Regret is not a bug. It's a feature. Pt II.

The Weight We Carry

This essay was inspired by two men who embodied the weight of regret in different ways. Sal, who initially tapped out at mile 16 of our ruck, later returned alone to finish all 26.2 miles with his full 35-pound pack, writing to our group: "I could give you excuses as to why, but I'm not built to wallow... I don't need a pat on the back. I just need to finish what I started. Pain or no pain, I'm using this fire."

And Uche, who despite intense suffering, pushed through the second leg predominantly by himself, limping forward when no one was watching. Their stories—one of redemption, one of solitary perseverance—compelled me to explore how the weight of potential regret can drive us through present pain.

It was mile 21 when the real battle began. Not against the distance, not against the darkness of an Austin night, but against the voice in my head offering what seemed like rational salvation: Stop now. The blister in your left boot is only getting worse. Your gait is already changing. One more day of recovery versus potentially a week.

With every step, I could feel the friction between sock and skin, the heat building, the humidity turning my groin into a swamp. My body was sending clear signals that something was wrong. Something needed to change. But there we were, on Lakeshore Boulevard, having veered off the trail after realizing our planned loop wouldn't get us to the full 26.2 miles. This unexpected detour added another layer of mental burden in the dark; passing abandoned scooters that whispered easy alternatives to our chosen struggle. Twenty nine men, twenty nine packs, each calibrated to 20% of our bodyweight, grinding forward in the humid Austin night.

The pain was immediate and visceral. The regret would be distant and abstract. And yet.

The Temporal Nature of Regret

In my original essay on regret, I referenced Daniel Gilbert's work in Stumbling on Happiness and Christopher Hitchens' admonition to "choose your future regrets." What I discovered on that concrete path, surrounded by abandoned scooters and the occasional curious onlooker, was the visceral, embodied truth of these intellectual concepts.

Psychologists Thomas Gilovich and Victoria Medvec ¹ discovered something profound about regret: it morphs over time. In the short term, we tend to regret actions things we did that caused pain or embarrassment. But as years pass, this pattern inverts. Our most enduring regrets become the roads not taken, the chances not seized, the conversations we never started.

This research suggests something crucial about human psychology: the pain of action is sharp but fades; the ache of inaction compounds with time. On mile 21, I was living this research in real time. The pain in my foot was undeniable, but so was the knowledge that quitting would plant a seed of regret that would only grow stronger with time.

The Weight That Defines Us

When we organized this ruck, we created an invitation that read: "We all carry weight some chosen, some inherited, some we need to let go." This wasn't just poetic language. It was the central truth we were testing.

The physical weight in our packs calibrated to exactly 20% of each man's body weight was merely the tangible representation of what we all carry daily: expectations, fears, responsibilities, and yes, regrets. The difference is that we chose this weight. We measured it, packed it, and shouldered it deliberately.

And in doing so, we were making a statement: some burdens are worth bearing.

Philosopher Albert Camus wrote that "one must imagine Sisyphus happy" as he eternally pushed his boulder up the hill. The meaningfulness of the struggle transforms the burden. Similarly, psychologist Jordan Peterson argues that the antidote to suffering isn't happiness, but meaning. When we shoulder a meaningful load whether physical or psychological we aren't diminished by it. We're defined.

The Mathematics of Regret

In my previous essay, I referenced Paul Millerd's breakdown of our behavior in the present state:

Uncertain Discomfort < Certain Discomfort + Coping Mechanism²

This equation captures how people tend to behave, choosing familiar discomfort with coping strategies over facing the unknown. But on the trail, with blisters forming and muscles protesting, I found myself considering a different equation:

Future Regret > Present Pain

When the inequality points this way when the weight of potential regret outweighs the intensity of present suffering the path becomes clear, even when it's painful. Each step becomes an investment against future remorse.

Bronnie Ware, who worked with the dying for years and documented their most common regrets, found that the most universal lament was not having lived authentically having let fear dictate choices instead of courage. No one at life's end wished they'd taken fewer risks or endured less temporary discomfort in service of their values.

