I Wouldn’t Wish Entrepreneurship On My Worst Enemy

“Entrepreneur” has turned into a buzzword.
Entrepreneurship isn’t sexy.
It’s not glamorous.
It isn’t really even fun.

It’s pain. It’s angst.
It’s often more stress than any human should have to endure.

And it doesn’t matter how “successful” you are.
You are still susceptible.
Cameron Herold told me that he got hit with a monstrous IRS tax bill he didn’t see coming.
What’s more stressful than a letter from the IRS demanding ungodly amounts of money by a certain date?
And by the way, if you can’t pay by this date you’ll have to pay late fees and interest on top of the total.

This doesn’t happen when you’re a W2 employee collecting a direct deposit paycheck every two weeks.

Doug Brackmann had a client that had achieved his dream of amassing $10MM and bought the plane and dream house.
He shot himself in the head with a 9mm leaving behind a wife and three kids.

Being a successful entrepreneur won’t solve all of your problems.

Want to be an entrepreneur because you saw a GaryVee rant?
GaryVee didn’t choose to be an entrepreneur.
He had no choice.
He couldn’t function any other way.

In a podcast episode with Facebook Ads genius Nicholas Kusmich, he says, “Entrepreneurship has been presented as this sexy thing. Be your own boss and set your own hours. And please no, just stop. It’s not that easy. Most people don’t have what it takes and they’re being lied to. It’s this lie being perpetrated that tells people to follow your passion and you’ll be rich and successful. It’s a complete disservice to most people and most people should not be entrepreneurs. Be thankful for your job.”

True entrepreneurs don’t do it because they want to.
They do it because they absolutely have to.

It’s this moment when the pain of not changing exceeds the pain of being comfortable and living in certainty.

Comfort kills dreams.

Certainty is the enemy of growth.

This is why you always hear “get outside your comfort zone.”
It’s why I embrace failure.
You can’t fail if you’re comfortable.
You can’t succeed if you don’t fail.

Entrepreneurship can take you to dark places.

While living in La Jolla this past April, I felt so much pain and so much overwhelm that I went to bed at 4pm to try to turn off my brain.

Our personal bank account was running on fumes and most of my business liquidity was being held by a third party.

I never knew if I’d see that money again.
And that was a completely devastating possibility.

After working so hard on the business for the last three years, our livelihood was being held hostage and could very well be murdered.

I couldn’t believe I put Jacklyn and I in this situation.

It wasn’t just money.

It was dear business relationships and friendships that had gone irreparably south.

I had a scary thought that day laying in bed.

About how the only way I could have a clear head, without all of this stacking overwhelm and stress, would be if I were dead.

I wasn’t planning to kill myself.

And to be clear, I’m typically very happy, go lucky.
Jacklyn usually calls me a human version of a golden retriever.

But at this point, I just thought that having a clear head without stress seemed really, really nice.

Maybe no one will relate to that.
Maybe a lot of you will.

If I keep it to myself, it helps no one.

This might be an atypical journey for an entrepreneur, I don’t know.

I made a lot of mistakes in business the past few years.
Mistakes that maybe most entrepreneurs don’t make.

I’d lost hundreds of thousands of dollars.
I’d given others more control over parts of the business than I should have.

As much as I hated having 14 different jobs in the past ten years, none of them had given me the stress, the pain and the dark thoughts that entrepreneurship has at times.

Jobs give you a level of certainty for the time you are employed.
Certainty gives you comfort, but it also stifles growth.

Even if you read a book each week, watch every GaryVee video and listen to every Tim Ferriss podcast, that isn’t growth.
They educate you, they don’t truly make you grow.

Practice always beats theory.

Joey Coleman shared in our podcast conversation that the quality of your life is in direct proportion to the amount of uncertainty you are willing to have in your life.
It’s a positive reframe that shows that I’m on the right track when the going gets tough.
Reflecting on our conversation helps me when I’m having a tough day.
Thanks Joey.

Entrepreneurship brings uncertainty.
Business and life constantly change.
Maybe you pay yourself one month and not the next.
Or maybe you can’t pay yourself for six months.
Hello current reality.

Uncertainty brings discomfort.
It also brings tremendous levels of growth.

How can you know what you are truly capable of unless you actually spend time in this state of discomfort and uncertainty?

Jacklyn asks me why I want to be an entrepreneur and live like this.
She sees firsthand the pain and angst I go through.
The pain that I’ve hidden from the outside world until now.
I think it sometimes scares her.
I tell her I’m an entrepreneur because I have no choice.
She understands.

And to be clear, it’s not always stress, pain and angst. There are moments of pure bliss and freedom that, for me, make it all worth it.

