The Working-Class Reality of Your Superstar Dreams

Whenever I’d meet new people during my three-year tenure as a professional basketball player in Israel, they’d be skeptical.

They’d look me up and down with a furrowed brow, as if I was playing a trick on them. It’s like I owed them something if I was going to say the words “pro athlete.” I should have been wearing really nice clothes or had a fancy watch. At the very least they expected a towering, polished, physical presence — not some short guy with big calves and messy hair.

Once they were satisfied that they weren’t on a hidden camera show, they’d inevitably start talking money and lifestyle. Despite my appearance, certain connotations still come to mind when you hear that someone is a professional basketball player: Ludicrously high salaries. Private jets. Front-of-the-line access to every nightclub.

Everyone’s eyes would glaze over when the truth came out. Salaries that were commensurate with an entry-level IT job. Looooong, cold bus rides through places like Bulgaria and Latvia. And not only did we wait in lines for clubs like everyone else, I once had a teammate get denied entry because the bouncer didn’t like his haircut. Somehow I feel like that wasn’t happening to the stars of the local soccer team.

Other than the 300 or so guys playing in the NBA, being a pro basketball player is not a glamourous job. You do it to see the world, make a little money, to have fun — and because you love it.

And you have to really love it. Not just anyone will be happy to play in a country where you don’t speak the language and where quite a few of the neighboring nations wouldn’t lose sleep if your country was wiped off the face of the earth.

I was happy to have my job, but it was still a tough adjustment. I was given a roommate even though my contract said that I would have my own place. I confronted management about it, but they just said (in their classic Israeli accents), “Don’t to be a worried! He’s good guy! Good guy!” And that was that.

We played in gyms that looked like a dust storm had just blown through. I think our uniforms were made out of a mesh-sandpaper hybrid polymer. Our team trainer was on loan from the local soccer team. When he showed up, he usually had us play soccer in the basketball gym to “practice on the footwork.”

After many months of this, the reality starts to sink in. You’re not going to be hitting game-winners for the Lakers anytime soon.

That’s when you can either get sad, because you’re failing the third grade version of yourself, or you can learn to embrace the struggle.

Appreciate the Journey

I slowly started to realize that I was never going to grow five inches, gain five inches on my vertical, or start shooting three-pointers like Steph Curry. All those things would have been nice, and could have allowed me to gain “big-time athlete” status. But, it wasn’t reality.

That was difficult for me to accept. In the beginning, I was still caught up in the idea that doing something non-traditional that you love would always be glamorous. That’s not the case.

Entrepreneurs, writers, artists, and freelancers of any kind are mostly slogging through in the “minor leagues” of life. As many as nine out of 10 startups will fail. Only 17% of baseball players drafted into the minor leagues will ever make the majors. And for every famous movie actor or big-name musician, there are hundreds more paying their dues while they wait tables and tend bar on the side — the notion of a “starving artist” isn’t cliche by accident. 

At my last job, I got a first-hand look at what it’s like to cast a network TV show. It’s not pretty. Well, the people are all beautiful beyond belief, but the process itself leaves you questioning why anyone would ever want to be a TV actor.

From what I could gather, this is a typical day for a low-level comedy actor during audition season:

Wake up. See which of your day’s appointments have already been cancelled because the show decided they want someone older, younger, skinnier, bigger, taller, funnier, more serious, or with a different sense of style. I mean, did you see what they wore at their last audition? 

Brush off the negativity. You still have an audition, and this could be your big break! Drive an hour across town. Park in the 5th floor of a parking garage that is a quarter mile from the casting room. Trudge through 90-degree heat until you find the right building. Sit and sweat in room full of 10 people who look just like you while you wait for your name to be called.

Perform your lines for the writers, executives, and casting directors. Start a scene over again after someone’s cellphone goes off. Get some polite chuckles and a “thank you,” head back to your car. Go to sleep, wake up, repeat.

It would be crazy for all these people to base their self worth and happiness on whether they book one of those impossibly-hard-to-land TV roles. The journey in and of itself has to be enough to fulfill and sustain them.

I finally came around to that idea over my final two years as a basketball player. I was getting paid to throw a ball through a hoop, and that’s not to be taken for granted.

I began to appreciate the little things that come along with playing in the Israeli professional basketball league: free travel, free housing, free car, free time. Like, serious free time. I could spend whole afternoons walking through the city, reading books, and studying for graduate school tests. 

You are doing what you’re doing because you love it and there are ancillary benefits. This is true of many pursuits.

Take, for example, freelance writing. Most working writers aren’t bestselling authors — they’re churning out web copy or marketing materials or magazine articles in the middle-class trenches of the industry. Most will never write the next great American novel or win a Peabody, but they’re getting paid to do something they enjoy, in their own time, and in their underwear if they want. (I swear I’m not doing that right now!)

writer with will write for food sign
Most working writers aren’t bestselling authors — they’re churning out words in the middle-class trenches of the industry. Photo: HowtoStartaBlogOnline

Understand the Role of Luck

If you’re going to go into an industry with high barriers of entry, you have to prepare yourself for the possibility that you will never quite attain your dream.

I’m not saying you shouldn’t try your best. I just think that part of the American Dream mythology is that the cream always rises to the top and that hard work always prevails. We’re taught that if you really want something, all you have to do is put in 100-hour weeks until it becomes a reality.

That is simply not true. Nothing is a purely merit-based. There will always be backstabbing and politics and accidents and lucky breaks and surprise benefactors and any number of other circumstances that will affect your chances of “success.”

If you don’t find joy in the day-to-day process of your pursuit, it’s probably not worth doing, no matter how high the potential payoff — because that payoff might never come.

Reframe Your Idea of Success

Any entrepreneurial or non-traditional pursuit is going to be fraught with peril. Yet, you can tweak your perception a tiny bit and see the whole thing in a different light.

Sure, if you want to be an actor, it’s going to be a slog. But if you got into that profession because you really love performing and being an artist, then it shouldn’t matter whether you ever get cast as some boring network-TV archetype. You love performing and you’d do it in a community theater if it meant you got to express yourself.

The Simple Dollar’s Mia Taylor once profiled a full-time musician named Will Dailey who perfectly sums up the ethos of doing a job many people think of as glamorous, but is often a grind just like any other profession:

“I will do this full time until I can’t give it my all anymore,” Dailey said. “I found the one thing where, when it really gets tough and I get kicked down, I can get back up, year after year.” 

Basically, you better love what you’re doing enough to endure the setbacks: You can’t just be chasing fame and fortune.

I may have played professional basketball, but I never signed an autograph or flew on a private jet. I never got paid seven figures or signed an endorsement deal.

What I did get was a unique set of life experiences and a newfound appreciation for all the people struggling to get by in jobs that are not as glorious as they once envisioned — but getting by nonetheless.

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Drew Housman


Drew is a former professional basketball player and a Harvard graduate. He is passionate about writing content that empowers people to improve their careers, save more money, and achieve financial independence. His writing has been featured on MarketWatch, Business Insider, and ESPN.