Another year has passed since I’ve sat down to write an update here. It’s been a reminder that if you aren’t intentional about making things happen, they won’t. The older I get, the more I recognize time is a rushing river that constantly flows past us. Since it’s also our most precious commodity, I’m going to try to hold myself more accountable to making time for the things I value and that are truly important to me. My dream is to eventually write full-time, so doing more of this is at the top of that list.
Anyway, I’ve been meaning to share an experience I had about a year ago in Colorado. In late August of 2025, my wife and I traveled out west for my buddy’s wedding. Since Colorado is one of my favorite places on Earth and my wife had never been, I decided to turn the trip into a two and a half week adventure of traversing the state and hitting up some of the best spots it has to offer.
We spent a few days in Denver and then hopped in the rental car to spend a long weekend in Boulder where I had spent one of the most formative years of my life washing dishes and sleeping on a free couch from Craigslist (that people had definitely vomited on). After that, we headed south to Manitou Springs for some real outdoorsy shit and finally all the way to Buena Vista to a remote Air BnB with a spectacular view of the mountains and lots of peace and quiet.
After living in Colorado for two years from 2014 to 2016 at a time when I was often fighting for my life (financially speaking), it was awesome to go back and get to experience it the way I had always dreamed of. It’s hard to put it into words, but there is something so satisfying when you wake up and realize you’re living a life your former self could have only imagined. Starting the day with a hot cup of coffee and stepping outside to an unobstructed view of the Collegiate Peaks was a top tier moment for me. Getting to fire up my laptop and work in that environment gave me a large sense of pride about my journey up until this point. It was a far cry from the late night walks home in the snow and ice in Boulder after washing dishes for $10.50/hr.
But the real point of this post is not about sharing a glorious vacation. It’s about unpacking another piece of the mental puzzle that I think has made these moments possible for me. A few years ago, I was introduced to the idea of the “Misogi Challenge” by the entrepreneur Jesse Itzler. Essentially, it’s a modern adaptation of an ancient Japanese ritual that is designed to push you past your limiting beliefs and enrich your personal development. In 2024, I did my first Misogi Challenge by hiking 10 miles through the Samaria Gorge on the island of Crete in Greece. It was certainly not an easy undertaking for me, but I found the experience to be overwhelmingly positive and I am so happy I did it.
Last year, while in Colorado, I did my second Misogi Challenge by hiking the Manitou Incline. This hike is 2,768 “steps” made of old railroad ties that gain 2,000 feet of vertical elevation in a little under a mile. It is a very steep climb essentially straight up the side of a mountain. If none of that paints a vivid picture for you, then I’ll add this: there have been at least 5 reported deaths on the trail since it was opened to the public and numerous other people have suffered either serious injuries (like broken legs/ankles) or experienced severe health crises such as strokes that necessitated being airlifted off of it by a rescue team.
Something I have struggled with most of my life and continue to struggle with currently, is my level of physical fitness and maintaining a healthy body weight. It’s estimated that only 40% of those who attempt this climb make it to the top, so this was another serious challenge that gave me a lot of pause and felt intimidating to do (which makes it perfect for a Misogi). My number one rule is if you’re not sure you can do it – you should definitely try to do it. The Manitou Incline fit the bill for me.
(Photo below for context).
We were in Manitou Springs for 4 days to see some old friends of mine, enjoy the quaint little mountain town, do some sightseeing at Garden of the Gods, and of course, bust our ass on this hike. The day I had initially planned to do the hike, I woke up feeling not quite rested and something internally told me “today is not the day” and so I (wisely) swapped the itinerary to go sightseeing that day and put the hike on the docket for the following morning.
We woke up early to beat the heat so we wouldn’t get stranded halfway up the “staircase” in direct midday sunlight (which ended up happening anyway). After eating a hearty breakfast at the hotel, we packed our hiking gear, some quick release energy snacks, and LOTS of water/sports drinks. Once the shuttle dropped us off at the base of the trail, we got out and walked with the rest of the brave crowd ready to test themselves.
The start of the hike is pretty easy and begins with a gradual curvature up the slope of the mountain. After about 15 or so minutes into it though, the real ascent begins. If you’ve ever climbed a really long steep staircase or done a grueling workout on the stairmaster, you know it’s no joke. Combine that with the added difficulty of exerting yourself in the Colorado altitude, and you’re in for a real treat. My heartrate started climbing faster than the elevation and I quickly realized that if I was going to get all 300+ pounds of me to the top of this mountain, I was going to have to pace myself and be strategic about it.
My wife is a former professional athlete, so she was handling the challenge of the hike much better than I was. After three or four times of stopping because of me, I encouraged her to take some extra water with her and go at her own pace and wait for me at the top. By the time I got 70% of the way up, the gradient had reached a similar percentage. I began stopping every 100 steps to catch my breath. Then every 50. Then every 25. I was hurting bad.
