Illustration of a woman looking back at a road she's just walked down

Daniel Pink, author of best-selling books like “Drive” and “When”, will join us this week at Team ’21 for a fireside chat on the state of work in this fast-changing era. We caught up with him ahead of time to dish about his recent research on regret and how it can affect us at work.

“The only people without regrets are people who have brain damage, people who are sociopaths, and people who have neurodegenerative diseases,” declares best-selling author Daniel Pink. “The rest of us have regrets. And when we reckon with them properly, they can point the way forward.”

It was this underappreciated aspect of regret that prompted Pink to embark on a multi-year study on the subject, culminating in a book coming out later this year (title TBD).

“The science of regret shows that looking backward can move you forward,” he says. “In many ways, though, and in the U.S. in particular, we are gripped by the philosophy of no regrets. We don’t talk about regrets. We think we should never have regrets. And that’s just nonsense.” 

The truth is, we experience plenty of regrets. Pink’s upcoming book includes over 15,000 individual stories collected by the World Regret Survey, alongside quantitative research into American attitudes about regret.

At a time when many of us are reflecting on everything from our careers to our lifestyles to our complicity in racial inequalities, understanding regret feels especially relevant. I caught up with Mr. Pink for a chat about how regret affects us at work and in our personal lives. (Our conversation has been lightly edited for clarity.)

Sarah: Let’s start by defining the concept. What is regret exactly? And how does it differ from disappointment? 

Daniel: Regret is an emotion. It’s an emotion that has a lot of cognition behind it, and it’s that kinda stomach-churning feeling when you realize that the decision you made, the choices that you took, the path you decided to pursue resulted in a suboptimal outcome.

Now, disappointment doesn’t involve agency in the way that regret does. That’s the big difference. With regret, you have agency. With disappointment, you don’t have agency.

Let’s say that there’s a kid who loses a tooth. And that night she goes to sleep, and she puts her tooth under her pillow waiting for the Tooth Fairy. But when she wakes up and looks under her pillow, the tooth is still there and the Tooth Fairy hasn’t come. The kid is disappointed. The parents regret their failure to be the Tooth Fairy. Hat-tip to Janet Landman from the University of Michigan – that’s the best example I’ve ever heard.

Sarah: Is there any difference in how we experience regret over doing something versus how we experience regret over not doing something?

Daniel: The research tells us that people tend to regret inactions more than actions, especially over the long term. Sometimes in the short term, people will regret actions more than inactions. But over the long term, it’s pretty clear that we regret what we didn’t do more than what we did.  

There are reasons for that. Actions can often be undone. So, I come over to your house, and I say, “Hey, let me test out your cool walking desk treadmill thing.” And I break it! I regret doing that. It’s an action, but it’s an action I have the possibility to undo. I can get your treadmill repaired.

Inactions are harder. Let’s say, that I didn’t learn to speak another language fluently. I can’t just instantly undo that.

5 questions about motivation with Daniel Pink

Sarah: So, I would regret inviting you over to my house because you broke my treadmill more than I’d regret not taking out the extended warranty on my treadmill – at least in the short term.

Daniel: Well, I haven’t done the full suite of research into treadmill-centered regrets.

Sarah: This really is opening up a full new body of work that could be explored.

Daniel: Indeed.

Sarah: Moving on! People sometimes hang on to regrets for years, or even decades. Does taking action to remedy your regret get harder with time? Or easier? 

Daniel: It depends on the nature of the regret, and it depends on your place in life. Some of the early research in regret showed that education regrets were the largest category. So if I regret, say, that I didn’t complete college and I’m 25 years old, I have a fighting chance at going back to complete college. If I regret that I didn’t get a graduate degree and I’m 85, it’s not impossible, obviously, but that might be harder.

And when you go into the core regrets that people have, they end up being largely about either opportunity or obligation. There was an opportunity I didn’t pursue. There was an obligation I didn’t fulfill.  

Sarah: What are people telling you in terms of things that they regret doing or not doing as it relates to their profession?

Daniel: I argue that there are four core regrets that people have. When you look at career regrets, the big one is not being bold enough – playing it safe. You do have people who say, “I tried to go out on my own and start a business, and it flopped. I really wish I hadn’t done that.” But they are outnumbered significantly – it’s not even close – by people who wish they had started a business rather than work for the man. “I wish I had pursued the riskier path in my career. I wish I had gone out on my own.” That’s a huge, huge career regret.

Another career-oriented regret is not investing in your human capital, to use a management-y term. A lot of people, especially in their 30s, look back and say, “I wish I had paid more attention in school. I wish I had made more effort.” Those are two of the big regrets in the realm of careers.

Sarah: You’re doing a fireside chat with our own Dom Price at Team ‘21. And I heard rumors that y’all might touch on this idea of coping with regrets by channeling them into a sense of purpose. So, I wondered if you might give us a little preview of your thoughts on that.

Daniel: I’ve been trying to crack the code on purpose for a long time, as you know. And regret yields some instances of that, particularly our regrets about not being bold enough, not leaving a legacy. 

I’ve always thought about the pandemic as a great unmasking. And I use that term intentionally. It’s a great unmasking of things that were already going on. What you see now in some of the labor-attitude data is that an enormous number of people are ready to quit their current jobs.

Why are smart companies so dumb about motivating employees?

In part, it’s because the pandemic has given them time to reflect and ask, “Am I making a contribution? Am I making a difference?” They’re not just going through the motions. And after a year of this, people are saying, “You know what? I’m not making a difference. I’m not making a contribution. I’m not growing in the way that I could. I’m going down a path that is probably not right for me. I gotta make a change.” And that turns into a sense of purpose.

Now, there are two different kinds of purpose. There is big, transcendent purpose: I am solving the climate crisis; I am arresting species loss; I am cleaning the waterways of the world, etc. But there’s also another kind of purpose, which I like to call “small-P” purpose: I felt a sense of purpose today because I helped a teammate solve a problem. I felt a sense of purpose today because there was a customer with an issue, and I helped resolve it. I felt a sense of purpose today because I earned some money, and I can support my family. And that is undersold as a career motivator.

So, if you’re a leader, you should ask your team if they feel like they’re making a contribution. And if you’re an individual, you’ll want to reflect on that same question periodically. I think the question of professional purpose will turn out to be one of the most significant consequences of this pandemic.

Daniel Pink on how regret can help you find your purpose