These Two Simple Exercises Can Help You Radically Rethink Your Career

Reverse-engineer your way into a career change you never would have considered possible.

These Two Simple Exercises Can Help You Radically Rethink Your Career
[Photo: Allef Vinicius/Unsplash]

You’re feeling stuck in your job, so you do the obvious thing: You sit down and brainstorm all the other positions you’re qualified for. It doesn’t go well. No matter which way you cut it, your options look limited.


Before you find the nearest wall to bang your head against, take a step back and turn the question inside out. Instead of, “What’s available to me?” ask yourself, “What type of work will make me happy?” It’s not as idealistic as it sounds. If you can come up with an answer–even a vague one–you may be able to reverse-engineer your way into a career change that you never would’ve considered possible.

Here are two exercises to help you do just that.

1. Plan Your Career In Reverse

Most of us know where we’d like to be next year or the year after, but when hiring managers ask, “Where do you see yourself in five years?” many of us already already start to wince. Robert Wong, the cofounder and VP of Google Creative Lab, thinks that’s a sign you need to contemplate the long-term more, not less.

“First,” he suggests, “imagine your most successful, self-actualized future self in 20 years and write it down. Once there, imagine what you would have had to achieve 10 years prior, and write that down. Then go back five years. Then two and a half years–until you get to one year from today.”

Related: Robert Wong On Inspiration And Creativity


Wong freely admits that this is hard. “It’s easy to fantasize about the future: ‘Oh, I can be retired in the Mediterranean!’ or, ‘I could be running a Fortune 500 company or have a restaurant in New Orleans!’ But if you go back assuming that happened,” he explains, “you realize that a year from now you would have to achieve something to get to that end state.

Robert Wong [Illustration: Eric Palma]
The point, however, isn’t to obsessively plan every detail of your professional life and then just spend the next several decades merrily executing them, Wong says. No one’s career works that way. Instead, it’s to get into the habit of translating your future goals–however distant, vague, or ever-shifting–into actions you can take right now. Wong doesn’t remember where he first heard about this exercise, but he knows that the instruction was to do it every week.

“It’s less about helping you get to like your goal as much as about propelling you forward,” he explains. Ultimately, Wong believes, “Most of us don’t really know what we want,” in part because we can’t possibly know what jobs of the future may await us to fulfill those wants. He sees this thought experiment as “a way to try on different artifacts of the future”–no matter how imaginary in the present–“and bring them back.”

Wong’s own “epiphany” after doing so, he says, “was that it wasn’t about what the end goal was at all. Even if you change the end thing, it was, ‘Oh shit, I have to do something different tomorrow.”

2. Ask “Who Am I?”–Your Job Notwithstanding

“You probably find it easy to say where you are from, what you do for a job, and the roles you play in life–father, teacher, plumber, etc. But when asked to describe who you are at the core, how easily do those words come?” asks Shantell Martin.


Martin, a British artist whose collaborations run the gamut from Kendrick Lamar to the MIT Media Lab, proposes a deceptively simple exercise to find out: “In five minutes, without describing where you are from, what you do, or the roles that you play, write down or record who you are.”

Related: Shantell Martin’s Business Models For A Modern Artist

“It may be a description; it may be an idea or an emotion; it may be a future vision,” she explains, “but I think a lot of people who are quite sure of themselves try this and they’re like, ‘Oh wait, who am I when I strip that back?'” Martin knows a key reason for that is how closely many of us identify with our careers–which she doesn’t necessarily think is a bad thing. But, like Wong, she suggests there’s a risk in getting it backward, allowing what we do to stand in for our sense of self.

Shantell Martin [Illustration: Eric Palma]
“Anyone who’s tried this challenge understands that there is no real easy, quick answer,” says Martin, which is why she finds it valuable. “Part of my work is asking who we are, and who you are, and ‘Are you you?‘”

“It’s bizarre to me that as we progress [into adulthood], this isn’t something we have the words or vocabulary for [any longer],” she she says. “When we’re kids we have these inclinations to do what we love . . . If you’re doing something obsessively as a kid, there’s a chance that your fight and your passion is tied up in there.” Martin believes grownups need to get back into that habit, mining our childhoods for “what those clues were at a young age that perhaps weren’t encouraged or promoted or even seen.”


At the same time, she believes this exercise can help you reconnect with your sense of self, even it has nothing to do with your work. “It depends on your personality and your understanding of what success means,” Martin says. “We shouldn’t be forcing people–like, ‘Find your passion and turn that into a job.’ If you’re happy with having a nine-to-five and having kids and being able to provide for them, then great!”

Martin’s own answer to her prompt? “I’m a curious, questioning individual who is always striving to figure out ‘self’ and figure out if progress exists . . . My core being is to make and to share–and that’s as far as I’ve got,” she says. But she’ll keep asking. “We have a lifetime to figure that stuff out. Being patient is good . . . Patience doesn’t mean standing still.” Martin adds, “It just means moving forward in the right direction.”

About the author

Rich Bellis was previously the Associate Editor of Fast Company's Leadership section.