The Introduction: Reflections on Career, Leadership, and Growth

As we move into 2026, I find myself staring at my screen thinking: "Oh god. What if this all goes wrong? Why now? Should I even do this?"

It’s a thought I’ve had more times than I’d like to admit — both personally and professionally. And if I’m being honest, that uncertainty is exactly why I’m here, writing this post.

For those who don’t know me — Hi! My name is Graydon McGowan.

I grew up in the small town of Grand Valley, Ontario. From a young age, I knew I was different. I wanted to dress differently, act differently, and express myself differently — which, as you can imagine, wasn’t always easy in a small hockey- and country-town in the early 2000s.

High school was especially challenging. I experienced persistent bullying — verbal and physical — at a time when I was also learning how to navigate life with type 1 diabetes. Looking back, those years forced me to develop resilience early. I learned how to be self-reliant, how to push forward when things were uncomfortable, and how to advocate for myself in environments that didn’t always feel welcoming. Those experiences shaped how I approach work, leadership, and people more than I realized at the time.

After high school, I went on to study Aviation Management — a natural path for someone who had been fascinated by aviation for as long as he could remember. The program blended business fundamentals with industry-specific knowledge, and for the first time, my interests and skills felt aligned. I believed aviation would be my entire career.

Through co-op placements and early professional roles — including time with Air Georgian, Sunwing Airlines, American Airlines, and eventually Porter Airlines — I had the opportunity to learn the industry from the inside and build a strong operational foundation.

In February 2020, I was offered a role with Metrolinx — an opportunity I hadn’t actively been seeking, but one that ultimately became a defining moment in my career. At the time, leaving aviation felt uncertain. In hindsight, it opened doors I couldn’t have anticipated.

Over the years at Metrolinx, my work evolved from being deeply embedded in day-to-day operations to operating as a connective tissue between frontline reality and executive decision-making. I’ve spent time close to the work itself — in operational environments where issues unfold in real time — while also supporting senior leaders by translating complexity into clear, actionable insights.

That dual exposure taught me how large, multi-layered organizations actually function under pressure: how information flows, where it breaks down, how accountability is created, and how decisions made at the top land on the ground. It shaped how I think about leadership, influence, and execution — not as abstract concepts, but as practical disciplines rooted in trust, clarity, and timing.

Alongside my professional career, I’ve always been drawn to entrepreneurship. Over the years, I’ve explored a number of side projects and business ideas — including BetesBox, a subscription service designed to support Canadians living with diabetes beyond traditional medical care. That curiosity has never fully gone away, even when perfectionism, timing, or the sheer noise of the internet made starting (or continuing) feel overwhelming.

And yet, as I enter 2026, I find myself feeling reflective.

On paper, everything looks right. I own a home. I have a stable, rewarding role. I work alongside talented people within one of North America’s largest public transportation agencies. So why does it still feel like I’m asking bigger questions?

I think this is where the idea of the millennial career crisis often shows up — not as dissatisfaction, but as quiet recalibration. It’s the realization that doing well and feeling fulfilled aren’t always the same thing, and that growth sometimes requires reflection rather than acceleration.

A lot of my recent thinking has been shaped by voices outside my immediate professional world. I’ve been particularly influenced by Stephen Bartlett, whose work consistently reinforces the idea that you don’t need a perfect plan or traditional credentials to begin — you just need to start. His emphasis on building, learning, and evolving in public resonates deeply with me.

I’ve also found alignment with thinkers like Aaron Spivak, who speak openly about discipline, self-awareness, and the difference between chasing validation and building something meaningful. Across long-form conversations, documentaries, and interviews with leaders and creatives, a consistent theme emerges: no amount of money or status guarantees fulfillment.

Earlier in my career, financial success was a primary motivator — and that focus served a purpose. It created stability, confidence, and opportunity. Over time, however, my priorities have shifted. What motivates me most now is impact: coaching and mentoring others, leading thoughtfully, and sharing what I’ve learned in ways that help people and organizations work better.

So why write a blog?

The honest answer is that I didn’t know where else to start.

Writing has always been something I’ve enjoyed, and this felt like a way to slow down, think more deliberately, and capture lessons that often get lost in the pace of day-to-day work. Over the holidays, I stepped back, spent time with people I care about, and gave myself space to reflect — not on what was next on the to-do list, but on how I want to grow as a leader.

Today marks my first day back at work after the holidays. The inbox is filling up again. The pace is picking back up. Before everything moves forward at full speed, I wanted to mark this moment and create a place to think out loud — carefully and honestly — about the work, the questions, and the lessons along the way.

I don’t have a grand reveal planned. What I do have is a growing belief that paying attention — to how we work, how we lead, and how we change — matters more than pretending we already know the answer.

This blog is simply a place to think out loud, honestly and carefully, about what I’m learning along the way.

If it helps someone else make sense of their own questions, then it’s worth writing.

Until Next Time,

-Graydon. AI disclosure: This piece was written by me whilst using AI tools to assist with structure, editing, clarity, and image creation — not to generate ideas or replace original thought.