Work Smarter, Live Better

When you spoke at The Council’s Employee Benefits Leadership Forum this past August, you said it felt like we were at the beginning of something and that “experimenting mattered more than knowing and discovering mattered more than deciding.” Should we still be operating in this mindset almost six months later? And, during this time, is there anything that you personally have discovered or experimented with that has been eye-opening?

Two interesting questions. The answer to the first question, I think, is yes. We should continue to be experimenting. One of the things that I talked about there, and that I continue to believe, is that we are in the midst of what I like to call “a great sorting,” where this conversation that we’ve been having about remote work or in-person work is in many ways a proxy for even bigger questions that have been unresolved in organizations—questions like, what should be collaborative and what should be solo in our workplace? We don’t really have a good answer to that. What should be done synchronously, and what should be done asynchronously?

I think there’s some open questions about what an office looks like and what an office is even for these days. I don’t think that we can answer any of those questions with certainty. It requires a different way of thinking. … I think that the approach remains to experiment our way to discovery—to try stuff, learn from that, adjust, try more stuff, learn from that, adjust. And I don’t know the time horizon of that.

On the second part of your question, I actually think, even more than I thought six months ago, that we’re going to end up with hybrid being what work is—to the point where we no longer call it hybrid; we just call it working. I’ve been surprised a little bit by how enduring some of these Zoom meetings and Zoom gatherings are and how well people have adjusted.

I feel like in the last several months, people have in some ways hit their groove and are using these technologies in this way of working together and communicating to each other very effectively. I had a Zoom meeting yesterday where we had a lot of graphics to look at. It worked fine. It was the kind of thing where, in the old days, we might have had to go all together in person or they would have had to ship me stuff (they were in California) and I would look at it. It worked fine.

We have regular art meetings where we look at images. We used to get in a big room and everybody would meet and pass around pieces of paper. Now we just screen share. And it works.

It works better. Your question was about what surprised me. I’m surprised at how well that kind of stuff worked.

The other thing about it is I’ve been a little surprised by how many people actually really like some form of remote work. The number of people who want to go back to the office full-time is relatively small; it’s not zero, but it’s relatively small. A lot of people want to have this so-called “remote work” as part of their lives. And we’ve done it for so long and done it so well, that that becomes a very hard egg to unscramble.

Are there other factors that leaders should consider as they work through what their own staff needs?

I think the big open question for leaders has to do with culture. We’ve always thought of building cultures as something that people did together. It’s unclear to me whether that’s because the only way to build a culture is for everybody to be together or because the only way we ever tried to build a culture was everybody being together. I don’t know. Even though I am somebody who has been working at home for 20 years, I actually am somewhat skeptical that many organizations, particularly large organizations, are going to be fully remote all the time. I just don’t think that’s how human beings roll. But I’m equally skeptical that we’re going to go back to a world where we are sending people on one-hour commutes in a fossil-fuel burning car so that they can sit at a laptop by themselves at a desk, and then come back an hour the other way. I think those days are over.

I think the real question is how we build a culture. If you look at some of the evidence on how cultures are built, they are built around a sense of belonging. I actually think that being in person is easier for a sense of belonging, but maybe there’s a way to build a sense of belonging online. One of the things that comes out in the work on culture is the importance of a purpose and, particularly, what some people call “simple beacons,” which is that people know why they’re doing what they’re doing—it’s in very simple language.

The quintessential example of this is the NASA program of the 1960s, where they had a very simple beacon: we’re going to put a man on the moon. Forgive the sexism of the time but, man on the moon. Four one syllable words. Very simple. And it seems like simple beacons, you can share and develop online as well. But I think that’s a really open question. It could be that the way you build culture is you basically do hybrid culture-building. You do some of the things to build a culture online, and then when people come together, you are much more intentional than we have been when we brought people together. So the days that people are in the office are more meaningful, they’re more intentional, they’re better structured, they’re more purposeful.

I really think that culture is an open question. As we were talking before, I think we experiment our way to that.

