Challenges: Knowing When To Say When
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Everyone has their vision of a perfect vacation. For some, it involves luxury and indulgence; for others, it is uninterrupted time with friends and family. For those who are more adventure-minded, it may include getting to know some faraway place. Regardless, we all seek a sabbatical from the busyness of the societal norm.
My wife, Diana, and I tend to gravitate toward the more adventurous side of the vacation spectrum. We enjoy dreaming up, planning, and attempting some wild exploit during our times of freedom from work. Last year, it was biking and packrafting the Great Divide Mountain Bike Route. A couple of years previous, it was mountain biking the Colorado Trail. We enjoy pursuing an objective and the physical exertion that comes with it — even when it occasionally involves some type 2 fun. Though not physically restful, these immersive experiences with the natural world are restorative, invigorating us to forge ahead with greater resilience to the stresses of our daily lives.

Given time constraints this year, we would take on a couple of micro-adventures separated by social time with friends. Completing a 120-mile bikepacking loop in southeast Montana would be our first objective. Once fully in vacation mode, we hoped to emerge with more stillness to enjoy the wedding festivities of our good friends. We would follow this revelry with more solitude as we traded wheels for packrafts and our own two feet to explore another part of Big Sky Country.

The steep, tree-lined hillsides slowly encroached upon us, turning the smooth gravel road into a flowy double track that continued ever upward. Filling our lungs with the fresh air of a healthy forest rich with moisture and abundance, my thoughts strayed to last year’s ride across Montana. It was a time of wildfires, temperatures over 100 degrees, and rivers gone nearly dry. The contrast between this summer and last was extreme.
An hour into the climb, we traded our spacious, groomed trail for an overgrown ribbon through the woods. Montana had a late spring with heavy snow in April and May, pushing the state’s snowpack to some of the highest levels in recent years. The moisture kept coming in the form of rain as the months progressed, causing severe flooding throughout the state. The snow usually melts off in Montana’s high country by late June, with trail crews and recreationalists venturing into the peaks to assess the toll of winter snows on the landscape.
It was July 3rd and from the looks of the trail ahead, it had yet to see much traffic. My hunch was confirmed as a mountain biker hiked his bike into view. “The trail crews haven’t got to it yet. There are lots of trees down. I finally turned around. The effort wasn’t worth it. Good luck.” With that, he was back on his saddle descending the manicured track we had just climbed.
As someone who is no stranger to the struggles of heaving loaded bikes over, under, and around trees, the rider’s comments didn’t elicit a sense of foreboding in me. Everyone has different tolerances for discomfort. Additionally, as strangers to the area, Diana and I had a mindset of exploration, which brings with it a willingness to experience some challenges along the way. It seemed that our first challenge would be downed trees.

As the mountain biker predicted, shortly after riding up the trail we were dismounting to begin the game of tree/bike twister. Accepting our fate, we worked together as team to unlock the many puzzles of getting our heavy bikes and ourselves through the trail-blocking brambles. It seemed with each puzzle solved that the trail began to clear up for longer and longer sections. Less than an hour after turning up the dreaded timber-strewn trail, we were pedaling over the crest of our first mountain pass.

In a clearing at the top, we glimpsed our next challenge of the day. The overcast skies had turned heavy with moisture and looked ready to unleash their liquid burden upon us at any minute. Keeping our wheels rolling, we began our descent away from the exposure of the pass. To our delight, the trail was clear, and we were able to stay on our bikes. Halfway through the plunge in gradient, the skies began to warn us with thunder that boomed louder and more frequently with each passing minute. Challenge two was nearly upon us.
At a decision point, we chose the more conservative doubletrack over the exposed hillside singletrack. Both trails would lead to the same spot on our map: a Forest Service bathroom where we could shelter from nature’s fury. As the first fat drops fell and electricity bolted overhead, we began the race down. Unfortunately, we weren’t going to make it to shelter in time.

The rain came in a torrent. Our riding surface became a stream moving with us downhill. Despite wearing good rain gear, all thoughts of staying dry and relatively mud-free vanished with each wheel revolution. When dime-sized hail started chattering on our helmets, it was time to abandon the bikes and huddle under some closely spaced trees. Soaked to the bone and squatting in lightning positions, Diana and I amusingly reflected upon our first day of “vacation.” It was a far cry from lounging beachside and sipping umbrella drinks. Choices.
As the sky lightened and the hail dissipated, we remounted our bikes and continued to our sought-after shelter. The trail surface was surprisingly intact, its rocky base preventing mud formation. It was still raining steadily and looked as though it would continue for some time. Cold and soggy, we finally rolled up to the bathroom and took shelter under its drab brown roof. Visions of warm, exotic locales still permeated our thoughts as we shivered together, watching moisture fall from the heavens.

A vibrant rainbow signaled the end of challenge two. Eager to ride in the sun and recoup some of the mileage lost due to sheltering, we began our next climb. Surprisingly, the track through the evergreen forest was in good shape despite the deluge. With the late-day sun shining overhead, we made our way upward, relishing in the warmth and dryness of the moment. We weren’t tanning on a beach, but after the past two challenges, the ease of our forward momentum felt rejuvenating.

