At the close of 2025, failure caught up to me.
I suddenly found myself starring it dead in the face. Like Jim Hopper sizing up the Mind Flayer in Season 5 of Stranger Things.
The reality sank in quickly… and the truth of it rocked my world.
OK, so it wasn’t the dust “off your resume”, life-upending kind of failure. But it wasn’t the polite kind either. This was crash-and-burn territory. The kind of failure that humiliates you if you let it. The kind that exposes your sense of self. The kind that forces you to sit with it long enough to ask yourself some pretty difficult questions.
It was humbling. And if I’m honest, brutal on my ego.
There’s a particular kind of failure that doesn’t just disappoint you—it dismantles the story you were telling yourself about who you are, what you’re doing and where you’re going. That’s right where I found myself in November.
Trying to reconcile massive amounts of effort with less then ideal outcomes, good intentions with a reality check, confidence and bravado with the consequences of my actions. Wondering how something I believed in so deeply and worked so hard to achieve could begin to unravel so rapidly. Luckily, it’s salvageable. Things are looking up. But, damn, did it rattle my cage.
In the aftermath, I did what many of us do. I replayed decisions. I judged myself harshly. I questioned my instincts. I tried to make sense of it all from inside a system that views failure as something to be really embarrassed about rather than simply understood.
And then, unexpectedly, I heard a conversation that helped me put this failure into some much needed perspective.
Failure in a Linear World
Recently, I listened to a discussion between Jay Shetty and Matthew McConaughey that found me at just the right time. What began as a reflection on embarrassment and missteps unfolded into something deeper—a revealing look at how our relationship with failure is shaped by how we understand time itself.
In much of the Western tradition, time is experienced as linear. There’s a beginning and an end. A starting point and a finish line. This worldview, deeply influenced by Christianity, imagines history unfolding along a straight arc: creation, fall, redemption, judgment. Birth. Life. Death. Heaven or Hell. Humans find life’s meaning in progress toward a definitive endpoint- When they ultimately reach the finish line, will they be welcomed at the pearly gates or cast down into the everlasting BBQ pit?
Within that framework, failure feels dangerous. When time is a straight line, mistakes feel like lost ground. Like slipping backward. Like lagging behind.
Progress means climbing higher.
Failure means falling lower.
So when we fail, we panic.
McConaughey reflects on looking back at moments that once felt embarrassing or misguided and realizing that those very moments were essential. He talks about learning lessons only because he was confident—or arrogant—enough to put himself in situations where he could fall flat on his face. In hindsight, the mistakes weren’t missteps; they were stepping stones.
He sums it up beautifully: life is a mystery going forward, but a science looking back. Hindsight being 20/20, we can always connect the dots in reverse. And almost without exception, those dots lead us back to pivotal moments in our lives when we tripped, failed, or made embarrassingly bad choices.
The irony is that many of the outcomes we’re grateful for today were fertilized by the very failures we once tried to avoid at all cost.
We resist integrating failure. We try to erase it instead.
In a linear worldview, we struggle to make peace with that reality. Failure becomes something to give a wide berth to rather than something to incorporate into our daily lives.
Avoiding the uncomfortable is a costly mistake that robs us of incredible opportunities for growth.
Failure in a Cyclical World
In contrast, Eastern traditions such as Hinduism and Buddhism offer us a very different perspective on time. Time is perceived as being cyclical rather than linear.
When time is cyclical, life isn’t a exam you take once and wait for the grade. It isn’t a courtroom drama building toward one big verdict or a “one shining moment” shot at the buzzer with eternity keeping score.
It’s part of an ongoing cycle of birth, death, and rebirth. Expansion and contraction like our Universe. Ebbing and flowing like the ocean tides surrounding us.
Existence is merely transitional. We’re all travelers, not settlers. Life’s a bridge between profound mysteries.
