. One of my earliest work experiences was working in Google’s communications department. We grew from 25 people to 125 people in a year. I was 23 or 24 at the time, and I was just trying to hold it together, but I made a bunch of friends while I was there. And interestingly, many of those people went on to become the Heads of Communications at all the other companies in the valley — Facebook, Square, Pinterest, Stripe, Tesla. It was my first education in the idea that every person you work with is going to go on an adventure of their own. And sometimes, you’ll want to go with them. 

So, make work friends, make sure they want to work with you again (be useful to them), and hopefully they’ll call you next time they go somewhere fun and interesting.

Building friendships can sometimes take a backseat to day-to-day work, so you really need to make time for it. You can set a goal of having coffee or an informal Zoom with someone interesting 1x per week or 1x per month. Make the space to get to know them as people, not just as employee robots.

When I left Facebook, I made a list of every single person I loved working with. Now I do it every time I leave a company. It’s just a spreadsheet of names but what I do is scan it once in a while and think, “have I talked to that person in a while?” I reach out in an informal way and try to stay connected with people. I’m not as methodical or systematic as other people I know, but I do, now, have a really powerful network. And building a powerful network is not more complicated than that. It is as simple as ensuring you stay connected to people you think are smart and talented, and it is invaluable to everything that will happen to you during your career.

I’ll also say that for me, almost all of the people in my support system – mentors, people I turn to for advice, the first people I think of for jobs – are people I’ve worked with before in some capacity or another. They’re the ones I call when I need to make a hard decision because people who know you and your work are better at helping you through the phases of your life. They’ve seen you in many different contexts over the decades, and that’s something you just can’t replace.

9. Learn what good looks like

When I see founders start companies right out of college, I think about how they’ve never actually experienced what a good company feels like from the inside. They’ve never had a manager, let alone managed anyone. They’ve never had to sit through an All Hands, let alone a good one. The list goes on. 

There is immense value in having one tour of duty at a well-run, medium-sized company, like a growing Stripe, Facebook, or Slack. Or the equivalent in another industry. I have a friend who worked at McKinsey for two years, and I saw how valuable that experience was to her — it taught her about management, how to be exceptional at execution, and professionalism. 

Beware of the badly run company :) But if you can gift yourself 2-4 years at a well-run company with a good manager, there’s no better training. None.

10. Don’t rush through the great managers

You’ll only have maybe two great managers in your life, so don’t take them for granted. I spent a lot of the first 10 years of my career trying to level up, but at some point, I became senior enough to realize that I would never have another manager who was a teacher and an advocate. I was always the most senior person in the room. 

Honestly, sometimes I just want to go back and be an intern for the smartest, most caring, most thoughtful leader I can find. I’m surprised at how many of my friends feel the same way. If I could go back in time, I would tell myself to slow down and love the moments when you have a real, exceptional manager — someone who takes pride in the craft of making others better.

To the point about following great people, if I could go back in time and do my 20s again, this is what I would optimize for: find exceptional managers that you want to be like when you “grow up” and go work for them. Almost doesn’t matter what job. 

Those people can be a force multiplier for your career and they can shape who you become as a leader. And they simply don’t come around all that often. Do NOT take them for granted.

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When I look back at this list, I realize there are two themes. One is about collecting experiences. The other is about collecting people — finding great people and traveling with them. Both will serve you in invaluable ways over your career. Both will guide you to places you could not have imagined when you started working. 

Focusing on people and learning about yourself is a much surer bet for success than trying to get it “right” immediately after college or trying to pick a rocketship company like Facebook to join early. It is definitely true that one stint at a well-run, fast growing company will change the trajectory of your career, but truly, those opportunities are hard to spot. I stumbled into Facebook by following Elliot Schrage. It was a lucky choice. Most people I know who have ended up at one of these “rocketships” didn’t end up there because they were a great picker, they feel like they ended up there by mistake. 

Instead, focus on the things you can control. Follow great people. Take risks. Focus on your strengths and learning about yourself. 

At the end of your 20s, you want to have clear lists — what you love, what you hate, what you’re good at, what you’re bad at. If you know yourself well, you will know what direction to point yourself in and what ladder to climb. You will know what makes you happy, fulfilled, and powerful at work. You also want to have a community – interesting people that you’re desperate to work with again, and wonderful people who want to help you grow and attain whatever goals you end up having. 

Collect people and experiences – that is the magic that can set you up for a long and fulfilling career.