The Single Best Piece of Career Advice No One Teaches You

You’re welcome.


I sat down with a fresh-faced MBA candidate intern this afternoon, at my office job deep in the heart of corporate America. It’s not uncommon for the leaders — or, middle managers, at least — of tomorrow to request 30 minutes of face time with “senior” “professionals” to “pick their brain,” and I often try to make myself available to shape the way these kids (can I say kids? are 22 year-olds “kids”?) … ahem, young adults see themselves and their greater role in society for the next few decades. Or, at least for the afternoon.

He asked me your garden-variety “brain picking” questions, like “what do you do?” “How does what you do impact the business?” “Where do you see your career in five years?” etc. I entertained them all, but I really wanted to know what drove this young man. I wanted to know why he chose his field of study, his career path, and this company. His answers were as dull as a rusty spoon.

“I like marketing.” “This seems like a great place to grow my career.” Etc. Etc. The platitudes you’ve all heard before by someone who’s started to die a little inside and doesn’t know it yet. I’m going to make navigating a career as simple as possible for you, but first, I am going to make two assumptions.

  1. If you’re reading this, you’re not destitute. (Although, even if you’re destitute, you can still follow this career advice, as I did — detailed here.)
  2. You’re not already fulfilled in your current gig.

I make these assumptions because, if you’re destitute, your choices and concerns become more immediate. It’s a lot harder to take a 32,000-ft view of your career when you’re in the weeds of student loan payments stacking up, not knowing where your next meal is, or the spectre of sleeping on the streets looming overhead. So, let’s table those scenarios and assume — hopefully! — that you’re not in danger of losing a home, starving or napalming your credit. (It’s 2018 in the US and we don’t have a safety net, so there’s no shame in any of those conditions being true for you. We’re not a tide designed to lift all boats.)

Okay, now that we’ve got that unpleasant business out of the way: Here’s how to find success in your work life.


1. “Do What You Love” isn’t bad advice, it’s just not that good.

I do what I love. I get that a lot of people don’t get to say that. I wake up every morning thrilled to death that I spend eight hours spitting words into a computer and, on occasion, those words get used in global marketing pieces that shape the way people perceive one of the world’s most well-known brands.

But “Do What You Love” has caught a lot of flack lately. Some of that backlash is understandable: it is rare to find a profession that speaks to you on a visceral level. It is hard to love a profession you haven’t yet mastered. It is rare to be well compensated for something you adore. And we’ll tie all those counterpoints together at later moment, but, know this: just doing what you “love” isn’t going far enough, and it’s also a little extra.


2. “Follow the Money” is, in a vacuum, the absolute fucking worst.

Donald Trump seems like a happy, healthy, well-adjusted man, doesn’t he? Sorry, is that answer too politically charged? Okay, then: let’s scale it back and talk about your dime-a-dozen upper management. They’re raking in the mid-six figures. Yet, suicide rates among the elite are higher than the middle class.

There’s boatloads of evidence that point to money being unable to buy you happiness beyond a reasonable cap. That cap is, roughly, $70,000-$75,000 per year in salary. So, if you’re already making that, (as of this writing, some 70% of you are not) then hitting on 17 at the blackjack table won’t get you much closer to an emotional 21.

Think, however, of the unhappy lawyers, c-level executives, bankers, salespeople, doctors, dentists, national news anchors and pop stars. With the exception of pop stars, how many of them pursued a career thinking, “well, if I can just break into this field, I can absolutely crush it.” Don’t be The Wolf of Wall Street. Don’t watch The Wolf of Wall Street 127 times in your studio apartment. (*side-eyes another prominent blogger on this site*) Money is nice, and it’ll change your life, and it changed mine, but it won’t quell your inner demons — it’ll exacerbate them.


3. “Do What You’re Good At” is a start.

… provided you, you know, like what you’re good at. I’m good at packing moving trucks. No fucking way would I make that a career. That sounds as fulfilling to me as working a factory floor — all due respect to people who work factory floors. Some people find real reward in working at the mills. Bless them.

Also, some of us are good at things that don’t pay: I’m a magician when it comes to geography trivia, making bolognese sauce and sexting. None of those are viable career paths. Though it’d be nice, America. It’d be nice.

Yes, developing marketable skills is probably your surest path to becoming upwardly mobile in your career — well, your surest path to becoming upwardly mobile in your career is being white, male and straight, but you didn’t come here for that heartbreaking nugget. You came here for a small sliver of hope. Let’s break that out before you go crying into your single-malt.


The Best Career Advice is All Of The Above.

Wait. What the fuck? John, you just said all t — … I know. I know. Let me explain. Let me use me as an example, because it’s my M.O., and because narcissism.

Remember my job? Well … I love to write. I’m good at it. People are willing to pay for it. And I am happy. I write for a Fortune 500 company (or what would be Fortune 500 company, if we were publicly traded). The work-life balance there is awesome, so I have some free time to do more of what I love. I also love to play music. I write for Medium. I write for a few startups as a freelancer. I write for a couple political campaigns. I write as a school board member. And that’s it.

Between all the gigs, I spend like 50% of my waking hours at my day job, 20% of them doing various side-hustles (including Medium, which I have not yet taken advantage of their paywall, because I believe in much of what I have to say being available to everyone), and 30% of my time being a functioning human — eating and running and showering and rabble-rousing with friends. That’s not just career fulfillment — that’s life fulfillment. That’s happiness and health. And that’s possible for you.

Here, I caught you this delicious Venn Diagram that illustrates the sweet spot where you want your career to be. (The center, in case you’re new to Venn Diagrams.)

Find the intersection of:

  1. What You Love
  2. What You’re Good At
  3. What People Want (or, “follow the money”)

That’s the single best piece of career advice. And I’ve yet to hear anyone tell you this. So, who told it to me?

My dad. He always told me, “you will naturally gravitate toward what you were meant to do.” And that, I think, is the most key takeaway from this entire piece. Most people think they need to map their careers out before they graduate from college: That’s simply not true.

I didn’t discover I loved writing things until I was 25. I didn’t get paid to do it until my 30th Birthday. I’m still not as good at it as I will be. So, how did I find my career?

Let’s queue up “Success Is A Myth.

I started by working at a telemarketing company, as a survey taker, and then I graduated to training, and then working in data analytics, before I did some bargain-basement actuarial work for them. I parlayed that gig into a telecommuting job working as a Traffic Manager at a tech-centric ad agency. I did that for four years, working with creative professionals on deliverables for Cisco. Because it was a telecommute job, no one was watching what I was doing, so I started blogging about sports. I then got a job at a publishing company as their marketing director, where I worked with more creative professionals and established a set of messaging parameters.

I wasn’t making money blogging about sports. I wasn’t good at being a marketing director. But I loved writing, and I loved working in marketing. I had experience in tech. And so my next career move, although one fueled by desperation, made total sense: work in tech, in marketing, as a writer. I got a job doing exactly that, I’ve gotten a few raises and a couple promotions since then, and here we are, six years later.

It was a natural career progression. And now I feel like I’m where I’m meant to be right now, at age 35, in the top 11% of income in the U.S., all my debt paid off and a small nest egg, with still a solid three decades left to make what I want out of my life.

Get good at doing something you love, and find people who are willing to pay for it. You’ll naturally gravitate toward that career path — and don’t let anyone sway you otherwise. Now … go tell all your interns.


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