Rewrite the Script After 50: Redefining Success

 Turning 50 has a way of quietly changing the conversation you have with yourself.

For many of us, it’s the first time we realize we are closer to the end of life than the beginning. Not dramatically or gloomily, but in a practical, honest one. You start to look back and take stock. For what did I hope? What did I actually do? And what, if anything, still feels unfinished?

For some people, that reflection feels unsettling. For others, it feels oddly freeing. For me, it became an invitation to rewrite the script.

When I turned 50, I made a decision that surprised a few people around me. I enrolled in a Master’s of Education program, focusing on how computers should be taught in schools. At the time, I didn’t frame it as a bold reinvention. I simply followed a question that wouldn’t let go. Schools were changing, technology was changing, and I wanted to understand how teaching needed to change with it.

That one step opened more doors than I ever expected.

After I graduated, the Ministry of Education asked me to help create a new computer curriculum from Kindergarten through Grade 12. Suddenly, I found myself working alongside curriculum experts, educators, and policy thinkers. For a full year, we debated not just what students should learn, but how learning itself should look in a rapidly changing world.

What shifted for me wasn’t just my résumé. It was my perspective.

I still worked in a school, but I no longer saw teaching only through the walls of a classroom. I began to see education as a system, a living thing shaped by culture, policy, values, and imagination. That change in perspective quietly altered my attitude toward my colleagues, my work, and even myself. I felt more liberated, more curious, more willing to explore ideas beyond my usual lane.

That sense of freedom showed up in my teaching. My lessons became more adventurous. I was more open to collaboration and risk. I started saying yes to conversations and opportunities that, earlier in my career, I might have dismissed as unrealistic or “not for someone like me.”

At one point, I even put together a team and bid on a contract to revamp an entire country’s curriculum from K to 12. We didn’t get the contract, but we were the runners-up. Years earlier, I wouldn’t have dared to imagine myself in that role. At 50, it felt possible, even natural, to try.

Redefining success gave me the courage to apply for a position at an international university. To my surprise and gratitude, I was successful. I went on to help create programs that trained teachers how to teach teachers. That sentence still makes me smile. It wasn’t part of any life plan I’d written in my thirties, but it fit perfectly with the person I had become.

Looking back now, I can see that redefining success was the most important first step in preparing for retirement ten years later.

Success stopped being about titles, routines, or staying on a predictable path. It became about alignment. Did my work feel meaningful? Did it energize me? Was I learning, contributing, and staying curious? Those questions mattered more than climbing any particular ladder.

Many of my readers are what I call “young seniors.” You may not be thinking about retirement yet. You may still be busy holding things together, careers, families, responsibilities, and expectations. But somewhere in the background, a quieter question may be forming: Is this still the life I want to be building?

Redefining success doesn’t require dramatic change. It doesn’t mean walking away from everything you’ve built. Often, it starts with noticing where your definition of success came from in the first place, and whether it still fits.

Over the next five posts I will explore some ideas that I should have looked at more deeply when I turned 50. In the next post, I’ll explore what happens when we begin to loosen our grip on old identities. The roles we’ve carried for decades don’t disappear overnight, and letting go can be emotional work. But it’s also where new space begins to form.

This is not a series about endings. It’s a series about possibility, and about giving yourself permission to write the next chapter with intention.

Living Well Without Conclusions

I started this series with a snowflake, a sunlit mountain, and a memory of skiing, desires that my body can no longer chase as it once could. Along the way, I have looked at knees that ache, choices that ask us to accept limits, burnout that teaches patience, and quieter adventures, such as writing a poem for Valentines Day, but no less meaningful. And yet, here I am, still asking questions.

Maybe that’s the point. Life doesn’t hand out final answers, and perhaps it never did. The tension between what we imagine and what we can do, between fear and curiosity, between caution and joy, these aren’t problems to solve. They are companions, guiding us to pay attention, to notice, and to act thoughtfully in the spaces we occupy.

Living well doesn’t require resolution. It asks for presence, discernment, and a willingness to embrace uncertainty with grace. It’s in the noticing of a snowflake, the warmth of the sun, the laughter shared with friends, or the quiet satisfaction of a day lived deliberately.

So, maybe the best way forward is to live with questions, not chase conclusions. To step into the world thoughtfully, with curiosity as our guide, and to let the journey itself teach us what matters most. After all, it’s in the living, not the solving, that we find the richness of our days.

