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 Editor-in-Chief and Director of 99U. Find him on Twitter: @SeanBlanda.
load comments (49)
  • Dimitra Zervaki

    Congratulations!!! Excellent article :)

    • Radz

      Awesome! eyeopener! I am a job seeker,and this saved me from taking a job that was off my track.. phew..

  • Chuckbluz

    Sounds like another excuse for not getting on with life. Being “aimless” is bad. There is no direction, no goal and ultimately no sense of accomplishment. Instead, be decisive in your choices, build experience in different areas. Don’t get that graduate degree right away – in most cases that’s just delaying the inevitable.

    • Sasha

      I think this is all about getting ahead in your life, but moving ahead with your own goals and aspirations, and not those people tell you you “need” to do.

      • Chris Douglas

        Exactly! IMO, people with this type of response have always done what was expected of them, are now in the “bullshit jobs”, and jealous of their inability/reluctance/fear to branch out. They’ve completely lost the ability to think/act for themselves, are jealous of those who do, and so respond as above in an attempt to get those they’re jealous of to “tow the line” and get a “bullshit job”. They’re completely blinded to the point of the article, and it’s just sad.

  • Mmm

    Time for uni in my 30’s after meaningless jobs over the last 15 years. As one person said you are never too old to dream of a different life….

  • clover

    The jobs I took in my early 20s weren’t “bullshit jobs” or “just because” jobs (unless “just because” is short for “just because I need to pay my rent,” in which case, yeah, they were). They were the jobs I could get. I wasn’t looking to check boxes. Frankly, I felt like I had no choices available. I was just trying to survive. And in the course of trying to survive, I learned a lot, had some great adventures (not all of them intentional) and cobbled together a resume that, in retrospect, has a more coherent narrative thread than it seemed to have while I was building it.

    I have no problem with an “all who wander are not lost” outlook as a way to make sense of past choices, but as an actual strategy for future choices, it seems a little precious to me.

    But I don’t think this is entirely what the article’s about. The really key point, to me, is the one about agency and independence. These are key qualities for success, and they can only be gained through experience broad enough to allow for some mistakes, some learnings, and some growth.

    • Sean Blanda

      I think you hit on my intention at the end of your comment. We hop into other “checkboxes” because we’re afraid of failure or disappointing others.

  • Idea Partner

    I had dinner recently with a friend who has just finished his final CGA exams. He told me he was looking forward a lighter workload once he gets his accreditation. He complained about how much extra work the partners of his firm were throwing at him. The late nights. The long hours. He’s 35 years old. Previous to that he lived his life as described in this article. Trying a bit of this and a bit of that. Going with the flow of the day with no real goals or concrete direction. I did notice that he was less happy than before, but I also remember the hard knocks of my career before being accepted as a pier. I started when I was 22 and don’t regret a moment. At 35 it’s a lot harder to put up with the shit. I like the thinking in this article however struggle guiding my own daughters though free spirit and discipline.

  • Matthew Trinetti

    Sean, I’m practically in tears over this. This is fantastic. Thanks for making me feel a little less crazy today.

    Although this talks more of metaphorical career wandering, I took some time to physically wander. I never felt so alive. It’s a truly remarkable feeling to be able to live, if even for a moment, a life absent of should-do’s and expectations. And it turned out that my physical wandering sparked some career wandering as well.

    It’s not that the aim in life is to be aimless, but I think magic is found in a little aimlessness from time to time. I find it much easier to listen to myself, and come to “know” things better while wandering.

  • Rebecca Merrifield

    Love this article, it sums up everything I believe about work and careers. So many people let their lives be dictated by what other people expect them to do and base their choices solely on what looks good to other people when it should be about what feels good to you. I’d rather fail 100 times doing stuff I believe in than living a soulless life based on what other people think I should do to ‘get ahead’. What I learn from failing gives me the kind of experience which could never be acquired by playing by the rules. Great stuff.

  • Brady Dale

    I didn’t manage to get around to really wandering till I was 35 years old. It is beginning to look like the best move I ever made.

  • Rachel Kats

    This article just went straight to my heart. I’ve currently checked off all the boxes and am pretty much aimless, but it is the time to decide what career choices to make: either to zig or to zag. Thanks a lot for the encouraging article!

  • Wilm

    I have been a wanderer for most of adult life, exploring and getting lost along the way. With every zig or zag I find out more about myself and have met extraordinary people as well. Thanks for a great article and affirmation to keep wandering.

