Can You Learn From Regret? Turning Past Mistakes Into Future Strengths

When Peter and Sjanna Leighton were in their early twenties, their marriage ended. Financial strain was a heavy burden, and both felt they were failing each other. Neither possessed the skills to effectively communicate their vulnerabilities and the pain they were experiencing.

Nearly a year after their wedding vows, Peter made the difficult decision to leave their San Antonio, Texas home. He moved into his own apartment, channeling his energy into building a career in the restaurant industry.

“To the outside world, it might have seemed like I had moved on from our failed marriage,” Peter reflects, who subsequently battled chronic depression. “But the memories of the intense connection we once shared, and the potential of what we could have built together if we had persevered – those thoughts constantly swirled within me.”

Both Peter and Sjanna carried the weight of regret for abandoning their relationship through subsequent marriages, raising children, and experiencing divorce. Then, in 2007, thirty-three years later, Sjanna searched for Peter’s name online and discovered his photography website. “The first image that appeared was a photograph he had taken of himself in our bathroom when we were married, and the second was a picture of me from our honeymoon, which he had titled ‘The Muse’,” Sjanna recounts. Realizing he was living in Austin, not far from her, she gathered the courage to email him a few weeks later. They arranged to meet for coffee. During their second meeting, Sjanna posed a direct question, “What happened to us, Peter?” His response was simple and profound, “I don’t know, but you were the love of my life.” Within a month of reconnecting, they were dating once more.

Today, at the ages of 75 and 72, Peter and Sjanna have been happily remarried for 16 years. “When we reunited, we embraced our past regrets and perceived errors,” Peter explains. “Because of this foundation, when challenges have arisen, we’ve been equipped to navigate them together.”

While few are granted a second chance like Peter and Sjanna, regret is a common human experience. We might not openly acknowledge them, perhaps not even to ourselves, but most of us harbor past actions we wish we could undo – whether it’s past actions such as unkindness towards a classmate, unspoken words of love to someone dear, or choosing a secure job over pursuing a creative passion. Yet, we seldom truly confront this universal emotion or understand its potential benefits. Since the past is immutable, regret can appear unproductive and self-pitying. However, this emotion can illuminate the gap between our current selves and our ideal selves. And, importantly, it can guide us toward positive change and personal growth.

Unpacking the Psychology of Regret

“Regret is composed of three key elements,” explains Amy Summerville, a research scientist who has conducted extensive studies on this emotion. “Firstly, it carries a negative feeling; secondly, it stems from contemplating how events could have unfolded more favorably; and thirdly, this contemplation centers on your own actions.” To clarify, feeling disappointment after a successful interview that doesn’t lead to a job offer is not regret. However, feeling negative emotions because choosing video games over sleep led to missing an interview, could certainly be categorized as regret.

Summerville’s research indicates that the most prevalent regrets are linked to career paths and romantic relationships. As individuals mature into their sixties and seventies, family and health concerns increasingly become sources of regret, though romantic regrets persist throughout all life stages.

Her findings also highlight that regrets of inaction are more frequent than regrets of action. In essence, we are more likely to regret what we didn’t do rather than what we did. “Human memory functions adaptively to remind us of pending tasks, rather than completed ones,” Summerville states, “This could explain why unmet goals are more readily recalled and linger longer in our minds.”

Another contributing factor is the tendency to idealize the paths not taken, focusing solely on potential positives while ignoring the inevitable challenges and disappointments. It’s more difficult to regret choices we actually made because they are grounded in specific realities. “With regrets about actions taken, you can often find a silver lining, but this is harder with regrets of inaction,” notes Daniel Pink, author of The Power of Regret: How Looking Backward Moves Us Forward. It’s easy to romanticize the idea of eloping with a captivating stranger at 22, without considering the potential conflicts and heartbreak. Conversely, regretting an unhappy marriage becomes more complex when it also brought wonderful children into your life.

Contextualizing Regret and Self-Compassion

When grappling with regret, self-compassion and realistic perspective are crucial first steps. It’s tempting to imagine acting differently with current knowledge, but at the time, we lacked that experience. “For someone middle-aged, with family and financial responsibilities, it’s easy to question, ‘Why didn’t I take a gap year to travel Europe after college?’” Summerville points out. “But realistically reflecting on your post-graduation self, facing student loan debts and societal pressures to start a career, reminds you of the responsibilities and stresses you were under then.”