A Different Kind of Adventure

Not long after we start asking whether life gets smaller when we “get it right,” another question sneaks in, usually unannounced: who decides what right even looks like now? Is it our doctors, our families, the well-meaning commercials, or the quiet voice in our own head that has learned to speak in warnings instead of possibilities?

Aging has a way of putting us in a room full of advice. Some of it is wise. Some of it is fear dressed up as concern. And somewhere in the middle, we are left to sort out what still gives us energy, what quietly drains it, and what we are doing simply because it seems expected. I meet people every week who are quietly negotiating this terrain.

One of them is a 92-year-old woman I serve with on a board. Some days she has more energy than I do, and yet she worries she isn’t doing enough. She’s become a quiet role model for me. Many people her age might be sitting at home, but she’s dancing the Maypole, walking in the May Day parade, sitting in the hot sun at our booth during the car show, encouraging other seniors to stay engaged, or advocating for our latest project supporting caregivers of people living with dementia.

She doesn’t overreach. When she’s tired, she rests. There’s no inner argument between caution and curiosity for her. She has learned something many of us are still working toward: excitement doesn’t have to be loud, fast, or risky to be real. For her, adventure has shifted from adrenaline to purpose, from speed to depth. Discernment, not fear, has become the skill that keeps her moving forward.

And as we reflect on our own lives, perhaps the most daring adventures now aren’t measured in miles run, slopes skied, or ladders climbed. They are measured in connection, nurturing relationships, exploring new ideas, trying creative projects, or simply being present in ways that matter. The bravest risks later in life are often quiet, emotional, or relational, and they can bring more meaning than any physical feat ever could.

So, I invite you to pause for a moment and ask yourself: Where has your adventure evolved? What risks now feel worth taking, and what joys are waiting just beyond your comfort zone? The answers may surprise you—and they may just lead to the richest, most unexpected adventures of all.

Adventure in later life doesn’t have to be loud or risky—it can be found in laughter, new ideas, and small acts of courage. What might happen if you tried something just because it sparks your curiosity? Step lightly, step boldly, and see where joy finds you next.

Life’s later chapters invite a different kind of daring, one that blends curiosity with care, connection with creativity. Ask yourself: what risks are worth taking now, and which joys are waiting just beyond your comfort zone? Step forward, the next adventure is yours to discover

If I Get This Right, Will Life Get Smaller?

As we age, we’re often reminded, sometimes gently, sometimes loudly, of the risks we face: falling, cognitive decline, chronic health conditions. Cautious, “prudent” behaviour is presented as the responsible response. Sensible advice, yes, but it can also raise an unspoken question: if I get this right, will life get smaller?

At lunch the other day, one of the guys announced he’d done a full “nose plant.” When I asked what happened, he said he was walking from his car into a store during heavy rain, misjudged the height of the curb, caught his foot, and went down. A few bruises, nothing serious, but, as he put it, a much larger bruise to his ego.

My wife and I often laugh at a local TV commercial for stair lifts. After a sobering montage about falls, the ad closes with the line, “We have a solution for that. Just don’t fall.”  We laugh, even though the message underneath is serious. It suggests that the safest life is the smallest one.

A friend told me his doctor advised that anyone over 65 should never climb a ladder. In theory, it’s good advice. In practice, it’s unworkable. A more realistic approach is using ladders wisely: have someone steady it, climb slowly, avoid the top rung, don’t overreach. Prudence doesn’t have to mean withdrawal.

By that same logic, someone might tell my friend who tripped at the curb, “Just don’t catch your toes,” or better yet, “Don’t go out in the rain.” But if we followed every fear-based instruction, we’d soon be living very carefully, and very quietly.

That’s the real worry behind being sensible. Not the bruises or the risks, but the fear that doing things “right” means doing less, seeing less, trying less. Yet life has never been about eliminating risk. It’s about adjusting how we move through it

Getting it right doesn’t have to mean life gets smaller. It can mean life becomes more intentional, slower, yes, and more deliberate, but still curious, still engaged, still willing to step out into the rain. The real work isn’t avoiding risk; it’s learning which risks are worth taking and which fears are quietly shrinking us without our consent. And that raises the next question: once we stop letting fear set the limits, how do we decide what “enough” looks like, and who gets to define it?