ABOUT CLAYTON

From The Road,
Not The Mountaintop

I work with entrepreneurs, creatives, and people in the middle of big transitions.

Most of the people I work with are not stuck in obvious ways. They are building things. Holding things together. Moving forward. Doing what they’re “supposed” to be doing.

And underneath that, there’s often something harder to name.

A sense that life is happening, but not fully being lived from the inside. A feeling of waiting for some future version of themselves to arrive before they can finally exhale. Or building something meaningful, but quietly questioning whether they are allowed to fully own it.

I know that place intimately.

I know what it’s like to spend years moving through life while still feeling like you are on the outside of it. To be capable, functional, even successful, and still not feel fully at home in yourself. To not just wonder “now what,” but to realize you may have been waiting for your life to begin for much longer than you thought.

And I know what it’s like to want more without yet fully trusting what you want, or whether you’re allowed to want it at all.

This work is not separate from my life. It is the same work I am still learning how to live.

Where I Come From

I grew up in a small western Massachusetts town that looked fine from the outside. Underneath that, there was a level of instability and complexity that shaped how I learned to move through the world.

For context, I’m a 9 out of 10 on the Adverse Childhood Experiences (ACE) scale (a framework used to understand the impact of early life stress and trauma). I don’t include that as a label, but as reference for the environment I was navigating early on.

Very early, I learned how to separate experience into what could be seen and what had to stay hidden. I got very good at that split.

Over time, that turned into a set of beliefs that quietly organized everything I did.

That if I stayed controlled enough, I could avoid being hurt.
If I kept distance, I wouldn’t have to fully feel loss.
If I judged myself first, no one else could land the blow.
If I didn’t fully let myself be seen, I couldn’t be rejected in a way that would break me.
And underneath all of it, a quieter belief that I was fundamentally different from other people in a way that made ease, belonging, or softness something I had to earn, if it was possible at all.

That pattern deepened when I came out as gay, and learned how to use humor as protection. If I could make something funny, I could control how close it got. People often felt like they knew me, but I was still carefully managing what was actually visible.

After a long string of deaths in my family, I began keeping a suit in my closet at all times. I would quietly practice eulogies for the people I loved. Not because I expected loss at every moment, but because some part of me believed preparation could reduce the impact of grief when it came.

That was the internal logic I was living inside. And for a long time, it worked well enough to keep me functioning.

The breaking open

I avoided therapy for years. Eventually the anxiety caught up. My chest felt like it was caving in. In one of my first sessions, my therapist asked almost casually: "But do you actually believe you're worthy of love?"

The answer was no. And that answer collapsed my entire world. It was also the moment I started to rebuild it.

Over the years that followed, I tried almost everything. Talk therapy, CBT, IFS, EMDR, Neurofeedback. One piece at a time, figuring out how I was actually wired underneath all of it. I was diagnosed with CPTSD, which validated why I showed up in the world the way I did.

Therapy saved my life. Eventually, I even reached the point where a brain scan revealed that I no longer fit the criteria for CPTSD. I had "healed" my trauma, but the real work came in learning to build a life that I wanted, which wasn't just based on surviving all that had happened to me before.

In 2020, I finally listened to the people who had been telling me for years to try stand-up comedy. I took classes at Second City. The first time I stepped on stage, I couldn't believe that the same kid who spent decades trying to fight off tremors in crowded spaces was the one on stage holding the microphone in front of hundreds of people.

How the work found me

Coaching found me the way everything important has. Through other people seeing something in me before I could see it myself. My first paid workshop was five dollars. Afterward, two people paid and I cried and tried to refund them. It felt wrong to charge for something that came naturally. It took me years to understand that what I was offering wasn't advice. It was a space.

Some of my greatest wins as a coach aren't dramatic. They're the entrepreneur who finally took a week off without her laptop. The cancer survivor who chose the lower-paying job because he understood he had earned the right to rest. A client learning to let a boundary stay in place even when someone pushed back.

One of my greatest personal wins wasn't reversing a diagnosis or moving across the country on my own, though both of those happened. It was a Thanksgiving, a few years before my mother died. I walked up behind her and hugged her, just because I felt called to. She was confused at first. Then I felt her settle. It lasted less than a minute. But it had taken decades of work from both of us to make it possible. That's what this is. Small moments that are anything but small.

What I Believe

I marvel at how much people have survived and still tell themselves they're not doing enough. I don't believe there's a moment where anyone could give themselves too much grace for who they are, how they show up, and everything they've been through.

The patterns that keep us small don't break overnight. But they do break. And every small shift, every moment of honesty, every choice that reflects what you actually want instead of what you think you're supposed to want, is worth naming.

That's what this work is. That's what I'm here for.

With Love,

Clayton