Try and Fail

The Value of Attempted Adventures #

There’s a fundamental distinction between hypothetical experiences and actual attempts—between wondering what might happen and discovering what does. I’ve developed a core philosophy that shapes my approach to life’s possibilities: attempting something meaningful and falling short creates infinitely more value than perfect execution of the safely achievable or, worse still, the perpetual contemplation of what might have been.

My life’s ledger contains both achievements and setbacks, with the latter significantly outnumbering the former. Yet I consider this imbalance not a record of inadequacy but rather evidence of a life lived at the edge of my capabilities—where meaningful growth occurs. Let me share one particularly instructive example from this collection of instructive failures.

During a recent social gathering, a conversation turned to my 2017 attempt to solo paddle the entire length of the Mississippi River—an adventure that didn’t unfold as planned. As we discussed this experience, our dialogue expanded into the broader pattern of my willingness to attempt challenging endeavors despite uncertain outcomes.

This conversation highlighted something I’ve observed repeatedly: the boundary between those who attempt difficult things and those who don’t rarely aligns with capability differences. Instead, this boundary often reflects a fundamental distinction in relationship with potential failure. Many highly capable people avoid ambitious challenges specifically because of the difficulty involved—creating a self-limiting pattern where comfort becomes preferred over growth and certainty over discovery.

The Mississippi Challenge: Context and Preparation #

The Mississippi River expedition represents a significant adventure by any standard—a 2,340-mile journey from Minnesota’s Lake Itasca to the Gulf of Mexico. While not unprecedented, successfully navigating the entire river remains a relatively rare achievement, particularly for solo paddlers who must manage all navigation, logistics, safety considerations, and mental challenges without companion support.

I approached this journey with both enthusiasm and documentation intentions, bringing camera equipment to create a daily video log—footage that remained largely unshared until now, partly because I questioned whether an incomplete journey would hold interest or value for others. This hesitation itself reflected a misconception about failure’s instructive potential that I’ve since reconsidered.

Day 1: Initial Optimism and Reality’s First Lessons #

My expedition began with characteristic optimism at Lake Itasca, the Mississippi’s headwaters. I embarked carrying equipment for what I anticipated would be a three-month river lifestyle—a collection that reflected certain assumptions about the journey’s nature. My approximately 200-pound cargo included solar charging equipment, comprehensive camera gear, computing technology, and even musical instruments (a ukulele and harmonica) for riverside relaxation.

This equipment selection, while aligned with my vision of leisurely river exploration, would quickly reveal itself as mismatched with the actual conditions I encountered—an early lesson in the gap between expectation and reality that often defines ambitious undertakings.

First Encounter with Reality’s Constraints #

As my first day progressed, the initial enthusiasm gradually transformed into a more complex emotional landscape. The upper Mississippi revealed itself not as the deep, navigable waterway of my imagination, but as an incredibly shallow stream requiring constant physical effort. Rather than paddling smoothly through picturesque landscapes, I found myself dragging a heavily laden canoe across rocky streambeds—a physically demanding activity for which I had neither physically prepared nor mentally anticipated.

This unexpected challenge created both physical exhaustion and a cognitive dissonance between my romanticized vision of river travel and the labor-intensive reality I was experiencing. The adventure was already revealing important lessons about preparation, research, and the gap between conceptual understanding and experiential knowledge.

Evening Reflections: The Psychological Dimension #

By day’s end, multiple dimensions of challenge had emerged simultaneously: physical fatigue from unexpected exertion, technological isolation without cellular connectivity, and the psychological weight of solitude in an environment that felt more demanding than nurturing. The night brought little relief as sleep proved elusive—my mind processing the day’s reality adjustments while anticipating the journey ahead.

This evening marked an important inflection point in my relationship with the expedition. The pre-journey anticipation had been replaced by direct experience, requiring real-time adaptation of expectations and plans. Before attempting to rest, I recorded thoughts that captured this transitional state between initial vision and emerging reality.

Day 2: Compounding Challenges and Decision Points #

The second day brought continued adaptation rather than the improvement I had hoped for. The challenges actually intensified—the landscape transformed into seemingly endless grasslands with no visible human infrastructure, creating an enhanced sense of isolation. My technological lifelines remained non-functional, with cellular connectivity absent and no offline navigation resources to supplement traditional wayfinding.

This phase of the journey introduced additional strategic considerations. Approaching Lake Bemidji presented both navigational challenges and a decision point. Lake crossings represent a distinct risk category for canoeists—open water creates vulnerability to wind conditions that can quickly transform calm surfaces into dangerous, choppy waters with powerful crosswinds. Simultaneously, Bemidji’s proximity offered the first reasonable exit point should I choose to conclude the expedition.

The river’s approaching infrastructure also foreshadowed increasing logistical complexity—a series of dams and weirs would soon require multiple portages (physically carrying the canoe and all equipment around obstacles). With my current gear configuration and physical condition, these portages would represent disproportionately difficult segments that would significantly slow overall progress.

After another challenging day, I established camp on what appeared to be cattle grazing land, creating a temporary haven while evaluating the journey’s trajectory and sustainability.

Day 3: The Decision Point and Conscious Conclusion #

The third morning became a moment of clarity and deliberate choice. Despite proximity to Bemidji (representing tangible progress), I recognized several important realities about the expedition:

1. Experience Quality: The journey had not generated the anticipated enjoyment or fulfillment—a fundamental consideration for voluntary adventures

2. Preparation Mismatch: My physical conditioning, equipment selection, and technical preparation had not aligned with the actual requirements of the expedition

3. Psychological Factors: Perhaps most significantly, I discovered I wasn’t mentally prepared for the particular combination of wilderness isolation, technological disconnection, and sustained self-reliance the journey demanded

This constellation of factors—particularly the unexpected anxiety about continuing deeper into remote areas—created a decision context where continuation would have represented persistence for its own sake rather than meaningful engagement with the experience.

The Wisdom of Attempted Adventures #

My relationship with this experience exists in a nuanced middle ground—neither characterized by particular pride in the expedition’s premature conclusion nor by shame regarding the outcome. What remains most valuable is the fundamental distinction between theoretical and experiential knowledge. I will never wonder what might have happened had I attempted to paddle the Mississippi, because I actually undertook the journey, encountered its realities, and made conscious choices based on direct experience rather than speculation.

The expedition’s most important outcome wasn’t distance covered but lessons internalized. I gained irreplaceable insights about:

• Preparation specificity: Understanding the particular demands of each environment and activity rather than generalizing across superficially similar experiences

• Gear-to-purpose alignment: Recognizing how equipment choices should prioritize essential functions over anticipated comforts or tangential activities

• Psychological preparation: Acknowledging that mental preparation for isolation, disconnection, and sustained self-reliance requires specific conditioning beyond general enthusiasm

• Decision-making frameworks: Developing clearer criteria for when continuation serves growth versus when recalibration represents wisdom rather than capitulation

This experience has been transformed from “failure” in the conventional sense to valuable data that informs future adventures. With this experiential knowledge now integrated, I can envision a potential future attempt—one that would benefit from precisely calibrated preparation, more appropriate equipment selection, and psychological readiness aligned with the actual demands of this specific journey.

The most significant insight remains this: the attempt itself, regardless of outcome, holds inherent value that perpetual contemplation can never provide. Through actually beginning the journey, I’ve gained membership in a category of experience that remains inaccessible to those who merely speculate about such adventures from a distance.