I also told Jacklyn that I don’t plan on going through these brutal low points every single year. I take the lessons and course correct.
The low points are guiding forces getting me closer to what I want my life to actually look like.

As stressed as I can get living this reality, I never felt as uninspired as I did through those 14 jobs.

And even though I go through incredibly hard times, I’m still living my dream right now.
I wake up every single day with a blank canvas.
I can slow down and read a book on my front porch in the morning.
I can take Lucy on a hike at anytime.
I can enjoy an extra long hot shower in the morning knowing I don’t have to beat rush hour traffic.
Jacklyn and I can go see a movie in the middle of a weekday to avoid the crowds.
I am able to leave the God forsaken beaches of La Jolla to move to the mountains!
Okay, La Jolla was great, but I love the mountains.

I am supporting myself without needing a job.

Outside of the daily “luxuries,” I can actually work on projects that truly matter to me.
Projects that I feel can change lives and help others.

As cliche as that sounds, to me, there is nothing greater.

I’m in control of my life.
Uncertainty is my certainty.

Through all of those jobs, someone else called the shots.
Someone else had the power over me.
Someone else could cut off my livelihood with a single conversation.

At least in this reality, I can do something about it.
I control my destiny.

My own decisions led me to those dark thoughts in bed that day.
I can deal with that.
And I can course correct.

If a job or a boss put me in the bed at 4pm and led me to those feelings, that’s an even scarier place.
Because they are in control.
Not me.

Reading this, you are in one of two situations.
One, you are an entrepreneur and fully support yourself without a job.
Two, you don’t do that.

Let’s say you’re in bucket two. You think the first bucket sounds better because you heard an amazing GaryVee rant, you like the idea of no rush hour traffic and not having to sit in your cubicle doing a job you dislike for a boss you can’t stand.
You should stay in the second bucket.
The first bucket won’t turn out well.

If you are in the second bucket, but know you have to be in the first bucket.
To your absolute core. Even if you don’t know what it is that will get you there.
Okay, maybe.
But, it still might not be in the cards for you.

If the pain of not being in bucket one doesn’t exceed the level of comfort and certainty you have in bucket two, you’ll never truly make it.

You just won’t.

Comfort kills dreams.

For me, and I tell this story often, there was a very specific moment when the pain of not being in bucket one exceeded the level of comfort I had in bucket two.

It happened while I was reading “How To Get Rich” by Felix Dennis sitting at Wake Up Coffee in St Simons Island, GA on a Tuesday morning in the winter of 2013.

I was at a breaking point.

The accumulation of failed business attempts and failed employments, while knowing to my core that I had the ability to create something powerful on my own, brought everything to a screeching halt for me.

I hit this moment of pure exhaustion and disappointment in myself.

How many books do I have to read?
How many podcasts do I have to listen to before I make this happen?
This type of education, for me, turned into mental masturbation.
It feels good to do it, but it’s not the real thing.

I knew that I had more to offer and was destined for greater things.
I also knew I hadn’t truly drawn my line in the sand.
I had a bunch of half ass attempts that would lead to the next thing. And then the next thing.

When would I truly focus and DECIDE?

After audibly crying in public for the first and only time in my life at this coffee shop, I decided things would change.
That I would focus on one thing and make it work or die trying.
My 50 Cent moment.

A true line in the sand.

The pain of knowing that I was destined for more finally exceeded the level of comfort and certainty in my life.

This is when everything changed.

Not overnight of course, but when I truly embraced uncertainty and became incredibly focused on one project, I knew I would never work for someone else again.

For eight years I thought entrepreneurship sounded cool and would be amazing if I could achieve that.
For eight years I dabbled and lived a life of indecision.
Indecision and uninspired effort.

In a single fleeting moment at a coffee shop in Georgia, I changed my life in an absolute instant.

As my bud Cole Hatter mentioned in our podcast recording, “Change happens in an instant, you DECIDE, and then it’s done. It’s a really powerful moment. How hard is it to quit smoking? Well, it’s in an instant that you quit, what comes next is the hard part. It’s stopping a habit and creating new habits.”

You can’t make a decision to be an entrepreneur.
It simply doesn’t work like that.

You have to DECIDE to be an entrepreneur.
You have to DECIDE to embrace the inevitable failures and uncertainty.

Reading this maybe you know you are destined for more than your current situation.

You that know you have to do it.
You know your sanity and life depend on it.
Mine did.

Do you want to be an entrepreneur or do you have to be an entrepreneur?

I DECIDED and had my line in the sand moment at that coffee shop.

What was the moment for you?