Regrets hurt. But they might not be as bad as you think.
“Youth is the most precious thing in life; it is too bad it has to be wasted on young folks.” — George Bernard Shaw
At some point, every person looks back on their life and thinks, “I wish I could have a do-over.”
Our regrets are saturated with all the things we should, could, and would have done differently if given the chance.
Relationships or jobs we would avoid or ditch earlier; conversations we’d do differently; careers or schools we would pursue instead of the ones we chose; people we might cherish and appreciate more next time around; hopes and dreams that were never fulfilled might come to fruition.
It would be nice to go back in time.
Or at least infuse our current perspective and wisdom into our younger selves to change the outcome of whatever we regret.
Gap Insight: Everyone can recall a moment, or several, they wish they could have back. The question is, are those moments still haunting you?
In Retrospect
I sat at lunch with my wife the other day musing about my past life as a tennis player. “I wish I could go back to when I was 17. I would approach tennis so differently.
I’d lose the fear and the doubt. I’d find a different coach. I’d put on much more sunscreen. I’d actually stretch. I would swear off other distractions (girlfriends), and I’d ditch the misguided notion that tennis players weren’t as cool as football players.
I’d go all in. Body, mind, heart, blood, sweat, glory, agony, and everything that comes with the pursuit of being one of the best tennis players in the world. All in.”
I didn’t ask what she would do. With tears streaming down her face as soon as I mentioned “Do over,” she already knew, and she didn’t need to tell me.
We all know. You know.
But how different would you really be if you could do it again, and would you change it after all?
Mitch Albom, famous author of Tuesdays With Morrie, tackles some of these questions in his latest book, Twice. The story follows a man who has the power to go back in time and redo any moment of his life.
(Spoiler alert) He discovers we’re not necessarily here to do it right, or perfectly. In fact, the whole point of our existence might be to do it all wrong.
Regrets might just work in our favor.
Think of it this way:
Name anything in your life you wish you could change. Behind the hurt, pain, or regret there’s a lesson – a message to uncover about how to create more love, happiness, fulfillment or success from now on.
From that perspective, growth is the point, not doing it right, and certainly not perfection.
Gap Insight: Regrets are like rearview mirrors – useful for a glance, dangerous if that’s where you keep your eyes.
A Few of Life’s Lessons
Looking back on a life spent pursuing athletic achievement that produced more than a few regrets – I let losses seriously bring me down, I wasn’t mentally tough enough, I could have trained harder – I’ve learned some personally valuable lessons.
- Happiness, self-esteem, and self-acceptance are more important than any athletic result.
- Your worth is not tied to the outcome of anything.
- Enjoy the journey – the destination matters less than you think.
These are just a few of the insights I’ve gleaned from my experience. I’ve learned them BECAUSE I failed, and because I have regrets – not because I was perfect.
I invite you to stop here and think about a seminal moment in your life that you wish you could do over.
Now think about what you’ve learned because you can’t.
Gap Insight: How much time, energy and emotion are wasted on wishing we could do things differently? After all, we can’t change the past, but we can shift our perspective.
The Argument to Keep Regrets Around
1. They highlight our imperfections and pave the way for connection.
I tell a story during my keynotes and workshops about the first time I played at Stanford in front of an entire stadium of students, the other team’s fraternity members, and anti-Cal enthusiasts.
I was so nervous that I hit my first two serves off the frame of my racket out the stadium. It was one of the most embarrassing moments I’ve ever had as a player.
I wished I had a do-over then, but now I use that experience to connect and relate to others who have allowed their nerves and stress to overwhelm them in important moments.
Our wish-I-could-haves are comprised of our mistakes, failures, flaws, and unfortunate choices, which prove that we are vulnerable, not perfect.
When we share that vulnerability with others, we invite connection, and connection paves the way for intimacy.
2. Our most painful moments – the ones we wish we could do over – often turn out to be our most valuable teachers.
Though we can learn much from success, pain and failure are often our greatest teachers. Something would be lost if we removed them from our memories or our lives, including our humanity.
We are shaped by our experiences both good and bad, and it’s hard to imagine we’d have the same wisdom and perspective without them. In fact, who would you be without them?
3. Sometimes, we need to process our emotions instead of a do-over.
Perhaps you disappointed, hurt, abandoned, or betrayed someone and wish you could take it back. You can’t. But rather than carry all that unresolved emotion around for the rest of your life, you can forgive yourself and process your emotional pain.
One way to process those emotions is write about them in a journal while feeling everything as you write, or close your eyes and feel the painful emotion (sadness, anger, rage, regret) to completion no matter how long it takes.
No emotion lasts forever, but they can stick around in our bodies and hearts for way too long.
Then remember that every day is a new opportunity to do things differently.
4. Do-overs actually exist. You’ve had many.
- You messed up in a relationship, they left you, and you applied what you learned to the next one.
- You plowed into someone’s back bumper because you weren’t paying attention, and every time you drove from then on, you swore off texting and driving.
- You made a major mistake at work that led to a disgruntled client, so you made sure never to make it again with your future clients.
I once had a coworker who placed a pregnant client in an exercise that required her to squeeze her shoulders back and hold her thighs tight for three minutes. Everything was great until she passed out. Talk about wanting a do-over.
She and the baby were 100% okay, but the therapist learned his lesson and never made that same mistake again with the hundreds of other pregnant women he worked with over the years.
In the end, our chance at a do-over is always the very next minute, the next day and every day after.
Instead of losing ourselves in the prison of past regrets, we are meant to take the lessons from our mistakes and apply them to how we live moving forward.
Gap Insight: Name a mistake you’ll never do again. That’s your do-over that’s already in play and working for you.
Final Thoughts
During COVID, I became the assistant tennis coach at Georgetown University.
In that brief six-month period of coaching both the men’s and women’s teams, I realized that my mistakes and regrets became valuable teachers for the young players who faced the same pressures, fears, and doubts that I experienced when I was their age.
My point is to help others. That’s one way to use your would-be do-overs and regrets for good.
Help yourself too, by processing any unresolved emotional passengers like anger, hurt, or disappointment still dragging you down, and by resolving to do things better the next time.
We can’t turn back time, but we can learn from our mistakes, forgive ourselves and others, and use our trespasses as vehicles for empathy, compassion, and connection with others.
Consider this final thought:
If you wouldn’t make the same decision today that you made back then, congratulations. You’re no longer the person who made it BECAUSE you made that decision.
See you inside the gap. Subscribe here!
I’m a keynote speaker, life counselor, and executive coach. If your organization or company is looking for a speaker for your next event, or if you’re working through a particular challenge and wish to work one-on-one with me, please reach out!
Yours in health and no more regrets, David
If this one landed, The One Thing Keeping You From Realizing Your Dreams picks up where regret leaves off — the difference between wishing and going all in.
FAQ
What does it mean when you say regrets are trying to teach you something?
Regret isn’t proof you did life wrong. It’s a signal pointing at what you value now that you didn’t fully act on then. Most regrets are unprocessed lessons — the pain is highlighting exactly what to do differently going forward. That’s a compass, not a life sentence.
How do you stop a regret from haunting you?
You don’t talk yourself out of it. You feel whatever’s still attached to it — write it out, or sit with the emotion until it passes — and then name the actual lesson it taught you. Once you can point to what you learned, the regret stops running the show.
Is it possible to have too many regrets to move past?
No. The number doesn’t matter — only whether you’re still avoiding what each one has to teach you. Even my most embarrassing moment as a player (the Stanford serve, above) turned into the exact experience that lets me connect with other people going through the same thing.
