I Have a Plan, But I'm Making It Up

The Air Force taught me to follow procedures exactly.

Until the moment you need to ignore them completely.

Sounds like a contradiction, right?

Twelve years of military discipline, regulations thick as phone books, everything spelled out to the letter.

But here's what they don't tell you in basic training: sometimes following the rules will get people killed.

When the Rules Don't Fit the Mission

I was a Fuels Specialist. My job was making sure jet fuel got where it needed to go, when it needed to be there.

Sounds simple until you're standing on a flight line at 2 AM with a MedEvac bird full of wounded soldiers and Marines, and your supervisor is telling you that you can't fuel it.

"They haven't followed proper procedures," the Master Sergeant said. "No exceptions."

The aircrew was frantic. They had critical patients who needed to get to a trauma center immediately. Every minute we stood there arguing about paperwork was a minute closer to someone's kid not making it home.

The regs were clear. Fuel procedures existed for good reasons: safety, accountability, chain of custody. But the mission was also clear: get these wounded warriors to medical care.

My troops looked at me. I looked at the aircraft full of people whose lives hung in the balance.

We fueled the bird.

The Aftermath

The MSgt was furious. Threatened to write us all up for insubordination. Said we'd violated every regulation in the book and put the entire operation at risk.

He wasn't wrong about the regulations. We had ignored proper procedures. But when the Wing King (a.k.a. the base commander) heard about what happened, something interesting occurred.

We got awards. The MSgt got a conversation about understanding when rules serve the mission and when they don't.

The commander's message was simple: "Rules exist to support the mission, not the other way around."

What This Taught Me About Real Planning

Military training gives you two things that seem contradictory but actually work together perfectly:

First, you learn systems inside and out. You know the procedures, understand the reasons behind them, practice them until they're muscle memory.

Second, you learn when to break those systems intelligently.

The key word is intelligently.

We didn't just ignore the MSgt because we felt like it. We understood the spirit of the regulations, weighed the real risks against the mission requirements, and made a calculated decision.

That's not chaos. That's adaptation.

We adapted. We overcame.

How This Shows Up in My Creator Work

Building a business feels exactly like being on that flight line. You've got your procedures: content calendars, posting schedules, marketing strategies.

Everything planned out, documented, ready to execute.

Then reality hits.

The algorithm changes. Your email platform crashes during a product launch. A global pandemic shuts down the economy. Your perfectly planned strategy suddenly doesn't fit the situation.

The old me would have either rigidly stuck to the plan (and watched it fail) or panicked and thrown everything out (and lost all progress).

You learn quickly that no plan survives contact with the enemy.

The Air Force taught me a better way.

The Framework That Actually Works

When your plan hits reality, ask these questions:

What's the actual mission here? Not the procedure, but the purpose. Are you trying to help people solve a real problem? Keep that front and center.

What are the real risks? Not the imaginary ones. What actually happens if you adjust course? Usually less than you think.

What would intelligent adaptation look like? Don't abandon everything. Adapt the tactics while keeping the mission intact.

What can you learn from this? Every plan that breaks teaches you something about building better plans.

The Real Plan

I still plan obsessively. Content strategies, product roadmaps, launch sequences. All documented, all thought through.

But I hold those plans differently now. They're frameworks for decision-making, not rigid scripts to follow regardless of circumstances.

When my newsletter platform went down during a product launch, I didn't panic. I adapted. Used social media, sent personal emails, found another way to serve the mission.

When Medium changed their algorithm and my traffic dropped 60%, I didn't abandon writing. I adapted. Focused more on my newsletter, tried different topics, found new ways to reach people.

The plan is never really the plan. The plan is what prepares you to make good decisions when everything changes.

Simple. Repeatable. Human.

Here's what I learned on that flight line: the best systems are designed to bend without breaking. The best procedures serve people, not the other way around.

Whether you're fueling aircraft or building a creator business, the principle is the same. Have a plan. Know why it matters. Be ready to adapt when it doesn't fit.

Because it won't always fit. And that's exactly when planning pays off.

What plan are you holding too tightly right now?