The Best Way to Follow Your Dreams Is by Keeping Your Day Job


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One of my favorite inspirationalbooks is The Crossroads of Should and Must: Find and Follow Your Passion, byElle Luna. The basic premise goes like this: Far too many people stick to “should” — the safe route, what they feel they ought to be doing and what is expected of them — rather than pursuing “must,” or the thing that truly excites and makes them come alive. Luna urges readers to chase after their “calling,” or work that is rewarding in itself.

For Luna, this meant leaving her job at a software start-up to make art, a decision that proved to be a good one. She authored a best-selling book and now spends her time painting, designing, and writing. She was able, as she puts it, to “choose must,” a choice that many people assume is required to get on a new path, to go after their dreams. Of course, this isn’t always possible — not everyone has the self-confidence, nor practical ability (bills to pay, food to buy) to make such a choice, to suddenly quit their job, for example. And yet it turns out that’s actually okay; it might even be advantageous. Because the best route to one’s calling is often not to choose must over should, but rather to choose must and should.

Consider an article published in the Academy of Management Journal, “Should I Quit My Day Job? A Hybrid Path to Entrepreneurship.” For the study, a pair of University of Wisconsin researchers set out to answer a question many have asked: If you want to do something entrepreneurial, are you better off keeping or quitting your day job? After interviewing thousands of entrepreneurs, they found that those who kept their day job while pursuing a personal venture on the side — or what the researchers called “hybrid entrepreneurship” — were 33 percent less likely to fail than those who quit their jobs altogether. As Harvard Business Reviewput it, “Going all-in on your start-up might not be the best idea.”

Though it may seem paradoxical, the most productive way to pursue your passion, for a time anyway, may very well be to do so on the side.

The author and investor Nassim Nicholas Taleb echoes this sentiment in his New York Times best-selling bookAntifragile, where he writes that going all-in on something — anything, really — makes you fragile. Taleb encourages readers to instead adopt what he calls a “barbell strategy.” The image of a barbell — two weights on opposite ends, creating stability — he writes, “describes a dual attitude of playing it safe in some areas and taking risks in others.” Such a strategy comes with two major benefits:

• You are more likely to take bigger and higher payoff risks when you know that failure won’t completely upend your life.

• Even if you do fail, you’ll still be okayand can take additional long-shots later on.

In other words, the barbell strategy — starting out as 10 percent rock star and 90 percent accountant — makes you antifragile. “It is the combination of aggressiveness plus paranoia,” writes Taleb. “Clip your downside, protect yourself from extreme harm, and let the upside, the positive Black Swans, take care of itself.”

I know the barbell strategy well. I followed it (and still do) pretty much to a T during my own foray into writing professionally. For me, “should” is a corporate consulting job. It pays pretty well; the work is in health care and I find it meaningful; and I like the people with whom I work. Yet ever since I was a kid (and this includes getting rejected from Northwestern University’s prestigious Medill School of Journalism), “must” was always writing. So when I had my first major column published in the Los Angeles Times and, soon after, started landing freelance gigs, I was tempted to quit my day job. But I didn’t. Instead, I wrote on the side. Sure, as the writing continued to pick up I went down in hours, but I never quit; I never went “all-in” on writing. To this day, I still consult part-time.

The barbell strategy allows me to be more selective about what and for whom I write. I’m also convinced it makes me a better writer. I feel like I am more relaxed and take shots that I otherwise might not because I know that failure is, in fact, a not-so-bad outcome. Do I long for the day when I can spend all of my time writing? Absolutely! It’s just that I think my best chance of getting (and staying) there is to do so incrementally.

There is, of course, a case to be made for going all-in on a passion; for choosing must over should. Perhaps for those who truly thrive under immense pressure this translates to better performance. But for the vast majority of people (at least according to the research), the best route to taking personal risks is to take them on the one hand while minimizing them on the other. Even Elle Luna tells the story of the international-best-selling author John Grisham, who started off as a “lawyer/author,” awaking every day at 5 a.m. “to write stories about harrowing crimes and evil doings all before going to his job at the courthouse.” According to Luna, it was only after three years of juggling writing and criminal defense that Grisham shaped his stories into a novel, which, after multiple rejections, was finally accepted for publication. And that, she writes, “is why John Grisham is a household name today.” In other words, for quite some time, Grisham chose must and should.

Though it may seem paradoxical, the most productive way to pursue your passion, for a time anyway, may very well be to do so on the side.

— Brad

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