Circles
Hiking the Timberline Trail
You.
When I think of stories, I think in circles. It’s Dan Harmon’s fault. Harmon, most notably the creator of Community, has this concept called the story circle, which is an adaptation of Joseph Campbell’s Monomyth, which is itself a theory on virtually all mythology and religion. To cover all of those at once would be “scope creep” as we say in corporate America, so let’s stick with Harmon’s. It’s the most digestible. Basically every summer blockbuster follows this formula. A million articles have been written about it. Like many people, it’s tattooed on my brain. It has eight pieces.
In Star Wars terms (specifically, A New Hope):
Sad kid on a desert planet.
Sad kid wants to leave the desert planet to fight the space nazis.
Old mentor in the desert conscripts the sad kid to go save a space princess.
Old mentor takes the kid on a galactic voyage with a space pirate and the space pirate’s hairy friend. Meanwhile, old mentor also teaches the kid how to use space magic.
They rescue the space princess.
Old mentor dies.
The rest escape, only to enlist in the space army.
Sad kid, now actually quite a happy guy, uses space magic to blow up space nazi’s spaceship.
I’ve been noodling on these story circles for awhile. At times I think they’re lazy. Not every great story follows these steps, at least not exactly. You could make the argument that they do and some steps are simply implied or are emphasized less than others. You could argue that sometimes the order gets mixed up.
But for me, when I think of a story, it starts to slot in these steps.
Need.
I ended a tough job a few weeks ago. I worked there for three years, which is both not that long and a lifetime. Within a year, I felt like I was hopping from lily pad to lily pad, my tenure there on borrowed time. Still, I managed to stay another two years for reasons I can’t fully explain. My résumé? A paycheck? Bias toward the familiar? All the above.
But the job ended and with it the Slack messages and the paychecks and the regular communications with corporate friends and corporate foes alike. You leave a job, but it’s all still there—the neural pathways that cause your adrenaline to spike when you hear a certain ringtone. Years of waking up at 2 am, stress buzzing at the need to send an email, don’t go away in an instant.
I had cobwebs that needed to be swept up.
Go.
My dad and stepdad are big on pilgrimages. They’ve done maybe one per year for a while now (sans covid, when they were very visibly itching to get back on the road). They’ve done all the big European pilgrimages and are working their way through the deep cuts. My dad made me and my sister promise that we’d carry his ashes on the Camino de Santiago after he dies.
Both my dad and stepdad believe in the walk’s ability to teach, but also the ability to help you process. When I told my dad about my upcoming departure from work, he suggested a walk. Specifically, a long one.
I poked around. Mainly by asking my friend Alex. The guy is a champion hiker. He once hiked forty miles in a day, just cuz he was feeling it. Most people spend months planning and preparing for the 90-something-mile Wonderland Trail. Alex, on the other hand, grabbed a walkup permit the day he set off and then knocked the thing out quicker than most.
So when Alex suggested the Timberline Trail, I didn’t need to look much further.
Trailhead located only an hour and a half from home? Awesome.
42 miles? Better than 90 miles.
Gorgeous views to rival the rest of the Pacific Northwest? Hell yeah.
And super easy logistics: the Timberline Trail circumnavigates Mount Hood. In other words, it’s one big circle. A lot of work just to get where you started.
Only a few days after wrapping up work, I threw my hiking pack and 6,000 calories of trail mix into the van and set out.
Search.
Tuesday morning meant lighter traffic on the roads and lighter traffic on the trails. I stopped off at Chipotle and ate a burrito in the parking lot, then continued on, to the Timberline Lodge. The asphalt was crawling with ski camp kids. Throughout the parking lot, ski bums slept in the open trunks of SUVs. I parked my van in the overnight-designated spaces. I took a deep breath. I put on my hiking boots. Shouldered my heavy pack.
I packed as light as I could, but still, enough supplies for three days and the comforts of a Kindle and a journal led to a heavy pack.
Game time.
I immediately started off in the wrong direction, on a trail that led to Mount Hood’s summit. I doubled back but felt a hint of regret—an extra half mile and, more crucial, 500 feet of vert on a hike that was already going to tax me to the brink. The right trail set my spirits soaring and I flew along at a quick pace.
