How to Win the Career Lottery

On Tuesday, April 5, Susan Cain chatted with Chris Guillebeau, author of Born for This: How to Find the Work You Were Meant to Do. Chris’s philosophy is simple in expression and vast in implication:

  • You don’t have to live your life the way other people expect you to.
  • You can do good things for yourself and help other people at the same time.
  • If you don’t decide for yourself what you want to get out of life, someone else will end up deciding for you.
  • There is usually more than one way to accomplish something.

Below are a few highlights from Susan and Chris’s discussion about how to win the “career lottery” and find the work you were born to do.

What do you want to be when you grow up?

When Orpah (and yes, that’s the original spelling of her name) Winfrey was a toddler in Mississippi, did she know she was going to grow up to be “Oprah, Queen of All Media”? Or was it something she figured out later? Today’s young people are expected to start making decisions about their life purpose at about the same time as choosing a retainer color. But while there are some exceptions, Chris’s research shows most people who win the career lottery do so by following a long and winding road that includes scenic turnouts, breakdown lanes, detours, and speed traps.

At 6 years old, Chris aspired to a career in fast food with an ultimate goal of working at Burger King, his favorite restaurant at the time. Instead, he grew up, traveled the world, and became a successful entrepreneur and author. So, yes—sometimes, it’s okay for a dream to die.

People who find a way to do what they were born to do are willing to experiment and regroup. They view their mistakes as guideposts to finding their eventual destination. So, unless you’re willing to settle for something that’s “okay” but not the amazing thing you’re looking for, be ready to make some kind of big change and encounter what most people see as failure along the way.

The conditions of work

When people think about their dream jobs or ideal work, they almost always think exclusively about a profession or vocation—the nature of the work. But per Chris, the way we work is just as important as the work itself. Working conditions include things such as how you prefer to spend your time, how much you like to work collaboratively versus independently, and how you like to be rewarded. Most people rarely think about the day-to-day ways in which they’ll be spending their time when they pick a career path. They just consider the overarching big picture or the difference they seek to make. But it’s really hard to keep the big picture in focus if you’re hating the moment-to-moment! We need to work in environments that challenge us (because challenge is good), but we also need to create space that allows us to thrive.

Do the side hustle

A “side hustle” is an additional income source that is separate from your paycheck. It’s not a part-time job as much as it’s something you create, and it’s disproportionately satisfying. Chris strongly recommends side hustles—they help you build confidence and security, especially if you’ve always been an employee and have never worked for yourself. Even a small amount of extra money feels great because you made it happen.

And even if you love your job and find your work to be fulfilling, you can still benefit from a side hustle, which will allow you to embrace your inner entrepreneur. If you love your work AND you have something else that produces income, you have the satisfaction of going to your job because you want to, not because you have to. Who wouldn’t want that scenario?

If you’re intrigued and want to figure out your own side hustle, there’s a guide in Chris’s book that can help you start something quickly (and with low risk and little to no investment).

Winners never quit, except when they do

“Winners never quit” is classic advice that also turns out to be terrible advice. There’s a huge difference between giving up and letting go, so if you’re doing something that isn’t working, you should stop. Successful people don’t necessarily flit from idea to idea without any evaluation or learning process, but they also aren’t afraid to walk away from a non-winning situation. In other words, the saying “Try, try again” should be modified to add “…but not in the same way.” That’s when you’re more likely to be successful.

Joy, money, flow: The key ingredients for a dream career

First, let’s define some terms. Joy comes from doing what you love; money is the result of a career that is sustainable and viable; and flow is the ability to use your unique skills to do work that makes you come alive. Flow is the most abstract of these concepts. To put it in other words, flow allows you to become so totally absorbed in your work that you forget the passage of time. The goal is to find the intersection of all three.

While each component is critical, flow tends to get less respect than it deserves. Flow is deeper than enjoyment or one’s ability to pay the bills (as important as these are). The immersive quality of flow results in the kind of deep satisfaction and feeling of ownership that produces the best work out there. 

Living in that sweet spot requires constant monitoring, evaluating, and improving. The more you orient yourself around these three qualities, the more fulfilled you’ll be. Anything else involves a compromise of one form or another.

You can keep up with Chris on Twitter and Facebook. If you would like to read additional excerpts, be sure to sign up for the QLI newsletter.

Chris Guillebeau Born for This cover

Chris Guillebeau’s Born for This was published by Crown Business, a division of Penguin Random House LLC. Copyright © 2016 by Chris Guillebeau. Learn more at