Shoulda, Woulda, Coulda

Over the last six months, I have been undergoing intense transformation as life has been schooling me on a variety of lessons that I neither asked for nor wanted. Yet here I am, all the better for having been put under pressure and forced to take on the world.

In this post, I desire to share just three of the many data points Life has bestowed upon me. I will share these life lessons by attaching them to three commonly used words. Remember, these are not the definitive uses of the words. These are specific uses that reflect destructive mindsets.

Shoulda“- Oh the power and destruction wrought by the misuse of the word “should.” The word implies a sense of obligation (usually a moral one.) Parents, pastors, and politicians throw the word around like a lacrosse ball, creating a culture of manipulative and unreachable expectations.

Taking a close look at my daily routines and my default thought processes, I’ve noted a lot of discontinuity in my actions and beliefs – usually connected to some “should-statement” that I’ve adopted from a former authority figure or someone that I let influence my life. I’m discovering that there are a lot of false “shoulds” acting out as a moral Mapquest that just can’t seem to get me where I need to be.

While I accept the feedback and concern, many of these imposers of life-requirements are often living in their own cages of obligation: obligations that are neither universal nor absolute.

I would implore you to understand your values and beliefs and to not put more obligatory rules and guidelines than there should be. I have removed a significant portion of these voices from my life and I have found freedom in doing so.

Woulda” – Life disappoints. We get thrown a few curve balls and we sometimes lack the resources to complete a project that ignited our passion. When these tragedies occur, we can find ourselves wallowing in the pit of defeatism. We begin pointing fingers at the things that inhibited our actions/prevented us from completing a task or achievement.

“I would have…”

“…gotten the promotion if I hadn’t been stabbed in the back.”

“…invested if I had had the resources.”

“…won the match if I hadn’t twisted my ankle”


We sit in self-pity, make excuses, and sometimes even play the victim. This is simply not a productive way to live. Plans go wrong, variables get missed, and people suck. Yet our responses to defeat and unfortunate circumstance belong to us and us alone: it is our responsibility. Accept what you had control over and stop dwelling on what you didn’t.

Coulda” – Lastly, we address the lesson of regret.

“I could have…”

“…saved her…I could have jumped in the way”

“…studied harder and maybe I would have aced that test.”

These phrases are all too common, and a significant amount of the time they are also false. We constantly beat ourselves into the gutter with some ill-conceived believe that everything that goes wrong is our own fault or that a disappointing outcome is somehow a sign of incompetence or flaws.

It is the dismissal of the present for the acknowledgment of a non-existent past. I have found this particular mindset to be most consistent in my life.

“I could have been a better Residential Manager if I had only __________”

“I could have helped that student if I had only known ____________

This energy-draining mindset is nothing more than a leech. It is possible to take these phrases and grow from them, yes. However, it is not ever beneficial to swim in the waters of possibilities lost unless we are seeking strictly to grow and prevent future repetition.


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