Why I’m Documenting the Messy Middle

Handwritten project questions in a notebook beside a laptop.

A couple of weeks ago, I was sitting on my couch wondering what in the hell I was doing.

I’d been working with Claude, trying to get all these AI agents to build things, fix problems, and handle different parts of my businesses.

I’d been throwing out ideas all night.

Build this. Send an agent there. Fix that. Start another one.

I was moving fast.

And for a while, I thought things were going pretty well.

The agents were working. Tasks were getting assigned. Things were happening.

At least that’s what it looked like.

Then I started checking what had actually been done.

And almost nothing was working the way I thought it was.

I had spent hours building what appeared to be a very efficient system for creating more problems.

An impressive accomplishment, really.

I sat there feeling defeated.

I was frustrated, overwhelmed, and wondering whether I was getting in over my head.

Because here’s the thing.

I’m trying to build something I haven’t built before.

I’m learning as I go.

And sometimes that means spending an entire night figuring out what you did wrong.

That’s the part of the story I want to document.

Not just the finished businesses.

Not just the things that work.

I want to show you what happens in the middle.

Nobody really shows you this part

Think about how people usually tell business stories.

They start with the struggle.

Then they skip ahead to the success.

One minute somebody is working out of their garage.

The next minute they’re standing in front of a nice house telling you how they built a million-dollar company.

And somewhere between those two scenes, apparently, everything just worked out.

Convenient.

But what happened during those years?

How many times did they get something wrong?

How many ideas didn’t work?

How many nights did they spend trying to solve a problem they thought they’d already solved?

That’s the part I find interesting.

Because that’s where most of us actually are.

We’re in the middle of building something.

We don’t know exactly how it’s going to turn out.

And we’re trying to make the best decisions we can with what we know today.

I don’t want to wait until I have some perfect success story to talk about what I’m learning.

I’d rather show you what happens while I’m learning it.

The problem wasn’t just the AI

When I started looking at why those agents weren’t doing what I wanted, I realized something uncomfortable.

A lot of the problem was me.

I was giving instructions too quickly.

I wasn’t being specific enough.

I didn’t have clear procedures for what the agents were supposed to do.

And I hadn’t defined what finished work actually meant.

So I was getting work back that didn’t match what I expected.

Now, I could have blamed the tools.

And believe me, I was tempted.

It’s much easier to blame a computer than admit you’ve spent six hours giving it bad directions.

But that wouldn’t have fixed anything.

I needed to change the way I was managing the work.

And that’s a lesson that applies to a lot more than AI.

If you’re running a business, you have to teach people how you want things done.

You need clear instructions.

You need a way to track the work.

And you need to know what finished looks like.

Otherwise, everybody can stay busy all day without actually moving the business forward.

I’ve seen that happen with people.

Now I’m learning how easily it can happen with AI.

Apparently, technology has found a way to automate confusion too.

You don’t have to know everything before you start

This is one of the biggest things I want people to understand.

You don’t have to be an expert before you begin building something.

You do need to learn.

You need to pay attention.

And when something goes wrong, you need to figure out what happened.

But you don’t have to sit around waiting until you know everything.

If I’d waited until I understood every part of AI, automation, software, marketing, and business operations, I wouldn’t have started any of this.

I’d still be researching.

Probably with forty-seven browser tabs open.

And somehow I’d have found three more businesses I wanted to start.

That’s part of the problem with having a lot of ideas.

It’s easy to get excited about what something could become.

It’s harder to slow down and build the process that makes it work.

That’s what I’m practicing now.

Instead of just throwing another idea into the system, I’m trying to ask what needs to happen first.

What information does the person or agent need?

What does a finished result look like?

How will we test it?

And how do we make sure the next person can follow the same process?

Those aren’t exciting questions.

But they’re the ones that make the work repeatable.

What the Army taught me about preparation

When I was in the Army, we trained on procedures over and over.

You didn’t practice something once and assume you’d remember it forever.

You repeated it.

You learned your role.

You learned what the people around you were responsible for.

And you practiced what to do when things went wrong.

There’s a reason for that.