There’s a “bail out” point at the 75% mark on the hike, which is typically where the lion’s share of the 60% of hikers who don’t make it stop. The first time I attempted this hike when I was 22, that is exactly what I did. My heart wasn’t in it at the time and I didn’t see the value in pushing myself the way I do now. I had equally bad habits of not giving a fuck and of not following through even when I did. I saw the off-ramp and I took it.
What was interesting this time around was how closely I felt this hike was a metaphor for life and business. Everyone who showed up that day to take on this challenge was of varying ages, fitness levels, body types, races, genders, nationalities, etc. What we all had in common was a shared goal of reaching the top. We all started the hike on step one. But only a certain percentage of us were going to make it to the top, and unlike what most people may think, it wasn’t the “most in shape” or fittest people that determined who made it.
What I observed was that the people who reached the top were actually the ones who possessed the most grit, determination, and willpower. I saw young healthy people turn back or hit the bail out point when they realized it was harder than they thought or that they didn’t really want it bad enough (like me ten years prior). I saw people who must have been in their mid sixties literally running up the mountain past everyone. Some people went up and down three times while I was contemplating sending up a smoke signal for a medivac helicopter at the halfway point.
In the midst of this, I had an enlightening realization. There may be people twice my age who can crush this hike faster and more elegantly than myself, but there’s also people who “should” be a lot better equipped for this than me who gave up already. As I was approaching the bailout point – hot, sweaty, tired, and sore – I committed to finishing what I started. I wasn’t leaving until the job was done, no matter what. I told myself, “I am going to make it to the top of this mountain or I am going to die on it.” And that was that.
I thought about all of the dreams and goals I’ve set for myself and how this steep climb was so similar. Instead of walking a mile straight up in the hot sun, I was walking a metaphorical thousand mile journey with varying degrees of difficulty throughout. My life and what I want it to be may never even have a “summit” or finish line to reach, but the same principle applies. It doesn’t matter what advantages other people have or if there’s someone doing what you dream of doing better than you right now. What matters is if you’re going to commit to the goal and refuse to stop short of it. I realized that I was running my own race and the only person I was actually competing against was myself and the part of me that wants to quit. I realized that the only thing that matters is whether I do what I set out to do or not.
From that point forward, it wasn’t just a hike I was completing anymore. Mentally, it felt like everything I wanted in my life was hanging in the balance. If I couldn’t handle this hike, how could I handle any of the other big dreams I have? They are certainly harder and more audacious than this. It was time to put up or shut up. So I took another sip of water, another deep breath, and I stood up and started climbing again. I passed the bail out point and laser focused on finishing what I had set out to do. I was determined to prove to myself that this was indeed a new and improved version of me. I wanted to prove to myself that my desire to succeed was stronger than how I felt.
There is a point on this hike that becomes so steep (and it occurs after you are well spent on your energy levels), that it necessitated me basically crawling on all fours. It was probably the last 500-600 steps that proved the hardest physically and mentally. As I was clawing my way up each railroad tie, telling myself each one amounted to meaningful progress (and that this trail from hell is not actually never-ending), I passed an older woman in a sun hat with a bright blue backpack and a hiking stick sitting on the edge of the trail taking in the view. She was probably in her late 50’s or early 60’s and certainly did not look like someone who was physically prepared for this type of strenuous activity.
There was a bit of shade near her and I felt like I was about to stroke out again, so I decided to make a pitstop in the same place. After sucking wind for a few minutes, I finally made some small talk and asked her how she was enjoying the hike. She smiled in a sort of whimsical way at first and took a moment to answer me. “Everything hurts,” she said plainly. “I’ve been climbing for over three hours already,” she added. (For context, it takes an average hiker about 1 to 2 hours to finish the Manitou Incline). I eventually summited about 2 hours and 10 minutes after starting. My wife took probably half that time. To be on the trail for over 3 hours and still have 20% of it left was definitely a slow go at it. I looked at her, slightly concerned, and asked if she had enough water and felt good to continue.
“Oh yes,” she replied. “I wouldn’t wait for me at the top as I’ll likely be taking quite a while to finish, but I’m not stopping until I’ve completed it. I’ll sleep out here if I have to,” she added matter-of-factly. I smiled and nodded my head at her while desperately chugging some powerade hoping to summon the energy necessary for the next 100 steps ahead of me. Before I left, I turned to her and said, “that’s the spirit. It’s not about how fast you get there, it’s just about getting there.” She nodded back with a grin and wished me good luck on the rest of my trek.
It wasn’t easy, but I eventually made it to the top of the mountain. There were groups of people waiting up there to give a big round of applause as each hiker reached the promised land. My beautiful wife was waiting with a big smile, ready to embrace me and talk shit about our finishing times. I could tell she had used her time waiting to think of ways to tease me about it. “I was starting to get worried… and hungry,” she said with a grin on her face. I might not have been the fastest, but it was still a hell of a test of my endurance and my willpower.
