There’s a little-known distinction between “fitting in and belonging” which can become an eye-opener on how we misspend our value across our careers and lives.
In this vlog, Dean shares his philosophy — along with two simple tips — to go from “failing to fit” to the deeper resolution of “truly belonging,” which promises to be a game changer for anyone stepping up to leadership or presentation.
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I want to talk about something powerful: the difference between fitting in and belonging. This idea came from someone in our organization—our superpower, Ellen Reiter. She has a way of cutting through the fog to the core truth of any situation. Today, in a meeting, she brought up this contrast, and suddenly my entire career—and honestly, my whole life—flashed before my eyes.
I spent more than half my life trying to fit in. Fitting in meant studying the rules of whatever group I was in and figuring out how to twist myself into what they wanted. As a filmmaker, I tried to fit in. As a game designer, a teacher, a trainer—same thing. In HR, in architecture, engineering, and construction, in consulting, on stage as a speaker—I was constantly asking, “How do I fit in here? Is this what a real professional looks like? Is this how I’m supposed to behave?”
Fitting in is contorting yourself to meet expectations. Belonging is something entirely different. Belonging is when who you authentically are naturally fits the place you’re in. It’s not about bending yourself—it’s about contributing your value as you are.
Somewhere along the line, after years of trying to fit in, I reached a point where I realized I simply belonged. Not because anyone told me so. Not because of external permission. But because I finally recognized the value I bring and stopped twisting myself into shapes that weren’t me.
For much of my life, I didn’t really want to be where I was. I was striving, pushing, contorting—and fulfillment always seemed out of reach. When I finally recognized that I belonged, everything shifted. I wanted to be here. With my family, with my clients, with my industry, with my work. I loved my whole life more because I wasn’t fighting myself anymore.
So how do you start moving from fitting in to belonging? One way is this: ask yourself, “What am I always the one doing that nobody else is doing?” In any room, any team, any meeting—what do you naturally bring? That’s your authenticity. That’s your differentiated gift. And when you offer that gift freely, you begin to belong.
This connects to an old SagePresence classic: you are the hero in the story. You don’t belong because someone invited you. You belong because you step up to help others. Belonging is earned through commitment to the people you serve—your team, your clients, your industry, your world.
When you are doing the thing that only you can do—your gift, your superpower—you rise out of contorting yourself to fit in and into a higher orbit of belonging. That’s where authenticity lives. That’s where purpose lives. And that’s where you find yourself becoming who you really are.
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