Can Career Regrets Be Avoided? 

This is one of a series of interviews by Bloomberg Opinion columnists on how to solve the world's most pressing policy challenges. It has been edited for length and clarity. Sarah Green Carmichael of Bloomberg interviewed Daniel H. Pink, author, "The Power of Regret: How Looking Backward Moves Us Forward."

When I started reading your new book, "The Power of Regret: How Looking Backward Moves Us Forward," I blithely assumed I didn't have very many regrets. By the time I finished, I realised I did — but so does everyone else. Your book is based in part on responses from 16,000 people who filled out your World Regret Survey. Most of their regrets fit into one of four categories: foundation regrets (financial instability), connection regrets (scuppered relationships), boldness regrets (insufficient risk-taking), and moral regrets (unfortunate transgressions). I'm curious specifically about career regrets. Did you see any trends in your survey?

The two that seemed to come out the most are not being bold enough and not speaking up. Being "bolder" could mean being more entrepreneurial on the job, not staying in a lacklustre job, or not starting a business. And there were a lot of regrets about not speaking up: "I wish I had said something" or "I had something to contribute, but I didn't" or "I wish I were more assertive."

What about regretting their choice of career?

There were not as many as you would think. And most of them were like, "I should have pursued my dream instead of taking this job." There were an even smaller number, an itty-bitty number, of people saying, "Oh, what a mistake becoming a fine artist. I should have become an accountant."

Is that because you don't have as many regrets if you do something that feels true to yourself, even if it's not the most remunerative?

A lot of times we evaluate our decisions based on how they turn out, rather than on the integrity of the decision at that moment. But I was surprised that people were not as outcome-ist as I expected. I remember one guy who said, "I started a business and it failed. But I'm glad that I did it. Because now I know. I don't have any 'What if?' questions lingering over me."

What else surprised you?

I was surprised that people who had more formal education were more likely to have career regrets than people who had less formal education. I think it's basically that if you have more opportunities, you have more opportunities to forgo.

In the book, you discuss the regrets of people who had not built a secure financial foundation. Did they regret not pursuing a career that would make more money?

The financial regrets were really about spending and saving more than earning. They were mostly regrets about buying stuff that made them feel good in the moment. And even worse, borrowing to buy stuff that made them feel good in the moment. I found people saying, "I can't believe I ate out all the time and I didn't save any money," and "I can't believe I didn't start putting money away when I was younger. I can't believe I didn't understand compound interest until it was too late."

If you have a decent foundation, you have the room to be bold, in more cases than not. Whereas if your foundation is unstable, it might be hard for you to even contemplate boldness.

Would it be easier for people to take some of these career risks to be bolder, if there was more of a financial safety net in the U.S.?

I can see you and raise you on that. If people had greater stability in their lives, they might be able not only to take more career risks, but they might actually be able to have more time with the people they love because they're not straining to earn a living. If you think about these four core regrets, they give us clues about what constitutes a good life: People want some stability; they want to be able to learn and grow and contribute; they want to have close relationships, and they want to be in conditions where they can do the right thing.

It also sounded like people regretted not getting more levels of education, even though education is so expensive. Did you hear from people regretting their education debt?

We're up to 19,000 responses so far, and only 38 people actually mentioned the words "student loan." Among this group, private universities came up a lot. One person said they regretted "attending a private university that I could not afford and majoring in something that does not make a lot of money." That was typical.

There's some evidence that young people today may be delaying having kids for financial or career reasons, or considering not having children at all. But in your book, fewer than 20 people out of more than 16,000 said they regretted having children. What's the takeaway there?

There are way more people who regret never having kids than having kids. It's not even close. I'm hesitant to say, "So go out and procreate, young men and women!" But I do think that tells us something about the importance of love and connection and meaning in our lives. There's data that shows that people's day-to-day happiness drops when they have kids, but their overall lifetime happiness increases significantly because they have somebody who they love, somebody who is in their life forever. They have a legacy.

Are there any lessons that you would like bosses to draw from the book or from the research?

When people tell you their regrets, they tell you what they value. And if they value these things — if they value a sense of stability, a sense of boldness, doing the right thing, connections to others — why would they not value those things in the hours they spend at work?

I do think that there are hints here about what makes an effective culture inside a company. One of them is a measure of stability. One reason for this "Great Resignation" is that people are leaving jobs because their jobs suck, because they're unpredictable, because they don't know their schedule, because they're not being treated well, because they're not getting paid enough.

One of the saddest regrets that I saw was a guy who talked about working at a place for 30 years and realising that he didn't have any colleagues who were friends. And I think that tells us that people want to have that kind of personal connection.

And business leaders should pay attention to the number of regrets I heard about speaking up, and how people feel like they can't speak up. When people are in a culture that doesn't provide psychological safety, they don't speak up. They worry more about not failing than they do about doing something cool and interesting. So I think there's a big lesson there.

Any other advice for leaders?

There is a lesson for leaders in disclosing their own regrets and normalising those rather than trying to live this kind of performative perfection. We know from the research on self-disclosure that when we disclose our vulnerabilities, people typically don't think less of us — they typically think more of us. A leader who reveals her regrets and reckons with them is going to be a more effective leader.

If someone has career regrets, what should they do?

Having career regrets is one of the most normal kinds of regrets that you can have, so treat yourself with kindness rather than contempt. I think there's a strong argument for talking about them with somebody else or even writing about them — when you convert it into concrete words, it's less fearsome. Try to extract a lesson from it.

This is why I'm a huge fan of the failure resume. I think that everybody should do a failure resume, where you list your setbacks and screw-ups, the lessons you learned from them, and what you're going to do about it.

Overall, in general, people are a little too risk-averse in their careers. There is a far greater number of people who regret playing it safe than there are people who regret taking a risk. It's not even close.

Sarah Green Carmichael is an editor with Bloomberg Opinion. She was previously managing editor of ideas and commentary at Barron's, and an executive editor at Harvard Business Review, where she hosted the HBR Ideacast.

Disclaimer: This article first appeared on Bloomberg, and is published by special syndication arrangement.