The “100-Mile Man” counts his days and what he does to make them epic.

Jesse Itzler counts every day—he literally writes down how many days he has left to live on his wrist every morning. He’s also not afraid to shake things up, to step outside of his comfort zone and challenge himself—and everyone he comes into contact with, to do the same.

That’s perhaps a large part of the reason he created 29029, an event that challenges participants to summit Stratton Mountain 17 times—with the intent of climbing the equivalent height of Mount Everest over one weekend, October 13-15, 2017. It’s the reason he ran 100 miles non-stop, for charity. It’s Itzler’s belief that we should all commit to doing difficult things whenever we can—on weekends, or every day if possible.

We asked Itzler to share his own experience summiting the peak, and why doing difficult things is how we set a precedent for facing and surmounting challenges in the other aspects our lives.

24Life: Why did you create the 29029 challenge?

Jesse Itzler (JI): I think it was a combination of just looking for new challenges and new kinds of races. Personally, I’m a little bit sick of obstacle courses.

I thought, “Let’s bring the hardest challenge like Mount Everest or the height of Everest to the States.” And that’s sort of where we came up with the idea. I mean, we wanted to do something seen and something that people would get really quickly, and could talk about, and train for, but just really be different. And that’s really where “Let’s climb Everest in Vermont” [came from].

24Life: What type of people are coming to climb?

JI: We were limited to 150 [due to the nature of Stratton Mountain]. We sold it out. And it’s an insanely diverse field. I would say 20 percent are amazing athletes that have done ultramarathons. There’s one guy who holds two world records in mountain climbing.

But the rest of the mix is people who wanted to challenge themselves and wanted a different kind of weekend adventure, and that’s everything from housewives to attorneys to Wall Street moguls. There’s three police officers and a firefighter. So it’s really diverse.

24Life: Have you always been a risk taker?

JI: I’ve always been in situations where—from a young age—I could be embarrassed, and that hasn’t stopped me from participating. And I think that fear of being embarrassed stops people from trying or participating. So you know, that could be everything from playing team sports at a young age or being in a play, or trying out, auditioning for something as a kid, all the way up to “I’m gonna go try to run 100 miles.” And you know in today’s world, there’s so much vulnerability because of social media.

24Life: Why are so many people averse to risk?

JI: I just think we’re wired for comfort. I mean, our whole life is around air conditioning, pillows, blankets, comfort and convenience. We’ll do anything for convenience. It’s just human nature. But I feel like most people feel most alive when they get out of that space.

24Life: If we’re wired for comfort, and the modern world makes life easy and us lazy—why bother to take on an epic physical challenge? What’s the motivation?

JI: People want more adventures, and memories, and more experiences with their free time. … You learn so much about yourself when you’re doing something for, you know, potentially 25 hours.

24Life: How did you prepare to climb the mountain, physically and mentally?

JI: I asked a lot of questions. I spent a lot of time on my feet because at the end of the day, there are no shortcuts. It’s gonna take hours, and hours and hours on your feet. So I walked up a lot of hills. And I tried to simulate, as best I could, what this would be like.

I tried to sleep a little bit less just to get used to it. I would try to train two times a day, and one of them would be late at night, just to get used to that kind of simulating an all-day situation.

24Life: You’ve done a few of these types of physical challenges. What are some of the life lessons that come from doing a challenge like this?

JI: I think there are so many lessons that come out of it. First of all, the discipline—the commitment to actually say, “I’m gonna do it.” And then the planning. [There are a] lot of correlations between business, too. Like you have a goal, and you have to become an expert. You have to learn, “How do I approach this? What do I eat? What do I drink? How do I train?” And you have to have a game plan. Then you have to execute your game plan, and then you have to have a B plan in case your game plan gets thrown off course. And then you have to fight through the challenges ’cause there’s always gonna be challenges in any business, journey, physical challenge, whatever. And then you have to, you know, go through those challenges and finish.

Just going through that process from the day you circle it on your calendar, all the way up to the preparation, to finishing it is super powerful. And it creates an amazing process to follow and a blueprint to follow, to do other things going forward.

24Life: How do physical challenges change us as humans?

JI: I think it just feels character-forward. You know, when you’re able to finish something like this or anything that’s really hard, it just creates an environment in your head when things get hard, [you] don’t stop. [You] keep going. And that translates into work. It translates into relationships. It translates into parenting.

But you know, after you jump in a freezing-cold lake, it’s hard to get agitated when your two-year-old cries over a toy. You’ve dealt with adversity already internally, so you just process challenges differently. And I think that’s the key. It helps you process challenges, obstacles and hurdles completely differently. I think the only way to really get that is to go through challenge.

24Life: What’s the benefit of doing challenges in social environments?

JI: You create a different kind of friendship and bond when you go through this with somebody.

Just from an encouragement standpoint, it helps push people. But when you go through something and someone’s had a similar journey, and it’s super hard, that’s a lifetime bond. So I think there’ll be some really good friendships made as well.

Follow Itzler on Instagram and Twitter, and follow our 29029 team as they summit “Everest”:

Chris Roussos on Facebook and Instagram

Amanda Russell on FacebookInstagram and Twitter

Micki Stary on FacebookInstagram and Twitter

Matt Novakovich on Facebook and Instagram

Photo credit: Jon Cornick