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Learning From the Roads You Didn’t Take

Updated: Jan 6, 2023

Author Daniel Pink
Bestselling author Daniel Pink, whose newest work is The Power of Regret

It's the end of the first week of the year. Have you already faltered on a new year’s resolution? Don't fret! Just take a listen to Daniel Pink on the newest episode of WorkLab, the podcast for Microsoft that I help produce with the team at Godfrey Dadich Partners.

Dan is a lucid and perceptive thinker whose best-selling books have explored topics like creativity, motivation, and timing. In his latest, The Power of Regret: How Looking Backward Moves Us Forward, he makes a compelling case for not brushing regrets under the rug, but examining them closely and using them to inform decision making on a personal and professional level.

As a leader I’ve always believed in openly owning my missteps. But I usually approached regrets—coulda, woulda, shoulda—in a nonconstructive way that lacked self compassion. In his conversation with WorkLab host Elise Hu, Dan recommends we should be “looking our regrets in the eye, using them as a signal, as information, as data, and then drawing lessons from them.”

As for those mistakes, don’t just own them, he says, draft your own “failure resume.” I’d already written a “highs and lows” of 2022 list to inform what I want more (and less) of in 2023. Now I’m going to dig deeper into times I’ve come up short in my past to glean from those moments moving ahead (Dan tells you how to do it).

If you’re beating yourself up about your resolutions, take a pause. Chances are, you’ve got too many of them. “If you have a giant list of resolutions, you’re screwed,” Dan says. He recommends making only one or two resolutions and offers concrete and actionable advice on how to do that.


Listening to Dan’s episode, I thought of how often regrets play a part in storytelling that sticks, especially in poetry and songs. Think of "The Road Not Taken" by Robert Frost, likely the most famous poem in American literature (and the first poem I remember reading and understanding). Of the two roads, Frost writes:

And both that morning equally lay

In leaves no step had trodden black.

Oh, I kept the first for another day!

Yet knowing how way leads on to way,

I doubted if I should ever come back.

Or the work of composer Stephen Sondheim. His lyrics often explore how we choose to go through one door over another—or never open the door at all—and the emotional toll those decisions can take on our psyches. Hear the late Broadway star John McMartin sing "The Road You Didn't Take" from Follies—where he looks back wistfully at the lives he could have lived:

Where I’d always seen regrets as another story we tell ourselves—about what could have been—I now see through Dan Pink’s research and writing that regrets actually offer a new way for us to see ourselves.

This episode caps off season three of the WorkLab podcast, which uses data and research to explore the transformation of work. Elise and cohost Tonya Mosley, who joined the show this season (hoorah!), led so many provocative conversations—I learned about the meaning of “productivity paranoia,” why there’s a human energy crisis, what Gen Z is looking for in the workplace, and much more. We are already drumming up ideas for season four. Please find us on Apple, Spotify, and wherever you get your podcasts. And don't forget: cut down that resolution list, stat!


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