Should’ve, Could’ve, Would’ve

Most men seem to be living in the past. They live with guilt, remorse, sorrow, and regret. What a shame that is because if they’d only realize that their past experiences don’t define who they are, I think we’d see a lot more men stepping up to the responsibilities they have today.

Believe it or not, I still have friends who are living out our high school glory days on the football field. I still have friends that regret decisions they made 20 years ago instead of learning from them, and becoming better men moving forward.

One of the most frequently asked questions I get is “what is the biggest regret that you have?”

Truth be told, I don’t have regrets. Because, if I did, and I would have done just one small thing differently, I wouldn’t be the same man and I wouldn’t be in the same position I am. I’m happy with where I am in my life so why would I want to change something that would potentially change where I am today?

Sure, there’s things that I could have done better. I would have played harder in high school sports. I would have treated my mom differently growing up. I wouldn’t have dated that one girl. I would have done a lot of things differently.

But, those are the “should’ve, would’ve, and could’ve” type things I’m talking about.

It reminds me of the movie, Napoleon Dynamite where Uncle Rico says, “If I could go back in time, we’d take state. No doubt in my mind.”

Good hell guys. Let it go. Move on. There is so much life to be enjoyed in the present. We’ve got to stop living in the past.

So, how do we do this? How do we let go of the past? How do we learn the lesson that needs to be learn?

Today, I want to share with you four steps I’ve incorporated in my life so that I live in the present moment. Yes, I learn from my experiences and reflect on the past but, only as a means to get better today, not to sit around feeling sorry for myself.


First things first, frame your experiences as lessons and accept the situations (good and bad) you find yourself in as just that – lessons.

Things are not happening to you. Things are happening for you. You might be thinking, “that’s easy for you to say Ryan. You’re not dealing with a bankruptcy, or divorce, or health problem.”

That’s right. I’m not. But I have. I have dealt with crappy situations. You can sit around and feel sorry for yourself and complain about how things should be or, you can accept the lesson you’re being taught, learn from them, and move to the next step I’m going to share with you here in a minute.

Look, I realize this isn’t going to happen overnight. You’ve spent decades getting you to where you are now. It’s going to take time to get you to somewhere new but, the longer you dwell on the injustices that you perceive as being done to you, the longer it’s going to take for you to get things right.


Step number two is to rectify the situation. The reason you may be dwelling on the past is because there are a few things left undone and unsaid.

You cannot change the past and you cannot change another person and how they respond to you but, you can do things on your end so that you’ll never wonder if you didn’t give it all you’ve got.

I remember when I was younger, I stole some candy from a convenient store. I know it sounds trivial but, it ate at me. And, I wasn’t able to get that right in my own head until I went back to the store and paid for it.

Some of you are dealing with far greater challenges. I know a lot of you are harboring some resentment towards an ex-spouse. I get that. And, while I can’t pretend to know all that goes into that relationship between you and her, I’d be willing to bet that there are a few things you know you should have done differently.

You may not be able to win her back. She may never trust you again. But, you can say you’re sorry for your own shortcomings in the relationship.

And, make no mistake, this is not for her benefit exclusively. This process of rectifying the situation is for your own well-being.


Next, correct the behavior. It’s not enough to say sorry. It’s not enough to rectify the situation, then keep doing the same thing you’ve always done. That’s a sure-fire way to keep living in the past – by continuing to make the same mistakes.

If I would have told my friend that I am sorry for missing the gym, then I missed the gym the next day, how sorry could I really have been? How easy would it be for me to fall into a state of guilt?

Correct the behavior. This is the best way to overcome “should’ve, could’ve, would’ve.” Yeah, you probably should have done it differently. Yes, you could have done something different. Of course, if you would have done it differently, you would have had a different result.

Great, do it! Stop talking. Stop dwelling. Do it and watch your remorse melt away.


And the fourth step is to drive on. At some point you have to forgive yourself. You have to live and let live. You have to come the conclusion that maybe you messed up, and it’s okay. We all do. We all misstep from time to time. It doesn’t make it okay. It doesn’t make it right. It just means you’re a human being with flaws and imperfections. Cool, now go to work on becoming something more.

I’ve found that, for me, life is a series of mess-ups and corrections. Mess-up, correct, mess-up correct. If I don’t mess up, I’m not pushing hard enough. If I don’t correct, I’m not getting any better.

At some point it’s time to hang up the varsity letterman jacket, put the trophy away, and let go of who you used to be so that you can become who you are meant to be.

Fellas, no more “should’ve.” No more “could’ve.” No more “would’ve.”

Accept the lessons that are given to you for what they are – an opportunity for growth.

When you get it wrong, make it right to the best of your ability (And, remember, just because you’re working to make something right does not mean you’re entitled to the person’s who’s been wronged respect and acceptance of your apology. You’re not doing it for them anyways.).

Correct your behavior and stop falling into the same traps. There’s the adage, “Fool me once, shame on you. Fool me twice, shame on me.” Don’t’ be a fool. Correct your behavior.

And, last, drive on with a new sense of growth, hope, and optimism as you are no longer a man who dwells on and lives in the past.

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