Mary-Hannah O
4 min readMay 1, 2024

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I have been working as an educator in the US public school system for the past two years. It is a role that has brought me equal parts laughter as I have witnessed the curious inner workings of the Gen Alpha mind, as it has brought me heartache. And headaches. And backaches.

The issue was never in the job itself. All things considered, my job responsibilities as a teacher within my specific subject area were manageable and I have had far more work-free evenings, weekends, and holidays than could be said by many of my professional counterparts across the nation. It has been noble work with decent pay. The ubiquitous ache that bored a hole through my confidence and sense of self was due to the disappointment of where my life was going, or rather where I thought it should go.

In Meg Jay’s landmark book, The Defining Decade, she writes of the ‘tyranny of the should’ and how it paralyzes the possibility of what is most true to oneself. Shoulds warn us of the regret of ‘lost potential’ and encourages the pursuit of all that has been prescribed as ‘excellent’, ‘valuable’, ‘proper’, ‘wealthy’, ‘important’, ‘uncommon’ so on and so forth. I was constantly vying with what my should should be, and acutely aware of how I didn’t seem to be living up to it.

I spent many planning periods in my classroom, which was until very recently an old outdoor trailer of which I grew quite fond of, minus the occasion six-legged critter, wondering of all the shoulds I should have done, and the shoulds I still could do. Should I go to law school? Should I stay in teaching and go for a doctorate? Should I move to London? Should I travel the world for a year? Should I be prioritizing money or fulfillment? Should I become a nurse? (That was incredibly short lived) Should I become a cloud systems engineer? (Even shorter-lived). The tyrannical voice of all my shoulds, some Tik-Tok-induced, some from cautious parental counsel, others still from an inner part of myself that still desperately desired to be seen, valued, never rejected, snarked at me daily.

More recently however, I have come to the understanding that the should of my life is never as meaningful, authentic or worthwhile as the what and better yet, what will be, of my life. What do I mean by this? Instead of seeing my years teaching as some sort of two year placement, an unanticipated odd-ball meant to fill the gap until I found the ‘right’ program, or the ‘perfect’ job, and consequently ‘arrived’, my experience within the classroom became the very bargaining table of my professional future. What I was doing and how it will shape my decisions and passions moving forward crystallized in importance.

The classroom is where I learned to discern the sort of interactions that excite and interest me, and contrarily those that drained and frustrated me, within the bounds of professional obligation. It is where I discovered my love for small group discussions, of witnessing the process of self-actualization, of articulating what age and sometimes confidence and ability made it difficult to say. It is where I remembered the joys of my own adolescence and was given a newfound appreciation for the awkwardness, messiness, and magicness of it all.

It’s a quintessential twentysomething experience I’m inclined to say — the constant bargaining with an adolescent self whose precocity and drive powered through high school and college — and the graduate self whose sudden thrust into adulthood makes us clamor for the chance to do it all over again, but better, with more freedom, more focus, etc. etc.

I write all this to say that living my life under the tyranny of the should made for a miserable existence, not least for my mind and the ears of those kind enough to humor me as I belabored my regrets, anxieties, and hopes about it all for the umpteenth time. The should was a shroud that I relentlessly clung to, hoping to resurrect the long-lost desires of a self that at her core had been ridden with insecurity and a fear of rejection, while masquerading as a ‘high-achieving’ well-to-do somebody.

To say that I have been preoccupied about my career, future, and the meaning of my life in light of it all for the past two years would be an understatement. There is nothing I have prayed more for or about, nothing I desired more than feeling like I had it figured it out. It is nothing less than a sigh of relief to no longer feel bound to the idea of what I should be, and rather feel free to conscientiously move towards the professional, and more importantly the person I desire to be. I now believe that there will be no one isolated moment in which I will feel that I have ‘arrived’ or ‘made it’, but rather a scrapbook of moments, decisions, and memories that have all played their part in my becoming. I look forward to one day recounting them all.

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