50-Mile Challenge: Coach Justin’s Journey

50-Mile Challenge: Coach Justin’s Journey

Our Tuesday morning coach, Justin, accomplished a feat recently that is not only extremely impressive but inspiring as well and I couldn’t help but make sure we shared it.

He walked 50 miles in 17 hours and 15 minutes!

Without giving the whole story away, I’ll just leave it there and let you know that we’re extremely proud of him, we’re looking forward to seeing if we can get a group to do it with him again next year, and we hope you enjoy the story below.

Where did you get the idea to walk 50 miles in a day?

The origin of the 50 miles in 20 hours challenge is a fascinating story of fitness in American life. If you want the full story, read this brilliant write up: https://www.artofmanliness.com/2017/05/24/take-trjfk-50-mile-challenge/

The summary is this:

  • Teddy Roosevelt observed weak soldiers in his tenure as President and issued a directive that required all officers of all military branches be able to march 50 miles within three days without more than 20 hours of effort.
  • As JFK became the President-Elect, he issued a similar challenge to a Marine commander, pointing out that, in Roosevelt’s time, many Marines were able to complete the effort in one day. JFK told the commander that, if he took up the challenge, member’s of JFK’s cabinet would probably do it as well. Before the commander could even attempt the challenge, Robert Kennedy (then the Attorney General), decided to give it a go himself. With a pair of Oxford dress shoes and no training, he left his at 5 o’clock with four staff members to walk from Virginia to Maryland. He was the only one that lasted the full 50 miles. His time? 17 hours 50 minutes. (That’s him getting his feet rubbed after the effort. Photo Source: Life Magazine)

When do you first hear/read about it?

I first heard about the challenge from a program I participate in called The Strenuous Life, which is best described as Boy Scouts for Adults. The program begins with 12 weeks of challenges, ranging from things like “Wake up every morning and do a max set of pushups before walking away from your bed” to “climb a tree” or “walk 1 mile with a 50-pound boulder.” To complete the first 12 weeks, you must complete all challenges… you only have one make up opportunity. I missed one challenge, and the makeup was, you guessed it, walk 50 miles in 20 hours.

How long have you been considering giving it a go?

When I started the program about 12 weeks ago, I saw it and thought “maybe someday.” Then I was dumb and didn’t complete an easy weekly challenge (read a 150-page book in a week), and found myself with a challenge to make up, and only one option. So after that, it was not if but when.

Once you read about it, what motivated you to go for it?

I felt this was an interesting challenge, for me especially. For where I’m at physically, I felt this wasn’t going to be impossible. It didn’t require me to train. At the same time, it wasn’t going to be easy. It came down to guts…did I have the guts to see it through?

So I felt I could do it. I asked myself, “should I do it?” I remembered a quote, “If you could, you should.”

I also think the scale of the effort didn’t sink in until much later…50 in 20 seemed like a nice round number.

After my first attempt on Black Friday, which ended just short of 28 miles, I knew I had to finish it. I hurt so bad at mile 27, I thought I couldn’t continue. But after a half hour of relaxing, and later that night, I felt fine physically. Mentally I was angry. Why did I stop? I could have kept going. That night I resolved that I would do it again, in the next two weeks, and I wouldn’t stop unless I couldn’t move.

What did you do to prepare for the walk?

From my experience backpacking and my current fitness, I felt I was physically prepared to make the walk. No specific training necessary.

Logistics, however, become important.

The first logistic was time… When was I going to do this? Luckily for me, Black Friday was coming up. I’m not a big fan of shopping, and the question of what to do while the ladies of the family are off shopping always causes a little frustration. So about two weeks before Thanksgiving I figured “Why not black Friday?” I passed the idea by Krystal (my wife), who would have to watch Juliet (our daughter) all day, and she was agreeable. (Luckily for me, the logistics of a supportive family who go along with crazy challenges was solved long ago when I met a wonderful woman).

The second logistic was location… Where was I going to walk 50 miles? Given I would be in Danville for Black Friday, the obvious choice was the Iron Horse Regional Trail, a 25-mile stretch of paved trail running from Dublin all the way to Concord.

The third logistic was stuff… What would I bring? I decided to bring 3 liters of water (my full water bladder), a spare water bottle with BCAAs, some candy bars and proteins bars, spare shorts and shirt, a headlamp for walking at night (I estimated 7 hours walking in the dark), a spare flashlight, my phone with a backup power bank, my GPS watch and my step counter for tracking distance, a hat and a pocket knife.

As I embarked on my first attempt, I made two major mistakes: I had the wrong stuff, and I picked the wrong route.

I had the wrong pants, wrong shorts, no headlamp, and the wrong watch. I also didn’t have the best socks (too thin), which would cause major problems later on. I had also overlooked one major consideration: chafing.

I had also picked the wrong route. The route had my leaving from my parent’s cushy house (complete with jacuzzi and lots of tasty food) and heading north, walking back by my parent’s house at 28 miles and heading south, then arriving back at my parent’s house to finish the walk.

The error was walking by my parent’s house halfway through. At 27 miles I started hurting bad, and then the negative talk started …
“Your back is going to get injured, you should stop.”
“It’s just a dumb challenge. Stop now and enjoy your day off.”
“You don’t have the right socks. Better to stop and do this again another time.”
Those thoughts combined with an easy way out led to me quitting early when I clearly could have continued.

