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Chris Szymanczyk

Santa’s Always Watching

By 29029 Everesting

June 6^th, 2025

If I don’t work out, I’m a bit like a dog that doesn’t get its exercise… I start causing problems!

Because of that, I’ve always been an active person. It’s kind of like my therapy.

My friend, Mike Boaz, called me during 2020 to see if I wanted to join him for some training he was doing for 29029.

This was the first I’d heard of it, and it sounded like a new, interesting challenge.

Maybe I’ll join Boaz and try it too…

That mountain was Snowbasin in 2021, and we got our Red Hats.

It felt like a big deal.

During those 13 ascents in Snowbasin, I noticed a few Black Bibs on the mountain.

That’s three Everests… pretty bad ass!

Right then and there, I decided I wanted to make a goal to earn one.

I decided my second 29029 would be a little more special than the first. I wanted to do it with my fiancé, Michelle.

It added pressure to me. If she didn’t finish, it would feel like I failed - not as an athlete, but as her support system.

We returned to Snowbasin in 2022. I earned another Red Hat, and Michelle came close.

I don’t like the word ‘fail’, and looking back, I won’t say we failed.

Michelle didn’t fail, she just learned the tools she’d need for success the next time. There was no doubt in my mind she would earn a Red Hat on her next mountain.

By 2023, I set my sights on Whistler.

It was a huge mountain, and the temperature swings were real. Mild temperatures at the base turned to full-on snowstorms at the summit.

I remember thinking that, mentally, eight ascents would be way easier than Snowbasin’s thirteen.

Boy, was I wrong.

Every single ascent was such a daunting task because as soon as you take that first step, you knew you were in it for at least three hours, if not much longer.

I still did it - another Red Hat, and this time, the right to wear the Black Bib on my next mountain.

Now, I’d achieved everything I set out to do after that first mountain.

I felt the pull of the 29029 community, so even though I didn’t have a clear what’s-next goal, I signed up for more in ‘24: Mont-Tremblant, TRAIL, and Stratton.

Mont-Tremblant was a special mountain. It felt less like Canada and more like Europe.

Michelle was with me again, and again, my goal was to get her to the summit.

We had a plan.

“Michelle, you have to get to 10 or 11 before bed. Then we’re going to get up early and keep going, because at 2 o’clock, it’s going to start raining. It’s going to be cold. You’re going to be wet. You’re going to be tired.”

I knew we could handle two of those things, but all three? That’s when those six inches between your ears can start breaking down, and the head games begin.

I climbed three extra ascents with her after I had Everested. I wanted to support her through those challenging last few ascents, which is exactly what I did.

As she pulled on her Red Hat, I realized that’s what I love about these events: finding something in yourself you didn’t know was there.

And when you help someone else find it too, that’s even better.

At Stratton, I finally checked the OG 29029 mountain off my list.

I’d always avoided it because I have poor circulation in my hands - cold weather can cause excruciating pain for me, and I’d heard more than a few stories of people going hypothermic on that late-season mountain.

But I finally went for it in 2024… and lucked out! It was the best weather they’d ever had.

I checked the box.

But the hardest experience I had at 29029 was actually the one that came before Stratton.

TRAIL.

Around Mile 48 - during Day 2 - I was ready to be f****** done!

I was tired, sore, and ready for rest.

On that downhill, not far from the finish line, I was absolutely flying. I just wanted the day to be over.

Then, I sprained my ankle.

I was moving too fast, and this is the consequence.

Then, at mile 50, since I was compensating for my newly sprained ankle, I sprained the other one.

No joke.

It was only Day 2…

The morning of Day 3, I could not take a step bigger than 6 inches…

It was tempting not to even bother showing up at the start line for that final day. Double sprained ankles were as real an excuse as you can have, but I’d already invested so much time, energy, and pain into getting here…

I may as well try!

I started Day 3, and when I’d get to a section of shale and loose rocks across the trail, I could only look down at it, then at my swollen ankles… then back to the shale.

