StartUp Founders: Planning vs Preparation
Dear Reader,
Your pitch deck promised X. Your roadmap outlined Y. But today, you’re building Z. And that’s exactly as it should be.
Founders write plans as if startups operate in predictable environments. They don’t. They operate in constant chaos.
Planning creates direction. Preparation creates options. You need both, but most founders over-index on the former and under-invest in the latter.
Your plans are fantasies until they collide with reality because the world rarely reacts how you expect….
We’ve all seen those founders with gantt charts, with detailed dependencies, overly complete notion sites, OKR maps formatted for investors. Looks so impressive, that must be the secret to what a great founder looks like, right?
Nope. When you have zero clue what’s around the next corner, it’s a waste of f’n time.
Planning assumes you know how everything is going to play out. Predictable, known, like a vacation. This street, this car, this hotel. We can plan because the constructs won’t change.
Preparation, however, assumes chaos. And chaos is almost always where the money hides.
đź“Ś Planning is how you want things to go. (structure)
​📌 Preparation is how you move through what you can’t predict. (resilience)
Preparation is NOT the fallback, it’s the entire framework.
Preparation is Pattern Recognition. Prepared founders don’t just react faster. They notice faster. The ability to actually see the signals, it’s attunement, its training to see the week signals. That’s the edge. The compounding.
This isn’t about hating plans, I’m NOT making a binary argument: Planning, bad – Preparation, good. You should plan. You need to plan.
Planning is how you reduce unstructured chaos, align the team, and move with intention in the same direction.
This issue is when founders start treating the plan as reality, instead of what it actually is, a best guess.
“Luck is what happens when preparation meets opportunity.” — Seneca
Preparation kicks in as soon as you start executing. It’s not a rejection of planning, it’s what makes planning useful under pressure.
I’m making this distinction between three related but fundamentally different things:
- PLAN: A static tool. A snapshot of what you think might happen.
- PLANNING: The process of organizing your thinking to align and get started.
- PREPARATION: Your ability to respond, adapt, and capture value when reality shifts.
Founders often think they’re choosing between planning and winging it. But that’s not the real tradeoff. You should plan. You should organize your thinking. Structure is good. Just don’t confuse that for being ready.
Planning is how you organize your thinking.
Preparation is how you condition your response.
Preparation is the muscle that you need to train, the one that really matters.
Plans MUST Break. Always.
Plans rarely survive that first contact with reality. Your investor doesn’t actually believe your pitch deck; they just want to see how you think, how you articulate, how you prioritize, how you organize.
You’re not building in a controlled environment. You don’t have perfect information. You’re making a thousand small bets on incomplete data.
So why do so many founders over plan? Because it feels like control.
The illusion of control is more dangerous than the admission of chaos.
Plans also assume some level of linearity that just does not exist.
Great founders know a plan is a hypothesis at best. So yes, have a plan, love a plan, as a baseline. Plan to learn, prepare to adapt.
You Are Not a General. Generals get time to plan. They have intel, resources, chains of command. You have none of that, it’s real time, limited cash, limited data, and everyone looking to you for direction.
Plan if you want to feel smart. Prepare if you want to be smart.
What Preparation Actually Looks Like
Preparation doesn’t mean you don’t have direction. It means you’ve built enough awareness and flexibility to adjust without chaos.
You still set guardrails on how you make decisions, how you think about your market, what you know, and where you think you’re going. And yes, you plan the immediate steps.
But preparation is:
🔥 Your team’s ability to hear, sense, pivot, and move.​
🔥 Your capacity to adapt without panic.​
🔥 Knowing how to respond, not needing to be right.
It’s readiness for surprise, the surprise you want, the surprise you are waiting for.
Four Filters I Consistently See….
1. Clarity on how you make decisions. Not what the decision is.​
Prepared founders don’t say, “Here’s what we’re building next.”
They say, “Here’s how we decide what to build next.”
2. A team that acts without waiting for permission.​
Prepared teams know the mission, the standard, the pace.
They ship, fix, and respond before the standup even starts.
3. Feedback loops that actually shift behavior.​
Data is not collected for data sake or slides.
They hear hesitation in a call today and change “something” tonight.
4. Conditioned for chaos, not surprised by it.​
They expect the weird stuff.
The platform crashing. The lead ghosting. The legal curveball.
It still hurts. But it doesn’t kill.
The Planning vs. Preparation Gap
This isn’t theory. The gap between planners and preparers shows up in how founders handle the exact same situations.
Planning is theory. Preparation is muscle memory. And in startups, muscle memory beats theory every time.
So with that….
1. Murphy’s Law: “Anything that can go wrong, will go wrong.”
The only founders who survive are the ones who expect chaos. Not as a pessimistic worldview, but as a practical reality. They’re not surprised by it and it doesn’t scare them.
2. The OODA Loop: Observe. Orient. Decide. Act.
Developed for fighter pilots in combat. It’s about decision velocity. Planning gives you a script. Preparation gives you speed. You don’t need to predict the future. You need to out-decide it.
3. Antifragility: Some things get stronger from disorder.
This is Taleb’s concept, and it’s perfect for startups. You shouldn’t just be able to survive volatility. You should get better from it.
Prepared teams get sharper with each unexpected turn, with each new data point, each failure a stepping stone.
TLDR; Don’t just write a plan. Train for the terrain.
As always, if I can be of service, feel free to grab time.
LFG.
— James