During the summer of 2020, when the COVID-19 pandemic caused most races to be canceled, I looked to my backyard mountains and local trails for running objectives to keep me motivated to continue training. After ticking off an “Everest in Place” vert challenge with a group of friends during the lockdown, a fastest known time (FKT) on a 26-mile section of nearby trail, and a couple of bucket list mountain runs, I set my sights on a challenge that I’d secretly dreamed about for years — but had never had the guts to tackle.

A Horizon of Volcanoes

From the vantage of Central Oregon’s high desert, volcanoes stretch across the western skyline. Unlike the sea of endless peaks in the North American Rockies or European Alps, the Cascades feature just one prominent volcano at a time. On a clear day in Central Oregon, you can count 10 or more dotting the horizon between Southern Oregon and Washington.

From almost anywhere in Bend, Oregon, where I live, the town’s backdrop includes five major volcanoes: North, Middle, and South Sister (the Three Sisters); Broken Top; and Mount Bachelor. Using a network of trails and off-trail scrambling, it’s possible to link this iconic skyline together in one point-to-point run. The route covers 35 miles and more than 15,000 feet of vertical gain. Locals call it the Five Sisters. In July 2020, this is where I set my sights.

Failure Is an Old Friend

I’m no stranger to failure. I’ve fallen short of my goals countless times in athletics and other aspects of my life, whether it was losing the water polo state championships my senior year of high school, getting rejection letters from my top choice law schools, or dropping from my first 100 miler at mile 80.

The accompanying disappointment and frustration can be painful, but it’s part of life. I’d always been able to shake it off and look ahead to my next goal.

A Complex Route and a Narrow Seasonal Window

When I chose the Five Sisters as my objective, no woman had yet posted an FKT. I’d heard through the running community that at least two women had previously completed the route, the fastest being around 14 hours and 44 minutes.

However, I had a lot of work to do before I could think about a time goal. I needed to get to know the route and get comfortable scrambling around on the crumbly peaks that have some exposed, no-fall sections.

Unlike the mostly-granite ranges of the North Cascades, Rockies, and Sierra Nevada, Oregon’s Cascade volcanoes consist of rotten rock that breaks apart easily, and slopes that resemble kitty litter. Learning to move quickly and safely over this type of delicate and unpredictable footing takes time and experience. If I wanted to put in a fast effort, I’d need to become efficient on surfaces that sometimes feel like a treadmill made of sand.

Additionally, before I could wrap my head around the entire project, I needed to make sure I’d feel comfortable doing it solo. By 2020, I’d summited most of the individual peaks on the route. Mount Bachelor is a ski area with a summertime hiking trail to the top. I’d climbed to Broken Top’s summit several times on my own and felt comfortable with its handful of fifth-class climbing moves on the summit block.

I’d also climbed Middle Sister and South Sister, though I hadn’t ventured onto South Sister’s north ridge, which looked steep and ominous. Nor had I climbed North Sister, which is notorious for exposed climbing, falling rock, and poor footing.

Near its summit, there’s a no-fall traverse (nicknamed the Terrible Traverse) across shattered shale, that often holds snow until mid-August. Between this, the wildfire season from July through October, and late summer snowstorms — which are not unusual in September — the window for attempting the Five Sisters is narrow.

Big Goals Require Vulnerability

Running has taught me that if you truly want to discover what you’re capable of, you need to set big goals that test your limits. These could include a time goal that feels like a reach, tackling a new distance that feels impossibly daunting, or undertaking a personal challenge, like a solo adventure run in the mountains.

A big, scary goal is one that has an uncertain outcome, yet it also has to have meaning. If the goal doesn’t mean something, it will be difficult to commit to the training required or the mental fortitude to succeed during the effort. Yet, to attempt something with the knowledge that you could try your very best and still fall short requires vulnerability. This is what makes big, scary goals both worthy and terrifying — falling short of this type of goal isn’t easy to shake off.

The Five Sisters was meaningful to me because I’d been thinking about it for years, but was intimidated by certain parts of the route. I didn’t know whether I’d be comfortable traveling sections of exposed, loose rock solo and unroped.

This gave the goal some uncertainty, but adding the sub-14:44 time goal really put it into the realm of big and scary. In July 2020, I was both overwhelmed and ready to throw my heart into it.

Getting Navigation and Terrain Dialed

During July and August, I spent weeks getting up close and personal with these mountains, focusing on the sections where I had the least experience. I climbed North Sister with a partner and a rope, and then climbed it again solo to make sure I could comfortably navigate the traverse to the summit.

I also climbed and descended a couple of different route options on South Sister’s north side. Initially, I was overwhelmed by the 2,500-foot ascent up the mountain’s seemingly impassable north ridge. When I finally worked up to climbing the north ridge by myself, it turned out to be a long slog with a delicate, exposed traverse that felt gripping for a few minutes but was over quickly.

The Process Is the Reward

While vulnerability can come with all sorts of discomfort, setting goals and going after them promises personal growth. During my training block, I got to know my backyard mountains better over two months than I had during the previous 11 years of living in Central Oregon.

I knew which moraines offered the most direct route to the base of North Sister, and which rocks were wobbly and best avoided on the descent off Middle Sister. I did workouts on the steepest, loosest dirt I could find, so that I’d be able to bomb down the long descent from the summit of South Sister. At home, I pored over maps and calculated the time breakdown for each segment to help me stay on pace throughout the day.

I loved the process of preparing for this mission. As I ticked smaller objectives off my list, I began to wrap my mind around this objective. While it still felt intimidating, my excitement and confidence were building. My fitness was, too.