Contextualizing regret within your environment is also essential, especially in cultures emphasizing personal choice and responsibility. “When we generalize about ‘people’s’ experience of regret, we are primarily referring to the experiences of white Americans and Western Europeans,” Summerville explains. More collectivist cultures, where decisions are often made within a family or community framework, can lessen the focus on individual choices. Arranged marriages or communal child-rearing can reduce the pressure associated with forging a completely individual path. Certain religions also offer established frameworks for processing regret, such as Catholic confession or Yom Kippur, the Jewish Day of Atonement. However, in individualistic societies like the US, where life is presented as a product of individual choices, missteps can feel catastrophic and entirely self-imposed.

Owning Up to Regret: The First Step to Growth

The initial step in reconciling with regret is acknowledging it, which can be challenging. “In the US, there’s an overemphasis on constant positivity,” says Pink, whose surveys have documented thousands of regrets across the US and globally. “We tend to believe that a fulfilling life is achieved by perpetual positivity, avoiding negativity, and always looking forward, never back.” When Pink began discussing regret in midlife, he anticipated resistance, expecting people to avoid the topic. He found the opposite: almost everyone harbored regrets but often felt social pressure to suppress them.

When Sjanna Leighton reunited with Peter in her fifties, it alleviated some of the sadness surrounding their past marital dissolution. However, as their love rekindled, she also experienced intense regret. She wondered: what if they had been more open and vulnerable in their twenties and persevered? What would their shared life have unfolded through their thirties and forties, as partners and parents?

“When we reconnected, I felt secure and validated, like he accepted me completely, which was an incredible sensation,” she recalls. “It also brought profound sadness. I wished we had stayed together, that we had understood each other better.”

Transforming Regret into a Catalyst for Positive Change

Initially, Sjanna found her regret painful. However, as she and Peter built a happy second marriage, she recognized how that regret shaped their current relationship, imbuing it with profound gratitude, empathy, and appreciation. “We had both experienced challenging marriages and raised children separately, and we understood the immense value of having a partner who loves you unconditionally,” she says. Occasionally, she still contemplates the life-long relationship they could have had, but witnessing couples their age arguing or appearing disengaged, she feels deep gratitude for the relationship she and Peter share. “We’ve faced difficulties, but ultimately, there is nowhere else we would rather be than together,” Sjanna affirms.

When constructively addressed, regret can clarify life’s direction. How is our current life deviating from our values? How do we want to act differently moving forward? “Regret can sharpen our thinking, improve our problem-solving abilities, and enhance our sense of purpose,” Pink suggests. “Some dismiss regret; others dwell in it. However, the optimal approach is to confront our regrets, using them as valuable data and information for future choices.”

For example, imagine a 60-year-old who regrets staying in an unfulfilling job instead of launching their own business. Instead of self-criticism, practice self-kindness and curiosity. Contextualize the decision: What were the reasons for staying in that job? What pressures and uncertainties were present at the time? Remember, this single choice doesn’t define your entire identity; reflect on choices you made that inspire pride.

Next, analyze and learn. What insights can you gain from this regret? For the 60-year-old, the lesson might be that with age, security and clarity, boldness and risk-taking are now more valued. Act on this realization. Perhaps start a creative side project, mentor young entrepreneurs, or take on a leadership role in a community organization.

“The process is about looking backward to propel yourself forward,” Pink explains. “You cannot undo the past, but you can leverage that intense negative feeling as a signal of your values and a guiding star for the rest of your life.”

Granting Yourself Grace and Moving Forward

Confronting regret can be emotionally challenging and daunting. Admitting past missteps means acknowledging imperfection. It challenges the unrealistic ideal of a “no regrets” existence, a flawless persona immune to failure. However, freeing yourself from this false dichotomy of success or failure allows for a more thoughtful and deliberate life, shaped by a deeper understanding of your strengths and values. It’s never too late to learn from regrets and use them to shape your present self. If you regret not prioritizing literature in college, seek book recommendations from friends and create your personalized reading list. If you regret long work hours during your children’s youth, initiate conversations about building stronger relationships now, perhaps with them and even your grandchildren. Owning your regrets is an act of vulnerability, but it’s the most effective strategy to minimize future regrets.

Sjanna and Peter still encounter disagreements and tense periods in their marriage. However, unlike their younger selves, they now possess the skills to navigate these challenges, recognizing the enduring value of their relationship. “Part of the shared regret we carry is that we simply weren’t ready then,” Peter concludes. “But now, we are.”

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