Illustration: Oscar Ramos Orozco

A Troublemaker’s Manifesto: The Benefits of Wandering

Psychologists are now seriously discussing extending the start of “adulthood” to 25. This is because, to them, young people are taking a while to “get started,” or to begin checking all of the boxes that used to define adulthood. To this I say: good.

When a young person doesn’t logically and immediately hop from one job to the next it is usually viewed as a bad thing, a sign that they’re just not ready to grow up. Oftentimes they’ll graduate and panic when they face the mountain of possibilities and uncertainty that is the modern career landscape.

That panic happens for good reason. From the ages of 5 to 22, most of us live what I call a “checkbox life,” one where our big-picture choices are made for us with the short-term focus of checking off the next box. We’re going to school, graduating college, and getting a job. Check, check, check.

But when we’re faced with no more boxes to check, many of us do one of two things. We either become paralyzed with options or we run back to find more checkboxes. We avoid the open-ended possibilities and instead go back to grad school, or get a job that “makes sense” with our degree.

But I’d like to offer a different mindset: those who are “aimless” have the right idea. The short-term thinking enabled by a checkbox life usually ends in what economist David Graeber calls “bullshit jobs.” Jobs you take “just because.” Jobs that seem to exist for the sole purpose of keeping us working. Jobs where we end up frustrated because we aren’t doing them for ourselves, we’re doing them to ease the expectations of those around us. We’re doing them to check boxes. As society gets more productive and technology advances, it is these jobs that will be the first to go. As young people, the rest of our lives will be spent outrunning automation and outsourcing. Going our own way isn’t just nice, it’s required.

Going our own way isn’t just nice, it’s required.

That means the way to succeed is through curiosity, by embracing the open-endedness of our careers to do something that makes a mark. To do this, we must decouple our innate talents from our goals. In the past, we used to look at our skills or talents and work forward to find a job that fits. Now, we’re better served by asking the big questions about our impact early and work backwards. It pays to reverse engineer our careers. And that takes time. It takes mistakes. To stodgy psychologists this looks like we’re in “extended adolescence.” In reality, it’s the only rational choice.

In fact, the more our career paths confuse people stuck in the old mindset, the better. Because the skills and tools required for most jobs changes too quickly, and we can move from novice to professional faster than ever. Amazon CEO Jeff Bezos uses a similar “mission over skills” framework for his company:

Eventually the existing skills will become outmoded. Working backwards … demands that we acquire new competencies and exercise new muscles, never mind how uncomfortable and awkward-feeling those first steps might be.

The panic we feel when we are lost shouldn’t be avoided. It should be embraced, because it’s in that wandering that we find what we want to do. Succumbing to the pressure of what others expect of you just delays the inevitable. It takes time to answer the big questions like: “What kind of impact do I want to make?” Finding your place in the world takes time. It’s a long-term play that often has some short-term pains.

To stodgy psychologists this looks like we’re in “extended adolescence.” In reality, it’s the only rational choice.

In an interview with Inc. Magazine, Y-Combinator founder Paul Graham discussed this fear of taking charge as the biggest issue he saw in young people today as they entered his incubator program:

They don’t realize how independent they can be. When you’re a child, your parents tell you what you’re supposed to do. Then, you’re in school, and you’re part of this institution that tells you what to do. Then, you go work for some company, and the company tells you what to do. So people come in like baby birds in the nest and open their mouths, as if they’re expecting us to drop food in. We have to tell them, “We’re not your bosses. You’re in charge now.” Some of them are freaked out by that. Some people are meant to be employees. Other people discover they have wings and start flapping them. There’s nothing like being thrown off a cliff to make you discover that you have wings. 

If you find yourself without many obligations and unsure of what’s next, celebrate. Revel in the chance to zig when everyone around you zags. It’s likely the only time when we’re not shackled by obligation. To feel pressured by others and run away is a massive waste of an opportunity. Worse, not taking a swing at what’s important to you defeats the purpose of this whole career thing.

The next checkbox will always be waiting. Though I suspect once you get the patience and courage to go your own way, you won’t ever want to go back.

How about you?

Did it take some wandering to find your career? How’d it go?

More insights on: Career Development

Sean Blanda

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Sean is the Managing Editor and Producer of 99U. You can also find him on his personal blog and on Twitter. Sean is a co-founder of Technically Philly and Philly Tech Week.
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