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What is Your Everest?

What is Your Everest?

October 05, 2023

Two months ago, I completed my second 29029 at Snow King Mountain in Jackson Hole, WY. I’ve had a lot of time to reflect on what happened during those 36 hours. It’s hard to process it all and put it into words, but here’s my attempt…

For those of you not familiar with 29029 (, it’s a hiking endurance event. You have 36 hours to climb the equivalent elevation of Mount Everest, 29,029 vertical feet. Each mountain at which this event is held is different, but for me this year it required a total of 19 ascents to reach 29,029 vertical feet. One key element is that you do not hike down the mountain. You get to ride a gondola down; therefore, only hiking up. Also noteworthy, once you arrive everything is taken care of in terms of food, water, electrolytes, aid station, etc. Hiking the mountain is hard enough; therefore, they want you solely focused on attaining that goal while you’re there. At the end of your final summit, you are given a red 29029 hat that symbolizes your completion of the challenge.

This year, as well as last year, I was part of a team raising money for the Kyle Pease Foundation (“KPF” - Kyle and his brother, Brent, have become dear friends over the years. They’ve greatly inspired me and thousands of others through their fight for inclusion. Kyle has Cerebral Palsy and they compete in different endurance events with Brent pushing/riding with/pulling Kyle whether it’s running, biking, or swimming. Their organization supports other disabled athletes to have the same experience with sports and competition. Brent is also the head coach for all the 29029 athletes. This KPF team consisted of 3 who quickly became new friends (Owen, Sarah, and Dani), a 4th – my longtime friend, Andy Dunagan, and myself.

In August of 2022, I completed 29029 at Snowbasin in Utah, but Jackson Hole was a very different experience for me. This year I arrived undertrained, but I was optimistic because this trail was about 9 miles shorter (21 miles) than Snowbasin (30 miles). This trail was single track and straight up the mountain until a few switchbacks at the top. In the Winter, it’s a Double Black Diamond ski run. We started at 6am and intentionally waited at the back of the pack to not be pushed by the faster climbers. We wanted to be patient and take our time on the first ascent. I started with 2 other KPF team members, Owen and Andy. It didn’t take long for Andy to lose us. I knew he was better prepared and didn’t expect for him to slow down and wait on me. Owen and I made our way up taking in the beautiful sunrise and the breathtaking views back over downtown Jackson and the Grand Tetons. One down 18 to go.

After riding the gondola down and branding the ascent board, Owen took off on his 2nd ascent while I quickly visited the gear tent. The ascent board is the board that tallies how many ascents you’ve completed. They have branding irons with the 29029 logo which you use to brand the wooden board by your name.

Four more ascents were accomplished before a lunch break. After lunch I visited with my wife and two girls before heading up for #6. About 50 yards up the mountain is when my stomach started to turn on me. I walked back down the mountain, took a short break to ease the discomfort, then kept moving and was able to complete four more before dinner. Last year at dinner Coach Brent suggested I make a plate of food and eat in the recovery boots, so I decided to do this again. I really struggled to eat. I couldn’t find any food that was appealing, but I knew I needed to keep my body fueled. I did my best, but that resulted in very few calories. Fueling your body is one of the most difficult aspects to this type of endurance event. Just imagine the amount of calories you’re burning while climbing over 1500 feet per hour. You have to refill your body with calories to have the energy to keep going. I headed back out for #10.

My goal was to complete 13 ascents before getting some rest. #10 was sunset and a fair amount of light, but #11 was the first true night hike in complete darkness. Only light was from my headlamp. Last year I really enjoyed the night hiking, but this year night hiking up a single track that’s 30%+ incline was brutal. Also, relative to last year, Friday was much more lonely. Ascents 2-11 were primarily solo. Yes, there were some segments with Andy, Owen, or other new friends met on the mountain, but the single track didn’t bode well for conversations and getting to know other participants. I felt like I met so many really cool people on the mountain the previous year due to the wider trail and longer segments of modest incline. Those conversations go a long way towards distracting your mind from what you’re putting your body through.

