Jack

Lately, I’ve been looking back. Not with regret, exactly, more with curiosity, with that quiet thoughtfulness of someone who's spent a lifetime working and now wonders what it all adds up to.

My career never climbed neatly upward. It zigzagged. It circled. There were so many detours, start-overs, Plan B's. Sometimes, Plan C's. There was reinvention. Always reinvention.

I've never had an aversion to success, or to money, but even after 30 years of working, I still cannot say for certain what my definition of success is.

Now, as I move towards a new phase, retirement (I'm hoping the R stands for rest, relaxation and rascality) I find myself wrestling with society's uncomfortable truths about aging. Am I now all of a sudden less capable? Do I no longer have anything of value to contribute? 

It appears western society has an aversion to aging. Aging is often seen as a dirty word; all signs of it needing to be eradicated (think plastic surgery, incessant dyeing of grey hairs and the multi-billion dollar anti-aging industry). Becoming elderly lacks reverence these days, and the wisdom that goes along with it, is under-valued.

So, I find myself returning to the same quiet question: Was any of it worthwhile? Was it, if the achievements doesn’t look the way we’re told it should?

To some, my career might look like it lacked direction. To me, it felt like necessity, survival, curiosity, and sometimes, just another mystery waiting around a different corner, one which would stretch and challenge me. And in every room I stepped into, I grew and learned and changed into something new. Every time. To others it might look like I lacked ambition. To me it felt like service, like most teachers, investing time, energy, personal funds, and an ocean’s worth of emotional labour into the work I did in the classroom. Teaching might have given me grey hairs, it might've stolen my weekends and, very often, my sleep. It isn’t glamorous. It isn’t lucrative. It hasn’t catapulted me into the kind of success people applaud at reunions.

But… it mattered, it still does!

Because there are students who found their voice in my classroom. There were teenagers who sat in my counsellor's office and finally felt heard. There were colleagues I mentored, younger teachers I encouraged. There is the quiet joy of knowing that maybe, just maybe, I'm helping someone believe they can grow, and question, and lead greater change.

These aren’t things you put on a CV. They don’t earn you headlines or hashtags. But they linger in lives, hearts, in ripple effects that I’ll never fully see.

Sometimes I still wonder if I could’ve gone further. If I’d been bolder, sharper, more strategic. If I’d demanded more, settled less. If I’d been the ruthless kind of ambitious. But then I remind myself that showing up with heart counts for something. That walking a non-linear path doesn't mean you went nowhere. It means you adapted. You responded. You cared.

Something so ordinary...

But what if the ordinary isn’t so ordinary after all?

What if the true measure of success isn’t how high you climbed, but how deeply you rooted yourself in the lives of others? What if all those lateral moves weren’t a failure to get ahead, but a refusal to stop growing?

I don’t know. I’m still wondering. Still circling the question. But I do know this: I’m not quite done.

A Collective Inquiry

I invite you to think about these issues too, and maybe we can redefine what it all means.

My personal reflections lead me to believe it is up to all of us to question the very nature of work and the elusive definition of success. For too long, the narrative has been clear: work equals income, titles equate to achievement, and a rising trajectory signifies a life well-lived. But what if that narrative is incomplete, or worse, fundamentally flawed?

Is our life's work simply about earning money? Undoubtedly, financial security is a necessity, a foundation upon which lives are built. Yet financial accumulation alone cannot be the full picture. If work is only about the bottom line, what happens when that line flattens, or dips? Does that invalidate the years of effort, the countless hours invested?

Or is our life's work primarily about contributing to society? Is the intrinsic value of service a truer measure of success than any external reward?

Perhaps our life's work is ultimately about finding personal purpose. This is where the journey gets complex. Is it driven by an inherent need to seek meaning, to continuously learn, adapt, and find new windows into possibility? If purpose is the guiding star, then every twist and turn, every "Plan B," becomes part of a richer, more authentic navigation. It’s a definition of success that prioritizes internal fulfillment over external validation, allowing for a life that might look "ordinary" on paper, but feels profoundly meaningful.

Or, could it be that we just don’t know any other way to be? From childhood, we are often taught that work is fundamental to identity, a non-negotiable aspect of adulthood. All about our Ego, rooted in our pride. We learn to measure ourselves, and others, by what we "do." This ingrained societal expectation can make it incredibly difficult to decouple our sense of self-worth from our professional roles. Is our relentless pursuit of work, in whatever form, merely a deeply conditioned response, an unquestioned default setting?

As I contemplate this new chapter, these questions aren't just personal reflections; they are an invitation: As a society, how do we begin to redefine success? Can we shift our collective understanding from purely economic or hierarchical achievements to encompass impact, purpose, and personal growth? Can we acknowledge that a life rich in diverse experiences, human connection, and genuine contribution might be the most valuable "work" of all, regardless of the titles or the zeroes in a bank account?

What is our life's work, truly? Perhaps the answer lies not in a singular definition, but in the courage to ask these questions, openly and honestly, as we navigate our own unique journeys.