Regretting The Past: 5 Ways To Help You Navigate Your Past Choices

Adam Bergen
Sep 23, 2019 · 6 min read

Whether you like it or not, where you are right now is the culmination of every past choice you’ve made. There’s a high probability you don’t like where you stand, and so you find yourself ruminating and wondering where you fucked up along the way. So you start reaching back, like way back, to pinpoint where things went haywire. This has a term: it’s called regretting the past.

You can pay me later for that incredible diagnosis.

Unfortunately, regret seeps into just about every facet of your life, and it takes you plus an army of 10,000 soldiers to even attempt to fend it off. You know, just long enough before it comes charging again. That is to say, you really don’t ever get rid of it. But the good news is you can defend against it.

Here’s five ways how.

Accept that you’re lost like everyone else

No one knows what they’re doing, That includes you, which I know you’ve beat yourself up over (see #2), but it also includes those people who supposedly “have it all”. Seriously, think about it.

On paper, some people look really good. They’ve got the money, the success, the great job, the perfect partner. But I’m telling you right now, everyone is dealing with bullshit in their life. And everyone, yes even them, are regretting the past to some degree. There’s plenty of times in life you’ve failed to make a change or do something, and now regret it. Everyone processes these feelings. Literally everyone. So in your quest to try and stand out as a millennial, stop thinking you’re all “different” and shit.

You’re lost like everyone else.

So why do some people manage to put it all together and kick ass in life? Well, there’s no easy answer. But first, define what “put it all together and kick ass in life” even means. It’s highly subjective. To some people, pulling it together means getting up in the morning and making their bed. To someone else, it may mean being the CEO of a business. It’s all relative to where you are, how you’re feeling, and what your goals are.

But my point stands: every single one of those people is lost in some facet of their life. It’s completely 100% human to be confused. It’s just whether or not you want to tackle it head on and keep pressing forward. And that’s why they appear to pull it together and dominate. They probably don’t feel sorry for themselves, they put their head down, and they continue forward (even with all the bullshit).

Guys, I get it. You let your girlfriend down. You aren’t as successful at your career as you thought. Hell, you’re probably in the wrong career. You don’t have as much money as you thought.

Keep moving, no matter what.

Accept you’re your own worst critic

You’ll never find someone more critical of you than your own self.

You’re the harshest critic. The strictest teacher. The meanest judge. The swift condemnation you’re capable of giving yourself for just being human; a crime you didn’t commit but your brain will tell you otherwise. What’s it all for, really?

You don’t have the car you want. You don’t have the partner you “deserve”. You don’t have the job you enjoy. You don’t live in the place you want. All sound familiar? By all intents and purposes, you’re a damn failure. At least you tell yourself that.

Wait, did you think this would help you?

First off, realize no one is going to surpass your innate skill of trashing yourself. Accept it. Once you can accept that, you can also start to understand every person thinks the exact same of themselves: they think they suck, for the most part. So really, do you think they have time to assess where you’re at and determine you’re supposedly a “failure”?

Nah, they’re too busy trashing themselves and regretting their past, too. Trust me when I say people are wrapped up in their own shit. Too much to worry about yours.

Realize it’s never too late and take action

If you’re regretting the past, here’s an idea: change it. Obviously you can’t literally change the past. Here’s what I mean.

If you regret a previous inaction, what makes you think it’s too late to try again now?

If you regret a previous decision, what makes you think you can’t take another step to reverse it?

Action is the best antidote to a regret. When you’re stewing over a failed endeavor, you have two options: either stew on it some more (the stupid choice), or take massive action to at least attempt to rewrite the story. Is this foolproof? No way. In life, nothing is.

Take a moment and understand one thing briefly: some decisions, or lack of decisions, end up being permanent. I hate when you always read the feel-good stuff. You know, the kind saying “anything’s possible”. It’s not, and it’s better if you know that now.

Here’s a random example to prove my point. Let’s say you spent your whole career doing something you didn’t really care for (and you knew it), but you stuck it out for whatever reasons: kids, wife, fear, or a concoction of all three. Now at 55 years old, you’re a bit early to retire so you want to become a lawyer. Is this possible? Sure, you can make it a reality.

Most people would say you can’t, but I disagree. They’re just scared and projecting their own insecurities on you. You could go back to school, get a law degree, and start practicing law. You’ll be close to 60 before it happens, but so what? If the idea of standing around in your retirement not doing shit sounds scary (which it can), why not pick up a new passion or purpose with the 20+ years you have left?

Now, on the flip side, if you’re 55 and you’ve always dreamt of becoming a professional tennis player, you’re shit out of luck. I’m sorry to tell you it’s not possible. You’ll have to accept a different outcome. That one was permanent; you lost your chance. But it doesn’t mean you still can’t take massive action and do something related. Like, for instance, become a tennis coach. Or get involved in the business side of tennis.

Learn to deal with some of the realities of life. The worst decision you can make, though, is regretting a past decision, or lack of one.

Try to connect the dots on why you’re regretting your past

Is it your ego? Jealousy? Failure to act? Combination of all three?

Everyone struggles with an ego, but I’d say men have more egotistical notions than women do. A lot of times, it comes down to pride. We’re supposed to be the alpha males. The ones who fuck shit up and don’t look twice. We feel, how do I say it, inadequate when another dude rolls through with all his shit in order, making us look like Ferris Bueller on his day off.

So you decided to switch careers before going down the deep, dark rabbit hole of getting stuck in a miserable career that makes you great money. You’re feeling good about your decision, until one day some schmuck in a tailor made Dolce & Gabbana suit pops up next to you in a Lamborghini Aventador. He’s good looking, his partner is good looking, and his bank account is good looking.

As you sit there stewing in your Toyota Prius, you instantly regret your decision. That could have been me.


Why? What makes you think he’s chummy and enjoying his life? Purely based on his car, partner, and career choice? Did you not just read my first few bullet points?

Talk to a therapist (or anyone)

And then hug it out.

Doesn’t necessarily have to be a therapist, but someone who you can get things off your chest with. The worst thing you can possible do is bottle it in.

Anger, resentment, bitterness, regret, all those juicy emotions…don’t hold them in to yourself all the time. I know men are supposed to somehow figure it out on their own and bottle up their emotions. Not sure why that became the status quo, but here we are in 2019 with that exact mentality.

What a time to be alive.

Talk to others. Regretting your past shouldn’t be a completely solo adventure. People are out there willing to help. Sometimes they require a little money up front, but it’s money well spent.

Mental health, like physical health, shouldn’t have a price tag on it.

Thanks for reading!

Originally published at on September 23, 2019.

Adam Bergen

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Chasing the Friday feeling on Mondays | Helping others focus on what’s important |

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