  • mvcvbro

    What if you aren’t going to college right out of high school?

    • Sean Blanda

      If that’s what you’d prefer, good!

  • mgrasewicz

    This article rules. Vagabonding is kind of the life philosophy behind it– i’ve started a company and am now in grad school and owe my life philosophy/career to being on the road. Regardless of checking boxes, do things on your accord. And don’t look to others to tell you what to do.

    A cool mini vacation:
    Just pick a place. Don’t plan. And go. Bring a Lonely Planet but don’t open it up until you’re on the plane. Figure out while you’re there how to survive. It will make you a much stronger person.

  • Melanie Wilson

    I’m one of those stodgy psychologists. :-) While it takes most people a while to make their way, especially where careers are concerned, I think we’ve done kids a real disservice by not allowing them to make their own decisions (and mistakes) when they’re young. That’s why they feel so vulnerable as young adults. I don’t think the answer is extending adolescence, but fostering maturity earlier.

    • Sean Blanda

      In my interview with Paul Tough a while back, he said that we have an “adversity gap.” Our children face either too much or too little adversity, and both have negative effects on growth.

  • Erik Abel Arts

    Making the decision to buy a one way ticket to New Zealand was the most liberating experience of my life. I ended up spending almost 2.5 years chasing waves around the world, making amazing friends, seeing amazing places and discovering myself. Finally one day I felt like it was time to go back home and continue building my art career. I tell every kid I know to pick a place and just GO before you have too many responsibilities and you wake up 75 yrs old wishing you would have had a better adventure.

  • Sosa

    There seems to be a lot of assumptions made here and a certain bias. I think it’s best to not put people into any box at all, such as those who start working at one job and don’t move on or those who keep moving every year. What’s best is to find what’s right for you, and I personally think that you can find that by understanding what has meaning to you and what legacy you’d like to leave. Also, I think that calling psychologists stodgy kind of diminished the quality of this work. Name calling is unnecessary to make your point! Overall, it was nice to read an opinion, but it’s not particularly new these days. Anyway, good luck to all! :)

    • Sean Blanda

      By “stodgy” I was referring to the measuring of today’s young people using standards that no longer exist.

      • Sosa

        Sure, but just like young people, not all psychologists are the same. There are quite a few psychologists and other academics looking at these current social conditions. I also haven’t really met a psychologist that used any specific measurements to characterize career success of a young adult. I don’t think this comes from psychologists but perhaps what you think people are expecting of you.

        I think these kinds of things make people feel good and affirmed, but I guess what I’m trying to say is that at the end of the day, there is no one correct path or right thing to do, and instead of calling everyone else conformist, it’s better to understand that everyone has a reason for what he or she is doing, whether you understand it or not. Discussion is a great way to get there!

  • Srinivas Rao

    That would be an understatement for me Sean. I didn’t just wander. Every job I had for the first part of my career was a bullshit job. I’m 35 now. You make some great points in this. The problem with a checkbox life is that your world becomes a cluttered canvas. Then you can’t create something new or something that’s never existed before.

    • Crystal Street

      Right there with you, Srini! My entire 20s was spend “wandering” and then I found my calling. Yet, I still wandered. ;) Perpetual reinvention and avoiding the checkboxes– that’s the sweet spot.

  • Mj Banzon

    I love reading 99u posts. These are simply eye-openers. Kudos to the writers.

  • Brooke Rothman

    I SO needed to see this today. Often times we make choices based on what is comfortable and safe. Really growth happens when we have the courage to try something new and unfamiliar. Thanks Sean for reminding us of that. This was an awesome and inspiring article.

  • Tama Lancaster

    I just loved this article, Sean. So many people seem so settled with their very first job that they tend to make the wanderers feel guilty and insecure. But, like you say, it’s totally okay to ‘Revel in the chance to zig when everyone around you zags.’

  • Stoleco

    I love this manifesto and think it is inspiring and applicable to people of all ages taking a new step in their professional lives.

  • Hifi1

    I wandered until 45. Until then no kids, no mortgage. So why not? Lived poor, but fulfilled.

  • Darci

    47 years old and still wandering.

  • Pierre

    74 and figuring I might keep wandering a few more years till I start stabilizing

  • Monique

    Definitely, working mind-numbing jobs was a killer for me, until I somehow stumbled upon a very unlikely career – life drawing modelling. I am my own boss, I take jobs when I am able to, I am in charge when I am on the stage, it is my job to come up with the creative poses, and I get to meet all kinds of interesting people from all walks of life. It doesn’t pay much but I do enjoy it. My next foray into a conscious kick-butt career is permaculture, the possibilities are endless!

