How to Grow From Your Regrets

Avoiding or ruminating on our regrets can ultimately make them more harmful and stop us from learning from them. The key, writes Diana Hill, is to turn to our regrets with compassion.


When clients end therapy with me, I like to share an exercise called Appreciations, Hopes, and Regrets. Sharing appreciations and hopes with clients feels good, but it’s the regrets that are the biggest teachers. “I regret not telling you sooner about my drinking,” says a client. “I regret not asking about your drinking when I suspected it,” I respond. Regrets can be powerful signposts. When approached with self-compassion, regrets can guide us in making the adjustments necessary to live a more meaningful life.

Regret Is Powerful

Looking back on your life, what do you wish you had done differently? Where do you wish you were more bold? Which relationships do you wish you didn’t let drift away? When you consider your unfulfilled dreams or things you wish you could change, it can lead to feelings of regret. Regrets are difficult to avoid. We all have them. But regret isn’t all bad. In fact, when held with compassionate inquiry, regret can remind us to stay true to ourselves, make repairs, and choose differently next time.

What we want to do is confront our regrets. Think about them. Use them as clues. And when we do that, this is a powerfully transformative emotion.

“Regret makes us human and regret makes us better,” says Daniel Pink, author of The Power of Regret. In the American Regret Project, Daniel Pink surveyed 4,489 people about different domains of regret such as health, relationships and work. He then created The World Regret Survey, where he’s collected over 19,000 stories of regrets from people across 105 countries. His results?

  • 82% of people say they experience regret at least occasionally
  • regret is one of our most common emotions
  • there are more similarities than differences in our regrets across age, race and gender
  • regret helps us make better decisions, perform better, and experience deeper meaning

When I interviewed Daniel Pink on the Your Life in Process Podcast, he offered a way to approach our regrets: “What we want to do is confront our regrets. Think about them. Use them as clues. And when we do that, this is a powerfully transformative emotion.”

Four Categories of Regrets

Daniel Pink asserts that what stands out most about regrets is their ubiquity and common underlying structure. Our regrets tend to fall into four main categories:

  1. Foundational regrets stem from our failure to attend to some aspect of our lives because we choose short term gain over long term benefits. Foundational regrets include statements such as, “If only I wore more sunscreen.”
  2. Boldness regrets come from not stepping up, speaking out, or showing up in our lives. With boldness regrets we may say, “I wish I was more true to myself.”
  3. Connection regrets occur when we don’t step through what psychologist and professor John Gottman calls the “sliding door moments” of relationships. They include the relationships that have drifted over time, or ended in rifts.
  4. Moral regrets are a product of acting in ways that go against our beliefs and values. The most common are cheating, harming someone, being unloyal, or dishonoring authority.

Why Avoidance Doesn’t Work

Reading through these categories of regret, you can begin to see why we have them. Regret teaches us to prepare for the future, be bold, connect with others, and be moral. According to evolutionary psychology, every emotion has a function, even our least favorite ones like regret. Regret functions to help us learn from our mistakes and grow. However, for many of us, we miss out on this opportunity because regret is so uncomfortable to feel! When faced with the discomfort of regret we often try and avoid or control them in one of two ways:  

  • Avoiding regrets by saying, “I have no regrets,” “never look backward,” or “think positive”
  • Getting stuck in regrets by ruminating on them, intellectualizing them, and blaming ourselves.

This form of experiential avoidance can lead us away from what we value. Avoiding regret may alleviate its sting short term, but your regrets inevitably will return. And when you don’t face them head on, you miss out on opportunities to learn from them.

Confronting Regrets With Self-Compassion

The best way to meet your regrets is with self-compassion. By bringing kindness, openness, and perspective taking to your regrets you can greet your past with curiosity and kindness and learn to:

  • Uncover the values that are hidden under your regrets
  • See pangs of regret as opportunities for growth
  • Stop ruminating on and rehashing regrets and start living your life
  • Begin a practice of self-forgiveness

3 Journalling Prompts to Explore Your Regrets:

1. Looking back on your life, what do you wish you had done differently? Consider the four main categories of regret listed above—(foundational regrets, boldness regrets, connection regrets, and moral regrets). Write about a domain of your life where you experience the most regret. Does your regret fall into any of these categories? How?

2. Consider the regrets you wrote about above. What role did context play in your actions or inactions? What role did your learning history, access to skills and resources, social network, or systemic factors like oppression play in your behavior? 

3. The most profound love we can give something is our attention. Learning to stay with your regrets longer allows you to bring some care and curiosity to them. What do your regrets teach you about what you value? How can you act on that value today?