4 Types of Regret and How to Leverage Them for a More Fulfilling Life


“Regret is not dangerous or abnormal, a deviation from the steady path to happiness. It is healthy and universal, an integral part of being human. Regret is also valuable. It clarifies. It instructs. Done right, it needn’t drag us down; it can lift us up.” ~Daniel H. Pink

It happened when I reached midlife.

I’d experienced regret before, but this was different.

In my forties, I struggled with several deep-seated regrets all at the same time.

And I didn’t handle it well.

If only I hadn’t chosen to fall into unhealthy habits that were hard to break, like smoking cigarettes and drinking too much alcohol.

If only I’d worked to understand myself and develop my identity earlier in life.

If only I’d gone after that degree in psychology I’d really wanted.

If only I’d taken charge of my own financial wellness rather than abdicating it to my husband.

Because I didn’t know better, I wallowed in these regrets, revisiting past mistakes and ramping up my self-criticism.

So many might-have-beens and what-ifs.

Heartbreak and grief ensued.

It’s safe to say I was well and truly stuck there for a while.

Thankfully, working with a therapist helped me safely face my feelings and reframe my regret as an opportunity for growth rather than a threat.

Over time, I learned to practice self-compassion and what my therapist called Neutralize the Negative – Promote the Positive.

I learned I could extract lessons from regret, use them to keep growing into the best version of myself, and create a more fulfilling life.

I learned that regret could be a positive force for good.

As the poet and wise woman Maya Angelou used to say, “Do the best you can until you know better. Then, when you know better, do better.”

Fast forward to 2022, when one of my favorite authors, Daniel H. Pink, published his remarkable book The Power of Regret: How Looking Backward Moves Us Forward.

Pink’s research, poignant stories, and practical takeaways had me thinking, “This is a guide for living better. I wish I’d understood all this back then.”

Understanding Regret

Unlike sadness or disappointment, regret is a unique emotion because it stems from our agency. It’s not something imposed upon us; rather, it arises from choices we made or opportunities we missed.

Intrigued by this powerful emotion, Pink embarked on a qualitative research journey, inviting people from all walks of life to share their regrets.

The response was overwhelming, with tens of thousands of stories pouring in. Through this process, Pink compiled, classified, and analyzed the regrets, unearthing valuable insights that can help us navigate life’s complexities.

One of the key findings was that regrets of inaction outnumber regrets of action by a ratio of two to on, and this tendency increases as people grow older.

Action regrets, such as marrying the wrong person, can often be tempered by finding solace in other aspects of life. For example, someone who feels they married the wrong person might say, “At least I have these wonderful kids.” However, regrets of inaction lack this silver lining.

Pink identified four main types of regrets that tend to cluster together. He calls them deep structure regrets. They all reveal a human need and yield a lesson.

Foundation Regrets

Foundation regrets emerge from neglecting to lay the groundwork for a stable and fulfilling life, like failing to save money for retirement or neglecting one’s physical well-being.

I now understand that most of my regrets, including those I shared above, fall under this category. Foundation regrets sound like this: If only I’d done the work.

The Human Need: Stability—a basic infrastructure of educational, financial, and physical well-being.

The Lesson: Think ahead. Do the work. Start now. Build your skills and connections.

Boldness Regrets 

As we grow older, the regrets that haunt us revolve around the missed opportunities we let slip away rather than the risks we took. The chances we didn’t seize, whether starting our own business, pursuing a genuine love, or exploring the world, weigh heavily on our hearts.

Boldness regrets sound like this: If only I’d taken that risk.

The Human Need: To grow as a person.

The Lesson: Start that business. Ask him out. Take that trip.

Moral Regrets

Moral regrets arise from actions that go against our sense of kindness and decency, such as bullying, infidelity, or disloyalty. They sound like this: If only I’d done the right thing.

The Human Need: To be good.

The Lesson: When in doubt, do the right thing.

Connection Regrets

Connection regrets center around missed opportunities to maintain relationships, often due to the fear of awkwardness. They sound like this: If only I’d reached out.

The Human Need: Love and meaningful connections.

The Lesson: If a relationship you care about has come undone, push past the awkwardness, and reach out.

Doing Regret Right

So how do we approach regret in a way that enhances our lives? How do we do it right? Pink suggests a three-part strategy: looking inward, looking outward, and moving forward.

Looking inward involves reframing how we think about our regrets and practicing self-compassion. We often judge ourselves harshly, but treating ourselves with kindness and understanding can lead to healing and growth.

Looking outward means sharing our regrets with others. We unburden ourselves and gain perspective by opening up and expressing our emotions. Talking or writing about our regrets can help us make sense of them.

Moving forward requires extracting lessons from our regrets. It’s essential to create distance and gain perspective. Pink offers practical exercises like speaking to ourselves in the third person, imagining conversations with our future selves, or considering what advice we would give our best friend in a similar situation.

In addition, Pink encourages us to “optimize” regret rather than trying to minimize it. He suggests creating a “failure résumé” to reflect on and learn from past missteps.

He also recommends combining our New Year’s resolutions with our regrets from the previous year, turning regret into a catalyst for self-improvement.

In a culture that promotes relentless positivity and a “no regrets” philosophy, I’ve learned that negative emotions have their place in a fulfilling life. I know better now, and I couldn’t agree more with Dan: “If we know what we truly regret, we know what we truly value. Regret—that maddening, perplexing, and undeniably real emotion—points the way to a life well lived.”

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