Ten Years In

A personal note to start the year

Hey friends, happy 2026!

I hope you’re feeling healthy and well.

It’s been a little while since I last posted, so I wanted to share a quick update and say thank you. Last year was my first full year running my coaching practice, and I’m so grateful for the people who trusted me, supported me, read along, or just reached out when something resonated.

The majority of my work revolves around people in the middle of something. Venture-backed founders raising money or thinking about what scaling looks like after the next round. Leaders stepping up to bigger roles, managing boards, or hiring their first executive team. People selling companies, winding things down, or trying to figure out what’s next after a big chapter closes. The work isn’t about having all the answers. It’s about creating space to think clearly and move forward with confidence.

On the personal side, Emily and I welcomed our third daughter last year. Adding another kid into the mix has been a big shift for our family - full of love, fun, and our fair share of chaos. For me, it’s also meant letting go of rigid routines and getting more comfortable adjusting on the fly.

I also wrapped up the year with something I’ve been working towards for a long time - I received my black belt in Brazilian Jiu-Jitsu. I’ve spent over a decade on the mats and what started as a way to exercise and manage stress has transformed into a lifestyle. I spent a lot of the holiday season reflecting on the journey so far, and I thought it would be fun to share a few lessons that Jiu Jitsu has taught me.

Consistency compounds.

People new to Jiu Jitsu often ask how to get good fast. My answer is usually to slow down. Pick something you can sustain - maybe two or three days a week - not seven. I’ve watched more people burn out their first year than stick with it. Secondly, remember that life is always changing so allow your habits to change with it. Some seasons you train a lot. Other seasons you’re sick, exhausted, or just trying to keep your head above water. The important part is not burning out, getting hurt, or disappearing altogether.

The real progress comes from sticking with something over a long period of time. Showing up on days when you don’t feel great, or when you feel like you’re getting worse. Going through stretches where you’re just reviewing the basics again. Then going a layer deeper. The journey is never a straight line. It’s more like a constant messy middle with occasional leaps forward that only make sense looking back.

Get comfortable being uncomfortable.

Jiu Jitsu puts you in tough spots constantly. You feel stuck, lost, and unsure, until you’re not and it just clicks. You’re constantly trying, failing and then trying again.

When you’re uncomfortable in a bad position, the natural reaction is to panic - to move fast, to force something. Most of the time, that’s exactly what gets you submitted. Learning Jiu Jitsu means learning to breathe and stay calm under pressure long enough to see what’s actually happening and figure out your next move. There’s almost always another step you can take. As one of my professors always says, “it’s just action and reaction.”

This applies to daily life and work too. We all end up in stressful, fight-or-flight situations. Our natural instincts often direct us to react quickly - to just do something! The better move is to slow down, breath, and respond or react with a clear mind. Calm doesn’t have to mean passivity. It means being able to think strategically when the situation feels intense or scary.

You don’t do this alone.

No one sticks with something for ten years without good people around them. Professors, training partners, and teammates make the hard days easier and the longer arc of mastery possible. Having people who notice when you’re gone (with a few guilt ridden texts!) and welcome you back matters more than most of us admit.

Getting a black belt didn’t change much. There were no new powers or sudden insights. It just marked the start of another phase, one where the focus shifts from chasing milestones to continuing to learn. Kind of like being a white belt again and I’m finally at the real starting line.

Thanks for being here and thanks for reading. Wherever this year is starting for you, I hope you give yourself permission to keep showing up in whatever way makes sense right now.

Dillon

PS: If this resonated, I’d love to hear what chapter you’re in right now.