The Imposter Syndrome Club: New Members Welcome

Some mornings, I wake up certain—confident in what I’m doing, why I’m doing it, and how we’re moving forward. Other mornings, I wake up wondering if I’m the right person for this work at all.

How can I be good at this if homelessness is still increasing? How can I have a day filled with clarity and progress, only to feel completely lost an hour later? How can I have moments of confidence, inspiration, and purpose—then, in the same day, question if I have any idea what I’m doing?

If you’ve felt this, too, you’re not alone.

Imposter syndrome is that creeping doubt that we don’t deserve to be here, that our successes are just luck, and that sooner or later, someone will realize we have no idea what we’re doing. It’s that nagging voice that whispers, You aren’t qualified enough. You aren’t smart enough. You aren’t making enough of a difference. And it’s shockingly common—even among people who are highly skilled, deeply committed, and outwardly confident.

If anything, it might be more common in the homelessness sector than almost anywhere else.

We’re in a field where urgency is constant and the stakes are incredibly high. People’s well-being, safety, and futures are on the line every single day. The work is never “done,” and the goal—ending homelessness—feels massive. Even when we make progress, it’s rarely as fast or as complete as we want it to be.

We focus on outcomes, and rightfully so. I’ve spent years emphasizing the need to measure success based on real, meaningful change rather than just tracking activities. And I still believe this—maybe now more than ever. We need to hold ourselves accountable to outcomes over outputs—fewer shelter stays and more permanent housing, reduced returns to homelessness, stronger system coordination. But there’s a trap in this thinking, too.

Because if we’re not careful, we start tying those high-level system-wide outcomes to our own personal worth. And that’s where imposter syndrome thrives.

No matter how hard we work, no one person alone can “end homelessness.” Progress depends on a hundred moving pieces, many of which are completely out of our control—housing availability, political will, funding cycles, economic conditions, public perception. If we judge ourselves solely by whether homelessness is solved at a provincial, national, or global level, we will always feel like we’re failing.

The worst part about imposter syndrome? It convinces us we’re the only ones feeling it.

I’ve had conversations with some of the most experienced and accomplished leaders in our sector—people I deeply admire—who have confessed they sometimes feel like frauds, too.

If even the best of the best wrestle with these feelings, what does that tell us?

This feeling doesn’t exist in isolation. It feeds into burnout—the exhaustion that comes from constantly feeling like we’re not doing enough.

And when we burn out, we don’t just suffer personally—we lose our ability to be effective, to think strategically, and to stay in this work long-term. That’s why acknowledging and addressing imposter syndrome matters.

The truth is: you are not an imposter.

If homelessness isn’t solved yet, it’s not because you’re failing. It’s because this is one of the most complex social challenges we face. And the fact that you care enough to question whether you’re doing enough? That’s proof that you belong here.

If you feel lost some days, that doesn’t mean you don’t deserve to be in this work. It just means you’re human.

So, let’s name the feeling, talk about it, and remind each other: we’re in this together.

In fact, maybe we should make this official. I propose we start a club—the Imposter Syndrome Club. No formal agenda, no PowerPoints, no icebreakers.  Just a space for some of the best leaders I know to say out loud, Yep, me too. Maybe we just start acknowledging it in every conference hallway conversation—or maybe, just maybe, we get matching Imposter Syndrome Club patches (like those Motley Crüe ones from the exhibition when we were kids) and start wearing it as a badge of honor. Not because we doubt ourselves, but because we keep showing up and forging ahead anyway.

Welcome to the club,