1 Big Idea to Think About

  •  Regret can play in inspiring role to help us make better choices in the future.

2 Ways You Can Apply This

  • Follow this process to let a regret fuel a positive change in your life:
    • Name a regret you have.
    • Look at the gap between what you wish it had been and what it has actually been.
    • Envision what the future will be if you don’t make a change.
    • Use the space you have to do something different.
  • Listen to Episode 88 Dan Pink on the Power of Regret and Living With It

3 Questions to Ask

  • What is one regret I have?
  • What can I do right now to use that regret to fuel a positive change in my life?
  • How will I feel in the future if I do not make a change in respect to this regret?

Key Moments From the Show 

  • Don’t miss what’s essential (1:32)
  • Two important lessons about what’s essential (2:28)
  • Expanding on an idea from Essentialism (3:49)
  • The positive role regret can play in helping us make positive choices in the future (4:55)
  • A moment of regret for Greg and how he is handling it (6:13)
  • Regret is a terrible thing to waste (9:14)
  • One way you can remedy a regret (11:38)
  • It’s not too late! (14:38)

Links and Resources You’ll Love from the Episode

Greg McKeown:

Welcome everyone. I’m your host, Greg McKeown, and I am here with you on this journey to learn. Have you ever had a wake-up call where you just suddenly realize you have missed what really mattered? Most of us have learned that we are supposed to live with no regrets, but this, I think, is wrong. What we know now is that regrets can produce the precise data we need to construct a meaningful, rich and essential life. Today, I will share a powerful story, something counterintuitive I’ve been learning, and some actionable advice. By the end of this episode, you will be able to use regret to design your most essential life. Let’s begin.

As you listen to this episode, I want you to be thinking about one person who you think could use this conversation and share it with them. Teach an idea from it so that they benefit and you also benefit. 

The life of an essentialist is a life of meaning. It’s a life that really matters. And when I need a reminder of this, I think of a story. It’s about a man whose three-year-old daughter died, and in his grief, he put together a video of her short little life, but as he went through all of his home videos, he realized something was missing. He had taken video of every outing they had gone on, and every trip they had taken. He had lots of footage. That wasn’t the problem. But then he realized that while he had plenty of footage of the places that they had gone, the sites they had seen, the views they had enjoyed, the meals that they’d eaten, and the landmarks they had visited, he had almost no closeup footage of his daughter herself.

He’d been so busy recording the surroundings. He had failed to record what was essential. Now, this story, to me, at least captures two immediately important and personal learnings. The first is the exquisitely important role of my family in my life, and I’m sure yours, in yours. At the very, very end, everything else will fade into insignificance by comparison. 

The second is the pathetically tiny amount of time we have left of our lives. Now, for me, this is not an inherently depressing thought, but in some ways, a thrilling one because it removes fear of choosing the wrong thing. In a way, it infuses courage into my bones. It challenges me to be even more unreasonably selective about how to use this precious, and precious really is too insepid of a word, but nevertheless, this precious time. 

I know of someone who used to visit cemeteries around the world when he traveled, and when I first heard that, I thought it was odd, but now I realized that this habit helped keep his own mortality front and center, and he’s gone now himself. But what a perspective, what a sense of clarity I think that must have given him. 

I’m reading here from the last couple of pages of Essentialism, and I want to continue, but I want to disagree with myself. The next sentence reads, “the life of an essentialist is a life lived without regret.” And as I read that now, I know what I meant, but I think it misses some nuance, and I want to explore that with you. I continue in this paragraph. “If you have currently identified what really matters, if you invest your time and energy in it, then it is difficult to regret the choices you make. You become proud of your life, proud of the life you have chosen to live.” 

I do agree. When we make trade-offs based on our highest, most important values, yeah, that is not something we will regret. I agree with that. I agree too that the life of an essentialist is the one that will produce almost certainly the least regrets. No one on their deathbed wishes that they just spent more time on social media, but I still think there’s something more here, something worthy of our exploration, and that is the positive role that regret can play in inspiring us to make better choices in the future.

