What If I Make The Wrong Choice: How to Eliminate Regrets

We all have regrets. Here is just a drop in the bucket of mine: I regret not taking the summer after my senior year of college to waitress on Cape Cod with a really good friend. I regret not telling that boy I liked him. I regret not seeing Whitney Houston in concert before she died. I regret not thinking about my college major ahead of time, and instead making one up six weeks before graduation.

As regrets are want to go, these probably show up more on the mild side. They aren’t on the level of not saying goodbye to someone before they left this earth. Or watching the love of your life marry someone else without saying how you felt. But they’re there. And they can accumulate. I think we should aim to minimize the accumulation.

I like to think of this as an “explored life” - a life with lots of stories; that we don’t have lots of questions about. A life that means there are very few circumstances where you can say, “should I have taken that trip to Ecuador?” Because the story is, “I actually almost didn’t make it out of Ecuador because they have a $25 exit tariff and I had no cash and none of the ATMS were working.” Or, “would that have been the perfect job for me?” And not because the story is: “Yes! I did and I loved it so much and I’m still with them today”, but because you can say with absolute certainty, “well, I now know where the expression ‘May the bridges I burn light the way’ comes from.” (Both true stories, BTW.)

“Should I do this or that?” is not a story. It’s not an interesting anecdote that that can help someone else or make sense of an experience for you. It’s just a question that needs an answer. And, honestly, it matters less what the actual answer is, but that you answer it so you can get onto the next question. Do you really want to spend a month on one question? Do you want the only thing to talk about with your friends be this one question? Do you want to be that girl who is *still* talking about this?

Maybe we thought some of the stories would different endings. But they all have answers. An explored life means we prefer answers to lingering questions no matter the outcomes (but bonus points for truly insane and unexpected outcomes).

Doing nothing is just as much of a decision as doing something. Choosing to do nothing means the situation in front of you probably didn’t matter that much in the long run, so it might have been less worth your time to engage with it rather than to set it free and let it live it’s life. Not choosing to do anything because you’re confused or relinquishing your agency is different. It’s the abdication of your power.

And while that’s fine to do every once in awhile, is it a habit that we want to build? As a practice, it tends to breed more questions and less stories. So if our end goal is stories, this really isn’t a helpful method.

Plus, think of all the stories you’ve heard. Aren’t the best the ones where everything goes terribly wrong? Or when someone rises from the ashes and rebuilds, stronger the second time around? Those are stories. I could listen to those all day long.

I fully believe that we regret the things we don’t do. No, it might not have been ideal to spend those three extra years in that dead end relationship, but at least now that person doesn’t get to take up space in your heart as some idealized version of themselves. Now *that* would be a real regret, so let’s take this opportunity to reframe how we think about regret.

I’ve spent money on clothes I didn’t need, trips I didn’t want to go on, and mentorships that weren’t helpful. Do I wish I could have back the thousands of dollars and hours spent on all these things? Sure.. But the catch is I would also be a different person. I would be a person racked with regret for the things I missed and wrong decisions I made. My energy of regret, self-doubt, and self-loathing would have radiated off me like a force field, repelling anyone who came within 10 feet.

So I like to think I spent the money becoming someone I could tolerate being around. And THAT is money well-spent. Even when it goes towards a flight that’s cancelled, and you end up on a bus and you never get the refund. Because the point is you took the trip. You got out of the country, or out of your own head and, maybe, grew as a person.

Take action about one thing you’re hesitating over whether or not you should do. Even if you can’t decide whether or not it’s a good idea, or if you can afford it, maybe the answer is simple: you’ll regret it if you don’t do it. Let that be enough of a reason. Because you don’t know what the experience actually is until you do it.

You could spend weeks or months (or years!) romanticizing it or dreading it, letting it build up to a status in your mind that it doesn’t deserve. Or maybe it will be an incredible experience you’ll love, and you’ll be validated in your choice. But if it’s actually terrible and you don’t do it, you won’t know that either. And then this terrible thing might live forever in your brain with an undeserved status as the “thing you should have done”.

Maybe stories about how it turned out should be the goal of our choices, as opposed to getting it “right” every time. Maybe evidence of what is real is more valuable than our meticulous assessments about how things might go.

So do the thing. Quit the job. Ask the person out. Buy the shoes. Hire the coach. Whatever it is, just do it. Because you have enough information. Because the only thing left to do is decide. You know what you’re doing.  And, even if you don’t, this is how you will learn. So you might as well write a new story for yourself.