Introduction:

“Business happens in real time. Planning happens before it.”

If you’ve ever felt like entrepreneurship turns into a nonstop series of problems you didn’t see coming, you’re not behind—you’re just building without a buffer. Most founders don’t fail because they’re lazy or incapable. They fail because they’re forced to make high-stakes decisions under pressure… without a plan they trust.

In this episode of The Strategic Thinkers Podcast, I sat down with Geoffrey Kent, a seasoned entrepreneur and strategist who has helped founders think through business models, risk, scaling, and the decisions that quietly shape whether a company survives. Geoffrey has a way of explaining complex business realities without talking over people—or dumbing anything down.

This article pulls one core thread from our conversation: business planning isn’t paperwork—it’s prevention. You’ll see why skipping this step creates avoidable chaos, how planning builds “mental muscle memory,” and one simple action you can take today to build a plan that actually supports you when things get real.

Real Story (One person, one action, one result)

Geoffrey shared a moment from his corporate career that put a spotlight on a truth many high-performing professionals feel—but can’t always name.

He had accomplished something no one else in the organization had ever done. The company asked him to present how he did it. So he prepared, delivered the presentation, and laid out the thinking behind the result. He walked people through the framework and the strategy.

Afterward, his boss’s boss pulled him aside and said something that didn’t sound like praise at first:

“You need to start looking for another job.”

Geoffrey was confused. He hadn’t broken a rule. He hadn’t failed. He’d done everything right. That’s when his leader explained the real issue:

“You just set the bar so high no one can get to it… People are going to collude to undermine your career because every time they look at you, they see what they can never become.”

That’s the part most people never hear out loud.

One action. Geoffrey didn’t shrink himself to fit the system. He made a decision: he needed an environment where his way of thinking wasn’t a threat—it was the product. Where seeing problems early wasn’t “rocking the boat,” it was the value clients paid for.

So he leaned fully into entrepreneurship—the environment where uncertainty is constant, but strategic foresight is rewarded.

One result. He described what happened after that shift with a clarity that matters for anyone trying to build:

When you stop optimizing for approval and start optimizing for outcomes, your thinking becomes an asset. You’re no longer punished for noticing blind spots. You’re paid for it.

And that connects directly to business planning: planning isn’t about being “formal.” It’s about building an operating manual for an environment that will not slow down to accommodate your stress.

The Truth (why it matters)

Here’s the truth most people don’t want to admit until they’ve lived it:

If you don’t plan in calm moments, you’ll be forced to decide in crisis moments.

Geoffrey framed business planning in a way that removes the usual resistance. He compared it to building a home: nobody buys random materials and starts hammering. They hire an architect. They create a blueprint. The blueprint dictates what you need—and how you’ll build it.

A business plan works the same way, especially when you treat it as an operating manual, not a document for someone else.

That matters because entrepreneurship doesn’t give you generous timelines for decision-making. Geoffrey said it plainly:

“Business happens in real time… you don’t have a lot of time to make decisions when you’re in the thick of building your business.”

So what does planning actually do?

It builds what he called mental muscle memory. Like a basketball player taking a thousand shots from the same spot so they don’t have to think during the game—planning trains your mind so when something happens, you can respond without panic.

That’s the difference between:

Preventative measures (you have bandwidth to address blind spots), and

Reactionary solutions (you’re scrambling, patching, and hoping nothing else breaks)

And when founders skip planning, the first thing that usually breaks isn’t motivation—it’s financial clarity. Cash flow surprises. Pricing gaps. Underestimating what it takes to deliver. Not understanding how many clients you need—or what you need to charge—to stay alive.

Skipping steps also makes the fall steeper. As we said in the conversation: once your name is out there, the stakes change. It’s not just “a project.” It’s reputation, trust, and momentum.

And here’s a related blind spot Geoffrey called out that matters early:

“Don’t ever tell an investor you don’t have competition.”

Why? Because it signals either you didn’t research—or you’re not being honest. But more importantly, it misses the deeper point:

Competition is market validation. It’s proof people want the outcome. Your job isn’t to pretend you’re alone. Your job is to understand what makes you distinct and why a specific customer should choose you.

Which brings us to the simplest, most grounding principle Geoffrey shared:

“You only need one customer to figure out what it takes to succeed.”

One customer who pays. One customer who uses it. One customer who can tell you why they bought, how it helped, and what would make it better. That’s not theory. That’s your first real dataset.

What To Do (one clear everyday action)

Write a “Plan A / Plan B” page—then pressure test it with one real customer.

If “write a business plan” feels heavy, start smaller—but start smarter.

Create a single page with four sections:

1) What am I building?
One sentence. No fluff. What is the business and who is it for?

2) What does success look like?
Not vague. Define the outcome you’re building toward (revenue, lifestyle, scale, impact, or transferability).

3) Plan A: What needs to go right?
List the 3–5 assumptions your business relies on (pricing, customer type, delivery capacity, lead source).

4) Plan B: What if one assumption is wrong?
Write one alternative move for each assumption. Not ten. One.

Then do the part most people skip: talk to one real customer or buyer-type person and ask:● What problem are you actually trying to solve right now?● What would make you pay for this?● What would stop you from paying for this?● How would you describe this problem in your own words?

This is how planning stops being “paperwork.” It becomes prevention with feedback.

You’re building a plan that holds up in the real world—before the real world forces your hand.

Conclusion

The goal isn’t to predict everything. The goal is to avoid being surprised by what was predictable.

Business planning, done right, isn’t a formality. It’s a way of thinking that turns chaos into choices. It gives you a working map when the terrain changes—and it keeps your confidence grounded in reality instead of hope.

Geoffrey put it in a way entrepreneurs can actually use: you won’t think of 100% of what could happen. But if you think through 95% and you’ve got a Plan A and Plan B, you’re operating with an advantage most people never build.

If you’ve been building on instinct alone, this is your permission to slow down long enough to see what you’re really building—and whether it can actually hold your goals.

And if you want guidance while you build it, Geoffrey’s created an environment specifically for founders who want clarity without hustle culture.
Ready to build the right business the right way—before the market forces a reset?
Join Geoffrey Kent’s Entrepreneur Academy (subscription-based mentoring community):
https://hi.volley.app/land?tk=KAyRbBp2hgYuCMVbwyqDcW-tk&utm_source=strategic-thinkers-podcast&utm_medium=article&utm_campaign=entrepreneur-academy

Entrepreneur Academy is built for founders who want clarity, leverage, and precision growth—and who are done guessing their way forward.

About the Guest

Geoffrey Kent is an entrepreneur and strategic advisor who helps founders think clearly about business models, risk, scaling, and long-term outcomes. His approach is direct, practical, and built around helping entrepreneurs plan before pressure hits—so they can build with intention instead of reacting in real time. He’s also the creator of Entrepreneur Academy, a private mentoring community designed for founders who want clarity and momentum without hustle culture.
Connect: Entrepreneur Academy (Volley) — https://hi.volley.app/land?tk=KAyRbBp2hgYuCMVbwyqDcW-tk

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