Andrew selfie during 29029 hike
Andrew selfie during 29029 hike
By 
Andrew Osterday
Learning & Development
5 minutes

What I learned climbing 29029 feet (the height of Mount Everest)

At first glance, the idea of climbing that high up seems almost impossible. But that’s exactly what the 29029 event challenges you to do: not by summiting Everest, but by hiking the equivalent vertical gain in 36 hours. When I signed up for this journey, I knew it wasn’t going to be easy, but I didn’t realize just how much of this challenge would test my mental strength more than my physical capabilities. 

The truth is, 29029 isn’t just a physical endurance event; it’s a crucible where mindset, preparation, and community collide to push you beyond what you thought was possible.

From the very first step, it became clear that this event was designed to do more than test your legs. It tests your commitment, your resilience, and your willingness to keep moving forward when everything in your body is screaming for you to stop. The tagline, “Keep Climbing”, isn’t just a slogan—it’s a philosophy. 

The journey to the summit is built on a foundation of mental fortitude. It’s why anyone who goes on this adventure isn’t the same person going up the mountain as they are coming back down.

When you push yourself beyond preconceived limits, you rediscover sheer grit you may have forgotten that you had. And you’re immediately reminded that you’re capable of far more than you give yourself credit for.

Jesse Itzler, one of the event’s founders, gave us a list of attitudes to carry us through because, as he put it, endurance isn’t about skills—it’s about mindset.

What follows is a reflection on the key lessons I learned throughout this journey. Lessons on commitment, resilience, teamwork, and the power of small victories. These lessons are universal—whether you’re climbing a mountain in life or business. And while the event may have ended with us crossing that final finish line, the insights gained will last for every new mountain range ahead.

1. Purpose is power

Before the event, I wrote my family’s initials on my wrist as a reminder of why I was pushing myself through such a grueling challenge. Those three little sets of initials became my anchor when things got tough, reminding me that this wasn’t just about physical endurance—it was about demonstrating commitment and resilience for myself and those I care about. 

Purpose is what turns discomfort into something meaningful; it’s what transforms pain into a worthwhile struggle. The deeper your purpose, the easier it is to silence the doubts and keep moving forward. For me, my family gives me infinite strength - it’s harder for me to give up when I think of them than it is to just keep going.

Whether it’s a challenge like this or any other life goal, connecting it to something bigger than yourself gives you strength and clarity when you need it most.

2. Rigid on the vision, flexible on the details

You can train to hit the road running, but you should also train your mental fortitude when the road inevitably hits back. I began this journey with a firm vision: to complete the 29,029-foot climb as fast as I could. I was in it for the experience, but I just wanted to get the physical challenge over with. If there’s one thing I learned though, it’s that things don’t always work out as you had intended. Sticking too rigidly to specific plans can sometimes hold you back. 

When unexpected challenges emerged like early physical exhaustion, night hiking, rough weather, or equipment issues, we had to think on the fly or simply just embrace an “oh well, f it” mentality. We’d redraw our mental maps and set out for hikes we didn’t realize we’d be doing.

Adaptability allowed me to keep moving forward without feeling derailed by each twist and turn. I had to adjust my pace, modify my strategies, and even change my gear choices—all without losing sight of the bigger goal. This flexibility also helped reduce stress and anxiety, as I focused less on “perfect execution” and more on making small, real-time adjustments. I learned that achieving big goals requires unwavering commitment to the end vision while remaining flexible about how to get there.

As Eisenhower once said, “Plans are worthless, but planning is everything.”

3. Struggle is your companion (be present through the pain)

Embracing discomfort was a mental shift I hadn’t anticipated but needed. Pain and exhaustion are inevitable in a challenge like this, but instead of viewing discomfort as something to avoid, I began to see it as part of the process—a companion that would teach me resilience. 

I learned to be present with the pain, knowing it was temporary and that the growth I’d gain from enduring it would last long after the event. This mindset shift helped me see each moment of struggle as a stepping stone to something greater. By reframing discomfort as an opportunity to grow stronger mentally and physically, I didn’t just gain new resilience, I gained a process to keep gaining more and more. This lesson applies well beyond mountain climbing: when we stop running from discomfort and lean into it instead, we find ourselves capable of far more than we ever thought possible.

This is what transformation looks like. It can feel like swimming upstream (or climbing a huge mountain), but it’s all about coming to trust - and falling in love with - the process. Admittedly it felt even better once I got to the top to see others cross that finish line. All wrapped up, with that lingering sense of victory and a hot chocolate in your hand, you get to relive that same feeling with every new person that crosses the finish line. “I did it!”

4. Small victories compound

Breaking down the enormous challenge into smaller goals helped me stay focused and motivated. Each ascent became its own mini-achievement. I celebrated each one as a small victory, which built up my momentum and made the overall task feel achievable. 

Focusing on these smaller wins kept me from getting overwhelmed by the daunting scale of the goal. Instead of looking at the total number of feet left to climb, I just focused on completing the next ascent. Then the next. And then the next.

These small victories didn’t just keep me moving physically—they reinforced my belief in my ability to reach the finish line. Every little success compounded, making me mentally stronger for the next step. In life, as in this challenge, celebrating incremental progress is a powerful motivator that fuels us for the bigger journey. Zoom in and cheer for every micro-completion you do, it’ll keep you going in the long run.

5. Keep climbing

The phrase “Keep Climbing” isn’t just a slogan; it’s a mantra that embodies resilience, persistence, and mental endurance. When you’re exhausted and every part of you wants to stop, focusing on simply taking the next step—no matter how small—makes all the difference. 

You may have heard the saying, “Life is like a bicycle, you have to keep peddling to stay on.” Well, that example applies here as well.

This mindset of relentless forward movement helped me push through moments when the challenge felt impossible. By staying present in the moment and examining everything while in motion, I found I could handle more than I thought. I was in a state of flow.

In both physical and metaphorical climbs, “Keep Climbing” is a reminder that consistent effort, no matter how small, adds up. It’s about building resilience and finding strength in progress, because time waits for no one.