The Trail Provides – The Workaround by Bob Gilbreath

Welcome back to The Workaround. I’m Bob 👋

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After completing the sale of his businesses, Marty heads out on his next journey…

NOTE: This is a Guest Post by Marty Boyer, a great friend and entrepreneur who just sold the second of two businesses he bought and turned around. After handing the keys over, Marty headed on a solo, month-long hike along the Pacific Crest Trail to clear his mind. I asked him to share something about his experience here. Hit the play button above to hear the audio version, which includes a discussion between Marty and me. And remember that you can listen to this and every post in the podcast (also available on iTunes and Spotify).

If you’ve ever heard the phrase, “the trail provides,” it’s an axiom among hikers. It’s repeated and relied on almost like a religion. It’s akin to the Christian belief that Christ will provide what you need. In this sense, the trail will give you what you need. At first, you might not buy in. But when the trail does provide, you better be damn well prepared to receive it. On a recent hike, the trail gave me what I needed, both physically and spiritually. Before I get to the “woo,” let’s start with the practical.

I’m a big believer that you must hit the reset button in life from time to time. I can’t prescribe when you should do it, but you know when that itch is there. Everyone resets differently. I won’t tell you how you should, but I typically need to get out and do some hard stuff. For me, that means hiking. And not just a casual stroll—I’m talking about covering 10–15 miles a day with everything I need on my back. Usually, that’s a 20–30-pound pack. I need solitude. I process life best when I’m alone and enjoy my own company. I want to be exchanging oxygen. It lights up my brain in ways nothing else can. That’s my formula. Yours might look different. Borrow whatever works for you. I was ready for my reset.

Over the last eight years, I owned a couple of businesses. I left a lot of vacations on the table and poured myself into those endeavors. That’s what you do. I was fortunate to have the opportunity to work that hard, and I don’t take that for granted. I gave it my all and had some success with those efforts. During the last year, I transitioned those companies to new owners.

I’m now a few days past fifty and feeling great. But I’m still fifty. In the words of my friend Jon, “49 years and 364 days feels a lot different than 50.” At this stage, you want proof that you can still do hard things, not just belief, but proof. Doing something challenging, like hiking a marathon a day for weeks, resets me. It restores vitality to my body, mind, and soul. So, after my companies transitioned, I set out to hike a few hundred miles on the Pacific Crest Trail. I had the “itch” to reset, and the timing worked out. Let’s go!

Most people would describe me, and I’d describe myself, as conscientious and responsible. But—and I shit you not—for whatever reason, I cannot hold onto tent stakes. When I set up camp after hiking 20 miles, I need eight stakes for my tent. I set it up at night, then in the morning I pack it down and count the stakes. Sounds simple. But somehow, I lose them. Always. A few extra stakes are worth their weight, especially when it’s windy. But on day three of my multi-week hike, I realized I’d damaged one stake and lost another. I was down to six. That’s enough to set up the tent, but not enough for the extra guy lines. I tied them off to rocks instead. So much for being responsible…

As I ambled into Warner Springs, California, I went to set up camp and realized I’d lost another stake. Curses. No clue how it happened, but my first reminder of the axiom, the trail provides was about to happen.

Warner Springs Community Center is a haven for hikers. They’ve got potable water, outdoor showers, laundry buckets, Wi-Fi, food resupply items, and power outlets. Basic amenities, sure, but for hikers it’s a mecca. I had to stop there because I’d sent a resupply box to their post office—my food for the next leg of the journey. That evening, I searched the hiker box for stakes. No such luck.

For the uninitiated, a hiker box is a collection of stuff that hikers discard. You’ll find food, unused clothing, water bottles, sometimes even a jar of pre-rolled joints—yes, I found these in a hiker box. When you’re carrying everything on your back, every ounce matters. You let go of what’s not worth carrying. It’s a beautiful metaphor for life. But I wasn’t looking to let go. I was hoping to find something worth carrying in that hiker box, tent stakes.

The next morning, I packed up to leave Warner Springs. The Community Center had fresh coffee—enough of a lure, along with indoor plumbing, to justify an extra mile on my day. I stopped in around 6:30 a.m. for that coffee, a total treat. For shits (literal) and grins, I checked the hiker box again. I don’t know if there was a cache of stakes that I missed or if someone dropped them in overnight, but the trail provided what I needed, and it was right on time, I might add.

Pictured below are my tent stakes. The ones on the right are the stakes I found in that box that morning. Yes, I took a couple extra (see above if you’re wondering why).

When I hike, I want to face the things that have been sitting heavy on my soul. Two years ago, I hiked the Sheltowee Trace in Kentucky for a week. On that hike, I decided to have conversations with the people who had passed but still occupied space in my head and heart. I didn’t want to carry those feelings anymore. While I talk to them out loud, I don’t hear voices back per se, as much as I try to stitch together the conversations we had over the years to see if I can glean any new insights. I won’t share all the names, but I’ll tell you one: my dad. My relationship with him felt unfinished.

I’m not a fan of my dad—wasn’t when he was alive, still not now. Yet I pray for his soul. For context, my dad died in 1995 of cancer when I was twenty. He was just 54 years old. The synopsis is that it was a complication from years of alcohol abuse. He wasn’t a great father to me, my brother, or my sister. He wasn’t a supportive husband to my mom. He battled alcoholism from an absurdly young age. He was married twice; my mom was his second wife. He abandoned his first three children from his first marriage. There was a lot to dislike.

