Dwelling on regret can make us miserable. But feelings of regret may also be able to teach us lessons. How can you turn the pain into a teacher?

The word alone can stir up strong emotions.

Take a moment to think about something you regret, or something you did regret at some point in time.

How do you feel when thinking about it? What shifts within your body?

It probably isn’t a great feeling. But is the pain of regret something that can be useful? And if so how?

My biggest regret involves quitting. At 18, I set out to pursue a long-held goal of completing the Pacific Crest Trail. A trail that travels from the Mexican border to the Canadian border through California, Oregon, and Washington.

The first couple of months were amazing. I had some rough times, but also met amazing people and got into a groove on the trail.

Then, in Northern California, I left the trail for a couple of weeks to help out a family member. When I returned to the trail, my young mind didn’t consider that I might be in worse shape than two weeks prior, and I essentially sprained my ankle from overuse that first day when I was so happy to be back on the trail and get moving.

It only took days to recover physically, but after the breaks from hiking, I never got back into the mental swing of hiking the trail. Not far north of the Oregon border, I made the decision to quit hiking. To call it quits. I decided I couldn’t, or wouldn’t, complete that goal.

I have now lived longer since that moment than I had lived up to it, and yet this moment is still raw for me. I told a group of people about it recently, and I couldn’t get through without beginning to cry.

Why? I wish that I had kept going. I was tired and lonely. It was difficult. But I think I gave up too easily.

So that sucks and I probably have some emotional baggage that I haven’t dealt with yet, but can there be a purpose to feelings of regret?

Brené Brown, who researches many different human emotions, says that regret is a fair but tough teacher. In her research, when asking people about their regrets in life, she found that most of them are either failures of kindness or failures of courage.

When we fail and feel regret, if it is a failure in these areas, that tells us that we were not living up to the person we want to be. From there we can challenge ourselves to lean in and grow to be that person who we want to be.

My lesson isn’t never to quit. I have quite many things in life, and I’m proud I did so. My lesson is not to quit just because something is difficult. In one night, when things were tough, I ended a deeply-held dream of mine. In hindsight that wasn’t the decision I wish I had made. In the future, I hope to sit with those decisions longer. To quit for the right reasons, not simply a desire for comfort.

Think back to the regret on your mind when you started reading this. Is it a failure of kindness or courage? What principles can you learn from the unsettling feeling of regret?

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