The “I Should” Game

Have you ever begun a sentence with “I should…”?  Yeah, I know, I’ve done it too.

“Should” is a funny word.  Here are some recent examples of how I’ve used the word over the last several of years and where the “should” thinking landed me.

– In reference to drinking: “I should be able to handle just one cocktail.”  Right.  Time and time again I would flirt with this “should” and ultimately end up drunk.  It’s no secret that, with time, this experiment ended with a complete emotional breakdown and the decision that I just couldn’t handle alcohol any longer without massive repercussion.  By figuring out this simple equation  I am, indeed, grateful.    

– In reference to ultra-running/racing: “I should be training as much as Bob did when in 2014 he won Pine to Palm 100.  So, if I train like Bob, I should be able to do well at Pine to Palm in 2017.”  I followed this “should” thread, trained well above my means at the time, got obsessed with STRAVA data, and ultimately experienced a severe bout of over-training and burnout, almost compromising my love for a ridiculously fun sport.  

– In reference to “living the dream”:  “I should get married, buy a house, and work seventy hour work weeks, so I can make a ton of money and get my piece of the American dream.”  Really, is this the American dream?  Who is saying that if I were to achieve all of these things then I would be living the dream?  Well, because I relentlessly chased this “should” thread at whatever the cost, I ended up with a dysfunctional relationship, a house that I couldn’t afford, cars that I couldn’t afford, and a lifestyle that ultimately led to me losing everything financially, physically, and mentally.

– In reference to body weight: “After reading Matt Fitzgerald’s book, Racing Weight, given my height I should be below 150lbs.”  This experiment went to hell, as, after several months of obsessing about food and my weight I ultimately got down to 149lbs (I’m close to 6’2″).  At first I took pride in being this light, until, I started to look emaciated and my body started to break down with injuries.  No disrespect to Matt’s book as I know it has helped many folks.  For me, at the time I read it, I was firmly steeped in transferring my addictions, so it didn’t really help me.  

– On being 38 without a steady paycheck: “I should be making $X because all of my friends are making lots of money, contributing to their 401k’s, buying houses, investing in the stock market, etc.”  When I get into this mindset I quickly lose the momentum that I am riding in pursuing my own individual passions. In reality, my current pursuits require long-term processes.  If I put my heart into every fabric of my pursuits the universe might just happen to conspire to make my dreams become a reality. 

So, who is telling me that I should be doing all of these things.  Is someone else putting these ideas into my head?  Are Facebook and Instagram making me compare myself to others which provoke the should mentality? Is someone else creating expectations for me to meet?  Maybe, but maybe not.  Ultimately, I have the power to control my own reality.  So, why would I continue to let someone else dictate how I should feel?  The answer is, I don’t have to if I don’t want to.

I wonder how many people have made life-altering decisions based on a simple “I should” thread that started out innocently and grew into a monster.  When I was so focused on living the dream and making money, which I based on someone else’s definition of living the dream, I became hell-bent on turning that “should” into a reality.  I ended up sacrificing everything to say that I got my piece of the dream, just so I could match up to some of my friends who had already achieved that notion. 

Currently, I am in a prime place to play the “should” game once again.  Luckily, I have fought against the temptation.   With the release of Appetite of Addiction I could very well have started comparing myself to other authors.  One of the ultimate benchmarks for success in self-publishing is E.L. James’ Fifty Shades of Grey.  In a previous world I would have dared to compare myself to the immense success that E.L.’s book has experienced.  Today it’s just not even a conversation I need to have with myself because it really doesn’t matter.  My mission in writing AFA wasn’t to sell millions of copies.  It was to write a book that people, who are experiencing their own struggles, can relate with and know, that whatever the demon, they are not alone.  

So, what are the drivers that help me fall into the “should” mindset?: 

One – Lack of self-confidence.   

Two – Ego. 

Three – Lack of mindfulness and appreciation of where I’m at, right here, right now.  

I’ve especially noticed the effect of mindfulness piece lately.  It seems that when I have a consistent practice of meditation the urge to play the “should” game dissipates.  In fact, there’s a very clear shift in my mentality when mindfulness sinks in.  Curiously, I focus less on the past as well as the future.  In reality, I have no idea where this new life of mine is going to take me.  So why bother stressing about what could or could not happen based on very little factual information.

I know I’m in a good place with the “should” game when I hear others say the word and I immediately cue in to if I am also in the “should” mindset.  

I’m curious, how have you been affected by playing the should game?  Have you followed a thread of “shoulds” that led to something more immense than you could have possibly imagined? 


2 thoughts on “The “I Should” Game

  1. Rebecca says:

    There’s a very good book- The Crossroads of Should and Must- super artsy, short, and fun to read. A few years ago it basically changed my entire mindset about shoulds and “societal expectations.” I refer back to it all the time, and probably would benefit from doing so a little more often!


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