Why You Should Never Feel Bad for Chasing the Money

I have had a wild ride the past couple of years, career-wise. I went from making just $22,000 per year working in the mailroom of a Hollywood talent agency to making far more than that at my current job at a startup.

Sure, I had to sell my soul and give up my artistic dreams, but that’s a small price to pay for a big raise, right?

I joke about selling my soul, but it’s something I actually think about. I was committed to making it as a TV writer, and now I pretty much do sales at my main gig. For a few months after making the decision to pursue a career with more immediate financial rewards, the thought that I was a “sellout” gnawed at me.

I imagined a younger version of myself, upon hearing that I’d taken a more corporate job, saying something like, “Good job, quitter. Have fun selling widgets the rest of your life.”

I think these are common, natural feelings for a 20-something to have after realizing that they’re making a career shift away from the creative and toward the traditional. The good part is that, after a while, the negative thoughts subside. And when they do, you’ll have the time to analyze your decision with more clarity. If you’re like me, you might come to the conclusion that you’re only a sellout if you think you’re a sellout.

Recognize That You Are Always Changing

Before I was trying to make it as a TV writer, I was trying to be a professional basketball player. And I succeeded! For three years, I actually got paid money to play a sport, which for many people would be a dream come true. But, I was never satisfied. I wanted to make the NBA. I felt like a failure.

When I eventually stopped playing basketball, I felt like I was giving up. Instead of realizing that I’d accomplished a lot and had much to be proud of, I wallowed in self-pity and stressed myself out thinking about my next career move.

But, as they always do, those feelings passed. I started to feel better about myself as I dove into the task of finding a job that would help me pursue my new passion: Becoming a big-time Hollywood writer.

There’s nothing wrong with that goal. I really believed at the time that TV writing was the path for me. My mistake, though, was not being able to apply the lessons I’d learned from ending my basketball career once I decided to end my TV writing career as well.

Rather than beating myself up for not pursuing the life of a starving artist, I should have been able to look at things more pragmatically. I mean, I’d pretty much gone through the exact same situation already with basketball!

But, I found that it’s hard for me to move on from pursuing lofty, shoot-for-the-moon-type career goals. And I’m sure it’s the case for many others out there as well.

The main thing I keep telling myself is that it’s okay to change. I’m happy I didn’t have all the same goals, principles, and dreams at age 12 that I did at age 18. Why is it such a big deal if I encountered similar changes between the ages of 22 and 24, or 25 and 28?

Your 20s are bound to be a time of growth, questioning, and reassessment. It’s better to embrace that than to stubbornly stick with Activity X because you were so sure you wanted to be the best in the world at Activity X a few years ago.

You’ll eventually want to settle on a set of core values and principles that matter more than anything, but it’s okay if takes you some work and some time to get there. I never appreciated that.

Trent made a great point along these lines a few months back, when he highlighted a quote by the philosopher Alan Watts: “You’re under no obligation to be the same person you were five minutes ago.”

Don’t Fall Victim to ‘Fading Affect Bias’

A problem I faced after leaving my old career was that I couldn’t stop remembering the good times. There was the the time I won an award for a script I wrote, the time one of my jokes made it into the finished pilot for a show on CBS, and countless positive memories associated with just hanging out with my bosses.

It took some active effort for me to snap out of it and think, “If it was so great, why did I leave?” Then I remember the aspects of the career I wasn’t so enamored with, such as the late nights spent in a dingy edit bay, the countless hours spent on my scripts even though there was no guarantee anyone important would ever read them, and the low wages.

I’ve learned that I’m not alone in emphasizing the positives when looking back on a situation. In fact, there’s even a name for it: The Fading Affect Bias. Studies have shown that across all cultures, bad memories tend to fade faster than good ones. Some researchers think the purging of bad memories could be an evolutionary adaptation to make sure our self esteem stays sufficiently high.

And to that I say: Not all adaptations are universally good across all circumstances. I think when making a big, profound career change — especially leaving a job you once considered your “passion” — you’d do well to remember exactly why you left.

It can help to take some time to write down in a journal your reasons for moving on. Then you can refer back to them the second you start thinking, “If I had just stuck it out a little longer, I’d be writing on Modern Family right now!”

There’s Always Time for Your Hobbies

Just because you’re no longer doing something “fun” for a living doesn’t mean you have to completely abandon your passions. I still write (obviously). I still play basketball (poorly). And the crazy thing is that I genuinely love doing these activities, even though they are now only done in my free time.

If I wanted to, I could have kept writing scripts even after I took my new job. In fact, the one script I wrote that won an award was written during the free time I had at one of my office jobs.

Heck, I could have even kept training for basketball. Just last year a former college basketball player left his job in public radio and signed a professional basketball contract to play in Poland.

The point is, if you really want to pursue something and you aren’t an on-call surgeon raising six kids by yourself, you probably have some time to get good at it and still maintain a day job. In many cases, it just requires rethinking how you spend your downtime: The average American spends four and a half hours a day watching TV and another few hours surfing the web, some of which could no doubt be devoted to a side project or passion.

Money Matters

People like to say that money doesn’t buy happiness, but a now-famous study showed that earning more money does increase happiness — to an extent, before leveling off after around $75,000 per year. Let’s just say low-level European basketball players and entry-level writer’s assistants aren’t very close to reaching that bar.

I’m not trying to imply that people earning below a certain amount of money are going to be less happy. There are people I know in both the careers I abandoned who are perfectly content doing what they love for very little pay.

I’m just saying that in my situation, with mounting student loan debt and the dream of being able to retire before age 70, it was plausible that I could be happier if I pursued a more lucrative career path. I’m very grateful that such avenues were open to me, and I’ve enjoyed learning something new in a different field.

Summing Up

If careers in sports and the arts were easy, everyone would do them. It takes a special kind of dedication to succeed in either arena. I’ve finally come to grips with the fact that it’s okay to not be one of those people. It’s not selling out to do what’s best for you financially, even if that means you end up in a career you would have once considered boring. Who knows, if you pursue your side hustles hard enough maybe they will eventually become your main hustle. In the meantime, take the time to appreciate you have a job at all, and hold your head high as you crank out those widgets.

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Drew Housman
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.

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