The Secret to Avoiding Life’s Biggest Regrets

Written by on 07 Oct 2014

A little over a year and a half ago, I found myself at a crossroads.


Yes, this happens to me a lot.


But this one was pretty unique.


It was more of a cross current than a cross road considering the fact that I was in the middle of the Atlantic Ocean when it happened.


It was April of 2013, and my trip around the world with Semester at Sea was coming to an end. As some of you know, I had quit my “cushy” Wall Street job and decided to set sail with 600 undergrads and a handful of entrepreneurs in the name of self/world exploration. I left with high ambitions—to learn about myself, to travel the world, to test out grad school, and oh-by-the-way-one-last-thing…


To find a new job.


The former three missions, I talked about a lot. The latter, well, notsomuch.


I avoided the topic because it was a huge source of anxiety for me. I had (mistakenly) decided that finding my next job would ultimately determine the value of my investment in the trip.


Old Wall Street habits die hard, I guess.


Basically, I reasoned like this:


If I get a job, this whole experience was worth it.

If I don’t…


I’ll get a job.


I didn’t even want to go through the mental exercise of what might happen without it.


But, as you might have guessed, that’s exactly where I found myself—one week from landing in Barcelona and still woefully unemployed.


Or funemployed. However you want to look at it.


So, during my last week on the ship, I found myself making the rounds with all of my new friends, mentors, and professors, doing what I do best—asking for advice.


It’s truly amazing the value another human being can add to your life if you just ask good questions and really listen to the answers.


And not just listen. REALLY FREAKIN' LISTEN.


People can save you time on the learning curve. They can save you money on bad bets. They can even save you from the pain and suffering of misguided decisions.


And sometimes, if you’re lucky (and REALLY FREAKIN' LISTENING) they can propose simple ideas that completely change the way you approach the world, and thus, literally save your life.


On my last week on the ship, I had one such conversation.


And I’d like to share that story with you today.


I actually met Professor Bill von Hippel on my very first day on the ship, before I even had time to set down a single one of my bags. He was gregarious and outgoing, walking up and down the line of students waiting to check in, introducing himself and asking questions of everyone he passed. When he got to me, I quickly learned we had two important things in common.


Yale and psychology.


Who would have thought, that thousands of miles from New Haven, while about to set sail, I would run into a fellow Bulldog? Who also loved people?




Unfortunately for me, I did not leverage this awesome bit of serendipity enough. I met with him only two other times on the ship—once as a guest in one of his classes and once during our final week at sea.


Fortunately for me, he decided to make both of those times incredibly valuable.


And for that, I will always be grateful.


I’ll save that first in-class meeting for another post. It’s well worth it.


So there we were, one week to go, sitting on the 7th deck, talking about life. I had sought him out for advice, but honestly didn’t know what (if anything) would come from our conversation. After all, I only had BA in psychology and zero interest in pursuing academia—both of which were his fields of expertise.


And I needed a job. (Remember?)


About an hour in to our conversation, I was feeling something that I did not expect—hopelessness. As well-intentioned as he was, we kept falling into the same kinds of solutions and nothing seemed to fit. With my background in psychology and my experience in business, the logical answers were Ph.D. or the corporate world—neither of which really piqued my interest.


Exasperated, I finally let it all out.


I told him how scared I was to go back to the life I was living before—hating Mondays and living for the weekends. I told him how worried I was that I would never “find my thing.” I told him that I truly believed that there was a way to do something I loved and do it sustainably, but I was nervous I would never figure it out.


It all just felt so elusive to me.


Out of absolute desperation, I just asked him—do I spend all of my energy trying to find the next “safe” job or do I jump in the deep end and go for something great, not really knowing what it is, and knowing that it could fail?


He didn’t even blink.


Absolutely go for it, he said. And I’ll tell you why.


Then he taught me one of the greatest lessons I have learned thus far in life. Our conversation went a little something like this:


Tracy, you must take a meaningful shot for the stars. If you don’t, you will regret it forever.


Here’s why.


Modern psychology breaks down regrets into two different categories. Yep, just two. Of all those awful things about which you could feel sadness, repentance, or disappointment, there are really only two kinds.


