Planning is Clean. Execution is Dirty.
Thoughts On The Strange World That Lives Beneath Every Plan
In Stranger Things—the Netflix show—the Upside Down is a shadow world: twisted, parallel, hidden just beneath the surface of the real one. And whenever the boundaries between the two worlds weaken, strange things happen. Lights flicker. Magnets fall off fridges. The laws of physics appear to be unraveling.
Strangely enough, it feels like a fitting metaphor for something far more familiar: the chasm we’ve been building between planning and execution.
On the one hand, we have the surface world, where we sketch ideas, set goals, and feel a sense of momentum. Everything’s clean. Everything’s fine. But then, the moment things get real, something shifts. The air thickens. The lights dim. The ground warps beneath your feet. And the battle begins.
If planning is our aboveground, execution is the Upside Down of Doing—the strange, disorienting space we all enter the moment our plans collide with reality. The messy, reactive, unpredictable world of getting shit done.
What if this isn’t just sci-fi?
What if this metaphor actually holds some weight and can teach us something?
The Comfort of Planning and the Monsters of Execution
Nobody cries in a plan. Besides minor hiccups or moments of uncertainty, when we plan, in our minds, problems dissolve neatly into logical steps. There’s little friction. No fatigue. Hardly any doubt.
Planning is calm. It’s clean. It trades in assumptions, predictions, and tidy outlines. It gives us the illusion of control, like we can outsmart chaos by color-coding our tasks and mapping out the next six weeks. Whiteboards get filled. Trello boards sparkle. Notebooks brim with excitement. But none of it breathes. None of it bleeds. Planning is a form of progress—but not the kind that moves things forward. In the end, it’s all rehearsal. Not the real show.
Execution, by contrast, is chaotic. Emotional. Raw. It’s where the magnets fall and the lights begin to flicker. It’s where confidence wobbles and the work reveals its true weight. It’s where the Demogorgons come out. The emotional ones. The invisible ones. Not monsters with teeth—but with choices. Too many ways forward. No clear signal. Just you, the blinking cursor, and the heavy silence of not knowing what comes next.
A premature plan rarely survives contact with reality. Doubt creeps in. Fatigue hits. Distractions multiply. You fumble forward, adjusting as you go. Execution doesn’t offer the tidy clarity of a blueprint—it offers truth, in all its tangled, unfiltered, and dirty form.
I tend to summarize all of this as: Planning is clean. Execution is dirty.
It’s a simple phrase, but it reveals deeper problems.
Two Worlds. Two Traps.
When we treat planning and execution as two entirely separate worlds, we fall into polarity. Some of us become planners who never start. Others become doers who never pause. Some cling to the surface, trapped in an endless state of preparation. Others dive headfirst into the fog—ungrounded, overcaffeinated, armed with nothing but a half-baked to-do list.
Overcommitting to either side throws us off course, just in different ways.
Too much planning leads to perfectionism and paralysis. We polish maps instead of walking trails—forgetting that clarity lives in the walking, not the watching. We become cartographers of intentions, map-makers of dreams. Afraid to step into The Forest, where the terrain begins to twist beneath our feet.
But too much execution is just as dangerous. We move fast but directionless, mistaking a flurry of steps for real movement. We burn energy on everything except what truly matters. We confuse motion for progress, noise for clarity. The result isn’t progress. It’s exhaustion.
The Rhythm of Engagement Is a Cycle, Not a Sequence
The real issue with these two separate worlds cuts deeper. It’s not just that we treat planning and execution as distinct—we treat them as sequential. We assume we can plan first, then execute. Clear the clutter, then face the fog. But this tidy division is an illusion. Life rarely grants us that kind of order. Plans leak. Execution bleeds back into strategy.
Like in Stranger Things, cracks begin to form—rifts in the walls between the aboveground and the Upside Down. And through those rifts, everything starts to interfere. The clean world of planning gets distorted by the pressure of action. The mess of execution echoes backward into the design. The line doesn’t hold. The real terrain refuses to match our sketches.
