Last Saturday I hiked 43 miles across the Grand Canyon and back, from the South Kaibab trailhead to the North Rim and back again, starting at 2 AM and finishing somewhere around 6 PM.

This is a newsletter about that hike, but it's really about a pattern I've only recently been able to relate to.

Hard things filter your life.

Yes, it’s something that I’ve known, we’ve all heard sayings that teach us that, but to experience it is another. When you commit to something big enough to be genuinely difficult, it quietly reorganizes everything underneath it, and life gets more fulfilling as a result. Business did that for me over a long season. Training for the Grand Canyon did it over a much shorter one. And right now I'm looking for the next thing that will.

As many of you know, a year ago I sold a company. Pneuma was the thing I built from zero to $3M in ARR in 36 months, and it consumed me in the best possible way. Every decision, every late night, every hard conversation ran through one question: does this move Pneuma forward?

Then it was gone.

Not in a bad way, because the exit was the right call, but I underestimated how much of my identity was wrapped up in the chase. When the company sold, the north star sold with it, and the mountain I'd been climbing for three years was suddenly behind me.

You still wake up early and still do the work. You show up, handle what's in front of you, and check the boxes. But there's no mountain ahead of you anymore, nothing pulling you forward, so you're just moving, and in my experience you're moving very unenthusiastically.

About three or four months after the sale, the honeymoon period of "retiring" wore off. I started looking for a mountain again. So I went back to what I knew before business, which was fitness.

I jumped into just about any workout I could find and went deep down the health optimization journey (which is one of the joys of owning a gym and a health clinic). But even that got boring after a while. It was better than doing nothing, but I kept circling the same question: what was all the training actually for?

Apparently, the Grand Canyon.

It started with a simple ask. A friend, Beau, asked if I wanted to do R2R2R. I was already looking for my next mountain, but I wasn't tied to it being fitness, and I genuinely believed I'd end up back in the business world and find it there. The offer to hike across the Grand Canyon just happened to be the first thing that truly scared me, so I said yes.

43 miles scared me. Twenty wouldn't have, fifteen certainly not, and thirty only maybe. I picked a number that felt so far out of reach that saying it out loud made me uncomfortable, and that discomfort was the entire point.

If the goal doesn't unsettle you a little when you name it, it isn't big enough to do the filtering you need it to do.

When the mountain is big enough, it simplifies everything.

I had good people in my corner who had done R2R2R before, and I had solid programming, but I didn't overthink any of it. The question was simple. What needs to happen for me to finish 43 miles on my feet?

Two things. Endurance in my legs, and cardio capacity.

So that's what I trained, nothing more complicated than that. More leg work, more endurance runs, more hiking, more walking, and more time on my feet in general. For 60 to 90 days, those two priorities filtered almost every training decision I made, which is the whole idea I keep coming back to. The goal was clear enough that it made the small decisions for me.

I didn't agonize over supplement stacks or perfect heart rate zones or gear reviews, because the mountain was clear enough that the path toward it was obvious. I just had to start hiking and running.

The real test was the Boulder Skyline Traverse, 17 miles across five summits west of Boulder with close to 6,000 feet of elevation gain. My friend Collin and I ran it twice and added another 15 mile hike on top of that, three long days on our feet over the course of training.

The last Skyline day was the turning point. I finished with heavy legs and sore feet, but it was only a training day, not a peak effort. I knew that on the real day, with adrenaline and ten people around me and the Grand Canyon itself in front of us, I'd have more in the tank than I did on a random Saturday in Boulder. That was the moment I knew I could finish.

We started at 2 AM from the South Kaibab trailhead at 7,260 feet, ten of us, all looking for our next hard thing. The group came together mostly through word of mouth and some social marketing, pulled together by none other than the aforementioned Beau.

It was in the upper 50s at the south rim, headlamps on. The first seven miles drop 4,800 feet straight to the canyon floor, switchback after switchback in the dark, and every step of that descent is a promise you'll have to pay back on the way out, two or three steps on the return for every one going down.

I was having a blast. There's something about hiking in the dark that makes time move quicker, because you can't see the scale of what's around you and the miles just pass. By the time the sun came up we were at Phantom Ranch at 2,460 feet, already pushing into the 80s and headed toward the mid 90s by afternoon, a 40 degree swing from where we'd started four hours earlier.

From Phantom Ranch we turned north, seven miles along Bright Angel Creek to Cottonwood at 4,080 feet, gradual enough that you barely notice the 1,600 feet of gain. That was the calm stretch, and it was easy to forget what I'd signed up for.

Then the trail tilted. The mile and a half from Cottonwood to Manzanita leads to the last reliable water before the steep switchbacks, and somewhere in there it got hard for the first time. Not "why did I sign up for this" hard, more like "how am I going to deal with this situation right now" hard, because my gut finally gave up on all the carbs and fuel I'd been loading in.

From Manzanita at 4,600 feet, it's 5.4 miles and 3,640 feet of gain straight up the North Kaibab switchbacks to the North Rim at 8,241 feet, the hardest section on the entire route. I climbed it while my stomach was telling me it was done cooperating, and this is exactly where a big enough goal earns its keep. I never gave myself the option of a Plan B. There was no version of this where I turned around, because that decision had been made months before I ever stepped on the trail. The mountain had already removed the exit for me.

Then you turn around and do 21+ miles back the way you came. Every foot you descended on the way out, you earn back, roughly 43 miles total and about 11,000 feet of elevation gain by the time you're done.

The last few miles climbing back up to the South Rim were joyful and a little bit sad at the same time. Joyful because I knew I was going to finish, and sad because the chapter was almost over. My only goal at that point was to keep putting one foot in front of the other and not stop, and even when the steps were slow, they were still steps forward. That was all it took.

In the months between selling Pneuma and committing to R2R2R, I was productive and I wasn't sitting around, but I had no filter. Every day was just a series of things to do, with no hierarchy and no sense that this mattered more than that because it served something bigger.

The moment I committed to 43 miles across the Grand Canyon, all of that changed. I changed how I ate, when I went to bed, when I woke up, and how I trained, and not because anyone told me to. The goal told me to.

That's the whole idea. When you have a mission big enough, it does the filtering for you. You stop asking "should I do this?" and start asking "does this serve the thing I'm chasing?" Those are two very different questions, because the first one has a thousand answers and the second one only has two.

Pneuma was that filter for three years. R2R2R was that filter for 90 days. The scale was wildly different, but the effect on my life was identical, and that's what I keep coming back to. The hard thing reorganizes everything underneath it, and life gets simpler and more fulfilling because of it.

I'm already thinking about the next one, though I'm less focused on what the mountain will be and more on who I become while training for it. The preparation is where the change actually happens, in the daily decisions that quietly stack up underneath a goal worth chasing. You point at the mountain, but the climbing toward it is what reshapes you.

Maybe you already have a mountain, and if you do, the only question worth asking is whether it's big enough. Does it unsettle you a little when you say it out loud? Does it filter the noise out of your week without you having to force it? If so, keep climbing.

(Good time to plug one of my favorite books - Chase The Lion by Mark Batterson. Go get a copy if you haven’t read it before)

If you don't have one, pick one, and it doesn't have to be fitness or business. It only has to be big enough that it reorganizes how you spend your time on its own, without you white-knuckling the discipline into place. The same group is going back to Grand Canyon in October - maybe that’s your mountain?

And if you can't find one, come join me on the next one. I don't know what it is yet, but I can promise it'll be big enough to be worth chasing.