What “Stepping In The Arena” REALLY Looks Like For Entrepreneurs — Not Understanding Is Why Nearly EVERY Entrepreneur Will Fail

Cody Dakota Wooten, C.B.C.
5 min readMay 19, 2023

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There is a great quote from Theodore Roosevelt that many people reference.

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better.

The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again; who spends himself in a worthy cause;

Who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

It’s a beautiful quote, inspirational in so many ways, and drives you to want to stand in the Arena!

But it is also extremely romanticized.

It speaks of achievement, triumph, and a worthy cause!

There is a lot of truth to it, but it doesn’t prepare you for the reality that is about to be faced in the Arena.

What Is Required To Get Into The Arena

Preparing to stand in the middle of the Arena is grueling.

Sweat, blood, and dust don’t even begin to express what will happen to you.

You will puke, have snot, tears, and indigestion, and it will continually require that you put stress on your body.

You must “master” your craft, whatever it is, for hours, months, years on end.

No one will care about you during this time, or if you are lucky only the few that are extremely close to you.

However, they likely won’t understand why you are even attempting to go into the Arena.

They may support you, but will never understand what it is you are trying to do.

They may try to give advice, but it won’t help, they have never been where you are trying to go.

This time will be lonely, people will tell you you’re crazy, they will say it will never work, and that you are hopeless.

You’ll need to fight on anyways.

Depression may soon follow, especially if you are listening to others who talk about how “easy” being in the Arena is.

What those people don’t tell you is that they are on the brink of collapse, and if you follow them, you will find yourself in the same holes they dug, 6 feet under.

From here, you will need to prove that you’re even worthy of having a place in the Arena.

Most people will tell you NO, you don’t have it, they don’t want you or anything you have.

They will bar access to the Arena.

If you keep going, you may eventually find someone who gives you a chance to step up, but it may be your only chance to have a place in the Arena.

Actually Being In The Arena

When you stand in the Arena, you will become overwhelmed.

No one can truly prepare you for everyone staring at you, expecting a show.

When everything begins in the Arena, things will become a bloody mess.

Not just your blood, but the blood of every other combatant in the Arena will flow like a river.

Can you stomach the bloodshed and chaos?

Most can’t — they either die or run in fear of being next.

They will think that no amount of accolades or triumphs or “worthy causes” are worth this.

80% will fail within 5 years.

Then, if you find yourself still standing, it’s not over.

No, it has only begun.

Now that you’ve stood in the Arena, people expect you to continue standing, fighting every new wave that enters.

Can you continue to fight?

If you choose not to, it will discredit everything you worked up to.

But if you choose to stay, there is a high likelihood that there will only be one way out.

How long can you keep pace?

When newer, younger individuals with new technology come along, can you handle the change?

Most can’t.

96% of businesses fail in their first 10 years.

You’ll begin to watch your greatest competitors, people you considered your peers, either break down or bow out.

When they do, they receive no pity, the Arena continues to demand something new, something better, a greater spectacle.

You’ll begin to wonder if you are next.

Is it only a matter of time?

Fear and panic will set in.

You’ll look in the mirror and you won’t recognize who you are anymore, the scars accumulate changing everything about you.

This is the REALITY of the Arena — it can have accolades and glory, but not without a cost.

WHY I’m Telling You This Now

I do not want you to misunderstand me.

I am not trying to keep you out of the Arena.

In fact, I think you NEED to step into the Arena.

Theodore Roosevelt was right, you DON’T want to be one of the “cold and timid souls” that never even attempt to enter.

However, I also know that you need to know the REALITY because that is the only way you will survive.

If you head toward the Arena thinking it will be easy, you’ll get beaten down, thrown to the side, and won’t understand why.

If I prepare you for reality, you have a much higher chance to stand tall and proud.

You KNEW what was coming — THIS is what you were preparing for the entire time.

You knew all the pressures that would be against you, so you steel yourself early.

You knew how disgusting the battle would be, so you studied reality instead of some fantasy from a snake oil salesman.

You knew how difficult things would become mentally and psychologically, so you got the right support to get you through those times.

You will see others fall, quit, and run, and you will stand firm knowing that this was bound to happen to just about everyone else who failed to know the truth — 96%.

THAT is what allows you to continue where others fall.

THAT is why I tell you — the REALITY and TRUTH are what you need to understand if you want to have any actual chance of getting to (and staying in) the Arena.

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Cody Dakota Wooten, C.B.C.
Cody Dakota Wooten, C.B.C.

Written by Cody Dakota Wooten, C.B.C.

"Legendary Leadership" Coach, Digital Writer (600+ Articles), Speaker | Faith, Family, Freedom, Future | Multi-Award-Winning Creator of "Legendary Leadership"