The Messy Middle: The Part of Entrepreneurship People Rarely See

The part people rarely see is everything that happens between starting and succeeding.

People usually see the beginning.

They see the announcement that you have started a business. They see the excitement, the new website, the logo, the first client, the first launch.

Then, if you are fortunate enough to build something successful, they see the result.

They see the revenue.

They see the team.

They see the growth.

They see the opportunities that come with having built something that works.

What they often do not see is everything that happened in between.

For me, that middle has been messy.

Very messy.

There have been incredible moments, but there have also been moments where I have genuinely questioned what I was doing.

I have trusted the wrong people.

I have made decisions that, looking back, I would never make today.

I have lost more than $100,000.

I have built products that did not work.

I have spent months working on ideas that eventually had to be abandoned.

I have started again more times than I can remember.

And I have failed more than once before finally getting something into the market that worked.

That is entrepreneurship too.

## You learn some lessons the expensive way

One of the biggest lessons I have learned is that not every lesson comes from a book, a mentor or a business course.

Some lessons cost you money.

Some cost you time.

Some cost you relationships.

And some cost you a piece of yourself before you really understand what they were trying to teach you.

I have trusted people because I wanted to believe that they had the same intentions I did.

I have entered business relationships believing that everyone was coming to the table with the same level of integrity, commitment and responsibility.

That has not always been the case.

There have been times where I have been taken for granted.

There have been situations where my willingness to give people the benefit of the doubt worked against me.

There have been moments where I should have asked harder questions, looked more closely at the numbers, protected myself better or walked away earlier.

At the time, those experiences were painful.

Today, I can see how much they changed me as a business owner.

I am still willing to trust people, but I understand that trust and good governance are not the same thing.

I have learned to verify.

I have learned to document.

I have learned to ask uncomfortable questions.

I have learned that being kind does not mean being naive.

And I have learned that protecting the business is part of protecting everyone who depends on it.

## There were times I did not know how I would make payroll

There is a particular kind of pressure that comes with having people depend on the business you have built.

It stops being just about you.

There have been moments where I have looked at the bank account and genuinely not known how we were going to make the next payroll.

That is probably one of the hardest experiences to explain to someone who has never run a business.

You know exactly when wages need to be paid.

You know people have mortgages, rent, children, bills and lives outside of work.

And you know that behind those numbers are real families depending on you to somehow figure it out.

There were times I didn't have the answer.

There was no secret reserve sitting somewhere.

No guaranteed money arriving tomorrow.

I simply had to keep going.

Call another person.

Follow up another opportunity.

Find another solution.

Look at the numbers again.

Make another decision.

Hold onto hope for one more day.

And somehow, something would shift.

A payment would come through.

A new client would arrive.

An opportunity would open.

We would find a way through.

I do not say that lightly because I think entrepreneurship can sometimes be romanticized in ways that are dangerous.

Hope by itself is not a business strategy.

There were practical decisions behind those moments too.

We had to make changes.

Reduce expenses.

Negotiate.

Restructure.

Work harder.

Sometimes admit that something we were doing simply wasn't working.

But there was always a small piece of me that believed we would find a way through.

That belief carried me through some very uncomfortable seasons.

## Building also means admitting when something isn't working

One of the hardest things I have had to learn is that persistence does not always mean continuing with the exact same idea.

Sometimes persistence means changing it.

Sometimes it means throwing months of work away.

Sometimes it means admitting that the thing you were convinced would work simply isn't working.

I have built things that I loved and still had to let them go.

I have invested money into ideas that never produced the outcome I expected.

I have launched things that did not get the response I thought they would.

There is a strange tension that comes with being a founder.

You are constantly told to believe in your vision.

To stay committed.

To ignore the doubters.

But you also have to be humble enough to listen when the market is telling you no.

That balance is difficult.

There is a difference between giving up too early and continuing with something simply because your ego does not want to admit that it needs to change.

I have had to learn the difference.

Sometimes the smartest thing I have done has been changing direction.

Starting again.

Building version two.

Then version three.