(Here’s the picture of us at the top)
After working our way down the mountain, which is another 3 mile winding trail down the other side of the stairs, and recuperating for a day (or two), I reflected on the experience. I realized that I only made it to the top of the mountain because I gave myself no other option. If I had listened to my body or my mind about how I was feeling through the toughest stretches, I would have quit on myself again. It would have been easy to rationalize or justify it or tell myself it wasn’t worth it or that it’s really not that important. But I didn’t let that happen. I told myself that nothing I wanted to accomplish in life would come true if I didn’t make it to the top of this mountain. The choice I gave myself was very simple: get there or die trying (50 cent would be proud).
It wasn’t until later that I realized I’ve been applying the same mindset to my life without thinking about it. After all, life and entrepreneurship can feel eerily similar to walking up a neverending staircase in the hot sun. Most of the time you can’t see the end of the trail and you’re so exhausted you want to fall flat on your face and say fuck it. But the key is remembering it’s just you versus you. The only thing that matters is getting to the top, not getting there first or before anybody else. If you can rid yourself of caring about the opinions of other people and stop comparing yourself to everyone around you (most of whom haven’t even started doing anything yet, let alone achieved anything), you can go all the way. But you have to commit to the goal and give it everything you’ve got. No Plan B.
I want you to think honestly about what would give you the motivation needed to endure the suffering necessary to reach the top of your personalized mountain (your dream life). What is worth the pain to you? What are you willing to crawl on your hands and knees for? What ultimate goal is worth dedicating your life to? That’s the real key to unlocking a whole new level of badassery within yourself. You need to know not just what to do, but why you’re doing it. Because at the end of the day, it’s only when shit gets hard that you find out how much you really care about your goals.
And remember the pace you choose is equally important. If you need to achieve your dream life in 24 months instead of 24 years, you’re probably going to collapse on that mountain well before you even whiff the top step. If I needed to climb the Manitou Incline in 20 minutes instead of 2+ hours, I wouldn’t be here to write about it. Sometimes you need to sit in the shade, rehydrate, and allow yourself to take in the view so that you can replenish your strength and energy to keep going. Last year and quarter one of 2026 gave me a royal beatdown and forced me to confront the fact that I was pushing myself too hard for too long and not taking care of myself properly. Something I’ve been learning the last few months is how to make space for productive rest so I can finish the journey ahead of me.
I tend to feel guilty if I’m not constantly working (I know, I know). I’ve made a lot of strides in my life over the last 8 years and made tons of progress, but I still have a long way to go to get to where I ultimately want to be. And what has shifted in my perspective lately was the same realization I had on the Manitou Incline: if I’m serious about reaching the top, I need to pace myself and do it strategically or I am going to crash and burn at the halfway point. I’ve been all-in, pedal to the metal, and firing on all cylinders constantly for years (which is admirable and was necessary for awhile). But when my health started to take a hit, I had to come to terms with the fact that even if I could brute force my way to the top like that… if I wasn’t healthy enough to enjoy it when I got there, what was the point?
I’ve been giving myself permission to take my foot off the gas a bit lately and focus on other areas of my life like health and relationships more. I still work hard and my goals haven’t changed, but I’m allowing for a season of sitting in the shade and taking in the view so that I can continue the climb in a way that is sustainable. I encourage you to think the same way about whatever mountain you’re attempting to climb yourself.
There is always going to be some 18 year old crypto billionaire or that person that seems to have it all figured out and is able to do it in a seemingly effortless way. The people who lap you three times while you’re checking your pulse halfway up. Fuck those people. They don’t matter. You need to get your mind dialed in on the task at hand and finish what you started. If you know you can push, then push. If you need to take a break, rest. Don’t overcomplicate things. Just don’t take it too easy when you know you have more to give.
Much like being the fittest person didn’t necessarily determine who made it to the top of the Manitou Incline, being the smartest, most confident, or naturally best looking person doesn’t guarantee you anything in the arena of life. I know tons of people smarter than me that cannot get out of their own way and overthink themselves into inaction. Better looking people may be treated better as a whole, but plenty of them lack healthy relationships and oftentimes end up having worse lives because of the drama it invites. Most goals that are truly beneficial for you require a lot of hard work to achieve, regardless of what natural talents or advantages you happen to be born with.
My point is this: you’re not in a competition with the rest of the world. Being successful isn’t zero-sum. There’s no one else like you, and that’s your advantage. Make sure your dream life is as unique to you as your own DNA, and you will give yourself a higher likelihood of achieving it. It should be tailormade for you and only you.
Once you define that dream and start climbing towards it, what matters is that you see it through. How fast you make it there or how effortless you make it look is irrelevant. No one is clocking you. The scoreboard is only in your head. Other people are going to laugh at you no matter what you do. So run your own race and focus on what you need to do to make your dreams become reality. The life you want is out there waiting for you. No one can walk the path for you and no one is going to feel sorry for you if you don’t get there. Keep climbing.
The Thought Project 