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How to Deal With “Should Have Done’s”

  • 8 min read

As the end of the year approaches and we’re thinking about our new year’s resolutions, many people are reflecting on the past year as well.

If you’re currently doing that, you may feel the occasional moment of regret for not doing something.

• Maybe you didn’t succeed in losing those 20 pounds even though you know you could’ve

• Maybe you’re still a smoker even though you said you would’ve quit by now.

• Maybe you forgot to run for elections this year because you overslept, when you could’ve been the only person fit to beat trump 

It’s tempting to be hard on yourself about these things.  But when you do,  be aware that you’re attacking your own self-esteem.  And a low self-esteem will increase the chances of you not doing those things the next time (because you don’t feel worthy or good enough).

So any form of anger directed at yourself for not doing what you “could have” or “should have” done will actually create a vicious cycle of more “should’ve dones”.

Another common feeling that comes up when thinking of these things is some form of grief.

Not the real grief you experience when your best friend dies or your girlfriend gets eaten by crocodiles, but the grief associated with imaginary loss.

I experienced this for the first when I hopped on a plane back to Belgium after becoming homeless.  Before I did this I was presented with the choice to go back or to stay there and have a permanent place to live in Los Angeles.

As soon as I came back in Belgium I experienced a deep grief over the “loss” of the future I hadn’t picked for myself.

I’m sure there is at least something you feel you could have or should have done this year that you didn’t. 

Whatever it is, think of that situation for a second.

Is it really, objectively true that it should’ve ended differently?  Or that you could’ve made a different choice?

It’s important to stay aware that the regret you experience in relationship to these things is a consequence of making the hypothetical a certain reality in your head, which you then think you stopped from happening.   

“If only you had chosen differently”,  the hypothetical better outcome would’ve made you happier.  Or so you think.  Because there’s no way of knowing.

You were not happy with the outcome, so you created a different one in your head that would’ve been more desirable.  But it’s just a fantasy.  If you’ve watched the movie “The Butterfly Effect”, you already know on a rational level there’s no way of knowing for sure which outcome would’ve “come out” of acting differently.

There are always unknown consequences of every action.  Both positive and negative.

On the other hand, you may be the kind of person who’s less concerned about the specific outcome your actions would’ve led to.  You just wish you had done it when you know you could’ve, because you’d be a little more like the person that you want to be.

This is still futile thinking. Why?

Even though we do it all the time, it doesn’t make sense to say that you “could have” or “should have” done something else.  Because, in reality, if you really “could have”, you obviously “would have”. 

Especially if everything pointed to the fact that it was the better choice.  If it wasn’t clear back then, you just didn’t have the necessary information so you couldn’t know what you should’ve done, which means you couldn’t have done it as well. And if it was, then something caused you to not be ready yet. That’s okay.

Whatever was holding you back:  Real (handcuffs, physical illness, lack of information about the wisest choice to make) or fake (limiting beliefs, fear, being a lazy cough potato), it was holding you back.  If you had wanted to push through that resistance, or if you had mental fortitude to do so, you would have done it.  No matter how easy it looked from an outside perspective.  Anything else is an illusion.

That doesn’t mean you won’t be able to make a better choice the next time.  In fact, this regret over past errors or misjudgments can play a vital role in leading to better choices and actions in the future.

They are just part of a learning process called “being human”.

Sometimes bashing your head against a glass door a couple of times is necessary to realize the door is there.

For example: After a period of meaningless one night stands that were fun but didn’t make me happy, I decided I had enough of it.  Even though I wasn’t interested in anything even closely resembling a relationships, I told myself that at least with the next woman I met that I was attracted to, I was going to make an effort to really connect with her.

A little later I unexpectedly met someone pretty with the personality I was looking for.  So I started hanging out with her without a real plan other than just being curious about who she was as a person and sharing my personality with her.

I made myself so vulnerable that it made me very uncomfortable.  I was an open book, and breaking every dating rule I had ever learned about.

All the signs pointed to it that she was receptive to me, but still I somehow didn’t take any action to get physical with her. Not even a kiss.

I don’t know why, perhaps I just went so far outside my comfort zone by going from 0% to 80% vulnerability in one go t. And I was simply not ready for that 1 outta 10 chance she’d reject me for my personality (whereas previous rejections couldn’t have to do anything with me, after all, random women in a club don’t know you deeply).  Before that, women could only reject me if my “game” hadn’t worked, which is a nice buffer to have if you want to protect yourself from getting hurt.  But it also protects you from truly being loved, so it’s pretty stupid.

In the end, I just didn’t get myself to do it.  It would be easy to turn that into a “should’ve done”, but instead it was exactly what I needed to never create such a situation again.  Since then, I don’t feel the slightest hint of doubt when it comes to kissing someone after they’ve seen me emotionally naked anymore.

I bashed my head against the glass door, and ever since that one bash, I opened it permanently because I don’t want my head to hurt again.

Now I’m with someone who has seen me more emotionally naked and vulnerable than anyone else I’ve met so far.  So I’m grateful for having gotten the chance to bash against that glass door once.  Otherwise I wouldn’t have learned the necessary lessons to create the beautiful bonds with the people I have in my life right now.

Another striking example of why “could have done’s” are just an illusion is this one:

In 2015 I wanted to write a book.  I invested a lot of time in it during the summer, but then I started to slack off.  When the year ended it felt like a big “could’ve done”.  Then all my files –including the back-ups- got stolen by cyber criminals and I never got them back.  So I wasn’t even able to continue writing it in 2016.

About 2 months ago, I started writing the book again from scratch.  I’m a little over halfway and it should be finished in January.

It’s kinda funny to look back at how I considered the book a “could have done” last year.

To be entirely honest, I probably couldn’t have done it.  As I said before, if I really could have, I would have.

Why couldn’t I do it, even though I thought I could?

Well, for starters:  I had no experience writing anything besides song lyrics and the occasional satiric poem.

However, in the first 4 months of 2016 people kept pushing me to start a blog, so in an effort to get them to stop nagging, I started one.  Because of that, I now have a full year of experience with writing non-fiction under my belt.  And I can clearly see my original book, while well-intended, would’ve sucked balls.

Looking back, what I thought I “could have” was something I obviously couldn’t have, but I am able to do it now because I was presented with the opportunity for constant practice.  Funny how life works sometimes.

Whatever it is you think you could have or should have done differently, realize that thought is simply not true.  There is no use in regretting or grieving over anything that never happened.  Things happened the way they were supposed to happen.  And there’s definitely no use in being angry at yourself for being a normal human being.

Life is just a constant growth process.  And there’s another year full of opportunities already on its way for you.

Whatever happened, happened.  And who you are now is a result of those choices and events.  You can’t change the past but you can always apply the lessons learned in the present and the entire next year.

If at first you don’t succeed, then dust yourself off and try again.

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