Learning from the Past to Live a Better Future


In the 1999 science fiction comedy, Galaxy Quest, a key plot line revolves around the “Omega 13,” a device allowing the user a 13 second jump to the past to repair a single mistake. When I first watched the movie, I was initially underwhelmed with the benefit offered. How much could you change your life with a 13 second do over? And then I thought about all the harmful accidents that could be prevented or even the opportunity to have never spoken words in anger that seemed to forever change an important relationship.


Yet, when most of us think about things we wish we could do over, we tend to think about longer life choices. Our decision to attend a certain college, pursue a particular relationship, or join a specific organization may haunt us as we consider how we would have benefitted from a different choice. And often it was not just our initial choice but our failure to truly take advantage of the opportunity.


In Dan Pink’s, The Power of Regret, he shares his research findings that take us on a deep dive on the “woulda,” “coulda” and “shoulda” of our lives. Most of his findings are not particularly surprising, such as that regrets are normal and even healthy when dealt with appropriately. Also, it turns out most people regret the things they didn’t do more so than the mistakes they committed. According to Pink, this is also driven by our natural ability to see all the positives of the road not taken compared to seeing clearly all the pain points in the choices we did make.


Pink categorizes regrets into four categories: foundation (if only I had done the work), boldness (if only I had taken that risk), moral (if only I had done the right thing), and connection (if only I had reached out.) Most of us can easily place our regrets into these categories. Regrets lead to positive outcomes if we either use them to correct a past wrong or to make better decisions going forward. When we allow regret to make us feel bitter, defeated, or stuck, we miss the opportunity that regret provides – the chance to begin again.


At the heart of a healthy response is the concept of grace. We often must be willing to forgive ourselves before we can move forward. Forgiveness does not mean forgetting mistakes, but accepting them as part of a learning process and, perhaps more importantly, recognizing mistakes are part of being human. Often, correcting a past wrong places us in the vulnerable position of admitting a mistake and asking the offended person for forgiveness. There is no guarantee that making that first move will result in restoring a relationship, but a failure to make any move does guarantee the relationship will remain broken.


When facing our next important decision, past regrets can be helpful guides, especially those that fall into the ‘bold’ category. Pink mentions two common sense approaches. The first is to ask what your future self five years later would advise. A future orientation may help make the immediate awkwardness or risks of pursuing a new opportunity seem less daunting. The second is to ask if your best friend was facing this same situation, what would you advise? Inserting some objectivity into our decisions can make all the difference. How often have you been quick to advise a friend to take what seems like the obvious next step towards a goal they really desire?


Perhaps the greatest lesson we can learn from regret is what really matters most to us. Pink’s category of foundation speaks most directly to this. In the moment we made what we now realize was an unwise decision, we often did so because we didn’t realize what was more important. We didn’t put in the effort in our studies, our work, or our relationships because in that moment something else seemed more valuable or attractive.


The best way to avoid the most painful regrets in the future is to take time today to clearly understand what is most valuable. In Pink’s book, he offers examples of regrets that demonstrate how our values can differ. Some people wished they had worked harder in school or pursued a more lucrative major so they could enjoy greater financial security. Others wished they had pursued their passions and not settled for careers that paid the bills but left them unfulfilled.


While we desire to live a life with no regrets, we will certainly have some, but our regrets don’t define us. Who we want to become and how we are becoming that person is the truest measure, and that is not about our past decisions, but our future ones.