Rewrite the Script After 50: Change, Transition, and the Messy Middle

We are good at talking about change. We are far less comfortable talking about transition.

Change is what happens on the outside. Retirement dates arrive. Jobs end. Routines shift. Calendars suddenly open up. Change is visible and often measurable. Transition, on the other hand, happens on the inside. It’s the emotional and psychological process of adjusting to those changes—and it doesn’t follow a schedule.

This is where many people get stuck, especially after 50.

In my first year of retirement, I was still trying to figure out what to do with all the time that had suddenly appeared in my life. For decades, my days had been structured by work, deadlines, and responsibility. When that structure disappeared, I felt unmoored, even though retirement was something I had looked forward to.

Around that time, I was asked to join the board of a local charity. Without overthinking it, I said yes. Part of me wanted to feel useful again. Another part wanted somewhere to go, something to belong to, while I figured out who I was becoming.

As I learned more about what the charity did and the impact it had on the people it served, something unexpected happened. I began to feel a connection to my community that I had never experienced before.

I had lived in that community for fifteen years, but I worked elsewhere. Like many people, I was a commuter. I left early, returned late, and spent most of my waking hours outside the place I called home. My relationship to the community was practical, not personal. I knew the roads, the shops, the routines, but not the deeper rhythms of the people who lived there.

In retirement, that changed.

As I coped with the external change of no longer working, I was also going through an internal transition. Slowly, almost without noticing, I stopped feeling like a stranger in a strange land. I began to feel rooted. I wasn’t just passing through anymore. I was participating. I was transitioning from commuter to citizen.

That experience helped me understand something important: change and transition are not the same thing, and confusing them can lead to frustration and self-doubt.

Most transitions move through three phases.

The first is endings. Even when change is positive, endings involve loss. You lose routines, status, daily interactions, and familiar ways of being seen. Endings ask us to let go, and that often brings grief, irritation, or numbness. Many people try to rush past this phase, telling themselves they should be grateful or relieved. But unacknowledged endings have a way of lingering.

The second phase is the messy middle. This is the part no one prepares us for. The old life no longer fits, but the new one hasn’t fully formed. You may feel restless, uncertain, or oddly invisible. Productivity drops. Confidence wavers. You might wonder if you’ve made a mistake or if something is wrong with you.

Nothing is wrong. You are in transition.

The messy middle is uncomfortable, but it’s also fertile ground. It’s where new identities begin to take shape, often quietly and imperfectly. It’s where you experiment, say yes to things that aren’t permanent, and learn what resonates now, not ten years ago.

The final phase is new beginnings. These don’t arrive with fanfare. They emerge gradually, as clarity replaces confusion and energy returns in different forms. New beginnings feel less like reinvention and more like recognition. You start to see where you fit again, even if the fit looks different than before.

As you move toward or into retirement, life will continue to bring change. You can accept it, resign yourself to it, or embrace it. Embracing doesn’t mean loving every moment. It means staying present, curious, and open while the transition unfolds.

In the next post, I’ll explore the power of purpose and voice, how being heard, being visible, and permitting yourself to want more can steady you during the messy middle and help shape what comes next.

If you’re feeling unsettled right now, take heart. You may not be lost. You may simply be between who you were and who you are becoming.

Rewrite the Script After 50: Letting Go of Old Identities

Letting go of old identities is easy to talk about and very hard to do.

We live in a world that encourages us to introduce ourselves by what we do. “I’m a teacher.” “I’m a nurse.” “I’m an accountant.” Over time, those labels stop being descriptions and start becoming definitions. They tell us who we are, where we belong, and why we matter. Walking away from them, or even loosening our grip, can feel like stepping into thin air.

I understand this personally.

Until I was 50, I saw myself as a classroom teacher. That was my identity, my anchor, and my shorthand explanation of who I was in the world. After 50, something shifted. I began to see myself not just as a teacher, but as an educator. It sounds like a small change, almost semantic, but it mattered deeply. “Teacher” tied me to a room, a schedule, a role. “Educator” gave me room to grow, to explore, and to imagine myself in new contexts.

That shift didn’t erase my past. It expanded it.

Not everyone finds that expansion easy, or even desirable. I think of my sister-in-law, who has been a nurse for 35 years and is now three years from retirement. Nursing isn’t just her job; it’s her identity. She cares deeply about her patients and feels responsible for them in a way that goes far beyond a paycheque. When her children were younger, she was actively involved in their Air Cadet adventures. She volunteered, supported, and showed up. As they grew up and her work demands increased, those outside roles slowly fell away.

Now, work fills most of her emotional space.

She has very few interests beyond nursing, and I worry about her, not because nursing isn’t valuable, but because it has become almost the only place where she feels useful and known. I once suggested to my brother that she might consider working part-time and returning to her love of knitting. His response was immediate and telling: she doesn’t want to leave her patients.

I understand that loyalty. I also understand the risk.

When she retires, she won’t just be leaving a job. She will be leaving an identity that has shaped her days, her relationships, and her sense of purpose. Finding a new one won’t be simple, and the loss may come as a shock.

I see this pattern often. I have friends who, even years into retirement, still think of themselves first as accountants, lawyers, teachers, or truck drivers. You name the occupation, and you’ll find people who wear it like a permanent name tag. Take away the role, and they’re left wondering who they are without it.

That question can be frightening, not just for the person asking it, but for the people around them.

Many of us, especially in midlife, are “the ones who hold everything together.” We are the reliable ones, the problem-solvers, the steady hands. Our identities are built around being needed. Stepping away from those roles can feel like abandoning responsibility or losing relevance. No wonder we resist.

But here’s the quiet truth: letting go of an old identity doesn’t mean erasing who you’ve been. It means making room for who you might still become.

This kind of letting go is emotional work. It involves grief, even when the change is chosen. There’s grief for routines that once gave structure, for recognition that once came easily, for certainty about where you fit. Ignoring that grief doesn’t make it disappear. It just makes the transition harder.

What helps is curiosity.

Instead of asking, “Who am I if I’m not this?” try asking, “What parts of me have been waiting for attention?” Often, the seeds of a new identity are already there, interests set aside, skills underused, voices muted by busyness. Knitting needles put down years ago. Ideas postponed. Questions unanswered.

You don’t need to rush this process, and you don’t need to have a replacement identity lined up before you loosen the old one. Midlife is not about instant reinvention. It’s about creating space, space to notice, to experiment, to breathe without a label attached.

In the next post, I’ll explore the difference between change and transition. Change happens on the outside: retirement dates, job shifts, new routines. Transition happens on the inside, and it has its own timeline. Understanding that difference can bring a great deal of relief, especially when letting go feels messier than you expected.

For now, it’s enough to notice the identities you carry, and to ask gently whether they still fit the life you want to live next.

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.