Thinking Through Time: A Conversation with Dan Pink

The bestselling author of Drive and A Whole New Mind explains why you should build a “failure resumé” — and discusses how he built his latest book out of a database of 18,000 regrets.

I’m truly grateful to Dan Pink for joining me to discuss his latest book, The Power Of Regret, which debuted last week at #3 on the New York Times bestseller list. It’s a terrific read, shining new light on both how our minds work generally, but also how we think about the individual trajectories of our lives. For more background on Dan and his career, see the introduction to Dan’s work that I wrote last week.

(Note: The second half of the interview — where Dan gets into the fascinating methodology he used to research and write the new book — is only available to paying subscribers to my email newsletter, Adjacent Possible. It connects in a number of ways with the series on creative workflows that I’ve been writing here at new newsletter over the past few months, so if you’re interested in those topics, now might be a good time to consider subscribing.)

Here’s our conversation:

Dan —

Congrats on another terrific book. I finished it yesterday morning, and ever since I’ve found myself mulling past events in my own life: paths not taken, opportunities missed, once strong connections that dissipated over time. I suspect it’s impossible to read the book and not end up retracing those turning points, imagining alternative timelines. (I’m also fascinated by the whole research methodology behind the book, which we will turn to later in our conversation.)

But in a way, the thing that struck me the most about The Power Of Regret didn’t revolve around my own personal history, but instead had to do with our evolutionary history as a species, the mental toolbox that makes us uniquely human. A few years ago I read an anthology of essays, written by Martin Seligman among others, called Homo Prospectus. The book argued that one of our defining characteristics as humans — right up there with language — was our seemingly effortless skill at “cognitive time travel”: mentally re-winding the clock back to an event that happened three weeks ago — or three decades ago — and then projecting forward a month to anticipate possible repercussions. The Homo Prospectus authors argued that this ability liberated us from the tyranny of the present, enabled us to imagine alternative pasts and futures, which laid the groundwork for all sorts of higher-order skills: creativity and imagination, counterfactual thinking, complex decision-making.

I was so entranced by this idea that I wrote a feature for the Times Magazine about it. But mostly my thinking had focused on the creativity and decision-making side of cognitive time travel. But your new book opened my eyes to a completely different side: the emotional resonance of cognitive time travel. The Power Of Regret made me realize that more than any other emotion, regret is anchored in this ability to seamlessly zip back in time to revisit a past decision, and then play it forward along an alternate timeline. The emotional weight of regret emerges out of the gap between the two timelines: the real timeline where you drop out of college and never reach financial security and the one where you go to grad school and become a successful pediatrician; or the real timeline where you don’t ask the woman on the train for her number, and the imagined one where you marry her and raise a family together. You can’t run those mental scenarios if you can’t project forwards and backwards in time, what you call a “mental trapeze act, swinging between past and present and between reality and imagination.”

There’s something very illuminating here on a general level. Other animals probably experience something similar to joy and grief and attachment and fear. But the time travel of regret may be one of our unique superpowers. And that raises the question of how we can get better at it. As far as I know we don’t have a way of measuring our aptitude at these kinds of temporal trapeze acts, but I would wager that aptitude has a significant impact on our ability to make important life decisions or sustain meaningful social connections. (As you point out, people who have brain lesions that limit their temporal imagination have massive difficulties in managing basic life choices.) In the last section of The Power Of Regret, you explore the ways that we can harness that power, through fascinating exercises like “anticipated regret,” “regret lotteries,” or even one of my favorite mental tools: the “pre-mortem.” So that’s my main question for you: to what extent can we improve our skills at cognitive time travel through deliberate practice? If you were to teach a gym class in the trapeze artistry of regret, what would be the standard workout?

Steven

Steven —

Thanks for taking time to read the book. I shouldn’t be surprised that you asked a question I’ve never really considered. (Very on brand, Mr. Johnson!) So, let me begin not by building a full-fledged time-travel gymnasium, but by assembling three initial backward-looking, at-home exercises while the full gym is being constructed.