During one of those trail conversations, he told me about his father—an old man when he was born. His dad made him a drinking buddy by the age of twelve and treated his mother poorly. In short, my dad never had a shot. He was fucked from the beginning—alcoholic, clueless about being a husband, never had a role model. At mile 98 on the Sheltowee Trace, I left that baggage. I asked the universe to take away the anger I carried. I can’t promise I like my dad, but I shoved as much grace across the table as I could. It was done.

Fast forward two years. Now I’m on the Pacific Crest Trail. Desert heat beating down, time to think. The thought of my dad pops into my mind. I wonder, “Would my dad even like me?” While I don’t feel the need to be liked, I wondered why I thought it. Did I have that unstated need? I don’t know. To be clear, my dad would have respected me, but like me—I’m not sure.

My dad would have respected me for taking care of my mom. A year after my dad passed, my brother was buried alive in a construction accident at the age of 28. Of course, my mom was heartbroken over that. She was 49 years old when her youngest son died horrifically.

In 2000, at 53 years of age, she had two strokes that left her unable to live alone. I was discharged from the US Army and took care of her. She lived with my wife and me for fifteen years until she needed long-term care. She spent two more years there before passing. My mom never worried about a thing after she moved in with my family. My wife is an angel for going through that with me while raising two kids. Taking care of my mom is my greatest achievement in life, next to raising my boys. My greatest act of rebellion and conceit is that I am a better son, father, and husband despite his guidance. My dad might not like me, but he sure as hell would respect me.

Still, that question haunted me: Would he like me? I didn’t expect an answer. But the trail provides.

On day six, I arrived in Julian, California. After hellacious winds on the backside of Mt. Laguna, it was my first “zero” day. I stayed at Banner Ranch, about eight miles from Downtown Julian. I had about 36 hours to rest, resupply, and hang out.

Banner Ranch isn’t much of a ranch. It’s a few acres along a stream with tiny houses, wagon-style rooms, campsites, outdoor showers, toilets, and laundry. A hiker’s paradise. They have a “saloon”—three pool tables, a convenience store that sells beer but no bar, and karaoke running all day.

I arrived Saturday afternoon after hiking 21 miles. I grabbed a campsite sheltered from the wind, showered for the first time on the trip, and washed my clothes. Then it was time for a beer. I hadn’t had one since starting, so a couple of light beers were in order. I wandered to the Lucky Dog Saloon and met Jim, the karaoke maestro.

Jim was about 67ish. He had a long gray beard that he stroked while thinking. I quickly nicknamed him Prophet Jim. Within minutes, I asked about his background as he had a command of complex topics and vocabulary only sharpened by academia. It turns out he was a retired PhD psychologist from a prominent California university.

Jim used a cane and occasionally stepped outside to smoke weed. “You must smoke with intention,” he said. I think Prophet Jim liked me because I listened with curiosity. I really wanted to hear his stories. As karaoke picked up, we got separated. Saturday came and went.

Sunday evening, after I resupplied in Julian, I went back to hang with Jim. He shared more wisdom: avoid the GERMS—Government, Education, Religion, Media, and Social Media. Smart advice. He told me about cannabinoid receptors in animals, claimed he “smokes out” the donkeys sometimes. Prophet Jim even said some invertebrates have cannabinoid receptors. Wild stuff. We also connected over psychedelics—psilocybin in particular, #iykyk. Jim had an amazing spirit. He enjoyed a friendly ear to listen.

Hikers are early risers. By 8 pm, you’re either in bed or you’ll pay for it the next day. You can’t drink too much, or you’ll dehydrate. It was 7:30 pm. I was ready to say goodbye. Jim stepped outside to smoke with other hikers. I don’t smoke—pot makes me puke—so I stayed back for a moment. After a few minutes, I had to go. Then I went outside to give Jim a proper goodbye.

He saw me and said, “Hold on, Slick. I want to tell you something,” gesturing with emphasis.

Right then, I didn’t know whether to piss myself or cry. Those were the EXACT words my dad used to say when he wanted to make a point, especially when he was drunk. I’m 100% sure my mouth dropped open. I wasn’t talking to Jim anymore. I was talking to my dad. Whatever Jim said after that blurred. I was in disbelief.

We chatted for about ten more minutes, and I took in his sage. I gave him a hug and told him he gave me more than he’d ever know. I left thinking only this one thing: I was exactly where I was supposed to be at that moment in time, and all the details of how I got there were immaterial. The universe was working to heal me.

To some degree, I wish I had the thought to take a picture of the moment. Too often, at least for me, I’m too busy living and being mesmerized by the gumption of the universe to put you where you’re supposed to be.

What I would tell you, when you have the audacity to face the universe, it seems to have grace waiting for you, in the form you need it. I thought I was out there hitting the reset button. Really, I was still pulling the pricks out of my soul AND hitting reset. I lost more than stakes on that trip. I lost the wonder of whether my dad liked me. I saw him again in a new form. And while I don’t think we’d be besties, he likes me. That much I’m sure of.

To that end, yes—100%—the trail provides. Be open to the universe.

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