The Power of Regret

How many times have you heard someone flippantly say “no regrets” or see life hack lists on how to live without regrets? The current culture narrative implies that there is some proactive way to live a life that will ensure we no longer experience them. At the end of the day, not only is this not realistic, but living without any form of regret (or at least ignoring it) can actually have a profoundly negative impact on our lives. 

In Dan Pink’s newest book, The Power Of Regret, he unpacks the real super power that comes from experiencing regret and how we can best use it to fuel significant change, adaptation or development within our personal and professional lives. 

Dan shares two stories to give insight into how we ultimately have two ways to respond to feelings of regret. 

One story refers to the life of Alfred Nobel. You may recognize the name as the man who donated roughly 94% of his wealth to create the entity that awards the Nobel Peace prize. Most of us don’t know that he was famous and grew very wealthy after inventing dynamite and other explosives, tools that have in many ways created as many negative impacts as positive ones. 

In 1888, a large newspaper accidentally confused him and his brother and published Alfred’s obituary. The headlines named him the merchant of death and ultimately painted a picture of a greedy man who chased wealth even at the expense of others. Supposedly, the picture painted of his life and the legacy he had created for himself saddened him and filled Alfred with regret. The story goes that those feelings of regret were a catalyst that Alfred used to change his life and the impact he would leave on the world. Eight years later, he really did die and his life was celebrated for all the positive things he had brought to the world. 

The second story is about an Olympian cyclist who took the silver medal in the 2016 Olympics. Her counterparts taking the gold and bronze celebrated their victories and took in their accomplishments while our second place Olympian buried her head in her hands and moved silently to consult with her husband. No celebration, just regret. 

According to Dan’s research, there is a common phenomenon that happens when someone experiences regret called counterfactual thinking. This is a process where we begin thinking about how things could have gone. We tell ourselves stories about how “if only”. We toil and focus on all the things we could have done differently that would have created the outcome we wanted. 

Ultimately, this “if only” spiral doesn’t serve us in any positive way and robs us from any joy or positive insights the current scenario presents. Unlike the cyclist’s example, Alfred Nobel used his experience as rocket fuel for positive change. He remained focused on the actions, behaviors and attitude he could deploy moving forward in order to prevent being in that same position again. Instead of diving deeper into “what if”, he aggressively moved forward with a new plan and a new set of priorities. 

Culture tells us that regret is evil and only serves to make us miserable. We’re told to ignore it, adopt slogans to “pep talk” ourselves away from it, and we even buy into the idea that we can make decisions so preemptively that we can ultimately avoid it. The issue is not with regret itself, it’s how we respond to it that either serves us or hinders us. It can become productive or non-productive in nature, based 100% on how we respond to it. 

Productive regret serves as a catalyst for change, shows us blind spots, and helps us mature for future responsibilities. Non-productive regret serves as a paralyzing choke hold that prevents us from moving forward and locks us into a spiral of negative emotions attached to “if only”. 

In the book, Dan lays out three steps we can take in order to use regret in the most effective way possible:

  1. “Undo it” – We need to take whatever immediate action we can to undo or stop whatever caused us to feel regret in the first place. Go apologize, say what you meant to, or go do the thing you had promised. This may not always be an option based on when the event or experience took place and that’s why he offers up the next two steps.
  2. “At Least it” – There is always a strong possibility that even though the scenario didn’t unfold exactly as you had planned there is a strong chance that something positive did come out of it. Try to find the positive “at least” and focus on it. Give it time in the light so you can appreciate it for what it is and how you have benefited from the experience.
  3. Analyze and strategize it” – This is the most important and most critical aspect of productive regret. This is where we begin asking ourselves what we can learn from the situation. Try to identify the concrete steps you can take to ensure the next time is different or that we walk away with a new skill, perspective or priority.

As leaders and business owners, we make hundreds of decisions weekly. We interact with employees, clients, families and partners constantly. It’s not realistic to think we will always make the right decision or handle a situation perfectly. We are human after all. There is no way for us to engineer our lives in such a way that the emotion of regret will not have a role. 

However, we all have 100% control on how we respond, and use those feelings of regret. Don’t ignore them. Don’t compartmentalize them. Don’t spiral into a pit of “if only”. Stop what you’re doing, and look that scenario in the eyes so you can properly take stock of what has unfolded. Step into the regret and use it as the super power for positive change that it’s meant to be.   

Click below and check out the Head Heart & Boots Podcast – In this episode we interview Dan Pink and gain a deeper understanding of the power of regret, the unprecedented data that was collected as part of his research on the topic and how best we can apply the positive catalyst of regret to better serve our employees, clients and selves.

Brandon Reece

Brandon has spent the last 12 years building and leading restoration companies with a focus on operations and organizational development. He’s a founder and Co-host of the Head Heart & Boots podcast, co-founder of the Floodlight Consulting Group, and co-leads the Floodlight Leadership Circles.  As Co-Owner of Floodlight Consulting Group, he works one-on-one with owners, managers and key personnel of restoration companies across the US.
Brandon resides in the beautiful state of Oregon with his wife of 25 years, Janna, and their 2 children – Alex and Abi. To reach him, visit or email
Listen to the Head Heart and Boots Podcast on Apple iTunes and Spotify.

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