Trying something different.

Listening more closely.

Taking the lesson and leaving the failed idea behind.

There are things I am working on today that took several attempts before they ever reached the market properly.

From the outside, someone may see the final product and assume there was a neat journey from idea to execution.

There wasn't.

There were false starts.

Bad decisions.

Changes in direction.

People who did not deliver what they promised.

Things that had to be rebuilt.

And moments where I wondered whether I was wasting my time.

Then eventually, something began to work.

## Entrepreneurship has changed me

I started entrepreneurship because I wanted to build a life that gave me more freedom.

What I did not realize was how much entrepreneurship would ask me to change as a person.

I have had to become more decisive.

More comfortable with uncertainty.

More willing to have difficult conversations.

More disciplined with money.

More protective of my time.

More selective about who I allow into certain rooms.

And much more comfortable with being wrong.

That last one has probably been one of the biggest lessons.

When you are the founder, people expect you to have the answer.

But sometimes you don't.

Sometimes your original idea is wrong.

Sometimes someone on your team sees something you missed.

Sometimes the strategy you were certain about needs to change.

I have learned that leadership is not about always being right.

It is about being willing to take responsibility when you aren't.

And then doing something about it.

## So why keep going?

I have asked myself this question many times.

Why continue?

Why take another risk after losing money?

Why build another product after something else did not work?

Why continue carrying the responsibility of a team, clients and families when sometimes it would be easier to choose a quieter life?

The answer for me has always come back to purpose.

There is a reward in entrepreneurship that I find difficult to explain.

And I am not talking about money.

Of course I want the businesses I build to be profitable.

A business needs to make money if it is going to survive.

But money alone would not have carried me through some of the hardest seasons.

The thing that has kept me going has been seeing what happens when something we build genuinely helps somebody.

The communities we have created.

The families who rely on us.

The people who have found employment through our businesses.

The people whose lives are different because something that once existed only as an idea in my head now exists in the real world.

That means something to me.

There is something incredibly rewarding about seeing people depend on something you created.

It also comes with enormous responsibility.

But that responsibility has given me a reason to keep trying.

## The messy middle never completely disappears

I used to think there would come a point where business became easy.

You reach a certain revenue.

You build the right team.

You learn enough.

You become experienced enough.

And somehow everything settles down.

I don't think that anymore.

The problems simply change.

In the beginning, you might be trying to get your first customer.

Later, you are trying to manage a team.

Then you are trying to protect culture.

Then growth creates new problems.

More employees.

More systems.

More risk.

More responsibility.

Then you start another business and suddenly you are a beginner again.

That has been humbling.

There are areas of business where I am incredibly experienced and areas where I still feel like I am figuring things out for the first time.

I think that is why I no longer see the messy middle as something I need to escape.

It is part of building.

There will always be something uncomfortable.

Something uncertain.

Something I do not yet know how to solve.

The difference now is that I trust myself more.

Not because I believe I will always make the right decision.

I know I won't.

I trust myself because I know that if I get it wrong, I can learn.

I can change.

I can rebuild.

I can start again.

## Building. Learning. Losing. Changing. Trying again.

If I had to describe entrepreneurship in a few words, it would probably be those.

Building.

Learning.

Losing.

Changing.

Trying again.

There has been nothing perfectly linear about my journey.

There have been incredible wins and very painful losses.

I have made money and lost money.

I have trusted people and been disappointed.

I have built things that worked and things that failed.

I have been confident and I have been terrified.

Sometimes both on the same day.

But through all of it, I have continued.

Not because I have some extraordinary ability to never be afraid.

Not because failure doesn't affect me.

And certainly not because I always know what I am doing.

I continue because I still believe there is something worth building.

I believe in the communities we are creating.

I believe in the people we serve.

I believe in the families who depend on what we do.

And I believe that some of the best things I will ever build are probably still ahead of me.

That is the messy middle.

It is crazy.

It is hard.

It changes you.

And sometimes it costs you far more than you expected.

But somehow, through all of it, I keep choosing to continue anyway.