Under a Full Moon

For my FKT attempt, I slept in my car at the trailhead on a weeknight in early September and hit the trail at 4 a.m. The full moon was bright enough to light up the mountains and minimize the need for a headlamp. In the gray, predawn light, I easily navigated the faint trail toward North Sister, in awe that I now knew this spiderweb of climber’s trails better than the palm of my hand.

I moved without hesitation over the rocky moraines, though I noticed with curiosity that the normally cool alpine landscape was holding pockets of hot air. Instinctively, I sipped on my electrolyte drink mix.

In no time at all, the sun was cresting the horizon to the east, and I was nearing the summit of North Sister.

A Hot, Dry Day and Two Key Mistakes

As the day warmed, I tagged North Sister’s summit, slid down the loose scree to a col, and then climbed up and over Middle Sister. I jogged across the rocky plateau between Middle and South, opting not to make a side trip to one of the nearby glacial lakes to filter water. I was making good time and didn’t want to waste a moment by going off-route.

This turned out to be a mistake. About halfway up South Sister’s north ridge, I ran out of water.

South Sister’s summit is dry in early September, but there’s a lake and a runoff stream about 1,000 feet below the top. I arrived at this stream absolutely parched. Still on pace for my goal time, I took my first break of the day, crouching down and dunking my head into the frigid water. I got my filter out and downed half a liter, and then refilled my water bottles. I felt okay, but I knew I’d gotten behind on hydration.

As I descended toward the glistening alpine waters of the Green Lakes basin, I felt the sun radiating off Broken Top’s west-facing slopes. Descending into the basin felt like stepping into an oven. The sun scorched me from behind while hot air rebounded off the mountain face and cooked my frontside.

As I splashed through a shallow creek that runs off Green Lakes, I contemplated stopping to fully submerge and bring my core temperature down. However, I’d just taken a break, and I didn’t have time to spare, so I kept moving.

This was my second major mistake.

Under a Magnifying Glass

As I started up the Broken Top climber’s trail, I felt like an insect under a magnifying glass. The sun’s heat and intensity were inescapable, and I began to wither.

Fully bonking, I dragged myself up the climber’s trail and literally crawled up Broken Top’s jagged north ridge. I knew I was hemorrhaging time, but I couldn’t move any faster. Watching the shadows grow longer, I held out hope that I could recover during the descent and a long section of runnable trail that leads to Mount Bachelor.

Somehow, I got myself to the summit and back down to the main trail. However, I plopped down on the trail feeling absolutely gassed. I hadn’t recovered any energy.

Goals Are a Privilege

It is a privilege to have the physical and emotional safety to set big goals that test your limits. While it takes emotional vulnerability to set a goal that’s both meaningful and uncertain, pushing to one’s limits (or beyond) in pursuit of that goal often involves both physical and emotional vulnerability. We see it all the time in sport, as athletes endure physical pain or injury or show heartbreak on their faces as their dreams crumble and fall out of reach.

Although I was putting myself physically at risk by undertaking a solo run across remote terrain with loose rock and no-fall zones, I’d enjoyed the freedom and access to train on the route every weekend for several weeks.

I’d also built up years of experience in climbing, ski mountaineering, and running up and down less-exposed volcanic trails. I also had first aid training, and I was carrying a communication device that allowed friends and family to track my progress and would enable me to signal for help if I got into trouble. While I was taking some risks, I also had a level of safety and support that allowed me to push my limits.

Accepting Failure

Below Broken Top, I was on a shaded trail for the first time since the sun came up. Yet, this wasn’t at all how I’d imagined this section of trail going. During training, I’d imagined cruising through this section, taking advantage of cooler conditions and soft light to make good time toward Mount Bachelor, where I’d give the final six miles up and down that mountain everything I had left.

Instead, I began to realize that my goal was slipping away, like my feet sliding through the sandy scree I’d slogged across all day.

I knew that I could finish the route, but it’d be an ugly, desperate shuffle that would take several more hours and conclude sometime in the middle of the night. I’ve limped to the finish of several ultras, opting for an epically slow finish over a DNF (did not finish.)

I didn’t want to do that on this day. I’d given this goal, and this day, everything I had. Getting to the finish at all costs didn’t feel like any sort of achievement for this particular objective.

Ultimately, I decided to call my friend Dani to ask for a pickup at the trailhead, my voice cracking as I conveyed my official decision to stop short of my goal. As I shuffled toward the trailhead where Dani would pick me up, I accepted my reality and began crying. I was overcome with gratitude for my friend who was willing to come get me, and for the friends who’d been tracking my progress via my Garmin inReach all day long.

When I saw Dani, she told me that my friends had been planning a surprise celebration for me at the finish, but they called it off when they learned I was in rough shape. Hearing this filled my heart and pushed tears through the dirt and sweat streaking my face.

The Beauty of Failing

The disappointment I felt was devastating. After pouring myself into this objective for so many weeks, I was heartbroken by how it was unfolding. Yet, in that moment, I was also in awe of my emotional capacity and the rawness of what I was feeling. I knew that pushing myself to the point where my emotions bubbled right to the surface was special.

There was nothing I could do in that moment but feel everything, and although it was overwhelming, I also knew it was a little bit magical.

The beauty of failing is in the vulnerability that it requires. If I hadn’t been willing to set a goal without knowing whether I could achieve it, I would have never realized what it feels like to push myself to my physical limits, discover my emotional capacity and mental tenacity, or get a glimpse of the incredible ways in which my friends are willing to show up to support me. It is a gift to gain even a small understanding of these things.

I’ve learned that taking on a big scary goal, whether it’s a solo FKT, a new project or relationship, or a commitment like marriage, is rewarding regardless of the outcome — and the people in my life will have my back if I come up short.

Call for Comments

Have you had any similar experiences? Tell us in the comments.