When you’re under pressure, you don’t always have time to stop and think through every step.

Training gives you something to fall back on.

It doesn’t remove fear or make everything predictable.

But it gives you a process when things get difficult.

I think about that now when I’m building businesses.

What happens if I’m not available?

What happens when somebody gets sick?

What happens when a customer needs help and the person who normally handles it isn’t there?

Does the business know what to do?

Or does everything stop until somebody can reach the owner?

That’s the kind of problem I’m trying to solve.

I want the systems to work even when I’m not sitting there watching them.

Not because I don’t care about the business.

Because I care about what the business is supposed to give me.

I’m not building all this just to work more

I’ve spent a lot of nights working late.

Trying to finish projects.

Trying to get systems running.

Trying to turn ideas into something real.

And sometimes, even after working all night, I look at what I finished and feel like I didn’t get enough done.

Meanwhile, there’s something else happening.

My kids are growing up.

Life is moving.

And I’m spending time sitting in front of a screen trying to get another piece of software to do what I asked.

That’s when I start asking myself whether I’m building the life I want or just creating more work.

Because I don’t want to spend the next ten years telling myself I’ll have more time later.

Later has a habit of staying later.

There’s always another project.

Another problem.

Another opportunity.

And if I don’t build the business differently, I can keep chasing those things forever.

That’s not what I want.

I want to build businesses that support the life I’m trying to create.

I want to travel.

I want to spend more time with my kids.

I want to get outside and experience things.

And I want to build things because I enjoy building them, not because every part of my life depends on me working all the time.

That’s the real experiment.

I want you to see the mistakes too

Ten years from now, somebody might read these articles and see how everything turned out.

Maybe some of these businesses will be successful.

Maybe some won’t.

Maybe we’ll build tools that help a lot of people.

Maybe we’ll find out that some of our ideas weren’t worth the trouble.

I don’t know yet.

But I want the record to show what actually happened.

What we tried.

What failed.

What we changed.

And what we learned along the way.

Because if you’re building something and you feel overwhelmed, I want you to know that the feeling doesn’t mean you have to quit.

Sometimes it means you’re trying to do too much.

Sometimes you don’t have a clear plan.

Sometimes the process you’re using just doesn’t work.

And sometimes you’re tired and need to stop for the night.

That last one has taken me a while to learn.

Not every problem needs to be solved at two in the morning.

Although I’ve certainly conducted enough research into that theory.

The point is to pay attention to what’s happening.

If something isn’t working, don’t just keep doing it harder.

Figure out why.

Then change what needs to change.

The goal is to build something you can repeat

One thing I’ve been thinking about is how successful businesses create systems that other people can follow.

Take McDonald’s.

You can go to different locations and recognize the same basic products and processes.

That’s part of the power of having a repeatable system.

You don’t need the founder standing in every restaurant explaining how to make a hamburger.

The company has procedures, training, and standards.

Now, I’m not trying to build a fast-food empire.

I have enough going on without adding a drive-through.

But I want that same basic principle in my businesses.

Clear instructions.

Repeatable work.

People who know what they’re responsible for.

And systems that don’t depend on me remembering every little thing.

That’s what I’m trying to build with AI too.

Not a collection of tools that look impressive.

A system that actually works.

We’re building the story right now

I don’t know exactly where The Wild Business Experiment is going to take us.

I have ideas.

A lot of them.

Probably more than I should be working on at once.

But I’m learning to slow down, define the work, and build things that can keep running without me having to manage every step.

Some days we’ll make progress.

Some days we’ll find out something we thought was finished doesn’t work.

And some days I’ll probably sit on that couch again wondering what in the hell I got myself into.

That’s okay.

I’m not trying to make this look perfect.

I’m trying to make it real.

And I want you to see that you have more control over the life you’re building than you might think.

You can change your process.

You can learn something new.

You can start again when something doesn’t work.

You don’t have to have the whole thing figured out today.

You just have to keep learning and make the next decision a little better than the last one.

That’s what I’m doing.

We’re practicing.

We’re building.

And we’re documenting the whole thing.

Later, we’ll have the story.

Go be wild.

—Michael


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