Lyrics from the Frank Sinatra song “My Way” share the final thoughts of someone before they die.  The song talks about living a life that’s full, traveling, doing what they had to do and sometimes biting off more than they could chew. That song is the battle cry for living, loving and laughing until one’s final breath.  It’s about living a life that you won’t have to regret later on.


In a study done by hospice care, the most common end-of-life regrets were:

  • Not spending more time or being kinder with people you love
  • Not being true to yourself
  • Letting fear stop you
  • Losing touch with certain people
  • Worrying too much


The wisdom of people who have lived a life that’s full tells you to not leave yourself open to saying on your deathbed, “I wish I had…”

But what if regret can be the impetus for changed behavior?  What if there is an upside to regret?  Regret doesn’t sound so bad if it can be used to shine a light on future desired action.  There’s always an opportunity to flip regret and change the future.

This week I’m going to discuss the downside to regret, the upside to regret and how to live a life that’s full.


The Downside to regret


I don’t know one person who doesn’t have something from the past that they regret.  It could be a past relationship, a past action or inaction or possibly a missed opportunity, but regret can become so all-consuming that it seems to color everything that you do.

For example, you had one bad relationship and now you can’t get back out into the dating world.  Or you experienced one knee-jerk reaction to an angry driver and now you have issues driving on that road.  Maybe you had the chance to send your resume but instead you allowed fear to convince you otherwise.

Regret can come from taking action, as in regretting saying something hurtful to someone or it can come from not taking action, as in regretting not saying yes to the invitation.

So why are some people able to move past things they initially felt regret about and some are stuck in the past?  It all comes down to what you choose to think about now.

By ruminating over the past, you create the feeling of regret in your present moment.  You relive that past moment, replaying the scenario and the negative feelings that come with it.  The feeling of regret can then lead to more negativity like shame which then leads to inaction.

By repeating this cycle, you have then created a “path” in your brain around the memory of this regret.  Once this path is established, your brain will automatically be triggered to reprocess that regret without your awareness of why.  Your brain now has a default setting when it comes to the emotion of regret and you aren’t even aware it’s there.

The downside to regret is that it’s backward-looking, can lead to more negativity, more self-blame and lingers in the brain becoming a well-worn path if not addressed.

Sounds pretty doom and gloom, but wait…there is an upside to regret!


The Upside to regret


One of my favorite quotes is by Wayne Gretsky “You miss 100% of the shots you don’t take”.  What that message says is that only by taking action can you have an opportunity for success.  By being focused on all the shots that didn’t go in, by obsessing about failed attempts or by using the past as a reason to not try now, you will never move forward.

It’s very interesting how we downplay the times we did something we are proud of and focus on the times we didn’t do what we wished we would have.  The reason we focus on those missed opportunities more than on the moments that worked out is because of our brains programming.

Your brain is naturally wired to protect you by focusing on threats (logical or illogical), to the detriment of all else.  This warning of potential “harm” is why you remember so many more moments of missed opportunities.  The part of the brain that makes good balanced decisions is temporarily switched off in favor of its protective default setting.

The good news is that there’s also a higher part of the brain that can override that default setting.  It allows humans to think about what they think about.  It’s where decision making and focus take place and it can be a huge help when you have regrets.

Anytime you can shine a light on something that is stopping you from being, doing or having what you want, it’s definitely worth taking a look at.  By flipping regret, it becomes possible to experience life in a way that regret has made it impossible.


If you do have regrets, there are actually a few ways that regret can be flipped:

When you can learn from a past moment of regret and take action to create a better result now:

Your daughter shares with you that there is some bullying going on in school.  You think back to when you were in school and regret being mean to one of the girls in your class.  You had joined in with others, teasing her about what she wore.

You know you can’t find that classmate from 30 years ago to make amends so you decide that you will support the local charity that helps teenage girls get prom dresses that otherwise would not be able to afford it; girls that are probably teased for not having the latest fashion.  You talk to your daughter about your experience and you decide to go speak at the local high school about learning how to treat others with respect now so that you don’t have regrets years from now.

When you decide that you don’t want to experience regret in some future moment so you take action in the present to avoid future regret:

You don’t like flying and avoid it whenever possible but your son is graduating and you’d like to take him on a trip for his graduation.  You start to tell yourself all the reasons why it’s probably not a great idea like it’s going to expensive, you don’t like flying, he doesn’t have a passport, etc.

You don’t want to regret an opportunity to take a great trip and spend quality time with your son so you decide to imagine creating a memory photo book that you will give him next Christmas, about all the great pictures you will take on the amazing trip together and about how he will tell his kids in the future about the great trip he took with his mom for his graduation.


In each of the above scenarios, the key is using your brain to plan instead of your brain using its default mode.  The more we use the decision making part of the brain, the more we override that “pathway” that leads to replaying the regret tapes.

By choosing deliberately with our thoughts, we can create any feeling we want and override any feeling we don’t want.  We can choose to learn from past regret or decide we don’t want to experience future regret.  In either case, the upside to regret is realizing that it doesn’t have to have power over you.

You are in charge of what you want to think about and how you want to feel about the past.


How to have a life that’s full


Thankfully we don’t need to be at the end of our life wishing we had done things differently.  We have the power to live a life that’s full right now.


Many of my clients want to rewrite the past in order to feel better now but before they start rewriting anything, I encourage them to ask themselves the following:

  • What happened in the past that you are wishing didn’t happen?
  • What if it was always meant to happen that way?


I worked with a client who had a horrible divorce.  Now years later she started regretting the divorce because she was about to go back out into the dating world and felt fear.  Her feeling of regret about the divorce was clouding her ability to realize that she could choose to think about the divorce any way she wanted to.

When I worked with her I explained that the divorce was always meant to happen.  How did I know this?  I knew this because it happened.  It was the reality of the situation and when we argue with reality, we lose.

Once she was able to choose to think about the divorce this way, she was able to see how she had been stopping herself from taking action and moving forward with her life.  The thought that the divorce shouldn’t have happened or that it was a mistake was keeping her from moving on.  She decided that planning for the future served her much more than arguing with the reality of the past.

I like to help my clients imagine a huge buffet table with every single thought you could possibly imagine thinking.  On that table are thoughts that lead to the feeling of regret and thoughts that lead to the feeling of acceptance and peace.  We always get to choose the thoughts that will service us from this buffet table of options.

Whether you choose to accept the past and learn from it or you choose to take action now to avoid future regret, just know that a life that’s full is always an option.



  • By ruminating over the past, you create the feeling of regret in your present moment
  • By repeating this cycle, you have then created a “path” in your brain around the memory of this regret
  • By flipping regret, it becomes possible to experience life in a way that regret has made it impossible
  • We can choose to learn from past regret or decide we don’t want to experience future regret
  • Instead of trying to rewrite history, we can always look at the past as if it was always meant to happen the way it did which serves us better in moving forward to live a life that’s full


If you’d like some help exploring the upside to any regrets you may have, please feel free to schedule a free mini session or email me at and we can get to work together.