In other words, it’s one thing to strive to live a life that we don’t regret, and quite another to always insist that the life we have chosen has no regrets in it. I remember even as a much younger man asking a colleague of mine, what would you do differently if you could have this experience over again? And without a heartbeat, the answer came back nothing. I would do everything exactly the same way again. And I just, I don’t know what I said on the outside, but on the inside, I just couldn’t find myself to think that was expressing great wisdom.

Yes, okay. Our experiences make us who we are, our past choices make who we are today, but surely there is something why isn’t admitting that we made a mistake? Surely there is something kept in its proper balance with allowing ourselves to regret a decision? After all, admitting that we made a mistake, admitting that we feel some regret only means that we’re wiser now than we used to be. 

I don’t know how much to tell of this experience now, but a few nights ago, as I was going to sleep or trying to go to sleep, a thought came to me, and it really hit me hard. It was a regret. A regret, not just in the making, but a regret for how I had spent time over the last few years. It was about someone who really matters to me. It wasn’t my wife Anna, although, of course, she really, really matters to me. But it was someone whose relationship to me is precious. And it wasn’t that I could look back and say, well, I haven’t been there for them. It wasn’t one of these relationships where the problem and regret is because of some strain, not because of some commission. And I think I could say quite truthfully that if you were to ask them about our relationship, they would say very positive things, but still, really, I could sense a gap. I could sense that I knew that they had a need and that I was the person supposed to meet that need, and I hadn’t. 

I’m not just trying to make myself feel better to position it this way, but it’s something like the regret between good and great. And there I was, feeling tired. It’s dark. I still want to get to sleep, but now sleep is not coming to me. And I started to reflect on all of the things I would need to do differently in the future to try and make this shift, to try and change the way I was using my time and every interaction to be able to bridge the gap, to meet that unmet need. And it was overwhelming. 

I’ve committed to do a lot, and I’ve tried to be thoughtful and curate those things, and so I wasn’t really sure how to go about it. And then an even sadder thought came to me, what if you’ve missed your chance? What if it’s too late, not too late to have a good relationship, but what if it’s too late to meet the precise need and to fulfill the precise relationship that was part of my unique mission to fulfill? 

Eventually, I did fall asleep, and the next morning, as soon as Anna and I were both awake, it was the first thing I talked to her about.

I do have regrets in my life, but I don’t live in them a lot. I try to learn from them and move forward. I try to understand what I did wrong and design around it, but this feeling was different. And as we talked, I started to really sense the possibility within the regret. Regret, let’s say, is a terrible thing to waste. 

As we talked about it, it brought me back to an episode. It’s episode 88 of this podcast. It was with Dan Pink who wrote, of course, the Marvelous book, the Power of Regret, in which he inverts almost everything we’ve ever been taught about regrets, something to avoid, something to feel shame about, something to be embarrassed about.

I would encourage you to go back and listen to it if any of this is resonating with you. But one of the key lessons that we discussed in that conversation was the idea of creating a failure resume. And the idea is that if you can study all of your regrets, they create like the negative of a photograph, the exact opposite of what it is that we really are trying to design. And so there is data deeply ingrained in the regrets of our lives for what it is we are really supposed to do. And if we just brush it aside, oh, talk about it in a sort of endlessly positive way, like lawyer our way through the past where we’ve made decisions, maybe they weren’t really the wisest decisions, or maybe they did cause problems, but instead of allowing the regret to teach us, to inform us, to inspire us, to encourage us to do better and be better, that if we don’t do that, we miss all of that design fodder. 

When I had Dan on the show, he shared with me that he’d created the world regret survey. So thousands of people from all over the world have taken this very simple survey. It’s basically, what is one thing that you really regret? And he’s collected those and organized them, and identified four core regrets that are more common than any other comments. And one of the four is what he calls connection regrets. That is the unmistakable importance of love and relationships. And that’s what it is right there. 

If we say we have no regrets whatsoever in any of the relationships of our whole life, it just seems to me we’re not being completely honest. We’re not learning deeply enough, not facing the choices and trade-offs that we’ve made. So I’d like to share what I’ve done since then just in these few days. 

The first thing I’ve done is I’ve taken this regret, stated it in the positive form, and put this as my number one priority. I don’t know how long it will remain the number one priority, but it’s going to remain there until the changes have been made, that means this is no longer a cause of regret, that the gap has been eliminated. 

