My Business Failed, But I Didn’t.

Why betting BIG on myself was the best decision I’ve made.

18 months ago, I left my job and started a tiny consulting business.

Last week, I pulled the plug on that business.

When measured in dollars and cents, I failed miserably.

That’s not to say that my little-engine-that-could business didn’t make any money.

It did.

It didn’t, however, make enough money to allow me to pay the bills, put money in the bank, and put myself at ease.

Each day was a challenge.

Each day was a struggle.

I had a love/hate relationship with my business.

I loved the freedom, flexibility, and the challenge. At times, I also hated the same things.

Most days I felt overwhelmed.

Even still, I tried to make things work.

I wanted so badly to succeed.

Boy, did I try hard.

I put in the hours.

I cold-called potential clients.

I took client calls at ungodly hours.

I took projects I otherwise would have rejected just to make ends meet (mistake #1).

I took some abuse from unreasonable clients who I should have fired much earlier (mistake #2).

I took on the role of business owner, lawyer, accountant, and many more (mistake #3).

And I reinvented my business more times than I can count (mistake #4).

Yet, up until now, I’ve measured success and/or failure in dollars and cents.

In business, that’s how things work.

Life, however, can’t be measured in such black and white terms.

When I put the letters “LLC” behind my name, I didn’t just start a business.

I took a gigantic step outside of my comfort zone.

I took a chance on myself.

Which brings me to the real point of this exercise in introspection.


Starting a business set off a chain reaction of AWESOME for which I’m eternally grateful.

After I decided to venture off on my own:

I took charge of my life.

I acquired new skills.

I traveled to new places.

I made new friends.

I reconnected with family.

I fell madly in love with a beautiful woman.

I lived in paradise.

I found out that my dreams are attainable.

And I figured out what I wanted in life.

And then I failed.

Nevertheless, here I am, still standing on my own two feet.

Two years ago, I remember asking myself:

“If you do decide to do this, what’s the worst thing that could happen?”

This is the answer I wrote in my notebook at the time:

“This whole thing fails, the business goes bankrupt, you lose all your money, and you go back, find a new job for a while, learn from your mistakes, and try it all over again.”

And wouldn’t ya’ know?

Minus the bankruptcy thing (thankfully), that’s exactly what happened.

As a matter of fact, I’m sitting at the kitchen table at my parents’ house right now.

I’ve spent the past three months here picking up the pieces and planning my next move.

I had to swallow my pride.

I had to sell my car to make some quick cash.

I had to ask my parents for a small loan.

I had to pull the plug on my failed business.

I had to find a job again.

And I had to rebuild my confidence.

I’m not gonna’ lie:

The past three months, in particular, have been the most difficult months of my life. My psyche took a serious hit, and I know for a fact that I haven’t been the best version of myself.

I can assure you that none of this was part of my plan at age 28.

But, that’s what happens when you live your life, right?

S — t happens.

So yeah, my first solo business venture failed.

Would I do it all over again?

Abso-freaking-lutely!

Will I do it all over again?

More than likely, but a little bit differently.


So, every now and then, take a chance.

Bet on yourself in a BIG way.

Take charge of your life even when you’re unsure of the outcome.

You might fail.

But you might just surprise yourself.

You might visit new places, make lifelong friends, fall in love, or find your purpose. Or, like me, you might do all of those things.

You might even accomplish a whole lot more.

And if you end up back at your parents’ house, give em’ a big hug and count your blessings.


You see, what I’ve gained over the past two years far outweighs what I’ve lost.

I start a new job next week, back in the same familiar place where this whole thing started nearly two years ago.

And so it goes.

I’ll continue to operate outside of my comfort zone.

I’ll continue to travel to new places and meet new people along the way.

I’ll continue to take calculated risks, and I’ll continue to pursue my dreams.

And I’ll do it all with a much bigger and brighter smile on my face.

This failed business venture (my first) probably won’t be my last.

Now that I’ve got the ball rolling, I’ll continue to bet on myself over and over and over again.

It’s simply too exciting not to :)