Volume 099

“The real failure isn’t falling down - it’s failing to learn the lesson that the fall was meant to teach.” - Sahil Bloom

I took my own advice and suggestions this week and spent some time pen and pad, reflecting on the year that was 2025. It’s amazing how much you can and do accomplish in a year. It’s always revealing how much good you just forget about throughout the year too.

As I looked back on the totality of the reflection, there was one lingering consistency to the most powerful lessons I feel like I am taking into 2026. That consistency was failure. Today, I want to pay a little homage to the lessons learned through falling on your face and figuring it out from there as you go.

2025 was a great year, but with the wrong headspace, could have very easily been viewed through a negative lens. So here it goes - an ode to failure.

An Ode to Failure

Failure doesn’t arrive loudly the way success often does. It doesn’t announce itself with celebration or validation. It tends to show up quietly, awkwardly, and without instruction. Most of us learn very early to move past it as fast as possible - to explain it away, to soften it with lessons, or to bury it beneath the next goal.

But as I’ve reflected, 2025 didn’t allow me that escape. It handed me two failures that refused to be rushed, reframed, or neatly packaged. One unfolded in public, on the pavement, in front of strangers. The other happened privately, behind closed doors, with only my own expectations watching. Both forced me into a kind of stillness I hadn’t practiced enough before. And both asked the same uncomfortable question: What will this result say about me as a person?

The first failure was physical. The second was professional. Together, they reshaped how I think about ambition, effort, and what success actually looks like in this season of life.

Mile 25

The irony of the marathon failure is that everything leading up to it had gone right. Sixteen weeks of disciplined training, consistent mileage, controlled workouts, and no major setbacks. It was my second attempt at breaking three hours, and unlike the year before, there was no guessing this time. I wasn’t hoping fitness would show up. I knew it was there. I had felt it through the back to back to back to back weeks of 65+ miles of training.

Race day only reinforced that belief. The early miles felt smooth and controlled. My pacing plan held. Breathing was steady. Every internal metric suggested I was executing exactly as intended. For most of the race, it felt less like chasing a goal and more like fulfilling one.

And then, at mile 25, my body made a decision my mind didn’t get a vote on.

The shutdown was sudden and complete. My legs stopped responding. My vision narrowed. The next thing I remember clearly is being on the ground, disoriented, waiting for EMTs, later learning I was experiencing rhabdomyolysis. What followed was a hospital bed, IVs, and the strange dissonance of having trained for months only to end the race not at the finish line, but in a medical ward.

There was a moment on the side of that trail, before help arrived, that stays with me. It wasn’t publicly dramatic, but it was deeply sobering. My body felt fragile in a way it never had before. Breathing didn’t feel guaranteed. Consciousness came and went. And in that liminal space, I remember being overwhelmed by emotions.

Frankly, I was feeling the fear for my life as I went in and out. I couldn’t stop thinking about my wife and my future kid. My family, my friends. The longing for things I still wanted and needed to accomplish. And as silly as it was in the moment all things considered, I felt disappointment that I had failed again.

Burred underneath it all to was a sense of gratitude. For the fact that I had cared enough to put myself in a position where failure was even possible. I told myself that I would not quickly forget these emotions. That it would be selfish to feel like you’re knocking at the pearly gates one second and then getting upset by some trivial life thing the next week.

Guess what? As life normally has it, I quickly forgot.

In the weeks that followed, embarrassment crept in. Then frustration. Then the familiar, dangerous thought pattern of tying personal worth to external results. The lesson didn’t stick the first time. Or the second. It had to be re-learned repeatedly.

What eventually settled wasn’t really relief, but clarity. I wasn’t ashamed of how hard I had tried. I was proud of it. And the disappointment came not from the effort, but from how narrowly I had defined success in the first place.

The Failure No One Saw

The second failure didn’t come with an ambulance or a visible collapse. It arrived quietly in May, after I applied for my former boss’s role when he was promoted to a broader leadership position. Vice President of U.S. Sales felt like a logical next step. The experience lined up. The timing seemed right. And professionally, I had never failed to land a role I seriously pursued.

