Hi, I’m Sterling.
Here’s the quick version of my story. Stick around for all the painful details.
I know what it feels like to build something extraordinary — and watch it collapse. To carry six figures of personal debt and the heavier weight of an approach that no longer worked.
That collapse was the best thing that ever happened to me. Not just because it built character. But because it forced the one confrontation that changes everything — with who I'd been, and who I needed to become. That's the No Matter What moment. And it's the reason I do this work.
Since then I've brought that methodology to Fortune 500 leadership teams, fast-growing startups, global organizations, and stages across six continents. My book Hunting Discomfort became a number one bestseller. And the No Matter What Movement has reached more than a million people worldwide. My work has been featured in The New York Times, Forbes, Fast Company, and Inc.
When I'm not on stage you'll find me leading No Matter What Leadership Adventures in Peru, Morocco, Chile, and the Colorado Rockies — living the philosophy, not just teaching it.
But none of that is the point.
The point is what becomes possible when you stop negotiating with who you've been.
If you're ready for that conversation — you're in the right place.
Here’s the story
behind my story.
I didn't set out to do this work. I set out to build something extraordinary — and for a while, I did.
I could have become the fifth generation to run my family's grocery business. Instead I co-founded a tech startup alongside my father, grew up fast in the world of innovation, and watched our company get acquired by a Silicon Valley group to become part of a multi-billion dollar valuation. More than 700 employees worldwide. A San Francisco penthouse. Life wasn't just great — it was everything I thought success was supposed to look like.
Then the housing market crashed. Funding dried up. The company went bankrupt.
And I collapsed with it.
In my thirties I moved back in with my parents — crippled by debt, shame, self-doubt, anxiety, and depression. I felt like I'd had my one shot and used it up. That I was now, permanently, the person who had failed.
The moment I still think about.
There was a meeting — after a major industry event — where everything was already going wrong and I knew it. I surfaced the red flags I'd been watching build for months. Political infighting. A culture of defensiveness instead of collaboration. People chasing credit while avoiding accountability. Money being used to buy the appearance of growth instead of building anything real.
I was told: we're on the right path, and you're either with us or not.
And I backed down.
Not because I didn't know the truth. Because the identity I was operating from — the loyal executive, the team player, the person who didn't make waves — couldn't hold the weight of what I actually knew. I told myself I must have been wrong. I sold out to the promise of going public, which never happened. And when I stopped being who I actually was, my heart was never fully in it again.
That moment was an identity failure. It was who I defaulted to who the situation told me to be instead of who I was.
That distinction took me years to understand. And it's the foundation of everything I do now.
Change is unsettling.
The work that came after.
From rock bottom I started over. This time, honestly. I began speaking about what we got wrong, what I got wrong, and what it actually takes to build organizations that don't collapse under their own culture.
What I found — working with businesses across just about every industry — was the same pattern repeating. Organizations investing in technology, restructuring, capital reallocation — everything except the one thing that actually determines whether any of it works. The identity running the show. The version of us that was built for a different moment and keeps defaulting to what it's always known.
It's like expecting a team to start winning by giving them better uniforms. The resource was never the problem. The identity & culture was.
That realization became the No Matter What philosophy. And it's the work I've been doing ever since — with leaders and organizations across six continents, in boardrooms and on mountainsides, in keynotes and in the most difficult conversations people have been avoiding for years.
The world didn't need to change. I did. And once I understood that — everything else became possible.
That insight became Hunting Discomfort. But the deeper I went — with leaders, organizations, and my own experience — the clearer it became: discomfort was never the destination. It was always the threshold. The signal that the No Matter What commitment needed to be made. And No Matter What is what happens when you stop treating that signal as something to manage and start treating it as the door.
What I've learned from going to the edge.
Change feels hard not because something is wrong. It feels hard because the identity you've built is being asked to become something it hasn't been yet. That resistance is not a signal to stop. It's a signal that the threshold is close — and the No Matter What commitment is what crosses it.
I've tested that belief — not just in boardrooms but in the field. On mountains in the Atacama and the Andes. In the Moroccan desert. On Colorado 14ers with leaders ready to confront their own threshold. To be clear, I don’t enjoy hardship. But I needed to know firsthand what it actually takes to transform — and whether it's possible to engineer that experience for other people.
The answer is yes. But not through strategy alone. Not through harder work or better habits or a new framework.
Through commitment. The No Matter What commitment — the moment you stop negotiating with who you've been and declare who you're becoming.
The version of you that got you here was built for a different moment. Real progress — the kind that sticks, that compounds, that changes what's possible — requires confronting that version. Not destroying it. Understanding it. And then making the No Matter What commitment about who comes next.
That's the work. That's why I do it. And everything I've built — the keynotes, the adventures, the methodology — is designed to create the conditions where that commitment becomes inevitable.
Here's what I know to be true.
Identity (and by extension culture) is the variable nobody's measuring. Organizations invest in strategy, technology and talent — and wonder why the results don't hold. Leaders work harder, learn more, and try differently — and find themselves back at the same ceiling.
The ceiling is always identity. The version of yourself — or your organization — that was built for a different moment, quietly running the show.
No Matter What is the moment that changes. Not gradually, not incrementally — but at the threshold. The moment you stop negotiating with who you've been and make the commitment that changes what comes next.
I've crossed that threshold personally. I've watched thousands of leaders cross it in real time. And I've spent two decades building the methodology that makes it not just possible but inevitable — in a room, on a mountain, in a single conversation.
That's the work. That's why I do it. And if something in this story resonates — if you recognize the ceiling, the default, the version of yourself that got you here but won't get you there — then you're already closer to the threshold than you think.
No Matter What.
Sterling’s BIO
IN THE MEDIA
Sterling Hawkins has worked with more than a million leaders and countless organizations worldwide — helping them create a No Matter What moment that makes transformation permanent.
See Sterling In Action
Two hundred organizations. Six continents. One consistent outcome — leaders and teams who leave as a fundamentally different version of themselves.
Named one of the world's top 30 leadership keynote speakers, Sterling brings the No Matter What methodology to life on stage in a way that has to be seen to be fully understood.