And on #11 it all hit me. The lack of energy due to fueling and stomach issues, the tiredness from climbing over 17,000 feet in 17 hours, and the loneliness. Thankfully, and to my surprise, my girls, Andy, and Andy’s family met me at the top after #11 at 11pm. They had been at the rodeo that evening and came to check on us before turning in. At that time, I was done. Done for the day. Andy had completed 13 and was ready for a break, and honestly, I thought I was likely done in terms of earning my 2nd red hat. I wasn’t going to quit, but didn’t see a way to feel well enough to get all 19 done. I started resigning myself to the idea that I am not going to finish.

We went back to the hotel, showered, and got ready for bed. I laid down about 12am and set my alarm clock for 4am. I knew I didn’t want to do another night hike but thought I could start as the sun began to come up. One of my biggest fears is oversleeping. When I was young, I overslept at a UGA basketball camp and I think about that often when it comes to important events. The reality in this type of situation is that it might be impossible to oversleep. There’s this looming 36 hour deadline coming that causes tension and anxiety, but also the significant steps taken to hydrate your body causes you to have to get up to go to the bathroom every hour. These hours simply turn into rest, not sleep.

At 4am I realize my stomach still doesn’t feel very well. Andy planned to get up at 5am so I set my alarm for then as well. I resigned to getting up at 5am, and fully resigned to the idea that no red hat was in store for me…

We get up at 5am and eat breakfast. Not much has changed in terms of how I feel, but after some food and coffee I have a little bit of hope things will get better. On my way to the base of the mountain Coach Brent texts me looking for me. He’s in the breakfast area trying to find me. Turns out this was a critical moment. Either go back to find him and lose time or forge ahead. I respond saying, “Gotta get rolling if I have a chance.” He responds, “You absolutely have a chance. Push the negative thoughts away and get this first one done.”

Many times in life you know what to do, but you don’t always do it. In fact, you do the opposite. I had heard things from coaches such as “push away negative thoughts”, “one step at a time”, “focus on 1 ascent at a time”, etc. But, at that time my headspace was pretty dark. I didn’t feel so bad as to simply quit, but I didn’t see a path to finish all 19 ascents. I knew the other members of the KPF team were crushing it and I didn’t want to embarrass myself. I resigned to at least making it to the height of Aconcagua (the tallest peak in South America), a total of 15 ascents. But, in the back of my mind, I knew each ascent was a little over an hour and that 1.5 hours round trip (including gondola and transition time) was reasonable. It’s now almost 6am. 12 hours left. 8 ascents to Everest. 8 x 1.5 hours = 12 hours. It’s possible. I haven’t timed myself out. I know this, but just don’t see it happening for me. I’d have to skip lunch. I wanted time in the recovery boots and that wouldn’t be possible. I kept moving, but the negative self talk continued.

The conversation in my head… “why am I doing this? Why am I putting myself through this? I’ve already done this last year. I’ve proven to myself I can do this. Why am I doing it again? This is stupid. I don’t enjoy this. This mountain just sucks. I’ve got plenty of reasons for not finishing. I didn’t have a chance to train as well this year. My stomach has caused me too many issues. I can’t make up for the lost time in the bathroom.”

This continues for ascents 12, 13, and 14. I resign myself to getting to Aconcagua before lunch between 12-1pm. At that point, a little food and time in the recovery boots and I’ll officially be timed out. I can relax. I’ll meet Andy, climb his last ascent with him, and celebrate with him. I’ll finish with a respectable 16 ascents, possibly 17 if I go back for another, and be proud of the effort.

But, deep down, I questioned myself. Would I really be proud of that effort? I’ve always heard, “leave it all out on the mountain.” Would that be leaving it all on the mountain? With this plan, if I kept going all the way to the 6pm deadline I could probably get in 18. To get to 18, but not 19 would really suck. So, maybe I could skip lunch and the recovery boots.