1. Save your past self.

There’s a reason that people keep journals, schools publish yearbooks, and cities bury time capsules on important anniversaries. They are gifts our past selves bestow on our future selves. So, I encourage you do to something, anything, beyond what you’re doing already to memorialize the you of this moment. Keep a journal, even for a week, then stash it away where you might randomly find it years from now. Or use FutureMe to draft a letter about how you’re doing right now that will automatically reach you some time in the future. And for your entrepreneurs out there, here’s a business idea: “family time capsules.” (Send a family a box. Ask them to place significant items it. Store the box for 25 years. Then ship it back to them, wherever they are, to provide them the glorious pleasure of discovering their former selves.) Our memories are leaky, including memories of who we were. These techniques seal some of those leaks. Future You will understand herself better if she has a more precise record of Past You.

2. Scrutinize your past self.

One of my favorite exercises is the failure resumé, which I learned about from Tina Seelig at Stanford University. Many of us labor endlessly on our resumés, scrubbing and buffing them until they shine. That’s cool. The marketing department has a job to do. But the research and development department is feeling a little left out. So, when you’re done Turtle-Waxing your LinkedIn Profile, try Tina’s technique. Compile all your failures, screwups, missteps and blunders. List them in a single column on a spreadsheet or document. Then next to each flub, write — in a single sentence — the lesson you learned from it. I’ve done this. It wasn’t fun. But it delivered two important insights. First, in some cases, there *wasn’t* lesson to be learned. Solid decisions don’t always produce fantastic outcomes. Fortune is fickle. Shit happens. That can be a relief — a way to move forward, unburdened by the setback and better informed about the vicissitudes of life. Second, in compiling the failure resumé, I discovered that at the core of many of the screwups were the same two decision-making mistakes. The failure resumé surfaced the two mega-errors Past Dan had been making, which helped Future Dan avoid them.

3. Forgive your past self.

Hal Herschfield at UCLA has conducted some fascinating research explaining why some of us don’t save for retirement. We see our future selves as entirely different people.(Why should I put aside money for 75-year-old me? I don’t even know the guy — and I probably can’t trust him!) Herschfield has discovered that we can improve our present decisions by closing that perceptual gap. When he showed people age-advanced images of themselves, they became far more likely to save — because the person they were saving for was no longer a stranger. The same cognitive wrinkle can help us when we look backward. For instance, Daniel Pink in his teens and twenties wasn’t an especially kind fellow. That bothers current Daniel Pink, who’s now in his fifties. This unpleasant feeling has been clarifying. It’s helped me understand how much I value kindness. It has also been instructive. It’s guided me becoming a (slightly) kinder person. But at a certain point, I need to stop looking backward and move on. The way to do that? To recognize that the Daniel Pink of, say, 1985 was a different person than the Daniel Pink of 2022. He’s not a complete stranger, but he’s someone who no longer exists. Once I learn from him, I should forgive him as I would someone who steps on my toe in the grocery store checkout line and then steps out of my life. And when I’m done forgiving, I should put some money into my 401(k) or the Daniel Pink of 2047 will be pissed.

Back to you, Current Steven.

Cheers

Dan

Dan —

Oh man, I love the idea of the failure resumé. I spent most of my morning walk to coffee compiling mine in my head. It’s impressive, I can assure you. (I actually think a version of it would make a good Adjacent Possible post down the line, so thanks for the suggestion.)

You and I have already spent some enjoyable time in the past nerding out about how we organize the ideas and research that ultimately culminate in our books — and the whole idea of “creative workflows” has been one of the central themes here at Adjacent Possible. So I was particularly struck by the approach you took in writing The Power of Regret, which was built on top of both extensive surveys and a resultant vast database of regrets that you compiled from people all around the world. I think we’d all like to hear more about how you came up with that approach, and what it entailed in practice. Do you think that’s a technique you’ll use in future books?

Steven

[You can read the rest of the conversation at Adjacent Possible…]