The Chipotle burrito fueled me for hours, way longer than I expected. I stayed in high spirits. The start was flat, but still offered a solid view of the craggy south face of Hood. Pines insulated the trail. Fields of lupine and columbine offered a constant, low-orbit fireworks display. Maybe six or seven miles in, my energy dipped slightly. At Paradise Park, I sat on a rock and watched the clouds as I ate trail mix.
I had no great revelations.
The first day, I hiked 12 miles and camped near Ramona Falls. One of the more popular stops, tents sprinkled in around me. I slept without a rainfly on my tent and spent the night worrying about ghouls slinking up in the night and hovering over me. Poorly rested, I filtered water and heated my freeze-dried breakfast.
The second day was the big one. I aimed to knock out the trail in three days. To have any hope of not making the last day a grueling haul, I needed to spend the second day in near-constant movement. Steeling myself for some big miles, big vert, and exhaustion, I set off.
It would be only half the truth to say that I hoped to avoid misery. My goal was to plumb the emotional depths: to stab into the onion of your own heart and figure out how deep shit goes. And you don’t get that way by staying comfy.
Find.
Eight miles into day two, I wondered why I was so foolish. I was in terrible shape. A futsal injury in June had left me virtually immobile for weeks prior to, and this late July hike required all the fitness I had while in good shape. Some plans are dumb and some plans are really dumb and this felt like it was increasingly a third option of extremely dumb and nearly dangerous. My knees were beginning to hurt. I was losing steam.
I was saved when I found a slow-moving stream, laden with deep pools. It was around noon and the day had committed to afternoon warmth. I dipped my whole body into the chilling snowmelt then warmed in the sun as I ate trail mix.
My thoughts flitted around. For a while, most of them were positive: I felt an immense appreciation for the community Amelia and I have found in Portland. For our health, for our families’ health. For Kona, the greatest dog we’ve ever known. An overwhelming sense of gratitude for life filled me up and carried me through the next few miles.
But then, my thoughts turned. I wondered how I could stay at a job I didn’t particularly love for three years. I pondered the question and kept coming up with “I’m dumb, I’m dumb, I’m dumb.”
Then the absurd thoughts. In Salinger’s (absolute banger) Franny and Zooey, Franny spends a portion of the story talking about a book she discovers—The Way of the Pilgrim—and with it, the Jesus Prayer. It’s a short prayer, repeated over and over, and in a way, Franny insists that it carries a propulsive, ecclesiastic energy; a spiritual enlightenment that allows one to endure the trials and tribulations of life. I found my own version of that. Mile after mile, uphill, downhill, sidehilling, my heavy pack never seeming to lose an ounce as I ate snack after snack, a new mantra took hold: “I am mostly piss and vinegar.”
Around mile 13 for the day, I hit a wall. I stopped and leaned on my hiking poles and stared out into the distance, toward the Columbia River Gorge. Everything seemed far away and so small and so strange.
Then at mile 14, I hit another one. I took off my pack and removed a thai curry backpacking meal and ate it as a late lunch. 400 exceedingly welcome calories. As the water boiled, I stared at the label. It noted a 2014 Winter Backpacking award. I had purchased it at Next Adventure’s Going Out of Business sale and did not think much of this out-of-date award. The meal expired in 2044 (whereas my other backpacking meals expired in 2055)—surely that earlier expiration date was a sign of quality. It was only hours later, as the stuff bubbled up uncomfortably in my stomach, that I realized what had happened: Next Adventure, in clearing out their inventory, had surely stumbled upon 2014/2015 era backpacking meals and, seeing them not yet expired, put them out for sale. I had eaten food packaged while I was still in undergrad.
Stomach grumbling—not quite upset but nonplussed—I hiked on with the clear understanding that surviving the apocalypse on decades-old MREs would be possible but not quite pleasant.
As the day grew late, more runoff pummelled the already treacherous river crossings. I spent more time plotting my rock hopping, especially at the Coe crossing, which is noted as the scariest of them all.
My spirits increased as I approached Cloud Cap, the checkpoint I had determined was the bare minimum, but then they plummeted at the Elliot Crossing, with an extended series of descending switchbacks to cross a shitty river, then back up even more switchbacks until you get to Cloud Cap. By the grace of Sour Patch Kids alone, I made it.
I kept on. Just shy of 19 miles, I stopped on an alpine plain. I made camp and lay in my tent and wondered why I had decided to put myself through such misery.