The trail gained a ridge and meandered for several miles. The clear trail and tacky dirt let us flow through the landscape uninterrupted. Moments like those make all the challenges worth it. With each mile, we forgot the stressors, anxieties, and busyness of the past months. Our efforts were rewarded with a sense of relaxation, contentment, and internal stillness. This is what we had hoped to experience while planning this trip. We had found our vacation mojo.
Screech! Diana let out a rare expletive. Looking up the road to her, I saw that her momentum had come to a muddy and sudden stop. Watching her balance momentarily, the bike finally shifted to the side. Catching herself, she extended her right leg for the ground, only to have it sink ankle deep into mud. A few more pedal strokes led me to the same demise. Arrrrgh. Our third challenge was upon us.
Getting off our bikes, I scanned the road ahead for firm and dry ground to no avail: the soul-sucking glop stretched into the next bend a half mile away. Just like the infamous caliche of New Mexico, this Montana muck was sticky, all-encompassing, and demoralizing. Within five pushes of the bike along the mud pit of a road, our drivetrains and wheels were useless for any kind of movement. The sludge had so thickly attached itself to our bikes and shoes that it was nearly impossible to move. Unable to roll, we picked up our bikes and began trudging to the road edge, hoping to find some relief.

The roadside provided little to no respite. In fact, it seemed that the grass, forest duff, and sticks only made things worse. Looking silently at each other, we both knew that a retreat was in order. We were going to have to find an alternate route, as this one would not be dry and rideable for days. We slogged back to where the road was supportive and began the tedious task of making our bikes rideable once again.


Upon freeing our bikes of mud, we found a drier alternate route that led us to an unremarkable camp. Relieved to have made it as far as we did despite the various tests, we settled in for an evening of welcome rest. Once again, Mother Nature had other plans for us.
At midnight, a large crack of energy right over our heads disturbed our slumber. The weather gods waged war in the clouds for the next five-and-a-half hours, lighting up the landscape and sending a barrage of moisture. Our sleep was erratic at best. Memories of the final challenge of the day and our route becoming completely unrealistic weaved themselves into the sporadic dreams we were lucky to have that night.
At 5:30 am, the land became quiet. For the next couple of hours, we dozed peacefully until the sun warmed our tent. The blue sky and fresh mountain air energized us for the day ahead. After the previous 24 hours, our expectations were low.
Step. Step. Push. Step. Step. Push. Those movements were the key to overcoming our fourth challenge. The sunny morning and surprisingly rideable trails led us near the high point of our route. As we got to the tree line, one of my worries about this trip due to the late Montana spring presented itself: the northern sides of the high peaks were still locked in snow. Diana and I were now postholing, slipping, and sliding ever upwards. With loaded bikes and in cycling shoes, it was no easy task.


Undeterred and motivated by our desire to make it over the pass before the afternoon moisture arrived, we continued forth. Step. Step. Push. Step. Step. Push. After a couple of hours of hard work, we finally encountered a trail and managed to pedal to the pass. Elated, we basked in the sun and looked down into our next drainage. Our emotions remained high as the trail looked snow-free. This was going to be a fun and well-earned descent.

As Diana mounted her bike, she discovered yet another challenge, as her rear brake had lost all hydraulic pressure. Upon a cursory inspection, the brake was unrepairable in the field and thus useless. The descents of the next couple of days were going to be harrowing for her, and we were concerned about our ability to complete the route. Thus far, the challenges were all surmountable with a little hard work and mental resolve. Having no rear brake on a heavily laden bike was a significant safety risk and potential trip stopper.
We began the descent with optimism, hoping naively that the problem would magically resolve itself. Ha! As we moved down into the next drainage, our first challenge of the trip reappeared. Winter had made its mark on the trees in this area, toppling many across the path. We began our second game of bike/tree twister.

The forced slow pace helped with Diana’s brake issue, but it was an overall detriment to our time frame for completing the route. One trial after another, visions of returning to our camper for a softer, more standard vacation experience began to dominate our thoughts. The previous summer, while riding and paddling for 40+ days down the Great Divide, we encountered very little resistance. This objective was far less audacious, but our continual struggles seemed to indicate that this wasn’t our time to complete this route.

Whether in my professional, personal, or adventure life, when I feel as if I am continually struggling against the current, I make it a habit to hit the “pause” button to listen to the universe. What can I do to change the situation? What lessons can I learn? How can I get back in the flow of the current? Sometimes the answers are obvious, requiring a change in behavior or mindset. Other times, the answer comes down to how much longer one wants to be challenged, which leads to yet more questions: Will pushing through these objections make me stronger and stimulate personal growth? What costs will I pay for these lessons?
Diana and I stood at a literal and figurative intersection debating whether we should continue or call it quits. We could stay on route and head back to the trails for another day and potentially complete our loop, or we could stop early and ride roads and town trails back to our home base. The drive to complete our intended route was strong; I believe in working hard and finishing what I start. But this four-day trip was just one segment of our vacation, and we were already experiencing what we sought: time together away from others and work; physical exertion in the great outdoors; and exploration of a new place. Continuing on with an inoperable crucial piece of equipment could lead to catastrophe.

We whipped through amazing meadows with wildflowers in full bloom, feeling better about our decision with each passing mile. Later that evening, we watched the spectacular Montana sunset dip below the mountains while we sipped fancy cocktails and lounged in comfortable camp chairs beside our camper. Choices.