On the 14th ascent I ran into two ladies that were on a pretty slow pace. I wanted some company and because I was in a dark headspace, I wanted to time myself out. At that point I was fully ready to implement my Aconcagua plan. These ladies had hiked through the night so they could take it slow. They were on pace to finish with a red hat. We took turns leading each other. One would take several steps up, step to the side for a breather, another would pass them and take a break, etc. We just kept rotating who was leading, but stayed pretty close together. This is where another critical moment takes place. I’m leading and get several steps ahead. When I stop to break I look back and realize they’ve let a large group by them and headed my way. If I wait and let this group pass me and then wait on them to catch up, I’ll be taking a very long break. I choose not to wait that long so I keep going in order to beat this group to the aid station up ahead.

After the aid station, I run into Marc Hodulich (CEO and Co-Founder of 29029) who is hiking with Thomas Zebley (29029 legend and adorner of many red hats). Marc and Thomas engage me and check on me. They encourage me and build me up. I’m still in a pretty dark spot mentally. They tell me I can still finish, but I’m telling myself that it’s not going to happen. I’m too embarrassed to tell them that in the moment. Marc gives me some great advice, “try taking shorter steps and fewer breaks.” This strategy allows me to get into a good rhythm. I hike with them a little longer until they outpace me and forge ahead.

At this time my stomach is starting to feel better. Even after having my slowest ascent yet, I haven’t timed myself out. I’m starting to get into better headspace. I’ve found a good rhythm. It’s 10:30am. I text my wife, “Feeling better. Odds are improving.”

Pulling up out of the negative headspace isn’t easy and I know that’s critical to the remaining time. I start focusing on positive thoughts. I think back to the personalized video Kyle Pease sent me that morning, encouraging me to push through. I think, “I GET to do this. Kyle can’t do this. He’s never been given a chance. Other KPF athletes will never have this chance. Who am I to waste my God given health? How could I possibly slow down, relax, get comfortable in recovery boots, etc.? The clock is ticking. I can do this. I can’t tell my girls, “Daddy didn’t finish.” If I’m not finishing it’s going to be something else knocking me out of it, but not because of a lack of effort. I WILL leave it all on the mountain.” My eyes start to tear up as I think about telling my girls, “Daddy didn’t quit. Daddy didn’t quit.” It’s time to go. Let’s GO!

The 15th ascent went well. Now I’m down to 4 ascents and 6 hours. It’s 12pm. I just need to skip lunch and keep fueling myself on the mountain. At this point the fueling is simply whatever it takes to get me through the 6 hours. It doesn’t matter if it’s all “space food” (energy gels) for 6 hours. I can deal with the consequences later. The daunting task of 19, or double digits, or even high single digits is gone. It’s only 4. It’s only 6 hours. I’ve got a chance. I have to keep pushing.

Ascent 16 went well. At this point I’m focused on transitions. I know each ascent is going to take around 70 minutes. I have been logging my data each ascent, start to finish. The real question is the gondola time, gear time, board branding, etc. I see Coach Brent and ask if he can pace me on the last ascent. It’d be great to have him with me to take my mind off everything and simply enjoy the last ascent, but I need margin. All I’m thinking is that I want to start the final ascent before 4:45pm, but ideally 4:30pm. I don’t have minutes to waste. I’m sticking with my schedule of water and electrolytes at each aid station, but I can’t sit around and rest. I have to keep moving. I want margin.

It’s 1:30pm and I’m headed up with Andy for #17. It’s his last ascent. He has his red bib on. He’s almost there. We meet up with Owen and he’s got his red bib on as well and ready for his last ascent. We have an enjoyable hike together. It was incredible witnessing them finish. I wanted to stop and celebrate with them. I wanted to give them hugs and enjoy the moment with them. But, I didn’t have minutes to spare.

It's 2:50pm and I’m texting my friend Thomas Hamm on my way down the gondola. Thomas is the friend everyone wishes for. He and I met through a mutual friend a few years ago, but really connected during 29029 training in 2022 and our time together on the mountain. When I told him I was going to sign up for Jackson 2023 he said, “I will be there for you. I promise.” He is a man of his word. He volunteered his time and spent his money to fly out to Jackson.

Throughout the event he and his friend, Sherman, were volunteers on the mountain. Supporting and encouraging me and every participant they could along their journey. In these final ascents, Thomas was 100% there for me. I’ll save minutes however I can. I asked Thomas to fill my water bottle so I could drink my Tailwind just as he had done on lap 16. He’s got it ready for me. I’m off for #18.