  1. Regrets of commission- things you did do.




  1. Regrets of omission- things you did not do.


Sins of commission are understandably painful. You do something wrong. You find out, realize, or come to terms with the fact that you did something wrong. You incur or endure some kind of consequence for doing something wrong. You regret doing whatever you did wrong.


This sort of thing happens all the time when people make bad decisions.


You cheat on your boyfriend. You get caught. You lose him. You regret it.


You invest some money in a new company. You learn that the company is going bankrupt. You lose a ton of money. You regret it.


You drink too much and drive. You get pulled over. You get a DUI that costs you $10k and your license. You regret it.


The form is basically the same—you make a decision, you take action, you get punished, you regret what you did.


The major thing these examples all have in common is a tangible outcome—some consequence—to be regretted. Yes, this outcome often sucks. That’s the definition of regret. But, at the end of the day, there is a resolution that you can (hopefully) come to terms with. Yes, acceptance and reconciliation may be very difficult, but they are possible.


That is the major difference between the two types of regret.


The second kind of regret—sins of omission or things you did not do—have no final, tangible outcome.


More accurately, they have an infinite amount of potential outcomes.


And it’s those potentials, those “what ifs,” that make this the worst kind of regret.


Let me show you.


Sins of omission go something like this: You have a decision to make. You decide not to do something. You can never know what would have happen had you chosen to do that thing. Your mind clings to the “what ifs” in search of resolution (#psychology). Eventually, you regret not doing that thing…



And over.

And over again.


I’ll give you a couple real life examples—maybe one of these will hit home.


You are in a relationship and you like the person so much, it scares you. You never say, “I love you,” because you don’t know if he will say it back and you’re scared of being rejected. The relationship ends. You can never know what might have happened had you told him how you felt, and your brain does something like this:


Maybe he would have said it.

Maybe we would still be together.

Maybe we would have gotten married.

Maybe I would have had kids by now.

Maybe I missed out on my soulmate.


The possibilities are limited only by your imagination.


Or how about this one:


You’re working at a job about which you are less-than-thrilled, but you are nervous about making a change. You get an opportunity to leave, but you pass because you’re scared it could be worse or less secure than what you have now. That opportunity expires. You can never know where that decision might have taken you had you said, “yes,” and your brain pulls one of these:


What if it was my dream job?

What if I could have advanced faster there?

What if I could have been making more money?

What if I missed out on someone who could see my talent?

What if I could have been happier?


Once again, this can go on for a while.


There are a million and one other examples I could use here, but I’ll stop. I don’t want to get you all hung up on the things you didn’t do. That’s not the point here. This is not a shaming party.


The point here is to get you to start saying, “yes” to the things you can do now, in order to avoid this fate in the future.


I will always be thankful to Bill for this incredibly valuable lesson. It’s never been so clear to me that letting fear guide your decisions—being afraid of an outcome that you could never predict—is actually the SCARIER route through life. Irony. It opens you up to a world of “what ifs” that could go on forever.


Sins of commission understandably hurt ourselves and others, but at least they have a resolution. Something tangible you can deal with. Something you can get over or fix.


Sins of omission have an endless supply of hurt, because there is no resolution—nothing tangible to deal with, get over, or fix. Just “what ifs” and “maybes” that never end.


So the next time you’re wondering whether or not you should do it, remember this:


Just try.


All you have to do is try.


Say “I love you.”

Quit that job you hate.

Take a trip you’ve been eyeing.

Start your dream business.

Do something.

Say yes to life.


Take your meaningful shot at the stars.


You can never know what might happen.


But at least you can know what did happen.




What can you say ”yes” to RIGHT NOW to avoid this type of regret? Who can you enlist to help you move forward?


Did this story resonate with you? Or did it make you think of a story of your own?


Share your story or your reaction in the comments below.


I believe that stories unite us. These stories can be traced back to one person, conversation, or observation that provided a turning point in our lives. I’d love to hear if you believe this, too.


If you do believe this, then share it with your friends! Because sharing stories an instinctual, powerful way to touch the hearts of others and change the world around us.

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