What’s your relationship with regret? 

Is it a fleeting emotion, or one you can’t shake because it is ever-present? 

In what area (or relationships) of your life or business do you have any regrets? 

How many money-related regrets do you have?

Here’s why I’m asking: The National Bureau of Economic Research (NBER) recently released a working paper about financial regrets. Specifically, regrets older people had about financial decisions and choices they made when they were younger. 

Last week I was interviewed about the results of the study. One of the questions the reporter asked me was how people can avoid having regrets. I told him how we shouldn’t have as our goal – “avoiding regrets.” 

And I could tell my answer caught him by surprise. Maybe you’re shocked by it, too? 

After all, you and I are often told to avoid emotions like worry and regret.

But, I think trying not to worry or trying not to have regrets is futile. It misdirects your energy and attention – and usually toward factors you can’t control. 

If you follow me on social media, you may have seen the brief video I posted the day of my media interview. Today, I am on your screen to elaborate on a few things I shared in that video and have been thinking about since the interview. 

My hope is that something I share today will help you make peace with the regrets you’ve already claimed and reduce future ones. 

Beginning with this…

The Problem With Regrets

The way I see it, regrets usually only surface after the fact. When some time has passed and the outcome of a decision made, action taken, or words spoken (or not) is now known and what you’d hoped for didn’t pan out. 

So now you are feeling sad, disappointed, repentant, or (fill in the blank). 

And now you wish you had done something differently; you wish you could travel back in time and get a do-over. 

My friend, therein lies part of the problem: 

  • The idea that you and I can foreshadow the future, with certainty. 
  • The idea that if we had a do-over, we’d prefer the result of the alternative decision made, action taken, or words spoken. Perhaps. But there’s no guarantee that that is true. 

Regret is a tricky emotion. Because you rarely regret what went “right.” Typically, it’s about what went “wrong” or what might have happened. 

If you’re not careful, it can lull you into believing you have a degree of control that you don’t…and never really did. 

That said…

Here’s An Idea

The future is uncertain. 

And with so many choices, comes many possibilities of potential outcomes – some of which you might embrace; others not so much.

Like I told the reporter, I don’t believe there is a way to avoid having any regrets. However, I do believe, with some intention, you can minimize them

First, you have to be honest with yourself about what you really, really want. 

Not what you think you should want. Not what others want for you. What you want. As you scan all the dimensions of your life and business, what do you really want? What role do you want money to play? 

Second, based on the above, identify the regrets you don’t want to have. Be specific. (By the way, the more courageous you are with your answers above, the easier it’ll be to create this list.) 

Third, identify what you need to do today to mitigate the possibility of the regrets you don’t want to have coming to fruition. 

The Beauty of Regret?

Since the interview, I haven’t stopped thinking about the cultural implications of the “no regrets” mantra. This mantra is incredibly powerful as it shapes how you and I tend to relate to our regrets.

Regrets are typically a concatenation of the passage of time, your expectations vs. the actual outcome (or result), and the process you experienced. 

Of these ingredients, the two you can control are your expectations and some of the process. 

It’s why I recommend naming the regrets you want to avoid. Because doing so will help you to be more intentional with your choices – today. It’ll help you focus on what’s in your power to do, right now, to avoid as many of them as possible! 

Another thing about regrets: they are a portal into other emotions. Usually of an unhealthy kind, like self-blame and guilt. 

But, what if you flipped the perception of regret?

Instead of viewing it only through the lens of it being a negative emotion that stings and is sometimes very painful, you began to pay attention to its positive traits, too.

The “no regrets” culture would have you believing that if you have regrets you’ve wasted time, energy, and effort. 

Yet, regrets can also be a source of incredible insight. It can remind: 

  • You of what’s most important to you 
  • You to prioritize processes over outcomes and results
  • You to practice acceptance and self-forgiveness
  • You not to live in the past

Ultimately, when it comes to regrets, I hope you remember that having them doesn’t mean something is wrong with you. 

My other hope? Well, it is that the words of the crooner, Frank Sinatra, are true for you in every way…

“Regrets, I’ve had a few. But then again, too few to mention.”

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