So I made some alternations for my second attempt:

First, I would leave from my house here in San Jose, and walk, and keep walking until I was 25 miles away. Then I would turn around and head home. Now quitting wasn’t so easy. I burned my boats.
Second, I had my stuff worked out. True, you don’t need the right gear (Robert Kennedy did it in freaking Oxfords), but at least I was more comfortable.
Finally, I fixed my strategy. On the first attempt, I had rushed through miles 10-27, without much rest or thought of fuel. My watch said I had burned 5,000 calories, and I had eaten a Reese’s Peanut Butter Cup and a small bag of M&M’s. So on my second attempt, I rested 5 minutes every 5 miles, and I ate nuts with a little bit of chocolate and jerky.

What was the route and give us a rundown of the plan.

The image above shows my rough route (compiled from phone data collected by Google). The route started at my house then went West to the Los Gatos Trail. From there, I headed North (in the dark), following the trail to the Diridon train station. I crossed over there and went to the Guadalupe River Trail, which picks up at the park across from the SAP Center. From there I went North all the way to the Southern end of the bay, past Levi Stadium, to a town called Alviso. Then I turned around and came back.

I stopped by Cróga to say hello, then headed back to the Los Gatos Trail. It was pitch black. I had my headlamp, but after a quarter of a mile with three homeless camps spotted, I decided it was unnecessarily risky to walk another several hours on that trail, so I backtracked and headed to downtown Willow Glen.

This presented a problem. I was too close to make a direct route to home, but I didn’t want to be on trails. It was about 7:30, and I was worried about loitering and drawing negative attention. Luckily for me, it’s near Christmas, and everyone in Willow Glen takes Christmas Lights seriously. This provided an excellent pretense for me to walk up and down every street in Willow Glen by myself at night… I was just looking at the lights! I got a few looks, but no one called the cops.

After a sufficient amount of wandering, I headed back to home. When I saw the house, I still had a half mile to go. I texted Krystal to tell her I was just going to drop my backpack at home then finish up. “Keep walking, I’m not unlocking the door” she texted back.

So I walked past the house for a quarter of a mile, turned around, and walked back. Total time, 17 hours 15 minutes.

Did you run into any obstacles along the way that threw a wrench in your plan?

The hardest part was finding a place to piss. The Guadalupe Trail is great for biking, terrible for hiking, for this exact reason. There’s a 7 mile stretch with 0 bathrooms and 0 stores or other accessible places with bathrooms. When you’re walking 3 miles in an hour and drinking plenty, this is a problem.

Two options presented themselves: trespass into corporate parks and use their bathrooms, or find a roughly covered area next to the trail. Sorry Nature.

The second obstacle I dealt with was the dark. I had planned to be on trails from 5 PM to 10 PM. The dark trail in the morning was fine, quiet. In the evening, there was lots of activity in the various campsites. I felt that wasn’t safe, so I had to make a route change. Once I was on streets I had to deal with crossings and sidewalks, but no big deal there.

18-20 hours is a long time to spend by yourself, did you learn anything about yourself?

I did. I learned I love my family. I missed lots of people, but them the most.

I learned that I’m good at these types of challenges (sustained efforts over long periods), but not as good at small efforts repeated consistently. Many of the things I want come from the small efforts, so I have something to work on.

What did you listen to?

Podcasts: Lionhearted Podcast of course, and Bill Burr’s Monday Morning podcast, which is hilarious.
Audiobooks: Discipline Equals Freedom Field Manual. I listen to the first half of this when I started walking, and again when I hit 27 miles (where I failed the first time). Jocko’s voice and words helped me push through.

Never Split the Difference by Chris Voss. A book about negotiating.

On my first attempt, I listened to Da Vinci, a biography about Leonardo. I’m sure it’s a fascinating read, but on the walk it was boring. I shelved that for this walk.
Music: During my last hour, Arctic Monkeys and Rush brought me home.

Did you meet anyone along the way?

Just a homeless guy: “Hey, I’ve got some weed if you want to smoke some.” I didn’t. There weren’t many others on the trail. I saw maybe 50 people total on the trail.

Any advice to other people that are thinking about giving it a shot?

First, prepare. Think about your feet, your route, your water, and your food. Plan breaks appropriate to your fitness level. It will feel like you’re moving slowly.

Second, go. Don’t wait for the right time or the right weather. Just go, and don’t stop until you’ve done it. If you set out to do 50 miles, kill any thought of “oh it’s fine if I just do 26.2, that’s a whole marathon!” If you want to do 26.2, great, do that. If you go for 50, the only way you make it is if you’re committed to 50.

Third, burn your boats. The critical mistake I made during the first attempt was having a way out (my parent’s house right off the trail halfway through.) Make your route such that it’s hard to quit. Avoid the situations that will make you want to stop (e.g. restaurants, meeting with other people, breaks that are too long.).

Will you do it again?


Well probably. Since attempting it, I’ve received 3 invitations from others to complete the challenge with them. Someone said it should be a Black Friday tradition.

How did you feel after it was over, physically & mentally? That night? The next couple days?

The moment it was over I felt great and really hungry. I didn’t plan for a post-walk meal. I took a quick shower, then I went to Wendy’s and had a Fast Food Glory Meal. I wore my bathrobe. And I drove. Krystal asked, “why didn’t you walk by Wendy’s on the way home?” I don’t know why I didn’t.

The next morning I was sore but no more sore than a good squat workout. My feet hurt like they had been hit hard repeatedly. But I could work, and no injuries. Sunday I was back to normal, just tired. Mentally I felt unburdened. I felt accomplished. And thankful for the opportunity to do something like this.

Anything else you’d like to add to this story?

Thank you to everyone at Cróga for the encouragement during both attempts, and the offers of support. It really helped, even just to see a “like” on a post.

Many of you have asked me other questions, so feel free to ask me on Facebook and I’ll be happy to answer them!