Asking yourself a simple question can help you get your dream career

Straight from NYU professor and business leader Suzy Welch.

Hello friends!

Work looks a whole lot different than it did 30 years ago. And thanks to AI’s abrupt rollout, it even looks different than it did three years ago. I’d be lying if I said the constantly shifting nature of work doesn’t freak me out—remember when people dreamed of writing for magazines instead of crafting algorithm-happy Instagram captions?—but Suzy Welch’s advice has been ENORMOUSLY helpful over the years.

Suzy is today’s pod guest, and she’s also a New York Times bestselling author, entrepreneur, and one of NYU’s most in-demand professors, where she teaches a wildly popular course on career and life design. A former Harvard Business Review editor and renowned thought leader, she’s helped millions navigate success in work and life. Her upcoming book, Becoming You: The Proven Method for Crafting Your Authentic Life and Career, distills her most powerful strategies to help you land a job you love, get paid what you're worth, and future-proof your career.

I’ve followed Suzy’s career for years, and there’s one career and life-related question that has been an absolute game-changer for me:

What would make you cry on your 85th birthday?

In other words, mentally fast-forward to the end of your life and ask yourself: What is the one thing I did—or didn’t do—that would fill me with so much regret that I would be tremendously sad?

Here’s why this is so effective in helping you take action steps toward your dream life and career:

❤️ It taps into deep personal values

This question forces you to reflect on what truly matters to you, beyond external pressures or short-term goals. The things that would bring you to tears—whether related to regret or fulfillment—can be really revealing when it comes to recognizing your core values.

👵 It brings long-term consequences into focus

By imagining yourself at 85, you’re able to bypass daily distractions and see the bigger, more life-encompassing picture. This perspective makes it easier to clarify which dreams and actions are worth prioritizing now.

😢 It connects emotions to motivation

Tears are a visceral response, signaling something profoundly important. When you identify what would make you cry—whether it's unfulfilled potential or a meaningful achievement—you create an emotional anchor that fuels real action toward your dream life and career.

I don’t think there are exactly 85 candles on this birthday cake, but we’re getting close. Photo cred: Betsie Van der Meer/Getty Images

From the episode:

“Stop being a naysayer. Stop being your mother, stop being your teacher, stop being the world, and just say, ‘I'm just going to pretend it all happened for me.’ And actually jot down that vision you see, and in fact, walk yourself through the day.

I've got X children or not, I get in X car and I drive to X place or not, or I go out and I lay on the beach or I continue ladling out food at a refugee camp in Somalia. Imagine that day 25 years from now, if you got everything you wanted. We never let ourselves do it. And that is our dream of a life.”

The takeaway:

If you’re having a hard time conjuring a clear vision of your dream career and life, ask yourself: What’s one thing that would make me cry on the morning of my 85th birthday? Write it down, talk about it out loud, and then start working to make sure it happens (or doesn’t!)

For more life-changing tips on figuring out your dream career and life and actually getting it, like the “10-10-10 rule for success” (I’m obsessed with this), what we don’t know about own personalities (apparently it’s a lot), and other crazy simple exercises for getting a better grasp on what we want, head to the Liz Moody podcast on Apple Podcasts, Spotify, or YouTube.

And let me know in the comments: What’s your biggest career hurdle at the moment?

Xo,

Liz

P.S. To access the full episode transcript plus key takeaways from the episode, hit the subscribe button below. And don’t forget: We’re on day 3 of the subscriber-only Liz Moody ‘reclaim your attention span’ challenge. I’m doing it right along with you, and it’s truly life-changing!