5 Things I Wish I'd Known About Careers When I Was Younger

by Jess Whittlestone
Originally Published: 
A man and woman with name tags talking about careers and smiling

In my final year of college, it seemed like everyone I knew had a pretty good idea what they wanted to do after graduation—except for me. Most of my friends had lined up jobs before they graduated, whereas I had avoided thinking about it. I majored in math and philosophy, and while the former certainly gave me options—finance and teaching being the most obvious ones—none of those options really appealed to me. Philosophy didn’t help me much, not exactly being a commonly-applied subject…

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Looking back, I realize that I was wrong in thinking everyone around me knew what they were doing. Now when I talk to those friends who seemed to have had everything planned out, many of them seem unhappy with their jobs. Sure, a few people decide at age 15 that they want to become a doctor or lawyer—and some of them really stick with it—but in my experience, those people are in the minority. Many people are still confused about “what to do with their lives” at age 40, let alone fresh out of college in their early 20s.

I was recently invited back to my college at Oxford to talk to the students about what it was like to graduate without a plan and what I’ve done since then—including a brief stint in finance, helping to set up and run a nonprofit, and starting a doctorate in Behavioral Science (plus writing for Cafe!). This got me thinking about the things I’ve learned over the past few years.

1. It’s totally fine and normal to be confused.


When kids are young, we often ask them what they want to be when they grow up, but we don’t take their answers too seriously. “Sure, you want to be an actor/truck driver/fairy princess now, but your preferences might just change a bit over time…” Once young people get to college, though, we expect them to know what career path they’re going to choose and to stick to it, more or less. Why is that?

If you’ve never had a full-time job in your life, you can’t possibly know what you’re going to want to do for the next 40 years. I think this should be more readily acknowledged. Pressure to pick a profession can cause a great deal of stress: A survey conducted by the National Union of Students last year found that “worries about graduate employment” are a significant factor in mental health issues among students.

Underlining the fact that these decisions can take time—and that that’s okay—might reduce this pressure. It would also prevent people from making panicked decisions (“I guess I’ll go to law school/become a teacher/go into banking, then!”) and ending up in jobs for which they’re actually not well suited.

2. Career choice isn’t a big, one-time decision.

Part of the reason there’s a lot of pressure on people to “pick a career” is that it’s framed as a big, one-time-only choice. The message we get is that when we graduate, we need to decide “what we’re going to do for the rest of our lives.”

I’ve found it helpful to think about this differently: Your career is made up of a series of small decisions, none of which is immediately set in stone. When you graduate, you don’t need to decide what you’re going to do for the rest of your life—only what you’re going to do for the next few months or years.

Of course, certain decisions will lead you to commit to a specific track more than others. For example, going to medical school is costly for someone who is unsure about wanting to be a doctor. But the more unsure you are about what you want to do, the more it makes sense to try many different things that keep your options open and allow you to learn about what you actually enjoy and are good at.

3. It’s hard to know what you’ll enjoy until you actually try things.

The summer after I graduated, I applied for a nannying job in London. I didn’t particularly want to be a nanny, but the job paid well, was only a few hours a week, and gave me lots of freedom, so it seemed like a good thing for the time being. In the end, I didn’t get the nannying job, but the father of the family I interviewed with offered me an internship at his corporate finance firm. (I’m not sure what this says about me as a person…)

At first, I was hesitant. I didn’t think I’d enjoy working in finance. But because I thought I might learn something (and I didn’t have any other, better plans at that stage), I took the job and stayed for a three-month internship. Although I decided not to continue after the internship (I couldn’t hack the long hours, and I wanted to do something that felt more meaningful), I enjoyed it a lot more than I expected. I found the work itself pretty interesting, challenging and rewarding.

On the flip side, I’m currently working towards my PhD, which I’d always thought I’d love (and mostly do!), but I now realize this path has several drawbacks. I don’t love the lack of structure and feedback or the solitariness of it all—things I hadn’t thought about much beforehand.

It’s hard to predict what you’ll enjoy until you actually try things. We often make judgements about different jobs based on our vague impressions of the work involved, but those impressions can turn out to be wrong. Which brings me to…

4. The first few years of your career are for trying things, learning, and building skills.

It takes most people years, sometimes even decades, of working to really learn what they enjoy. But what if you could massively speed up this process? Since it’s hard to predict which jobs we’ll enjoy without firsthand knowledge, the best way to find out what really suits you is to try lots of different things. You might not like the first thing you try—and that’s fine, even expected. By the time you’ve done a few different jobs or internships in different industries, you’ll have a much better picture of what suits you and what doesn’t.

If you don’t have a career path already laid out, one of the best post-graduation strategies might be to spend a year or two in a series of short-term jobs or internships in different industries. You’ll quickly learn what matters to you in a job, what doesn’t work so well, and where you can excel.

I actually planned to do this myself, but then after my finance internship I started working for an organization called 80,000 Hours, which I enjoyed so much I ended up staying for a year. It was a small nonprofit that was just getting started at the time, so I took on a lot of responsibility very quickly and was able to work in a variety of different roles. This made the job a really fun, challenging learning opportunity in my first year out of school.

5. Don’t let yourself be constrained by conventional career paths

A friend of mine graduated around the same time as I did and, like me, found most of the traditional career paths unappealing, so he decided to write a book on popular statistics. The book did much better than he expected, and he has been able to live off the royalties for the past few years, while he travels around the world writing and working on different projects that interest him. Now he’s starting his own business in London.

The point here is not to go write a book if you’re at a loss as to what else to do, but simply that you don’t have to be constrained by what’s typically considered a normal “career.” There are plenty of ways to make money that don’t necessarily take up all of your time—tutoring or freelancing, for example. If you can find a way to make enough money to live on, you can spend the rest of your time doing what you really care about, whether that’s learning new skills, writing or creating things, or starting your own business.

©john ivar andresen/Flickr

The common thread in all these points is that you should treat your 20s as a time to learn: Learn about yourself; learn about the world; learn new skills. Give yourself a few years before you expect anything indelible of yourself—and especially before you expect to “know what you want to do.”

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