Jordan Schilleci
3 min readJun 16, 2024

A conundrum is a difficult or intricate problem. It is a paradoxical, insoluble, or difficult dilemma.

co·nun·drum | \ kə-ˈnən-drəm

1: a riddle whose answer is or involves a pun // The conundrum “Where does Friday come before Thursday?” has the answer “In the dictionary.”

2a: an intricate and difficult problem // The coach faced the ultimate conundrum when two star players got into a fistfight.

b: a dilemma // She faced the conundrum of choosing between her career and her family.

The word comes from a dialectal form of the English word “conning” meaning to study or learn, combined with the Greek “ainos” meaning a riddle. So a conundrum is essentially a knotty or perplexing riddle or problem to study out and solve.

Having expectations for your tomorrow can place you inside of a paradoxical thought.

I hate being let down, but I love having a plan. I am someone who, when my plan shatters, I get into a funk. I don’t agree with my emotions, so I fight them, but I am rarely successful.

I have always viewed myself as a person with high expectations. I think there is right and wrong within that, but more right than wrong.

But if you have no expectations, do you struggle to find pleasure and happiness throughout the day? Are you letting yourself down by not having any expectations?

Maybe it isn’t about having expectations about others and experiences. Perhaps it is about having expectations of ourselves. Expectations can motivate us to achieve more and strive for more. Expectations can push us outside our comfort zones.

The bad comes with unrealistic expectations. When things don't go as planned, they can set us up for disappointment, self-criticism, and emotional distress. Yes, I am talking from experience. One that dominates me, is overwhelm.

But the answer must be, that one must find the right balance. We must find alignment within our expectations. I am sure my attachment to how things “should” unfold robs me of more than I realize. Leaning into the moment and the possibilities might be the key to avoiding the frustrations when things don’t go my way.

But a complete lack of expectations may make it harder to derive satisfaction. So, would an open, expectation-free mindset allow us to stay present, allowing us to appreciate the moment as it unfolds?

Hence the conundrum I have been feeling.

A middle-ground approach recognizes that some expectations are inevitable, but holding them lightly may be the answer. I want to build resilience and emotional calmness, so I must live presently in the moment.

If one were to stay grounded in the present moment with an open mindset, one could easily work towards one's peace and happiness while also embracing life’s unpredictability. With self-awareness and intention, the conundrum of expectations can evolve into a catalyst for growth — motivating us to strive for more.

Welcome to my late-night ramblings. I have taken a break from my early mornings while being carried moment by moment. Love y’all.



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