Forty Years Later
Recently, I attended my 40th high school reunion.
Just writing that sentence feels strange. Forty years. How is that even possible?
I graduated from Grass Lake High School in 1986. There were only 42 students in my graduating class. About half of us showed up for the reunion, and as I walked into the room, I wasn't quite sure what to expect.
What I didn't expect was how much the evening would cause me to reflect on my own life.
One of the first things that struck me was how many people had maintained friendships with classmates over the years. Many of them still spend time together, know each other's families, and remain connected in a way that I found both admirable and fascinating. Other than Facebook, I have maintained virtually no friendships from high school and very few from college. Yet I have maintained many relationships through entrepreneurship, coaching, and [EO](https://eonetwork.org/) over the years.
It made me curious.
Why is that?
Am I someone who naturally moves forward rather than stays connected to the past? Have I spent my life seeking growth and new experiences while others invested more deeply in long-term community? I don't know the answer, but I found myself thinking about it long after the reunion ended.
The other thing that struck me was how different my experience of high school was from many of the people in the room.
As stories were shared, I often felt like I was listening to memories from someone else's high school experience. People remembered me, and everyone was warm and friendly, but many of the stories being told weren't stories I was part of. It was almost as if I attended Grass Lake High School without ever fully belonging to Grass Lake High School.
The Space Between Groups
I wasn't part of a particular clique. I didn't go to parties. I didn't drink. The girl I dated most seriously went to another school. I moved between groups and got along with most people, but looking back, I realize I often occupied the space between groups rather than fully inside any of them.
That realization surprised me.
Reconnecting With Old Versions of Myself
As I reflected on it, I began to understand why the reunion felt so emotional. It wasn't about reconnecting with old classmates. It was about reconnecting with old versions of myself.
The C student.
The kid from a small town.
The boy who was convinced there had to be something bigger waiting for him somewhere beyond Grass Lake.
Is Pride Really Dangerous?
I was also reminded of something that may sound a little uncomfortable to admit.
Part of me felt proud.
Very proud.
I started a company and eventually sold it. I've written [books](https://extraordinaryadvisors.com/books/from-suck-to-success/. I've spoken on stages. I've been an [executive coach](https://extraordinaryadvisors.com/executive-coaching/) to leaders around the country. I've built a life that younger Todd never could have imagined.
There was a part of me that looked around the room and thought, "Wow, I actually did it."
And then, almost immediately, another part of me felt guilty for feeling that way.
Why?
Because many of us were taught that pride is dangerous. That we're not supposed to acknowledge our accomplishments. That confidence somehow makes us arrogant.
But I don't think what I felt was arrogance.
I wasn't celebrating anyone else's failures.
I was appreciating my own journey.
Achievement Questions vs. Belonging Questions
What became clear to me as the evening unfolded was that the reunion wasn't really stirring up questions about success. It was stirring up questions about belonging.
As I reflected on the conversations, the memories, and the emotions that surfaced, I realized the strongest feelings I experienced had very little to do with money, career achievements, books, business accomplishments, or any of the traditional markers of success. Instead, they were connected to something much deeper. They were connected to being seen. To be known. To feel like I mattered.
One of the most unexpected moments of the evening came when I saw the girl I went on my very first date with in seventh grade. Not only did she remember the date, but I immediately remembered the disappointment I felt when she didn't want to go on another one. More than forty years later, that memory was still there. Not because I'm still carrying the hurt, but because that younger version of me is still part of who I am. The reunion reminded me that we never completely leave those earlier versions of ourselves behind. They come along for the ride, quietly influencing how we see ourselves and how we experience the world.
The longer I sat with my thoughts after the reunion, the more I realized that much of my adult life has been spent trying to prove that the boy from Grass Lake mattered. As uncomfortable as that is to admit, I suspect I'm not alone. Many of us spend decades building careers, businesses, wealth, accomplishments, and identities. We tell ourselves we're pursuing success, but underneath it all, we're often pursuing something much more fundamental. We're looking for evidence that we are significant, that we are worthy, and that our lives matter.
The irony is that achievement can never fully answer those questions because they aren't achievement questions. They are attachment questions. They are belonging questions. At their core, they are questions about whether we are worthy of being seen, heard, known, and accepted.
As Jennifer and I drove home that evening, I found myself feeling grateful. Grateful for the life we've built together. Grateful for the risks I've taken. Grateful for the people who have walked alongside me throughout the journey. And strangely, I found myself feeling grateful for the boy from Grass Lake—the boy who wasn't always sure where he fit, the boy who wanted something more for his life, and the boy who spent years trying to prove himself.
Because somewhere along the way, I learned something I wish he had known much earlier. He mattered long before he became successful. The reunion didn't teach me that lesson. It simply reminded me of something that had been true all along.
