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When Your Dream Job Just Isn’t Your Reality

Struggling through a tedious 9 to 5 is valuable — but not in the way you might think

Jonathan Warner
Dec 18, 2018 · 5 min read
Photo: Q Yi Chn / EyeEm / Getty Images

I reconnected with a college buddy of mine a few weeks ago for the first time in almost 10 years. I found him on LinkedIn one day: Jeff, with his scruffy beard and longish hair. “Writer at Motorcycle Group,” his profile read.

What? Jeff? A writer for a motorcycle company?

We’d been English majors together back in 2008, nerding out on our favorite poets and essayists. I sent him a message.

It was true. That was his gig. “Dude, no lie. I travel the world to test ride all these bikes and then get paid to write about them for Cycle World! Most days I still can’t believe it—it’s pretty sweet, for sure, man!”

I offered my congratulations, poking fun at him about how truly unjust our world must be if he could weasel his way into such cushy employment. I couldn’t believe it. I read a couple of his recent articles. They were good. No, they were damn good—so much better than anything I’ve written. His turns of phrase, his unexpected insights about the particulars of each motorcycle, captivated me. After 800 words, I was ready to buy a Triumph Bonneville because it was a “custom heartbreaker” with iconic Britishness and lovable, temperamental mechanics.

America loves dream jobs.

The whole thing kind of shook me. I wasn’t jealous—well, actually, I was a little jealous. But Jeff is a great, humble guy, and I was genuinely happy for him. It was more that Jeff’s success, his joyful fulfillment in doing his dream job, made the gray clouds of dissatisfaction and disillusionment around my own employment seem darker.

Jeff and I had gotten along in college because we were both creative free spirits who never saw ourselves taking a typical career track. We loved the outdoors, adventures, international travel, philosophy, and writing. We both loved motorcycles, too.

Jeff had made it. He was riding and writing, spending his hours on his passion and honing his craft to an extremely high level. Meanwhile, I was selling medical software in a sterile seven-by-six-foot cubicle in western Pennsylvania. Monday through Friday, I drowned in emails, languished through lists of cold calls, and blinked my way blankly through tedious corporate contracts.

The reality is that most of us do not have dream jobs.

I’d flouted a conventional career for a few years, but student loans had caught up with me while I was traipsing through Central America, so I’d come back and reluctantly gotten a real job. Now, I dreaded eight hours of almost every weekday. I felt like it was wrong—morally wrong—for me to spend my time slumped in an ergonomically correct office chair, pecking at a plastic keyboard, while squinting into a bright computer screen. I should be doing something active and inspired, outdoorsy and creative. But it just hadn’t worked out. I didn’t have my dream job, and I was stuck.

America loves dream jobs. America loves talking about dream jobs. “Do what makes your heart sing.” “Find a job that you love, and you’ll never work a day in your life.” The tired adages go on and on. The reality is that most of us do not have dream jobs. Most of us will never land our dream jobs. How do we face that? How do we navigate that bleak reality without giving in to despair?

Though “dream jobs” are elusive, it’s still valuable to identify where our passions, interests, and sources of fulfillment intersect with the market. It’s healthy to strive to make reality as close to your personal ideal as possible. You can be realistic and aspire to have more than you currently do — and never give up on those aspirations — at the same time.

It’s also important to remember that struggle has value.

We’re all going to struggle; some of us more than others. It isn’t fun, but it’s almost guaranteed. But there’s an inherent value in the daily work struggles, discouragements, and frustrations that dream jobbers might miss out on entirely.

I love to have fun like anyone else, but I don’t learn much when I’m zipping along. I don’t think deeply when I’m enjoying myself. I focus on the face value of what’s in front of me, and I’m fully entertained. I float along passively in blissful preoccupation, not nearly as innovative or creative as I could be.

But when I’m stuck slogging away in lackluster trenches, it motivates me. It stretches me, it goads me into questioning my life and larger purpose. I consider change, weigh risks and rewards, and plot my escape strategy.

The depths of our woes bring out the zeniths of our human capacities — capacities that lie dormant when we’re happily entertained.

This kind of fortitude and preparedness serves us not only in work, but also in life in general.

Consider, too, the strength we actively build through day-job drudgery; this is a pain tolerance, a certain threshold of ability and will to endure that increases with each day persevered. People who love what they do don’t have the same opportunity to develop this. It’s a hidden, but significant, downside to dream jobs. If a person isn’t familiar with hardship, if they haven’t faced difficulty on a daily basis, they are often bewildered and panicked when trials finally come along. They don’t have the repository of mental strength to flex their way through adversity. Those of us who fight through disappointing, often-trying jobs, we’re well acquainted with misery. We’re ready to battle with blazing eyes. This kind of fortitude serves us not only in work, but also in life.

Beyond the opportunities for innovation, learning, and fortitude that non-dream jobs can lend us, there’s a specific pleasure in earning your way out of unpleasant employment with hard work. We all know this, but it’s easy to forget when we’re in the teeth of the grind. Notice how many super successful entrepreneurs, athletes, and celebrities recount their humble, hard, boring, and impoverished beginnings with wistful fondness. The uber-successful who don’t rags-to-riches or negative-to-positive stories seem almost embarrassed. Their journeys are predictable and uninteresting. Those of us who start low have an opportunity to gloriously fight our way out of the mud. Someday, we’ll tell our stories with flair. Taking the long way around leaves us with a rare wisdom about success and a deeper capacity for gratitude.

Recognize where you are. Press into the beast of your misery. Let it fuel your thoughts and actions with strategic fever and know that, someday, you may actually look back on these moments with a half-smile.

I want to catch up to what I feel like I’m missing. I hope to realize my “dream-ish job” in about two-and-a-half years. It might take four or it might take 10—I might not make it there at all. But as long as I know how to struggle mindfully, I think it’ll be okay.

Jonathan Warner

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Jonathan lives in a New York studio smaller than your bathroom and writes on http://thescrapjournal.com/. Connect with him on Instagram or Twitter. @JParkWarner