The second thing I’ve done is to take immediate action. So I’m not waiting for the full master plan to be figured out and clarified. It’s what’s the first thing I can do? And I’ve taken action every day. And for me, in this instance, it has had immediate effect. It has had great beneficial memories made. I think I want to put it this way. I have seen an immediate improvement, and I am encouraged and buoyed up with the idea that I can help this to go from good to great, that I can address this warning that maybe this regret in the nighttime can be experienced, something like a mini Christmas Carol, you remember this story as it happens, we re-listened to the whole story over the holidays. Ebenezer Scrooge, the elderly miser, he’s visited by the ghost of his former business partner, Jacob Marley, and then the spirits of Christmas past, present, and yet to come.

Well, that’s a pretty good metaphor for the role of regret. You regret the past. You see something that wasn’t invested in the way you wish it had been, that you see the gap as it exists today if it still exists. And then you see the regret of not making a change over the future. What is the pain you will experience in the future if you still don’t learn this lesson now? It really is an ultimate turnaround story that, in a single night, his life is transformed, and he has that most precious of things. As he wakes up the next morning, suddenly aware that the future has not been written, that his story can still be changed, that the next chapter must literally now play out that most precious of things, hope. 

And that, I think, is the dynamic combination, the regret plus the hope, the discovery he makes, that it’s not too late. It’s too late for him not to regret the past. It might be too late for him not to regret the present. It is not too late for him to regret the future. And at least that’s where I’ve come to, and that’s what I wanted to share with you today because I know I’m not alone in having regrets about something essential that was underinvested in. 

Maybe you have a relationship in your life where you feel regret. Maybe you have come to feel it is too late. And see, that’s the thing. That’s the killer combination to feel the regret, but to not feel hope. And what I want to say to you is that there is hope that it’s not too late. And I’m not saying every single situation from the past can somehow be completely redone the way that you wish it had been done. But I’m saying that gap between our current regret and this future regret, there’s space to change that.

Now Scrooge can’t go back and change how he was as a young man. He can’t go back and change the fact he made a decision never to be married, to get out of his engagement with the love of his life, the person who actually would’ve made his life so happy. He can’t change it all, but he has hope, the space with which to design again, and he can let that lesson of deep regret fuel his change. And that’s the same for me, and it’s the same for you. 

Name what you regret. Look at the gap. Face it between what you wish it had been and what it’s actually been. Look it square in the face of what the future will be if you don’t make a change and that stronger feeling of regret that you will have at that time if you don’t change, knowing what you know now. And then use that space that you have to do something different, reorganize and reprioritize and make an immediate action today to do something about it and then another tomorrow and see if you can’t build momentum around that, that matters most.

I’m going to come back to those last couple of paragraphs now from Essentialism. Will you choose to live a life of purpose and meaning, or will you look back on your one single life with twines of regret? See, this is the theme. It’s not too late for you to design a life that really matters. It’s not too late for you to change in a way that you can build relationships, perhaps with the very person that you are concerned about, or perhaps just in a way that you change so that you can be different for all the people in the future. It’s not too late to ask what’s essential. It’s not too late to ask who’s essential. 

Combining now that thought with almost the last page of Effortless, “Whatever has happened to you in life, whatever hardship, whatever pain,” I’ll add now, whatever regret, “these things pale in comparison to the power you have to choose what to do now.” I’ll say it again so the people in the back can hear. It’s not too late. I’m saying it to you as you’re walking along. I’m saying it to you as you’re driving in your car. I’m saying it to you as you tidy up. I’m saying it to you as you run on the beach. I’m saying it to you as you’re sitting there. I’m seeing you now. It’s not too late. So lets you and I get to it. Let’s begin.

Thank you, really, thank you for listening. What is one idea you heard today that caught your attention? Why does that matter to you? And who is one person you can share this with? 

Please be sure to take advantage of all the tools that I’m creating to be able to help you to live a life that really matters. The 1-Minute Wednesday newsletter. Sign up and subscribe to this podcast so that you can receive it every Tuesday and Thursday. Sign up for the Essentialism Academy if it speaks to you, and please give me your feedback in the review on Apple Podcast so that I can understand what’s relating to you, what’s connecting, and so that I can make sure that we’re doing this as well as it can possibly be done for you. I’ll see you next time.