You have a book coming out that’s based on regret, called The Power of Regret: How Looking Backward Moves Us Forward. Why did you decide to focus on regret?

I decided to focus on regret because I had regrets. This is the kind of book that I don’t think I would have written in my 30s. But I think that, in my 50s, it felt a little bit inevitable—as you get more experience and have more scars. The catalyzing event was my older daughter graduated from college. I had that feeling that parents have, which is, “Oh my gosh, she was just born. How did this even happen?” But then I also had this more narcissistic, human thing where it’s like, “Wait a second, how can I have a kid who graduated from college? I’m like 27. I only graduated from college a couple of years ago. This is not even physically possible.” So I’m dealing with those kinds of things in the course of this day-long graduation at a large university. And I started thinking about my own regrets. For whatever reason, I started mentioning it to people. And I found that it was a topic where people really leaned in. They wanted to hear my regrets, and then they wanted to share theirs. So I found it a very rich topic. I also was just curious myself about the kinds of things that people regretted. So I ended up doing two big social science research projects to try to crack that nut.

It is interesting that you say that people really leaned into it, because when I was doing some research for this conversation, I was very tempted to take the survey for myself. So I can see how people immediately attach to it.

I’ve had plenty of hunches and ideas that didn’t go anywhere; this is one that did. I set up this site called the World Regret Survey, where we just ask people to share their regrets. With almost no publicity, we have collected about 17,000 regrets from 105 countries. This collection of thousands of regrets from all over the world ended up being this incredibly rich trove of stories and emotions and insight. I spent two years going through a lot of those to try to figure it out and found that, around the world, there is a great deal of commonality. Across the world, people seem to have the same four regrets over and over and over again.

You mentioned that you had found four core regrets when you talked with us about this, and you shared one and said it was particularly relevant to the workplace. Tell us about that one.

One of the regrets that people have, and this is an overwhelming finding not only in the research that I did but also in the existing academic research in human behavior—it’s as sturdy an insight as you can find—and it’s that people regret inactions more than actions. We regret what we didn’t do much more than what we did do. There are all kinds of reasons for that, but that’s at the core. What I found in looking at things is that people regret not taking a chance. It doesn’t really matter the domain of life. There’s one category that I call boldness regrets, and boldness regrets are, “If only I’d taken that chance.” They cut across the different domains of our lives. So I have a lot of regrets about people who, I mean, literally, like 20, 30, 40 years later, say, “Oh, I met this person who I really liked, and I wanted to ask them out, and I didn’t do it, and I still regret it.”

A lot of people regret, and they use the same phrase, “I wish I had spoken up.” You have a lot of regrets about speaking up about assertiveness and very few regrets about people asserting themselves or speaking up and then regretting having done that. When it comes to careers, this is a prominent one. You think about starting a business. I had plenty of people in this database who regretted starting a business because it failed, or they realize they weren’t entrepreneurs. But for every one of those folks, I had 25 who said, “Oh, I can’t believe I stayed at this soul-sucking job for so long. I can’t believe I never went out on my own. I can’t believe I never took a chance. I wish I had started a business.” You have a lot of regrets in the workplace domain, the career domain, from people who said, “I wish I had been bolder in my career.” Even if they didn’t want to start a business, they say, “I wish I would have taken more chances in my job. I wish I would have been more entrepreneurial. I wish I would have spoken up. I wish I would have asserted myself. I wish I would have tried some stuff.” I think there’s a really big lesson for us there.

This book had a huge number of lessons for me. It made me reflect on my own regrets and realize that a lot of the stuff that I was regretting was actually pretty common. I think we can look at these regrets about boldness and it’s giving us clues. It’s giving us information about what we really want out of life, and what you find is, in most cases, the move is to take the chance.

The lesson to me is these four core regrets give us, in some ways, the reverse image of what makes life worth living. One of the things that makes life worth living is we all want the chance to do something, to grow, to try stuff, to lead psychologically rich lives. And when we don’t take that chance, later in our lives, we look back on it with regret. The antidote to that is you’re at a juncture and you can take a chance. You know, be smart about it. Don’t go crazy. But in general, I think we want to err toward taking that chance. I think that makes life worth living.