In a cyclical worldview, failure’s just another turn of the wheel. Seasons change, the sun rises and then sets on a fresh new day, lessons are learned and they repeat. Growth happens in spirals rather than straight lines. Nothing is wasted. Everything returns with new, deeper understanding.
Hearing this distinction helped something click for me.
When I viewed my recent failure through a linear lens, it felt catastrophic -like I had fallen irreparably behind. But when I allowed myself to see it through a cyclical lens, something softened.
It wasn’t an ending. It was part of a pattern. A lesson asking to be integrated into my life rather than erased from it.
That shift in mindset didn’t magically fix anything. But it brought me some much need peace of mind. It allowed me to stop arguing with reality and start learning from it. It helped me lift my head, dust myself off and regain some clarity. It helped me look inward first before focusing attention on the task at hand.
The Inner Journey
If Western success is outward and upward, Eastern success is inward. The focus isn’t just on achievement, but on awareness. Not just on the progressive realization of a worthy ideal, but on gaining the necessary wisdom along the way.
We live in a culture intoxicated by titles, milestones, and optics. We often overlook the inner journey entirely. We become experts at managing appearances while remaining beginners at understanding ourselves (it’s pretty hard to post pictures of your inner enlightenment on Instagram.)
But failure doesn’t care about optics.
It reveals clinging and attachment.
It exposes our fears and anxieties.
It surfaces our blind spots.
Those revelations are the real lesson. And continuous learning, it turns out, is the real measure of progress.
Language Matters
One of the most striking moments in the conversation centered on language.
McConaughey shared how he struggled for decades with the word humility. To him, it felt like shrinking—head down, shoulders slumped, confidence erased. (This must have been what I looked like to others a few months back).
Until he heard a redefinition—humility is simply admitting you have more to learn.
Suddenly, humility wasn’t passive. It wasn’t weakness. It was expansive. It didn’t diminish him; it energized him.
The same is true of failure.
If failure means humiliation, we’ll hide from it. But if failure means information—feedback from the universe —then it becomes something we can face with curiosity instead of fear. Heck, we may even learn to seek opportunities for failure in our effort to grow.
These subtle shifts in language are revolutionary. They don’t change the events of our lives, but they radically change how we relate to them.
Relearning Failure
Many of us were taught to fear failure early. We learned that mistakes meant disappointment, judgment, or loss of approval. Over time, that fear calcified. We stopped taking risks. We aimed for safety instead of growth.
Yet when people reflect on their lives, they rarely wish they had played smaller. More often, they wish they had risked more. Tried sooner. Failed bigger.
As my friend Paul Osting likes to say, maybe we should learn to run a little more toward the roar – quit living as if the purpose of life is to arrive safely at our death. Let’s get a little more comfortable being uncomfortable.
Failure isn’t the opposite of success. It’s embedded in the path like a stepping stone on our life story.
A Different Way Forward
So, yes. At the end of 2025, I was rattled by failure. Through a linear lens, it looked to me like regression. But, viewing that same failure through a cyclical lens, it now looks like a critical step in my constant “becoming”.
- What if failure isn’t a step backward, but a necessary turn in the cycle?
- What if the moments you’re most embarrassed by are quietly responsible for the clarity you carry with you today?
- And what if growth isn’t about avoiding failure—but about learning how to meet it without flinching?
When we loosen our attachment to straight-line progress, we give ourselves permission to experiment, to stumble, to evolve. We stop demanding perfection from a process that was never meant to be neat and tidy.
Failure will happen. If it doesn’t, you’re probably not stretching far enough.
So here’s the invitation:
- Laugh at yourself before you judge too harshly.
- Reflect before you retreat.
- Let failure teach you what success never could.
- And, then Go Be Great! (Again)
Because in the long arc of the human story, failure isn’t proof that you’re behind.
It’s proof that you’re still becoming… and yes, failure is always an option.
This post was inspired by a conversation between Jay Shetty and Matthew McConaughey on the podcast On Purpose (episode discussion on failure, time, humility, and growth).
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