“Monday 5 Things” ….. Messy Middle …..
September 29, 2025 by D. Paul Graham
Ever curious and always amused by the quirks of life, join D. Paul Graham each Monday for more M5T pondering.
“Wheels Up” photo D. Paul Graham, 24 Hours of Rolex, Daytona International Speedway, circa 2018
It was 2018, my first time photographing the Rolex 24 at Daytona. I didn’t have full media credentials, but I managed to stake out a spot at Turn 3, the International Horseshoe, where the action is as quick as it gets. I still remember watching one driver for several laps. He seemed hesitant, tentative through the corner, leaving the rear of the car just a little loose, never quite committing on exit.
Then in an instant, there was a scream of tires, the violent snap of carbon fiber, and gasps from the grandstand. My viewfinder was filled with the airborne fury directly in front of me. The image I captured was raw, imperfect, and undeniably alive.
Since that day, I’ve taken my glass to some of the most storied circuits in the world. I’ve seen victories etched into history and crashes that will never leave my mind’s eye. That photograph taught me something deeper than shutter speed and composition. The image is a metaphor for growth that is rarely polished and predictable. It can be violent, uncertain, out of control, and profoundly human. And yet, precisely there, in that chaotic messy middle, is where deep and meaningful change can begin.
This morning’s M5T shares five realities to carry with you this week when the middle feels messy.
1. CONFIDENCE COMES LATER. Confidence is often mythologized as something you start with, but more often it’s the patina, the hard-earned surface that forms only after repeated friction. Every confident person that looks like they have everything under control, once stood disoriented in the haze of doubt, searching for direction and meaning, and questioning whether they had the strength for what lay ahead of them. Stoics Seneca and Epictetus both taught that courage isn’t the absence of fear but the decision to act despite trepidation. Confidence is no different. It’s not a light waiting to be found and seen. Confidence is a fire born from sparks of small, uncertain actions, growing quietly at first and then building into something undeniable. Doubt isn’t a sign you’re failing. It’s the challenge that builds strength and the winding road that teaches you how to steer with intention.
2. HARD IS THE ROAD. We grow up believing passion will feel like a tailwind, that we’re meant to do something, and that it will carry us effortlessly forward. But purpose is rarely smooth asphalt. It’s more often a road full of climbs, curves, and unmarked detours. It demands sweat, sacrifice, and setbacks. Most people don’t quit because it’s hard. They quit at the first unexpected turn, the first major setback, because they thought it wouldn’t be difficult. They confuse resistance with a wrong turn, assuming struggle means they’re off course. Marcus Aurelius warned against this illusion. “The impediment to action advances action. What stands in the way becomes the way.” Hard isn’t a detour. Ease was never the promise. The difficulty is the point. It’s the route itself.
3. SYSTEMS ARE BUILT. It’s easy to look at someone else’s company, their lifestyles, their seamless habits, their airtight routine, and assume it was always this way. But such things don’t start perfect. They are the product of bruised knuckles, broken prototypes, painful discipline, and a thousand late-night improvisations. I’ve built businesses and creative practices both, and none of them started with elegant frameworks or systems. They started with chaos, sticky notes covering the computer monitor, legal pads strewn on the floor, mistakes on repeat, and that faint inner voice and heartbeat of panic at 2:17 AM. Order emerges slowly. One painful iteration at a time. The Greek word Kosmos means both “order” and “beauty.” Systems, like art, are not discovered. They are sculpted from a chisel. Keep carving.
4. GROWTH FEELS LIKE CHAOS. In the messy middle of growth, it rarely feels like you’re advancing. More often, it feels like you’re unraveling. You question decisions you were once sure of, dismantling more than you’re building. That’s because growth, by its very nature, is destabilizing. It unsettles the ground beneath you and demolishes the stability your built. Not to break you, but to make room for a larger version of you. It asks you to outgrow the familiar, to loosen your grip on what once felt certain and comfortable, to step into spaces that feel unsteady, and compels you to adapt before growth can occur. You don’t become who you’re meant to be without first letting go of who you were. The Stoics called this metanoia, which is the painful turning of the mind toward something higher. If your progress seems chaotic, it’s evidence that you’re broadening beyond the edges of the life you’ve already lived.
5. THE MESS MAKES YOU. We all crave the clean lines of certainty, comfort, and clarity. The blueprint, the quick fix, the step-by-step plan. But clarity isn’t the starting point. It’s what emerges from movement. The mess, the doubt, the fear, and the confusion aren’t detours. They’re the terrain that shapes us. The messy middle is where stories are written and rewritten, where identities are dismantled and reborn, and where potential stops being theory and starts becoming reality. And it’s also where most people give up and walk away. Not because they lack what it takes, but because they mistake discomfort for disaster. Discomfort is sacred ground where transformation begins. The mess isn’t the obstacle. It’s the shaping and making of all you were created to be.
Here's to a week of embracing the messy middle because that’s exactly where you need to be for the good stuff to start.
© 2025 D. Paul Graham, All Rights Reserved
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