Should-ing All Over Yourself (What it is and How to Stop)

Should-ing All Over Yourself (What it is and How to Stop)

This Fascinating Adventure

Image of a road with construction cones in the background. In the foreground is a red street sign with the lettering “Wrong Way”
“‎Though nobody can go back and make a new beginning… Anyone can start over and make a new ending.” 
― Chico Xavier

I have made a ton of baloney decisions in my life. Among these include developing a drinking problem in my late teens/early twenties (arguably genetics played a role in this), all of the dating choices I’ve ever made (except for my current partner of course), and spending every dime of money I earned up until age 27-ish. I “should’ve” done a ton of things differently. I didn’t and yet, here I am. 

The Should-ing Mentality is the idea that a person should’ve done things differently. She should’ve been more aggressive in that raise negotiation. He should’ve worked through college and paid his tuition in cash, thereby not taking out any student loans. They should’ve waited to have kids. And so on. 

Not only is judging other’s choices by Should-ing them not insightful, it’s backward. Let’s apply it to ourselves. When I tell myself, or say aloud, “I should’ve started saving money at 22 when I began my career,” I reek of shame. Shame that I didn’t know, what I didn’t know. Frankly, I didn’t know a damn thing about money back then. Why, on God’s green earth, would I berate myself for not knowing something? And why would I do this to someone else?

You may be able to gather, this gets me fired up. Not so much in an angry way, but in an indignant, crestfallen way. Why the heck are we so mean to ourselves, and so mean to each other?! When we blame ourselves, or blame others, for a lack of knowledge and skills, we forget our humanity entirely. We were all born not knowing very much at all. Life is a hands-on learning experience. Let us not be upset with ourselves (or others) for not having learned something yet. 


Example One:

When I was 25 years old, I entered Recovery for my alcoholism. I thought my world was over. How had I become like…this? Heartbroken was an understatement. I knew I had a genetic predisposition for the disease, and every drink I took brought me closer to the line. Then, as I drank more, I crossed it, never to return to my non-alcoholic state. Because I can’t drink responsibly, I choose to not drink at all. If I were to drink again today, I have no doubt I would drink alcoholically. 

As a youth, knowing what I knew about my family history, should I have not drank at all? Or perhaps, should I have tried to manage my drinking, be aware of every drink I ingested, knowing I probably have a finite number of drinks before I cross that line? Maybe. 

Brace yourself for my true self. My corny self, that loves with my whole heart wide open, and thinks emotionally before I think logically: recovery showed me who I was.

The inner work I had to do to get sober, and the continuous inner work I have to do to stay sober, has brought me so much closer to the person I love most in this world: me. Throughout the process I learned how strong and fierce I am, and how loving and empathic I am. These are things I didn’t know about myself before. I wouldn’t trade that knowledge to be able to drink like a “normal” drinker. 

To go back in time and do things differently (like I should’ve), means I wouldn’t be who I am now. Hard pass. 

Example Two: 

When I was 27 years old, I decided to buck up and get my finances in order. I owed some money to the IRS, was living paycheck to paycheck, and couldn’t build money in my savings account to save my life. 

At the time, should I have not blown through all of my earnings for the last nine years (back to age 18 when I was working and had excess scholarship money to spend)? Maybe. The problem was, I didn’t know how to budget or save. In fact, it never even occurred to me to Google it and try and figure it out. Just like with my alcoholism, at first, I didn’t even know I had a problem. I knew what drowning felt like, but didn’t know that was the name for what I was experiencing, so I didn’t know where to start in finding a solution.

It’s like having an itch in your nose, and no matter how much you rub it, nothing will ease the itch. I had no idea I had a big booger, and the itch wouldn’t be relieved until I cleaned out my nose. How was I supposed to know?! I didn’t have a mirror. 

And we don’t have a crystal ball. So how were we supposed to know how each decision would play out? Simply put, we didn’t. So what?

Not to mention the financial literacy I gained through my ass being on fire at the age of 27. It got bad enough that I wanted a change. I read everything I could get my hands on about personal finance and financial freedom. This has absolutely shaped how I approach my finances today. Would I have found all of those life changing resources (like this and this) if I hadn’t reached my financial bottom? Probably not.

Why The Should-ing Mentality is Trash

For starters, using this framework to approach our past is unkind to ourselves (and others). Thinking this way only sets us up to pick on ourselves and denies us something that is innately human: permission to make mistakes. Frankly folks, we’re all going to make mistakes, so why deny that it’s a natural part of growth? This teeters dangerously close to perfectionism which is unattainable and detrimental. It’s unrealistic to expect ourselves to make the exact “right” decision all the time. It’s just as unrealistic to hold others to this standard.

Secondly, research shows using the phrasing “should” instead of “could”, or “would like to”, is shame-laden and puts us on the defensive. Even to myself, when I say, “I should be working out more” I set myself up to resent the act of working out, because I already feel I failed at it. Instead when I say, “I would like to be working out more” I set myself up to start looking for solutions. Perhaps I look at my calendar to see when I have time to schedule a work-out date with myself, or I set a goal to increase my work-outs for the week. 

Thirdly, it’s unrealistic. If I say, “I should be saving more money every month” I feel dejected that I am not doing enough. That I am lacking in some way. If I say instead, “I could be saving more money every month”, I fact-check myself. Could I? If after all my budgeting, cutting unnecessary expenses, and a small monthly allowance to keep my sanity (personal choice), I can save more money, then great! I might just review my income and my spending to see how much more I can bump up my month savings rate.

But, if I review everything and realize actually, I couldn’t save more money without forgoing sleep and family time to work more hours, I can relax. I am doing my best. Every time the thought “I should be saving more” crops up, I can counter this thought with “No, I reviewed this. I am doing my best. I am so awesome.” Shame spiral arrested!

What to do Instead

So instead of Should-ing ourselves, or someone else, let’s step back. We can choose to use the words “would like to”, or “could”. This helps us fact-check ourselves to see if, indeed, we could be taking different actions. Our options stay open this way. 

Diminishing the use of this word also aids us in taking in the entire context of a situation. Yes, my husband could’ve worked his way through college rather than taking out student loans. But he would’ve had to spread himself very thin to make enough money to pay for each semester’s tuition, and also remain a full-time student.

He also could’ve chosen to be a part-time student to reduce the burden of tuition due per semester, but he would’ve had to graduate later. This would’ve postponed his entry into his current career, and reduced his lifetime earning potential. I am not arguing for or against student loans. It really depends on your personal situation. But, by shifting from should’ve, to could’ve, we realize we’ve always had choices, and there was always a trade off to be made. How empowering!

If we find, ultimately, that we just made an unfavorable choice, and if we could go back in time, we’d do it differently, let’s have some compassion for ourselves. Remember, we don’t know what we don’t know. If you didn’t know, so what? That was your thing to not know. Someone else has something else they didn’t know. We’re all just kinda hanging out on this earth winging it. At least we’re in it together! 

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