How to Create the Work and Life You Want – Using the Power of Regret: A Conversation with Daniel Pink

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Photo credit: (Yutthana Gaetgeaw)

Daniel Pink, a speaker at the Massachusetts Conference for Women, is one of the best-selling nonfiction authors of the last decade with his books on work, business, and behavior. He joined us recently for a conversation about his latest book, Power of Regret, and what leaders need to know about the power of purpose in a post-COVID world. 

Q: Your latest book is called the Power of Regret, which is a direct challenge to the association more often made to this emotion: “No regrets!” What is the truth about the role of regret that you want people to understand? 

There are two truths I want people to understand. The first is that regret makes us human. Everybody has regrets. I can’t stress this enough. Regret is one of the most common emotions that human beings have. It is arguably the most common negative emotion that human beings have. It is ubiquitous in the human experience. Truly, the only people who don’t have regrets are little kids, people with brain disorders, and sociopaths. 

The second thing I want people to take away is that regret can make us better if we treat it right. This is a really important point. We shouldn’t be ignoring our regrets. We shouldn’t be wallowing in our regrets. Instead, we should be confronting our regrets – using them as information, data, and signals. And when we do that, there’s a pile of evidence showing that it helps us on a whole range of things. It helps us become better negotiators, better problem solvers, clearer thinkers, and more astute strategists. 

So regret makes us human, and regret done right can make us better.

Q: It seems important to note that while many people imagine deathbed reckonings with regret, that’s not what you’re talking about. You’re encouraging people to identify their regrets now – as a motivator for future action. How specifically do you recommend we do that?

Deathbed regrets – that’s a little late. I want people to start thinking about their regrets much sooner. And what I want them to do is not ignore them and not wallow in them but confront them, and I think there’s a systematic way to do that. 

I think identifying our regrets is fairly easy because we feel them. Regret is an emotion that makes us feel bad. Think about it. Think about the decisions that any of us made today, yesterday or last week. We made all of these decisions, most of which we don’t even remember. 

But there are a few decisions and indecisions in life that stick with us. And that bug us for a year or 10 years or 20 years. That’s a very strong signal. We need to listen to that. When we hear the sound of that regret, we shouldn’t put our fingers in our ears and try to block it out. We shouldn’t let it bring us down. We shouldn’t say, ‘Oh my god, I’ve got this regret. I’m the worst person in the world. This fully defines who I am as a human being.’

Think of it as a knock at the door: clunk, clunk, clunk. Regret is trying to tell you something. Then we can derive lessons from it that can guide our path in the future.

Q: You identify four types of regret. I’d like to ask you about two of them. The first is boldness – or, as you put it, regret over the thwarted possibility for growth. Since most people reading this are committed to growth, what advice do you have for how women can fully embrace their boldest ambitions?

That’s a great question. One of the most critical distinctions in the architecture of regret is the regret of action in the regret of inaction – regrets about what we did and regrets about what we didn’t do. What I saw in some of my research was a very, very, very strong age effect here. When we’re young, we have a generally equal number of regrets about what we did and didn’t do. As we age and not even age that much – in our 30s, 40s, 50s, and beyond – inaction regrets take over. We are much more likely to regret what we didn’t do than what we did do.

A lesson from that, especially from these bold regrets, is that we should have a slight bias toward action. That means, in many cases, looking at things like feelings of awkwardness and apprehension and trying to reframe them as signals, as in: ‘Oh, I am feeling a little awkward. I’m feeling a little uncomfortable. Those are the situations in which I grow. So I want to lean into those.’

Too often, we think we have to figure things out and then do them. I’m going to change careers. I’m going to figure out what my new career is going to be, and then I’m going to do it. It doesn’t work that way. Doing is a form of thinking. So, if we have a bias toward doing and trying stuff, and using the feelings of awkwardness and apprehension as feelings of opportunity, I think that’s the solution.

Q: Another significant category of regret concerns connections or relationships. What does the research show are the most common regrets in this domain? And how can we use this information to move forward to more satisfying future connections? 

I don’t think there’s a specific kind of relationship most prevalent among the connection regrets. I think the interesting thing there is that they’re often not romantic relationships. It’s the full spectrum of relationships with our friends, our family, and our colleagues. And I think the interesting insight there is how these relationships come apart.

If you watch Netflix, you think the way these relationships come apart is in these dramatic ways where people are throwing things or swearing at each other. But most of these relationships come apart in less traumatic, slow, drifting ways. What happens is that people don’t want to reach out because they think it’s going to be awkward or that the other side is not going to care. And those are honestly two colossal mistakes.

Whenever we reach out, it’s almost always less awkward than we think, and the other side almost always welcomes that overture. And so, to me, what gives life meaning is the relationships we have with other people. So, you have to push past. For me, the lesson is if I’m at this juncture where I’m wondering whether I should reach out or should I not reach out – being at that juncture is answering the question for me. You should reach out.

Q: Finally, since you’re the guy who wrote the seminal book Drive, I’d like to end with your thoughts about the rising search for work that feels meaningful. What are employers missing on this? Or to put it more positively, what are the most important things they should be doing now to help employees feel more connected to a true sense of purpose?

There are a few things that employers should do. First, they should understand that this is a huge deciding factor among the most talented people in the workplace. Talented people need organizations a lot less than organizations need talented people. When talented people choose a place to work, most of them want to choose a place that is decent and has a sense of purpose and is honest and transparent and doing something worthwhile. So, it’s not this like nicey-nice. It’s fundamental to attracting great talent.

Think about meaning and purpose in a hard-headed way, as something essential to attracting the very best talent. There are also things employers can do on a day-to-day basis to cultivate, nurture, and feed the sense of purpose. One of the things that I like and try to do myself is to have two fewer conversations about how and two more conversations about why with your team. “Here’s why we’re doing this; here’s how your piece fits into the larger whole”. It’s easy to do, and I think people will see results quickly.

Daniel Pink

Daniel Pink’s other books include: When: The Scientific Secrets of Perfect Timing; To Sell is Human: The Surprising Truth About Moving Others; Drive: The Surprising Truth About What Motivates Us; A Whole New Mind: Why Right-Brainers Will Rule the Future; The Adventures of Johnny Bunko: The Last Career Guide You’ll Ever Need; and Free Agent Nation: The Future of Working for Yourself.