Stories

To Be Unsure You’ll Succeed

November 11, 2019

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To Be Unsure You’ll Succeed

“Digging really—really—deep unearths gems about ourselves that we never knew existed.”


Underneath, all was well. On the other side of the quilt, though, biting coldness awaited amidst a world painted in gray, dull light.

I didn’t even need to glance through our room’s lead-glass window to know that it was raining—the humidity penetrating the walls of our 1800s-era bed, and breakfast declared it loud and clear:

“Today will be uncomfortable!”

We dressed quickly, packed our bags, mounted them to our bikes, and rolled into the hallway. I grabbed a muffin near the door and stuffed it into my mouth as we walked out onto the glistening second story deck.

The raised cleats on my bike shoes clacked loudly as I walked a few feet toward the stairs—and combined with the drizzle, created a surface that might as well have been greased with Crisco. So, after taking my first step down, I promptly slipped and traversed the remainder of the flight on my ass.

The first discomfort in a day sure to be filled with them.

“I’m good,” I said to Jamie, smiling at her, and the small crowd gathered below.

“Thank goodness for padded shorts,” I chose not to say aloud. “Otherwise, my ass would be sore instead of just my ego.”

After picking myself up, we rolled our bikes to the front of the building. There, the B&B’s owner snapped a few pictures before we embarked on our third—and longest—day along the Katy Trail.

Immediately, the unceasing drizzle clung to our clothes, weighed them down, and rendered them incapable of retaining warmth. Cold wind reddened our skin underneath.

Water pooled across the crushed limestone trail, which repeatedly sucked any momentum we managed to build. Even when avoided, a thin layer of mud created ever-present resistance.

Our back tires kicked up this soily mixture and created skunk stripes on our backs that extended from our heads down to our ass cracks; a freezing cold version of swamp ass. Not shivering was impossible.

“How far have we ridden?” Jamie asked.

“20 miles.”

“How many miles to go?”

We looked at each other in the eyes. “55,” I grimly replied.

Reticent, willing, and with steely gazes, we bowed our heads in opposition to the wind, rain, and discomfort, and pedaled onward.


Not too much farther along, we rescued a coal-black kitten meowing in the middle of the trail. It would have surely perished if left exposed to the elements much longer.

Two retired women, who we met at our B&B the previous night, caught up to our trailside rescue effort. One, who had recently lost her beloved cat, decided to adopt the orphan and in honor of its rescuer, named the kitten Jamie.

After gently placing the furball inside her bike’s front basket and covering her with a warm sweatshirt, she rode toward the horizon with her new passenger aboard.

A few hours later, Jamie, who’s a decades-long vegetarian and was on her first bike tour, bonked in the middle of nowhere. With nothing but a local bar to choose from, she nearly ate chicken strips to continue pedaling.

The last remnants of daylight were fading when we finally pulled onto the gravel road leading to our Airbnb. In the low light, we missed the property’s turnoff by a couple of miles and rode up a steep hill before realizing our mistake and turning around.

Finally, as icing on the cake, our host for the evening—while perfectly pleasant—lacked crucial social skills and left us with a serious case of the creeps.

Still, we were grateful for the day’s conclusion. We peeled off our second skin of drenched clothes, took hot showers, climbed into our warm bed, and almost immediately fell into a deep, dreamless sleep.


Granted, putting these situations into their proper perspective, our lives were never in danger. We could have called for a warm, dry—and expensive—van ride to our destination at any time, and filled our bellies along the way.

Bailing out wouldn’t have just blown through our budget, though. We would have also missed the lesson we set out to learn: precisely what we’re capable of when maximally uncomfortable. Digging really—really—deep unearths gems about ourselves that we never knew existed.

Whatever the task, it’s healthy to be unsure that we’ll succeed. In fact, although trite, it’s during these times when we learn how to embrace irritation, hardship, distress, and unpleasantness, change our perspectives, and use these experiences as teachers.

Maximizing fatigue and exhausting every last ounce of energy peels back our syrupy egos, strips us bare, and allows the universe’s lessons to alight upon our consciousnesses.

Embrace the awkwardness. Revel in the disquiet. Find centeredness in the chaos. Pushing against your boundaries is always worthwhile.

Derek has more than two decades of experience as a cyclist, and is the founder of TreadBikely. He currently travels full-time with his family via RV, enjoying the country's best biking destinations. A secular Buddhist, Derek frequently explores the intersection of cycling, mindfulness, and compassion in his writing. #rolloutblissout
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