'Follow your dreams' is bad advice - how to make your job suck less

Phil Rosen

Issue #23

August 29, 2022

Reading time:

5 mins

Welcome back, readers. Phil here, writing to you from a cafe in New York.

I’ve spent the last few weeks asking people whether they’re happy in their careers. Conversations touched on job satisfaction, bad bosses, a longing for something new.

But nobody who told me they wanted to quit offered a plan to do anything else except get a new job — which can repackage the same problems all over again.

Escaping a job doesn’t necessarily mean more happiness. It might not even mean a better job.

The cliché is to drop everything and follow your dreams, but that’s bad advice.

Below, I break down what to do instead — and how to give yourself the best shot at doing more meaningful work, more often.

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You can’t do nothing

Even if you have an insufferable manager or a job you hate, abandoning work entirely creates too large a vacuum.

If you had a spare 40 hours a week, what would you do to fill the time?

Retiring early might sound nice, but that’s more avoidance than an actual strategy for happiness.

Without a doubt, work certainly can suck. But that shouldn’t convince you that work can’t be meaningful.

‘Follow your passion’ is bad advice

Broadly speaking, the tiny number of passions you may have — let’s pretend you have two or three — don’t align with the job market.

People dream of starring on Broadway, not waking up as a corporate foot soldier.

Because there are so few “passion” jobs, they are more competitive, and employers can afford to pay you less.

(The starving artist trope is alive and well.)

Plus, people in those sectors usually are forced to tolerate a lot of horrible things, because the belief is that only those passionate enough can stomach it.

But, as writer Cal Newport points out, following a passion isn’t actually how people get jobs they’re passionate about.

Instead, he argues, most people fall into work they love by becoming extremely good at specific skills.

Building a high level of competence in a select number of skills makes you valuable and marketable, which means you offer high human capital.

While it’s easier said than done, dedicating yourself to specific skills gives you a far better chance of deriving happiness from your work.

Work feels more meaningful and enjoyable when you can be a confident, valuable contributor. Plus, you’ll be better positioned for managers to take notice.

It takes time and strategy to develop real-world skills. The most obvious option is to start a side project that gives you plenty of room to practice.

Like a blog to improve your writing, or a podcast for public speaking.

In time, not only will your skills compound, but you’ll have a body of work to show for it — which you can leverage in job negotiations.

It’s worth noting that highly-skilled individuals are magnets for opportunity. That means the more focus you put toward your own development, the better the odds someone else will notice.

So if you’re unhappy at work, your first reaction shouldn’t be to find an escape route. The grass isn’t always greener.

Instead, prioritize becoming a master at one or two specific skills. Then, use those to map out your next steps.

Remember: Rarely do people dislike doing things they are excellent at.

Until next time.

— Phil

Tip Jar Recs

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Relevant business: How Amazon turned “Lord of the Rings” into the most expensive show of all time. (The Wall Street Journal)
Something different: The grammar of exile and teaching English to asylum-seekers in Rome. (VQR)