The One Question to Ask Yourself When You're Feeling Stuck in Your Career

We all have moments in which we need to make a difficult career decision.

Do you go for that promotion?

Should you go back to school?

Do you want to change careers?

Are you ready to take the leap into freelancing?

Finding yourself at a crossroads can be a confusing—especially when you don’t know which path to take. Sure, you can turn to classic approaches like pro-con lists, but what should you do if you still feel stuck?

To move forward, you need to find clarity on your long-term aspirations.

Yuko Shimizu, an award-winning illustrator, shares the answer in her 99U talk. As she described her career path, she includes a pivotal assignment she was given as a graduate student.

Write a detailed essay about an ideal day exactly five years from now.

Shimizu advises getting specific—really specific. You should cover your entire day (not just the part where you’re at work) and include your personal life, too.

That’s because if you simply write, “I’m in a management position at a good company making $10,000 more than I am now,” you still might not have clarity on your career question. But if you include what’s happening in the hours before and after work, you’ll know where you want to be as far as work-life balance. Are you answering emails on your exercise bike first thing? Or sleeping in because your day starts later? Or having breakfast with your kids before a day of scattered freelance work?

Additionally, she suggests getting into the nitty-gritty of your work. For example, instead of saying, “I’ll be working in design,” you should include who your boss is, who your clients are, what awards you’re in the running for, what salary you’re making, and so forth.

This practice can give you some valuable insights on what you really want to be doing in your career, and how you want to do it. It’s a fresh way to think about what projects you really enjoy working on, your ideal working arrangements, team, clients, and so on.

Of course, in order for this exercise to be valuable, you want to think broadly—and within reason.

For example, writing an essay about playing in the NBA All Star game, while it may be your ideal day because the sport’s been your favorite hobby since you were a kid, isn’t going to help you decide whether or not to quit your job (assuming you’re not an exceptionally talented basketball player who’s likely to be drafted by the NBA).

On the flipside, you don’t have to limit yourself to simply saying you’ll have moved five years up the career ladder. Maybe the first answer that comes to mind for you is that you’re on vacation. Dig into that. Are you working for a company with an unlimited vacation policy? Did you make enough extra money from your side gig?

The idea is that, if you keep asking the same question: “Should I work in Field A or Field B?” You may keep arriving at the same answer. “I can’t decide.” But by thinking about your future self, you’ll gain clarity on your career goals. It also gives you direction, so you’ll be able to think what the first step would be that will enable you to make progress towards that ideal day.

Use this exercise to create goals that will help you get to your ideal day in ways you are comfortable with. (And use this worksheet to help you complete the exercise without having to do too much work.)

Shimizu set high goals, but she only committed to “one small risk every single day” to get there.

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