Should I Try to Make a Career Out of Doing What I Love?

It depends a bit on what you love to do

Dear Daughters,

Well-intentioned people sometimes point out that “if you do what you love, you’ll never work a day in your life.” They rarely go on to note that many of us (probably the vast majority of us) don’t really have the option of getting paid to do what we love.

Take me, for example. I love to sit on the beach with a beer in one hand and a good book in the other (as above), but no one’s going to pay me for that. I also love to go on dates with your mother—to dinner or a movie or whatever else, really—but those dates all come with price tags, not pay stubs. I also love to play soccer and drums, but I wasn’t born with the talent to make a living at either.

I could go on, but you get the point. In the real world, the admonition to “do what you love” often has to be qualified with the recognition that no one’s going to pay you to entertain yourself. You’re only going to be able to “not work a day in your life” if what you love doing happens to be something that other people are willing to pay you to do.

And here’s the kicker: people mostly pay others to do things that they either can’t do or don’t want to do. This reality has some important implications as you consider your career path. One is that, whatever you wind up doing, your job isn’t likely to be filled with fun and games (sorry!). Another is that the best chance to combine good prospects for employment with jobs that bring at least some enjoyment lies in understanding your own comparative likes and strengths—knowing what you like to do more than most other people, and what you’re better at than they are. (This is where the kernel of truth in the “do what you love” advice lies for most of us.)

Working at What You Like

Again, take me as an example. I’m comparatively good with words, and I like working with them. Many other people—comfortable as they may be chatting with friends—absolutely hate writing and/or public speaking. They’re happy to offload those tasks to someone like me. And that creates a space for me—really a variety of different spaces—in the workforce.

I’m hardly alone. A friend of mine is great at schmoozing: he knows how to quickly connect with people and make them feel comfortable talking to him. He’s converted these skills into a successful career in business development. Another friend is super organized and detail focused and has become a highly valued project manager. Another has always been great with numbers, and she’s now a corporate controller (which is basically a fancy accountant).

None of them would report that they’ve “never worked a day in their lives,” but they’re all doing just fine, thank you. And that’s really another way of saying that they’re living fuller, more comfortable lives than nearly any other humans in the history of our planet.

If you’re like most of us, and what you truly love to do isn’t exactly marketable, then this is the basic opportunity you want to give yourself—the opportunity to make a living doing something you like and doing it well. You’ll still have to work, but at least you’ll have a chance to build on your strengths, provide real value to others, and earn their appreciation and respect.

Finding Your Path

It’s worth pausing to reckon with this reality, if not today then at some point in your teenage years–and periodically after that, too. Ask yourself, “Where’s the overlap between what I like to do, what I do well, and what people will pay for?” If you’re not sure, ask for help mapping this area out. Then plot a course toward it.

If you head in this direction, you’ll find that you get to do a lot of stuff you like along the way—even chasing your ultimate dream if you have one. But you’ll do it with both an appreciation of what “work” really is and a sense of your own best options, given that reality.

Pick a path that leads toward doing good work as one part of leading a good life. If you’re not sure exactly which path that is, don’t worry. There’s no huge rush. I’m actually still finding my way myself—which doesn’t mean I haven’t enjoyed the journey, including some books and beers on the beach along the way.

Work hard at doing what you like, and do it well. Your path will continue to reveal itself.

I love you,


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