The Shared Load

What made this ruck different from a solitary marathon wasn't just the added weight in our packs. It was the presence of other men shouldering the same burden, facing the same inner dialogue between comfort and commitment.

Contemporary society has created a peculiar problem for men. We're still expected to carry significant burdens financial, familial, social but now often in isolation, without the tribal structures that once distributed the psychological weight. The result is predictable: rising rates of depression, anxiety, and suicide among men who feel they must bear their burdens alone.

Our ruck offered an alternative: shared struggle, witnessed vulnerability, collective resilience. When my foot was screaming at mile 21, I wasn't just continuing for myself. I was continuing because I saw Zakk grimacing through his own pain. He was wearing his ruck pack shirtless, and the welts on his body were growing bigger with each mile. I was continuing because I knew the men around me would do the same. We had made a pact without words: no one carries this weight alone.

The research backs this up. Studies on "communal coping" show that facing adversity collectively changes our neurological response to stress. The presence of others who understand and share our struggle literally changes how our bodies process pain.

The Rite of Passage

Traditional cultures recognized something our efficiency-obsessed society has forgotten: transformation requires ordeal. From vision quests to walkabouts to various initiation ceremonies, cultures worldwide created structured challenges that forced young people (particularly young men) to confront their limitations and emerge with new self-knowledge.

Our ruck was a modern version of this ancient wisdom. The physical challenge was merely the container; the real work was internal. With each mile, we were asking ourselves: What am I capable of? What weight can I carry? What discomfort can I transcend?

Viktor Frankl, having survived the unimaginable suffering of Nazi concentration camps, concluded that humans can endure almost any "how" if they have a compelling "why." Our "why" that night wasn't just completing a distance or carrying a weight. It was proving to ourselves that we could choose discomfort when it aligned with our deeper values.

The Feature, Not the Bug

As I pushed through miles 21, 22, and beyond, I began to understand regret not as something to be avoided at all costs, but as a navigational tool a feature of our psychological architecture that points us toward what we truly value.

If I feel anticipatory regret at the thought of quitting, that's valuable information. It tells me that beneath the surface pain is a deeper commitment worth honoring. The potential regret becomes a compass, not a threat.

By mile 25, the pain hadn't diminished. If anything, it had intensified. The physical pain became so overwhelming that I reached for my phone and started playing Ben Lionel Scott's "Weekly Motivation."³ Those voices speaking about perseverance and purpose became the soundtrack to my struggle. I needed something external to reinforce what my exhausted mind was starting to forget: that this temporary suffering was building something permanent within me. That the pain coursing through my foot was insignificant compared to the regret I'd feel tomorrow, next week, next year if I surrendered now.

And when we all finished sweaty, sore, but intact I realized that we had collectively enacted what philosopher William James called "the moral equivalent of war." We had voluntarily embraced hardship not because we had to, but because we chose to. We had looked at the weight of potential regret and decided it was heavier than any physical burden we could shoulder.

Choosing Our Weights

There's the weight of expectations which can crush or elevate. There's the weight of responsibility which can burden or dignify. There's the weight of regret which can paralyze or propel.

The question isn't whether we'll carry weight. We all do. The question is which weights we choose to carry, which we share with others, and which we deliberately set down.

The blisters from the ruck healed within two days. The knowledge that we pushed through when every instinct screamed stop that's a weight we'll gladly carry forward.

Regret isn't a bug in our psychological software. It's a feature that helps us align our actions with our values. And sometimes, the way to minimize its weight in the long run is to shoulder a different kind of weight in the present the weight of discomfort, vulnerability, and growth.

So here's to the weights we choose, the paths we take when comfort beckons elsewhere, and the men who walk beside us, carrying their own loads, nodding in silent recognition of the shared journey.

1. https://www.researchgate.net/publication/15459284_The_Experience_of_Regret_What_When_and_Why

2. https://arc.net/l/quote/dpqscija

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