It’s great stuff to think about.

It’s great stuff to tell our kids, too. A lot of times, with our regrets, we don’t necessarily have a chance to repair what we did, and then if it’s things that we didn’t do, we don’t always have a chance to do things differently in the future, although many times we do, but in the advice that we transmit to others, it’s really powerful.

You write a lot about these big ideas—motivation, timing, regret. Is there anything more that motivates you to dig deep into these really big topics? And then, have you thought about what might be next?

I’ll answer your second question first: no way. I barely survived this one. On the first part of the question, I like figuring stuff out. I typically come to a topic that I’m curious about, and I feel like if I’m curious about it, other people are curious about it, too. It’s no more elaborate than that. I said, “Wow, wait a second. I have regrets, and all these other people have regrets, and what do we know about regret. It’s this negative emotion, but it seems like there’s a positive side to it. What do we know about it?”

Same thing with timing. I wrote a book on timing, the impetus of that was coming into this office, where I’m talking to you from right now, making up when I did stuff, and realizing that was no way to do it. And looking around for guidance and not seeing the guidance out there. And saying, “Oh, God, you know, this is a book I want to read. So I’m going to have to write it.” It’s really no more elaborate than trying to follow my curiosity and find stuff out. As I said, if I’m curious about it, other people will be curious about it, and if I do it well, I can sate some of the curiosity for people and maybe give them one or two or three things that they can do to work a little smarter and live a little better.

One more for you. On your website, you have all of these great short snippets of really valuable information. Like, here’s how to stay healthy when you travel and here’s the best time for you to exercise. I was fascinated by it. What are the top three pieces of advice that you think you’ve given in these small tidbits?

I have to think about it. At some level, I love all my children. And I’ve done probably 75 of these things, so I’m not even sure if I remember them all. But I love the question, so I’ll take it on. One thing that I like is—and this is a tip from [productivity consultant] David Allen—if you can do something that takes less than two minutes, do it now. Don’t put it on a list, don’t let it linger. It’s a game changer. It has dramatically changed my life.

There’s another one, it’s a tip from software engineers. Your listeners and readers won’t know this, but I’m now holding up a tiny, little rubber duck. One of the things that software engineers do when they get stuck is try to explain what they’re doing to this rubber duck. That explaining to someone else, even an inanimate object like a rubber duck, ends up unlocking some of the secrets to that. So, when you’re stuck, explain things to a rubber duck.

There’s another one that I really like that we did just recently. It’s a tip from Vanessa Bond—she’s a social psychologist at Cornell who encourages us to give more compliments. The reason for that is we resist giving other people compliments because we think it’s going to feel awkward and that they’re not going to really appreciate it. Vanessa’s evidence is we’re wrong on both of those fronts. It actually doesn’t feel awkward, and people do appreciate it.

So those are three—two minutes, rubber duck, and compliments—that I think can be super helpful in just small wins to help you do a little bit better each day.

Those are great. I think I’m absolutely going to immediately employ the two-minute one because I am always saying, “Oh, I gotta respond to that, that’ll take a second,” and then I don’t do it.

I’m telling you, I’m very serious about that one. There’s a reason that one came to me first, because I probably use that one, not joking, every single day. Truly. David Allen’s book is called Getting Things Done, and at the core of it is this idea that you want to get things out of your head into a system. There has subsequently been some really interesting research in neuroscience about that. Dan Levitin wrote a book about it that validates that.

I recently had this experience, I had an annoying email that somebody had sent me, and I needed to respond to it. I happened to be with my wife at the time, and I said, “I’m gonna respond to it right now.” And my wife was like, “No, you don’t need to respond to him right now.” And I said, “I’m not doing it for him. I’m doing it for me.” Because I knew it was only going to take me 30 seconds and, once I respond, I’m not going to think about it again. If I had let it linger, it would have been different. So two-minute drill, ladies and gentlemen.