It was like some sort of practical joke.

You couldn’t design a trail worse than this for a sprained ankle if you tried!

More than a few tears fell down my face that day.

But I knew I wasn’t going to stop.

The only question was if I’d make it to the finish before the cut-off time.

I did.

Not easy.

Definitely not pretty.

Not smooth.

Not the way I envisioned it.

Hard.

Painful.

Awful.

But great.

That was the proudest I’d ever felt at 29029.

Those three TRAIL medals mean more to me than any of my Red Hats.

I really had to earn those.

With five mountains and TRAIL in the rearview mirror now, I had to ask the question again: What’s next?

In the late 2000s, I did a few triathlons. I finished them, mostly just surviving, often not spectacular, but I was proud of them nonetheless.

After the mountains and TRAILs of 29029, I realized something.

I wanted to go back and do an Ironman.

But I wanted to do it better.

I wanted to feel comfortable when I crossed the finish line.

And I wanted to use 29029 to help get me there.

I texted Coach Brent Pease.

“I signed up for Ironman Madison, and I think I could use some coaching. Will you help me out?”

No reply.

After he finished Ironman Kona with his brother, Kyle, I texted him again.

“Super proud of you. Great job!”

Still no reply.

I called Boaz and told him that Brent probably hated me or something.

“He keeps blowing me off. I can see he’s reading my messages, but he never replies!”

“Are you sure you’re texting the right number?” Boaz asked me.

I looked, and sure enough, for two entire months, every few days, I had been texting the DNR Warden for Door County, Wisconsin, where I have a lake house.

His name was also Brent.

My mistake, although it does seem a little strange that DNR Warden Brent never replied to ask what the heck I was talking about...

Anyways, in Tucson, at a Black Bib retreat, Coach Brent was there, so I decided to tell him in person to avoid any other potential texting mishaps.

He would coach me, and in 2025, with Coach Brent's help, I was going to do 29029 Jackson Hole, 29029 Aspen, Ironman Madison, and one other event that hits closer to home than the rest.

A buddy of mine has a daughter with cerebral palsy, and over the years, he has been doing the Triple Bypass ride in Colorado to raise money and awareness.

It's 118 miles through the mountains, and over time, the crew has raised over $1.9 million!

This year, they invited me to ride with them. We're aiming to raise $500,000. It's a new kind of challenge, but the mission behind it? That's what makes it matter!

I’m pretty deep into Brent’s coaching now, and the accountability has definitely been the most impactful part.

I missed a workout once, and he texted me.

“I see that you were up at 1 in the morning. What were you doing?”

My watch was linked to the training platform we use for the training, and that’s when I realized something - Santa was always watching.

That’s what I call Coach Brent: Santa.

Because he’s always watching, he knows when I’m sleeping, he knows when I’m awake, and he knows when I’ve been bad or good…

It’s been great for me from a discipline perspective. He helps me make the right choices, and everything has kind of entered into a flow state.

When you feel good and make good choices, you get more rest. When you get more rest, you have more energy. When you have more energy, you do better workouts, so you feel better.

And when you feel better, it’s easier to keep making those good choices.

It all builds off itself, and I’ve quickly realized that the impact of training with Brent won’t simply be me getting my Ironman finish - it’s about building a better lifestyle.

One other benefit from all this?

My kids have been watching all of this. They see me head out for hours to run, bike, or swim.

They used to be scared of the lake, but now they jump in with me and see how far they can swim.

They race each other up the driveway, challenge each other to pull-ups, and spend hours practicing their sports - sometimes in the rain.

I never sat them down and told them to train or chase goals. They just see what Michelle and I do, and they follow our lead. It's been one of the coolest things to watch!

I’m fully expecting 2025 to be the peak for me.

Jackson Hole.

Aspen.

Ironman.

The Triple-Bypass.

Those are some big events.

And with Coach Brent in my corner - someone who not only leads by example, but gives back through the Kyle Pease Foundation - I know I'll be showing up as my best self with his help!