“What Makes You Cry?” and Other Unexpected Questions to Help You Find Your Dream Job
Magazine / “What Makes You Cry?” and Other Unexpected Questions to Help You Find Your Dream Job

“What Makes You Cry?” and Other Unexpected Questions to Help You Find Your Dream Job

“What Makes You Cry?” and Other Unexpected Questions to Help You Find Your Dream Job

In my book research, I noticed that introverts often spend so much of their lives conforming to extroverted norms that by the time they choose a career, it feels perfectly normal to ignore their own preferences. So here are four questions to help you find work you love:

1. What or whom do you envy?


Jealousy is an ugly emotion, but it tells the truth. You only envy those who have what you desire. Back when I was a Wall Street lawyer, some of my former law school classmates got together one evening, and compared notes on alumni career tracks. They spoke with admiration but also jealousy of a classmate who argued regularly before the Supreme Court. More power to that classmate! I thought, congratulating myself on my magnanimity. Then I realized that my largesse came cheap, because deep down I didn’t aspire to the accolades of lawyering. When I asked myself whom I did envy, the answer came back instantly. My college classmates who’d grown up to be writers, or psychologists.

2. What did you love to do when you were a child?


How did you answer the question of what you wanted to be when you grew up? The specific answer you gave may have been off the mark, but the underlying impulse was not. If you wanted to be a fireman, what did a fireman mean to you? A good man who rescued people in distress? A daredevil? Or the simple pleasure of operating a truck? If you wanted to be a dancer, was it because you got to wear a costume, or because you craved applause, or was it the pure joy of twirling around at lightning speed? You may have known more about who you were then than you do now.

3. What work do you gravitate to, even when it’s unpaid or unnecessary?


When I was a lawyer, I never once volunteered to take on an extra corporate legal assignment, but I spent a lot of time doing pro bono work for a women’s leadership organization. I also sat on several law firm committees dedicated to mentoring and training young lawyers in the firm. Now I am not the committee type, but the goals of those committees lit me up, so that’s what I did. Today I’m doing a version of this kind of work with my writing and consulting, and I wake up every day excited to get started.

4. What makes you cry?


This one comes courtesy of Steve Pavlina, over at Personal Development for Smart People. He advises that you sit down with a blank sheet of paper, ask yourself what your life purpose is, and keep writing down answers until you come to the one that makes you cry.

I experienced a variation of this many years ago. I was having dinner with my good friend Katie Orenstein. I mentioned that I’d always wanted to be a writer but could never find the time to actually write anything. We were having a casual conversation, but I saw the depth of my emotions reflected back in Katie’s face. And burst into tears. Check out Katie’s inspiring Op-Ed project here; she may change your life too.

This last question conflates work with life purpose, of course. In an ideal world they will be one and the same, or at least work will be a subset of a larger life purpose. For many people, however, it’s not an ideal world. In that case, try to earn your income from work that doesn’t take too much time and energy. Then you can spend the rest of the time doing your thing.



This post previously appeared on Susan Cain’s former blog, The Power of Introverts. For additional content like this, check out Quiet Revolution.


the Next Big Idea App

app-store play-market

Also in Magazine