You’re Allowed to Outgrow the Version of You That Started the Business

Spending some time in Nashville had me thinking about reinvention.

Maybe it's because this is a city filled with people who came here carrying a dream. Some arrived with talent nobody knew about yet. Some probably heard “no” hundreds of times. Some became successful. Others changed directions entirely.

That feels a lot like entrepreneurship.

When you start a business, you become whatever the business needs.

You're the salesperson because there isn't a sales team.

You're customer service because nobody else is answering.

You're marketing, accounting, operations and sometimes the janitor.

You learn to survive.

And if you do it long enough, those survival skills become part of your identity.

That's where things get interesting.

Because the person capable of starting your company isn't always the person capable of taking it where you want it to go next.

And that's okay.

I don't want to be the same businessman I was five years ago.

I hope I'm not.

I hope I make decisions differently.

I hope I recognize bad opportunities faster.

I hope I'm slower to react emotionally and faster to act when the answer is obvious.

I hope I understand money better.

People better.

Contracts better.

Leadership better.

My own weaknesses better.

Experience is expensive. You should at least get something for what you paid.

I've made decisions in business that I would never make today.

I've trusted situations I would evaluate differently now. I've spent money differently. I've taken on things I probably should have declined. I've also taken chances that looked crazy at the time and became some of the best decisions I've made.

I don't look at all of that as contradiction.

I look at it as tuition.

The goal isn't to build a career without mistakes. The goal is to stop paying tuition for the same class.

That distinction matters.

Sometimes your old strengths become your new limitations.

This is something I don't hear discussed enough.

Maybe hustle built your company.

There was a season when answering the phone at midnight, saying yes to everything and personally making sure every detail was right was exactly what you needed.

But what happens when there are employees?

Departments?

More customers?

Bigger contracts?

More money at risk?

You can't solve a 50-person company's problems with the habits you developed when it was just you and a laptop.

At some point, hustle has to become leadership.

Instinct has to become process.

Being involved in everything has to become knowing where your involvement actually matters.

And maybe the hardest transition of all:

You have to become comfortable watching other people do things differently than you would have done them.

Not worse.

Different.

That one has taken some learning for me.

Your company will usually wait for you.

I've started believing businesses rarely grow very far beyond the owner's personal development.

You can buy software.

Hire consultants.

Run more ads.

Open another office.

Hire more people.

But eventually the business catches up to the limitations of the person leading it.

If you avoid difficult conversations, the company eventually feels it.

If you don't understand your numbers, eventually the company exposes it.

If you can't delegate, eventually growth becomes exhausting.

If your ego needs to be involved in every decision, talented people eventually stop making decisions.

If you can't admit when something isn't working, you'll keep financing your own mistake.

That's why some of the most important work you can do on your company doesn't happen at the company.

It's becoming better at being the person responsible for it.

Here's a question I've started liking more than goal-setting.

Instead of only asking:

“What do I want my company to look like three years from now?”

Ask:

“What would have to be true about me for that company to exist?”

That's a very different conversation.

If you want a company doing $20 million a year, what does the person running that company know that you don't know today?

What do they no longer spend time doing?

What kind of people have they learned to hire?

What numbers do they understand?

What problems don't scare them anymore?

What do they say no to?

How do they handle pressure?

How do they treat people when things go wrong?

Now you've got something useful.

Instead of only building toward the future company, start practicing becoming the future owner.

Don't be embarrassed by an old version of yourself.

This is where I think entrepreneurship can become unnecessarily heavy.

People look backward and cringe.

At the old website.

The first office.

The cheap business cards.

The terrible logo.

The tiny customer.

The mistakes.

The way they used to talk.

The amount of money they thought was “a lot of money.”

I actually think there's something beautiful about it.

You were doing the best you knew how to do with the information, resources and experience you had at the time.

That version of you got you here.

Respect him.

Just don't make him CEO forever.

That's the part.

You don't owe your old habits permanent employment.

And don't move the finish line so often that you forget what happened.

This is something I'm trying to remain conscious of in my own life.

Entrepreneurs are incredibly good at normalizing answered prayers.

The first big client was once unbelievable.

Then it became normal.

The office you dreamed about becomes where you complain about meetings.

The revenue number you once wanted becomes the number you're disappointed wasn't higher.

The places you once dreamed about visiting become another flight on the calendar.

The opportunities that would have blown your mind ten years ago become Tuesday.

Be careful with that.

Ambition is a gift.

But ambition without gratitude can make an incredibly blessed life feel strangely insufficient.

I'm in my 30s. I still have enormous things I want to build. I still feel like I'm early in the story.

But I also want to be intelligent enough to recognize that some of the things surrounding me today were once things I was working toward.

I don't want to miss them because I'm too busy staring at the next mountain.

Maybe you're in an awkward chapter right now.

Your business might not look like you thought it would.

Maybe revenue is down.

Maybe you're changing industries.

Maybe an employee left.

Maybe a partnership didn't work.

Maybe you're rebuilding.

Maybe you're doing well financially but you've realized you're no longer excited about what you've built.

Don't automatically assume something has gone wrong.

Sometimes growth feels strange because your old identity is becoming too small for where you're going.

There's nothing wrong with changing the plan.

There's nothing wrong with becoming more selective.

There's nothing wrong with deciding money isn't worth a particular headache anymore.

There's nothing wrong with building differently at 40 than you did at 25.

And there's definitely nothing wrong with admitting:

“I know more now.”

That's what experience is supposed to do.

Nashville made me think about how many songs probably existed in completely different versions before anybody ever heard the one that mattered.

Business is like that.

There are drafts.

Bad versions.

Rewrites.

Things that never get released.

Unexpected hits.

And occasionally, something you've been working on for years finally sounds the way you always heard it in your head.

Keep building.

Keep learning.

Change what needs changing.

Keep the parts of yourself that got you through the hard years, but don't be afraid to leave behind the habits that belonged to them.

And every once in a while, look around.

You may still have a long way to go.

But don't disrespect the distance you've already traveled just because you haven't reached the destination yet.

That's worth celebrating too.

Writing from Nashville, Tennessee.

— Corey Flores
Founder, Flores Marketing Firm