I prepared with intensity and certainty. And it didn’t feel like hope…it felt like certainty. I walked into the process already imagining the life on the other side of the decision.

When the call call that I wasn’t getting the job, the emotion that surprised me most wasn’t disappointment. It was almost a shame.

There’s something uniquely unsettling about professional failure when your identity has been built on forward momentum. When the next rung on the ladder you assumed you were climbing suddenly isn’t under your feet anymore. I didn’t talk about it for a long time - not because it hurt too much, but because I didn’t know how to hold it without feeling smaller.

Initially, my focus was on what I lacked. I replayed the process, dissected conversations, compared myself to invisible competitors, and searched for the exact reason it hadn’t worked out. But over time, a quieter question emerged - one that had nothing to do with readiness or credentials.

What would this job actually cost me right now?

With my first child on the way, time stopped being theoretical. It became tangible. Finite. Expensive. The role would have demanded more travel, more nights, more emotional bandwidth. And while that tradeoff might have made sense in another season, it didn’t align with the life I was actively building. It took some serious time for this to settle in as a realistic point of view.

That realization didn’t arrive as comfort. It arrived as discomfort. I guess because ambition doesn’t like to be told to wait. It doesn’t like being redirected. And it certainly doesn’t like being asked whether it’s chasing growth or just validation.

What Failure Reveals

Failure doesn’t automatically teach lessons. That’s the part we often skip over. It reveals things, but only if you’re willing to stay present long enough to see them clearly.

The marathon exposed how tightly I had continually wrapped my identity around outcomes. How easy it is to confuse effort with entitlement, and ambition with control. The job rejection exposed something more subtle but equally important: there were gaps I hadn’t fully acknowledged yet.

Not glamorous gaps. Not résumé bullet points. But foundational ones: optimizing team performance at scale, deepening key account relationships, building tenure that can’t be rushed, and moving faster on hard conversations and decisions even when the data isn’t perfect.

Failure didn’t disqualify me. It clarified the work that still matters. And the reality of the situation that only settled in after a long period of honest reflection. What punched as a failure quickly became the realization that I both had work to do, and that I also have an addition to my family upcoming that deserves my full attention and energy.

And perhaps most importantly, both failures forced an honest reckoning with the idea that success isn’t static. It evolves. What looks like progress in one season can feel misaligned in another. Recognizing that doesn’t mean shrinking ambition as I have often viewed it as - it means aiming it with intention.

A Quietly Successful Year

If you isolate the moments themselves, 2025 could easily be labeled a step backward. A missed goal. A missed promotion. Two visible points of friction in an otherwise forward-moving life.

But when viewed with the lens of time, it was one of the most grounding and formative years I’ve had. Physically stronger. Mentally clearer. More aware of what I’m willing (and unwilling) to trade. Better prepared for the responsibilities ahead.

Failure didn’t derail the year. It refined it. It stripped away assumptions I’d been carrying about speed, timing, and what winning is supposed to look like.

An Invitation

Most people will end this year highlighting what went right. The promotions. The milestones. The curated versions of progress.

But nearly everyone has a mile 25 moment from 2025 - a goal that didn’t materialize, a door that stayed closed, an effort that didn’t get rewarded the way it was supposed to.

Instead of rushing to redeem it, try sitting with it a little longer. Ask what it revealed about how you measure yourself, what it clarified about what you want right now, and what effort you’re still proud of even without the outcome.

Failure doesn’t demand optimism. It asks for honesty. And if you give it that, it often returns something quieter but more durable in return.

Clarity.

As you move toward 2026, don’t just audit your wins. Write your own ode to failure. There’s wisdom there, waiting patiently, for anyone willing to listen.

I’m not one to sit here and glorify failure. I invite it these days, because I am not afraid of it. But let’s call a spade a spade - I would probably have loved to be sitting here as the VP of Sales who also ran a sub-3 hour marathon. But without failing at both of those things, I don’t know that I would have been afforded the opportunity to sit with that pain and dissect what it is I really want moving forward.

And if the cost of that realization is some failure - public or private - then bring it on again 2026.

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