A retraction of every “live your dreams” screed I ever wrote

Confession time! I used to write some of those “Quit your job! Follow your dreams!” articles. You won’t find any of them in my Medium history now, though, because I deleted them all months ago.

Looking back on my smugness now feels like looking back on my goth phase in high school: I’m not exactly ashamed of it, because I can understand the motivation behind it; the need to craft a public identity that would validate my perspective on the world— but it still makes me cringe a little,

Because I wasn’t nearly as cool as I thought I was.

Like a lot of people — not everyone, but a lot of people — I had a day job that I hated. A succession of them, actually.

I kept trying to fit in throughout my twenties, but I never could get the hang of getting up at seven every morning, working beneath fluorescent lights for eight hours, making small talk at the coffee maker, sitting in rush-hour traffic on the way home… nothing I accomplished at any of those jobs was worth any of that.

But that’s not everyone. That was just me.

You can probably guess the rest of this story: I hit the freelance work hard, saved up a safety net, quit my day job, sold ninety percent of my stuff, and backpacked around the world for two years, and it was incredible. Transformative. Eye-opening. I got tattoos. All the usual stuff.

I’ve had some genuine Peak Experiences™ — often in the most unexpected places. I’ve also had some “why am I here and what the hell am I doing with my life” experiences — often while lying on a beach, sipping a cocktail, feeling like this is a complete waste of time.

And now that I sound like I’m pushing the “Smug Privilege” meter completely into the red, let me make my meaning very clear:

The “run off to paradise” lifestyle is just another narrative — just as the “day job” lifestyle is a narrative — and so is the “tortured artist” lifestyle, and the “open-air park ranger” lifestyle, and the “Buddhist monk” lifestyle, and dozens more.

Some of those narratives sound cooler than others —

But none of them is inherently “the most fulfilling.”

Fulfillment comes from finding meaning in your work.

From having skills you enjoy using.

Practicing and perfecting those skills.

Applying those skills to problems you care about.

I think the reason so many people claim to have found fulfillment in the “run off to paradise” lifestyle is that they knew what kind of work they wanted to do — maybe writing or photography or teaching — and that lifestyle provided them with opportunities to do it full-time.

But the point isn’t to choose a lifestyle because someone else says it’s cool. That’s ridiculous. You have to start from the work. The skills. The meaning you enjoy creating in the world.

The work has to come first. Everything else follows from that.

Traveling to places where no one speaks English and the culture is totally different from anything you’ve ever experienced… really is genuinely cool. I highly recommend it — as part of whatever lifestyle enables you to do the work you find fulfilling.

I wish I could take back every “quit your job” message I ever put out there, and replace it with this one:

Do not quit your job.

Do your job.

It’s just, here’s the thing:

Make sure you’re doing YOUR job — not someone else’s.

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