Take.
A critical juncture occurs in the story circle toward the end—the protagonist loses something vital to their survival and past way of living and must face the conflict head on. In Campbell’s view, this was the Atonement with the Father, the moment of sacrificial bloodshed.
On my hike, I didn’t experience anything like this. I had everything I needed. I was getting low on food, sure. But overall I was good. That is, with the notable exception of my overall health and wellness and sanity and sense of purpose. I was not feeling good. In fact I was feeling quite bad. And tired. And also pretty cranky.
So yeah, it got a bit dire toward the end.
For the second night in a row, I slept terribly (this time with the rainfly on the tent), and when I woke up on the third day, I realized that I had a haul ahead. Thirteen miles to go. Thirteen, brutal miles.
With small, heavy steps, I took off.
Emotionally, I hit a new low. I felt I hadn’t actually learned anything on this hike. Hiking maestro Alex had been the one to tell me not to expect any grand revelations. And even before setting out, I knew he was right. But still, I was hoping that I might have gleaned something. Some little piece of wisdom. Yet all I could think about was the desire to not be hiking anymore.
I trudged on and encountered the first major snowbanks of the trip. Careful steps kept me from chuting down to the rocky crash pad below.
I wondered about narratives. My old Flagstaff neighbor—the one who, in a fit of mania, shot someone before being carted off to jail—mentioned the concept of “limiting beliefs” to me once. I took it as some Tony Robbins bullshit, but up on the mountain, I gave it a fresh ponder and wondered about the assumptions I make about myself. I wished I could chart them all on Post It notes and spread them across my office wall. Bad at science. Ok at writing. Ok at math. More soft skills, less hard skills.
Surely some things are true at an atomic level. For example, I am not seven feet tall. But surely some, maybe the majority, are assumptions so situational as to be almost pointless. I had no doubt that some of my assumptions could be left behind.
And I started to wonder about other assumptions. How was I navigating other aspects of life with these narratives? Had I crafted stories about friends that limited my interactions with them? Of course I had. I’m sure everyone has. I vowed to limit that, to let the vibrancy of those around me—good traits and bad, full of nuance—shine past any cheap heuristics.
Not even halfway through the third day, my knees began to grind in pain with each step. It was not a casual soreness but sharp pain, the kind any physical therapist will tell you to avoid. My mind worried about permanent damage or a months-long recovery. I tried to distract myself, but my nerves continued their dissonant shrieks of pain. Clinging to my hiking poles, I tried to put as much weight on my arms as possible. It was a losing strategy. I stopped often and panted for air.
With small steps I moved forward, uphill and downhill. At each stream crossing, I splashed water on my sunburnt face and arms.
Return.
The car chase. The run to the airport.
But for me, it was just a really, really long uphill.
The last two miles found me in a dazed, exhausted state. Too tired to think, I failed to fill up my water bottle at the last river crossing. My hydration bladder ran out just as I made the final push, hot and steep. A group passed me in the other direction. Their looks of shock and disgust told me I appeared exactly as I felt: a miserable, sweaty zombie.
The last mile was the longest mile. But I hiked on. Nothing else to do.
I am, after all, mostly piss and vinegar.
Change.
Back to where I started. Just as I left it, the van waited for me in the parking lot.
Legs shot to hell, I drove home. I stopped at Wendy’s on the way—my first time eating a Baconator in close to a decade. I spent the following day half awake, building out a Lego painting of Hokusai’s The Great Wave.
Of course I had no startling revelations. I’m not much different. But I am a little different—when I came off the mountain, I was done thinking about work. The worries were gone. And astoundingly, the bitterness, of which there had been a lot the past three years, was gone too. The middle of the night wake ups stopped. The bitterness largely dissipated. I caught a glimpse of myself a few years in the future, barely able to remember what this job had been like or what had filled my days or why I was so stressed all the time.
And even though it took two weeks, my knees finally stopped hurting. I’m back to running like normal.
Thanks for reading!
xoxo
Steve
P.S. if you want more on Story Circles, here’s my favorite video on them:
And more from Dan Harmon.












Great story--everything, the shitty work stress, the grueling slog around Hood--so relatable. You might also want to find and follow Marc Cordon. He coaches people on creating their TED talks and he has a lot to say about storytelling. Fun read.