The Gift Inside Regret

In 1985, something unexpected happened in a neuroscience lab at the University of Iowa. A man named Elliot had survived a brain tumor, but the surgery damaged part of his brain called the orbitofrontal cortex.

Afterward, he could still do math. Argue logic. Explain ethics. But he couldn’t make decisions. Not because he lost reason. Because he lost the ability to feel regret. And without regret, he got stuck—unable to weigh what mattered, unable to move forward.

That’s when scientists realized: Regret isn’t a flaw in the system. It is an essential part of the system. It’s how we learn. How we choose. How we grow.

Regret doesn’t always shout. Sometimes it whispers—so faintly we miss it for years. But unheard regret doesn’t vanish. It lingers. And over time, it can quietly reroute the course of our lives—how we live, how we lead, how we love.

Looking back, I can see this in my own story. I grew up in a home where I felt deeply loved. But when things got hard—whether it was school or a new habit or a tough conversation—I had a go-to strategy: I bailed.

I’d rationalize, argue, distract myself, do anything to get back to my comfort zone. I didn’t yet know how to sit in discomfort long enough to let it transform me.

A few months ago, my wife Teresa said something that landed like truth often does—gently, and then all at once. She said, “Honey, I don’t think you really learned how to lean into discomfort when you were younger.”

It was like someone quietly turned on a light in a room I didn’t know I’d been living in.

And suddenly, I could see it: decades of moments—missed growth, stunted courage, held-back words, half-formed risks. Not because I was lazy or afraid of effort. But because I didn’t yet have a framework for what discomfort could offer me.

I felt regret. Not just about one thing, but about a pattern. A missed muscle I wish I’d started building earlier. And I wondered: What would have been different if I had felt that regret sooner, and let it teach me something?

Because here's the thing: regret that gets ignored doesn’t go away. It calcifies.

A few weeks ago, I walked into our dining room. We have this beautiful old reclaimed wood table—a gift from a friend—but the leaves don’t slide together easily. There’s a certain way to do it so they don’t jam, and I’ve (probably too often) reminded the family “how to do it the right way!”

That day, I saw the leaves half-closed and stuck. And without even thinking, I blurted out: “Who would be so stupid as to do this the wrong way? I can’t believe how ignorant someone would have to be to not figure this out!”

As I was muttering to myself, Teresa walked around the corner. She looked at me and simply said, “It was me.”

The wave of regret hit instantly.

Not because I got caught. But because I had just spoken with contempt and superiority about someone I love deeply. I heard the tone. I felt the impact. And I hated what it revealed.

That’s what regret does. It gives you a flash of clarity—a window of opportunity to course-correct.

And while I don’t always recognize those windows, this time I did.

I apologized. I did a repair. And thankfully, Teresa—gracious as always—was quick to forgive… and equally quick to point out the contempt in my voice. She wasn’t wrong.

Two different stories. One was quiet and years in the making. The other exploded in a single sentence. But in both cases, regret wasn’t there to punish me. It was there to teach me. To hold up a mirror. To offer a better way forward.

And it made me wonder: Why do we resist regret so much? Why do we downplay it, stuff it down, or try to outrun it altogether?

Because somewhere along the way, we started telling ourselves that regret is weakness. That it’s something to avoid at all costs. That “no regrets” is the mantra of the strong, the successful, the self-assured.

But what if that’s completely backward?

You’ve heard the phrases. Maybe you’ve even said them:

“No regrets.”

“I did what I had to do.”

“You can’t change the past, so why dwell on it?”

At face value, they sound like strength. But look again. These are not declarations of confidence. They’re defenses. Defenses against vulnerability. Against feeling the sting of imperfection. And most of all, defenses against the transformational gift of regret.

Because regret, when held honestly, is a compass.

It points us toward the kind of person we want to be. It’s not there to shame us. It’s there to shape us.

According to neuroscientist Lisa Feldman Barrett, emotions aren’t reactions to the world—they’re predictions.

Your brain is constantly comparing what’s happening now to what has happened before, making educated guesses to keep you safe, connected, and aligned with your internal map of meaning.

In this model, regret isn’t a malfunction—it’s a message. It’s your brain’s way of saying:

“That moment? That choice? That wasn’t in alignment with who you want to be.”

So when regret shows up, it’s not a sign of weakness. It’s an invitation.
An opportunity to pause, reflect, and recalibrate your course.

As therapist and author Terry Real says, “All healthy relationships move in a rhythm of harmony, disharmony, and repair.”

The goal isn’t to live in constant harmony—that’s a myth. The real work is recognizing when disconnection happens, allowing regret to awaken us, and then leaning into the work of repair.

And the research backs this up.

Relationship scientists, Drs. John and Julie Gottman found that what distinguishes the “masters of relationships” from the “disasters of relationships” isn’t the absence of conflict or missteps. It’s the work that goes into repair after a regrettable incident. Repair—not perfection—is the secret ingredient to thriving connection. 

And regret is what helps us get there. It’s like a quiet inner compass, gently signalling when we’ve drifted from our values or our connection with others. Rather than a flaw to avoid, regret becomes a form of wisdom—an invitation to pause, reflect, and realign with who you want to be and how you want to show up in your relationships and in life.

When partnered with love, it guides you from breakdown to breakthrough.

The Rule of Regret is simple, and transformative:

You can’t change the past. But you can learn from it.

There’s no power in shame, and no growth in blame. But there is incredible power in allowing regret to teach you how to show up differently.

3 Ways to Turn Regret Into Relational Power

Regret isn’t weakness—it’s healthy feedback. A high-functioning internal system alerting you when something isn’t aligned with who you say you are. 

It doesn’t exist to shame you.
It exists to sharpen you.

To help you recalibrate, reconnect, and lead with greater integrity.

Let go of the “no regrets” myth. It’s not strength to ignore what matters.
Real strength is being honest with yourself, owning your impact, and choosing to lead—at work and in life—with clarity, courage, and care.

Let regret be a teacher.
Let love be the strategy.
And let who you become be the real win.

Until next week,

Jonathan Penner | Co-Founder & Executive Director of LifeApp

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