The Trail Provides

“The trail provides”. This simple saying ranks up there with “Hike your own hike” and “Last one to Katahdin wins” as one of the most frequently repeated and fundamentally true bits of wisdom I came across on my Appalachian Trail thru hike. The trail provided in many Big Ways–providing solace and companionship, solitude and space to heal, struggle that brought me to me knees and empowerment to stand right back up.

The trail also provided in countless seemingly mundane ways. Spotting a perfect campsite moments before a downpour. Catching a much-needed hitch into town the second you arrive at a remote road crossing. Losing a piece of gear and meeting another hiker with an identical spare. Stumbling upon a trail magic feast when you’ve never felt hungrier. Finding that extra scrap of toilet paper in the privy when you profoundly need it.

I finished my thru hike over a year ago and the trail has yet to stop providing. This weekend, I move to Alaska to house sit for the winter. If you told me three years ago I would voluntarily choose to spend six months in one of the most brutal climates on Earth…well, I don’t know what the hell I’d say. But here we are! In many ways, this unexpected turn of events feels like a logical, direct extension of the AT.

Back in March, I posted about my pending summer of tour directing in Alaska. To refresh, a close friend recommended I apply for the job nearly a decade ago, but I worried about “taking time off from my life” or something overly-rational like that. Thru hiking redefined what my time is worth and taught me to lean into opportunities for adventure. The trail provided me the headspace to say Yes.

Everything about my summer was a smashing success. I visited so many new places, experienced a laundry list of firsts, and met an abundance of wonderful people. Greetings to any readers from my first Alaskan summer!

I lead groups of 30-40 vacationers on land tours throughout Alaska and the Yukon. We spent over a week together, traveled by train, motor coach, and plane, regularly basking in stunning sights. I highly suggest adding Alaska and Denali National Park to your Must Visit list*. Essentially, I coordinated the group’s travel logistics (itineraries, transportation, lodging, etc) so they could focus on enjoying their vacation. Many of my guests had been anticipating the trip for years and I found it genuinely rewarding to foster an atmosphere of excitement and comfort as their travel dreams came to life.

Of all the jobs I’ve worked (and what sprawling a list it is), tour directing is perhaps the best match yet for my personality, skills, and interests. I had a blast and made great strides in settling my finances post-divorce. I expended a decent amount of mental energy on the AT considering ways to combine my professional pursuits with time in nature. Major check mark in that box.

I quickly made friends with many of my new co-workers, but one relationship holds particular significance. Leah, a fellow first year tour director, also thru hiked the AT last year! Her trail name was Junior. We started only 3 days apart and never ran into one another, though we knew several hikers in common. Leah was first thru hiker I met in person after the trail, and we took full advantage of each other’s insatiable desire to ask every question and pore over every detail.

Like Leah, I still think about the AT every day. I’ve written before about feeling self-indulgent bringing it up too often in conversation with most people. As with most aspects of life, it felt so refreshing to speak with another human being who just gets it. I fully believe we would make good friends regardless, but we shared a special, immediate bond of common struggle, triumph, and respect (I’m tempted to write “unspoken bond”, but like, we spoke a loooot). The trail provides an entirely new dimension on which to build relationships and an endless supply of conversation fuel.

Luck would have it that Leah’s and my tour schedules synced up for the first half of the season. We spent much time together hiking, decompressing, and trying not to monopolize group conversations with AT talk. Leah grew up in Fairbanks, one of the regular stops on our route. I met Leah’s lovely parents at their house for her birthday dinner. They have lived in Fairbanks for decades.

During one of my trips to town, they asked if I would like to house sit during the harsh winter months while they travel abroad. Someone needs to run water in the pipes daily, ensure the oil heat is delivered properly, manage broken pipes, things of that nature. I want to spend another summer tour directing in Alaska, and at the time of the offer I didn’t have firm plans for the interim. It did not take long for me to seize the opportunity.

Fairbanks and the surrounding North Star Borough have a dispersed population of roughly 100,000, with 32,000 in the city center where I will be living. It’s the second most populated city in Alaska. The main part of town has the feel of a small metropolitan suburb, though it is encircled by vast wilderness. During the winter months, Fairbanks receives only 2-4 hours of sunlight, with temperatures ranging from 0 to -50F. I’ll have easy access to groceries, a movie theatre, and killer thai food, so I’ll be just fine. Plus, I’ll be spoiled with Northern Lights sightings. Can’t wait for that. I have some strong leads on part time work and volunteer opportunities in town. I look forward to calling Fairbanks home.

I’m approaching house sitting as something of an artistic retreat. When I think back on the major accomplishments of my life, my path to success seems obnoxiously straightforward. I wanted to make a horror movie, so I wrote, crowdfunded, and co-produced a short film. I wanted to be someone who backpacked, so I backpacked my ass off. This winter I want to live up the the self-proclaimed title of “writer”, so I will write every dark, frigid day.

I am my own worst enemy when it comes to self-imposed productivity. This blog is a part of my push to write daily. Several of my current projects are long term endeavors, during which I tend to get distracted and lazy, so I hope updating the blog will help me stick to achievable deadlines. I plan to post frequent updates about life in Alaska, so check back regularly. Feel free to shame me if I don’t stick to it.

Though my life has seemed all over the place the past three years, I can clearly track the dominoes that bring me to this moment, researching ways to prepare a car for arctic winter. Divorce lead me to the AT, which led me to work in Alaska, which led me to Leah, who led me to her family, who are now entrusting me with their home. What a wild ride. I can already sense the trail arranging a future row of dominoes, providing more white blazes to guide me if I keep my ears open and eyes forward.

Stay warm!

*If you’re planning a trip Alaska, hit me up for some recommendations! Especially if you want to hike.

Tormented Valley
Tormented Valley. Along the South Klondike Highway in Yukon Territory, Canada. One of the best pictures I’ve ever snapped.

6 thoughts on “The Trail Provides

  1. you look amazing and I am so excited to see you being so happy. Work is a bitch back here in SF and I want to plan to visit you. I wanted so much to come this summer. Take care …man you look good. bo ___________________

    *Billy Boughton, RPh * *Sr. Field Managed Care Trainer – MPMC* *CMG Training & Development* (o)*650-225-4411* (c) *214-728-4545*

    Check out the training support site by Clicking Here where you can find the most helpful resources to assist you in resolving your training and LSO questions.


  2. Good stuff, Jake. Even though I don’t necessarily believe in Fate, it’s very curious how often certain unexpected things happen and naturally flow from one life event/course to something completely different but “right”. It’s really exciting to read about all the cool things you’re doing and the adventure that you’ve experienced.

    Earlier this year, I listened to the Shining, and I can’t help giggling about how you will be a caretaker of an Alaska property this winter. Stay sane! And send me your mailing address once you’ve landed.




  3. Love your post. The trail does provide. My PCT hike has changed my own perspective 100%. Sometimes expressing to others (non thru hikers) is challenging. Have an adventurous and amazing winter. I’ll put Alaska on my list to visit one day soon! Best


    1. I know this is a huge question, but what would you say is the biggest change to your perspective you left the PCT with?Mine was that I need to be way more supportive, patient, and kind to myself when I’m struggling. That’s what will
      help pull me through rough spots.


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