    Thank you for a stellar read, and for the oh-so true information of our times.


  • Ianah Maia

    Wow! I’m exactly at this moment in life. Felt desperate since I graduated exactly because there was no more checkboxes. And the steady job checkbox wasn’t fulfilling me. Since I was feeling like this for almost a year, I started to allow myself to wander and let the answer to “what am I supposed to do” simply appear on my path. Great text!! Thanks!

  • Anon

    Interesting, provided someone’s willing to help pay for all those wanderings and changes. What about rent plus course fees plus spiralling cost of living? Wandering is for those whose parents made money through precisely that ‘outmoded’ thinking.

    • Keith

      I disagree… Wandering is not about avoiding responsibility and not being able to support yourself. And it is not about creating no value and mooching off of the resources of others. Wandering is about being ok with not know where the path will end. It is about trusting your instincts and your genuine interest to lead you in the right direction, the place where you can make an impact like no other.

      I am a designer… I love making leather bags. I started skateboarding a year ago and recently started doing custom artwork on skateboard decks. And I have always been in love with the idea of becoming a Japanese sword maker, even though I have no connection to Japanese culture. Now I am studying in Japan and trying to find someone to teach me swordmaking. I have no idea of how these disparate loves in my life will connect. But when they do connect, it will a combination that is almost unheard of.

      It’s important to really take the time and develop your own path, regardless of the cost because when the path you take is truly your own, you have the greatest chance to create the greatest impact. And not just for yourself, but for all live that are connected to yours. So I’d urge you to take the time and explore your world… you find your path, monetizing it is easy.

    • Kristen

      Anon, your statement is a common misconception that a lot of people hold about “wanderers”. If you are a resourceful and hard-working person with a can-do attitude, there is no limit to the amount of “wandering” and self-discovery you can do on your own. Especially as an English speaking person, you have bountiful opportunities of working abroad. The key is to not get yourself into too much debt before embarking on an adventure, which I know, is hard to avoid. I spent 6 years “wandering” as a 20-something, all on my own dime, and all the while earned a college degree for free in France.

  • joão augusto

    usefull and smart, the way i’m going will not take too long for me to move after my job as waiter now and work as a designer, hope of getting a new job, never end. This skill of write or speak english was something but in “auadays” that’s justa a common language every body must know, thanks for the advices

  • Ahmed Radwan

    I left my high paying team lead position at a respectable company and took an entry level job at a much smaller one for half the pay. I’m now in terms with being fully lost in life and able to enjoy the journey rather than have my short term pains consume me. I don’t feel like I’m where I want to be in life at all but somehow I have faith that it’ll come for sure, with some sweat and tears of course.

    For everyone who read this article I recommend reading “The art of possibility” by benjamin zander

    P.S. Travelling always helps !

  • Kacper

    Great post! I have been wandering for the past two years of my life. It is challenging, it makes me anxious, it is hard. However, for these two years I have never seriously considered coming back to the “checkbox” world. I left it- I didn’t know what to do with my life yet- but I have already known what I didn’t want…

    Again- great text- great insights, thanks Sean!

  • Liese

    I love this article!! This is exactly what I’m doing at this moment in my life, and will be continuing wandering until I know what I want to do.

  • Nana

    Love this article Sean. I just turned 26 and been wandering since 16…and it’s still as exciting a journey now as it was 10 years ago…I can’t imagine living life any other way. I have done many things, did a degree in business and technology, worked as a data journalist in a national media house, helped run the first tech hub in Nairobi, and co-founded a couple of other startups which have since grown into ‘mature businesses’. Am now running my own startup which works with young people to teach business and life skills…hoping to spark a bit of the wanderlust in the young’uns .

    Question: can one traverse both sides…? ie, be a wanderer and have a satisfied life, without necessarily being poor? I think so.

  • Carmilla5

    Soul food reading this Sean. I felt like you were writing about me! Still trying to find that square hole! Thank you x

  • binocularface

    The bigger question… why do we have to become an “adult?” I mean, at the end of the day it’s just a word created by people before us. Why can’t I just be myself? Why is it blasphemy to not want or need to “grow up?!”

  • Stina

    Amazing piece that made my day, I am wondering around right now but life is good and I am going to embrace it and find my edge. Tkanks for this

  • Az Calleja

    Quickly becoming my new favourite writer.

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