After winning the state championship my sophomore year of high school, we lost in crushing fashion the next year — a semifinal heartbreak that lived rent-free in our heads for months…admittedly, it might have been longer than that.
Over the next several months, at the dinner table, my dad and occasionally a few teammates would, with obvious regret, repeat the same refrain: “Shoulda won that game.”
In short, we were living a shouldy life.
I wouldn’t go as far as to say “should” is a dirty word, but it definitely muddies things up (pun intended).
The problem with “should”
“Should” when focused on the past leads to regret, shame, and rumination. It keeps us replaying moments we can’t change instead of learning from them.
“Should” when focused on the future leads to rigidity, anger and unnecessary pressure — expectations disguised as goals. It traps us in an imagined standard rather than actualizing the process in front of us.
Better alternatives
Try swapping “should” for “prefer” or “want.” Those words create space for flexibility, curiosity, and growth — they shift your mindset from judgment to ownership.
Exchange curiosity for judgment. Instead of “I should’ve made that putt,” try “What can I learn from that moment?”
“Should” shames you for not being where you think you ought to be. Curiosity and flexibility pull you toward where you can go.
Remain in the present- it’s only a moment in time
Remind yourself that “It’s okay” (it is not actually life or death to have missed a putt or to not make the cut).
Focus on resilience and agility more than perfection or rigid expectations.
I will leave you with a final warning—Excessive “shoulding” could cause emotional constipation.