Ascent #18 goes well. The end is in sight. Keep moving. Coach Brent, Thomas, and Sherman meet me at the top and ride the gondola down with me. More silence in that gondola than I’m anticipating. I’m not sure why. I’m focused. I’m ready. Let’s go.

With the clock ticking, I make a quick transition. I put on my red bib quickly, grab some water, and yell “I’ll brand the board for ascent #18 when I brand it for #19.” I’m on my way.

It’s 4:22pm. I’m ahead of schedule. Unless something crazy happens, there’s no reason I’m not finishing this last hike. I know my data. I’ve been averaging around 70 minutes per hike. I’ve got this… Coach Brent sends me on my way and says he’ll catch up with me. Come to find out, I was the last finisher to start my last ascent. Shortly after hiking I pass my (new) friend Caryn in her red bib. At this point, I’m in such a rhythm with my short steps and few breaks I’m just rolling along. Brent catches up with me. He helps pass the time as we talk about 29029, family, and golf. Towards the top we run into Wolfman (another 29029 Snowbasin 2022 finisher whom I had met last year). Brent and I hike together with him for the remaining 20 minutes taking our sweet time now that we have the clock on our side.

At the very top of the mountain you enter a service road for about 50 yards before entering the red carpet. Not wanting to ruin Wolfman’s moment by arriving together, I decide to speed up and separate myself.

Last year I remember being amongst the crowd at the top cheering on finishers in the final minutes. It was really cool to be there for them. This year, they were all there for me.

As I approach the red carpet I see the crowd and start to get chills. Cheers. Cowbells ringing. They’re here for me. In the final yards I garner the energy to start jogging. As I enter the red carpet lined with people I see my wife and girls on the other end. I bump fist after fist on both sides as I walk down the red carpet. Greeted at the end by my girls, my wife, Thomas Hamm, Thomas Zebley, Marc Hodulich, Andy, and my KPF teammates. I’m overwhelmed with mixed feelings of joy, exhaustion, gratitude, and excitement. Hand shakes and hugs of celebration. I’m handed a red hat and place it on my head with a big smile and sense of pride.

I did it. 36 hours and it’s all over. Daddy didn’t quit.

Grit. Determination. Vulnerability. Perseverance. Inspiration. Support. Encouragement. Teamwork. Toughness. Growth. Transformation. Excitement. Hugs. Tears. Joy. Relentlessness. Community. Patience. Endurance. Love. A different mountain, a different year, a different experience. But, “the mountain”, once again, was a beautiful display of humanity.

You may have no desire to experience this event yourself, and I don’t blame you. (ha!)

But… What is your Everest? 29029 always asks this question.

They describe Everest as “a metaphor for a goal that is so big that it scares you to even speak it out loud. That goal that takes more than a season, a year, or maybe takes a lifetime to even accomplish.”

I describe it as a goal so big and challenging that it pushes you beyond your perceived limits. Something that is so difficult that it may cause you pain, suffering, and discomfort temporarily, but the end result is a beautiful, personal growth that will impact you for the rest of your life.

So, what is your Everest?

(Please reach out to me with any questions about this experience or any way I can help. So many people have been impactful to me during this journey and I’m always happy to pay it forward.)

All the Best,



Reagan H. Wolfe, Registered Representative and Financial Advisor of Park Avenue Securities LLC (PAS). Securities products and advisory services offered through PAS, member FINRA, SIPC. Financial Representative of The Guardian Life Insurance Company of America® (Guardian), New York, NY. PAS is a wholly owned subsidiary of Guardian. Ashford Advisors, Inc. is not an affiliate or subsidiary of PAS or Guardian. Ashford Advisors, Inc. is not registered in any state or with the U.S. Securities and Exchange Commission as a Registered Investment Advisor. AR Insurance License Number - 15783316.  Guardian and its subsidiaries do not endorse or have any direct or indirect responsibility with respect to this activity. 2023-161944 exp 09/2025