If we look closely, we realize the aboveground and the Upside Down aren’t separate worlds at all. They’re not distinct phases. They’re modes—like inhaling and exhaling. They’re not the same, but they belong together, like two sides of the same coin. They loop, blur, and merge into one another.
Planning isn’t a one-time launchpad—it’s an ongoing dialogue with possibility.
And execution isn’t just doing—it’s sensing, listening, adjusting. It’s discovering what’s real. And feeding that back into the evolving plan.
Where clean is ideal, dirty is real. And real plans are revealed by doing.
That back-and-forth rhythm—between clarity and chaos, between map and mud—is what I call engagement with the work. It’s the moment you stop theorizing and start exploring. When you peer into the Upside Down not just to glance at the monsters—but to understand them. And only then does your plan begin to matter.
The HOW Emerges Through Motion (Make a WHAT Plan)
In a VUCA world—volatile, uncertain, complex, ambiguous—the HOW rarely shows up in advance. In fact, the eventual HOW might not even exist yet.
In a world like this, the HOW reveals itself through movement. Terrain first. Map second.
That’s why in my work, I advocate for a declarative approach to productivity. Instead of scripting every step, we name the mountain. We define the WHAT. Then we let the HOW emerge through motion, feedback, and friction.
Because a rigid HOW dies fast. And flexible WHAT endures.
To be clear—HOWs aren’t ignored in this system. They’re discovered. Shaped in motion, not in meetings. A good plan isn’t perfect—it’s alive.
Another way to say all of this: Make a WHAT plan, not a HOW plan.
Of course, there are times when upfront planning is crucial, especially when navigating a complex situation, dealing with critical deadlines, or when coordination with others is essential. But most of the time, especially in your personal projects, you don’t need the full path ahead. You just need to be directionally correct. In such cases, a strong WHAT acts like a compass, not a turn-by-turn navigation system. It won’t provide you with every detail, but it will draw you toward what truly matters.
And if you really find yourself stuck on a HOW, shift the question. Ask yourself instead:
What needs to happen next?
Because most HOWs aren’t puzzles to solve in advance. They’re just a series of smaller WHATs—waiting to surface, one step at a time. You don’t need to map them all up front. You need to move forward honestly and let each next step reveal itself when it’s ready.
Execution Isn’t a Step. It’s a Rhythm.
Execution isn’t a single act. It becomes a rhythm. A relationship with the unknown. Not blind hustle, but tuned responsiveness. Not blueprint compliance, but feedback-driven engagement. A kind of resilience that doesn’t come from control, but from connection.
So, yes—planning is clean and execution is dirty—but that’s not a warning; it’s an invitation.
We don’t grow through spotless performance. We grow by learning how to show up without it, by dancing with the mess. By committing—and then letting the friction, tension, and surprise teach us how to honor that commitment. Growth and progress don’t come from having it all figured out. It comes from returning—again and again—to the work that matters, despite not having it all figured out.
Unlike the protagonists in Stranger Things, we’re not trying to shut the Upside Down away. We need to enter it, without losing touch with the surface.
The Upside Down of Doing isn’t the enemy. It’s the proving ground.
The real trick isn’t choosing one world over the other. It’s learning to move gracefully between them. To know when to zoom out and reflect—and when to stop sketching and step boldly into the fog.
Final Thought
This dance isn’t linear.
It’s recursive. Cyclical.
A rhythm of vision and feedback.
Imagination and engagement.
So here’s what I’ll leave you with:
Expect the mud.
Strength, clarity, and trust aren’t born in clean rooms.
They’re forged in the dirt.
Planning and execution aren’t stages—they’re two ways of moving forward.
Execution isn’t the second step of a process. It’s the continuation of a dialogue—with your work, with the world, and with yourself.
Progress lies in the ability to shift between the surface and the Upside Down—frequently, fluidly, and with grace.
Planning is clean. Execution is dirty.
Progress is made by choosing a direction with heart—and then taking the next, beautifully messy step.
If this piece spoke to you, please crack that ❤️ button.
And if you want to go deeper, check out my book Scale Smart. It goes deeper into declarative planning, feedback-driven systems, and how to stay close to what matters—without getting lost in the map.