Making Peace With Regret

Learning to live with the choices we make

In my last book, Consider This, I offer some advice on regret:

“Is it possible to live with no regrets? It’s more likely to live with manageable regrets. When we make a choice, we can’t be certain we have made the right one. So, mistakes are inevitable.

Regret springs from guilt. Regret springs from not living fully. Regret springs from living inauthentically.

Intentional living might lead to fewer regrets, but it won’t completely eliminate them.”

When I’m facing a decision, I often ask myself, “Will I regret this later?” That question helps me center myself and often leads to deeper reflection. Sometimes, when we say yes to something—like moving to a new city or taking a new job—we still leave ourselves room to change our minds. Other times, saying no can mean losing an opportunity forever. It helps to think about what’s flexible in a decision and whether there’s room to pivot if you have a change of heart later.

For example, when we apply to college, we might apply to several schools, even if we know we really want to attend just one. We apply to others to give ourselves options and avoid the regret of not leaving room for a backup plan. Sometimes, saying yes to opportunities is about minimizing future regret.

We also have to learn to live with the idea that, “I made the best decision I could at the time with the information I had.” This reframing helps us ask, “Is it really a regret, or was it a lesson I needed to learn?” When you reflect on an experience you regret, ask yourself: What else came out of it?

Looking back, I can see that even people who are no longer in my life—introduced me to things. For example:

• My favorite pizza place

• The habit of wearing socks with my loafers

• WizKid’s first album

• Making chicken with fresh garlic

When situations don’t work out the way we hope, instead of focusing on regret, we can search for the small good that came from them. It might not be life-changing, but it can still be meaningful.

In one of my favorite holiday movies, The Family Man, Nicolas Cage plays a character who has chosen a demanding, fast-paced corporate life. In the movie, he gets a glimpse of what life would’ve been like if he had made different choices—choosing love and family over career. In this alternate life, he has less money but more love and security. Sometimes, our choices aren’t about what’s “better” or “worse”; they’re simply different.

Regret can also be a tool for growth. If a relationship ends because of something we did, we might regret our actions—but that regret can motivate us to do better next time. It’s a painful but powerful way to learn. Sometimes, regret is what fine-tunes who we are.

That said, some regrets have harmful impacts on others, and the path to self-forgiveness can be difficult. For instance, I’ve seen people who were incarcerated express deep regret for their actions and the harm they caused. That kind of regret makes sense, but the past can’t be undone. The challenge becomes finding a way to move forward despite it.

Regret can be a life-giving teaching tool if we let it. To reframe regret, we can ask ourselves:

• How can I create a self that can live in this world despite what I did?

• What can I do about the situation now?

• Who can I help?

• Who can I be of service to?

• Who can I become in light of what I regret?

• How can I show myself grace?

• How do I forgive myself?

Journal Prompt

How can you reframe something you regret?

A Few Things That Caught My Attention This Week

• The Power of Regret, by Daniel H. Pink. You can find this book on Amazon or Bookshop. 

• How Therapy Speak is Ruining Your Love Life, by Isabelle Morley Psy.D., in Psychology Today. 

• How to Complain Better and Strengthen Relationships, According to Experts, by Joshua Coleman in The Washington Post. 

• There’s One Lie I Will Never Tell My Children, by Allison Sweet Grant in The New York Times.