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How AJ Jacobs Manufactures An Interesting Life And How I May Be Sabotaging Mine

AJ Jacobs fails. A lot.

He pushes outside his comfort zone for a living and then writes about it.

Spend a year living by the laws and times of The Bible. Read the entire Encyclopedia Britannica. Create the world’s largest family tree.

And he does it pretty damn well.

To the tune of writing four New York Times bestsellers.

Want to have interesting writing? Insert yourself into interesting circumstances.

Through this approach, anyone can create audacious experiments that people would love to follow along with.
Or read about.
Or listen to.
Or watch videos on.

There’s a beauty in being open to failure.
There’s comfort in the ability to turn failure into story.
A complete win-win.

Sharing the failures, successes, struggles and wins forces you to learn from them.
Masking failure is true failure.

The last six months have been an absolute roller coaster for Jacklyn (wife) and I.
Often fulfilling and more often terrifying.

Fail On is an experiment that might fail.
It might succeed.
I don’t really know.

All I can control is giving it my best shot.
So, I’ll do that.

Similar to the extraordinary circumstances that AJ creates…
In January, I quit a five to six figure per month profit business because I felt out of alignment in the work that I was doing.

Many would call me crazy. Many have.

I have one life. How do I want to live it?

I haven’t had income since January.

It hurts. Like, really hurts.

No unemployment checks, no salary, no dividends.

Oh, but your business did so well people might say.

As my income increased, my lifestyle increased.
Travel increased.
Spending increased.

Suffice to say, managing money is not a strong suit.
I’ve always been of the philosophy that I can go create money faster than it would be to simply save it.
Should it be a combo of the two?
And I’ll learn from this.

I own an ad network that does well.
On paper, I do well financially.
Liquidity vs on paper are two different things.

Revenue is vanity. Profit is sanity. Cashflow is reality.

To be clear, we are fine financially even if Fail On keeps failing for awhile.

My wife thought we were going broke when she read this.

However, there is a fire that is lit when money is solely outgoing and not incoming.

It’s been tempting to go back to the “easy money.”
I haven’t, but I’d be lying if I said I hadn’t considered it.

Will I ever truly decide to swim all the way to the island if the safety of the shore is still in sight?

Probably not.

If you swim far enough out where you can faintly see the island in the distance, and the shore you left is no longer in sight behind you, you can’t go back.

This is the true inflection point.
The point of no return.
The line in the sand.

I’d also be lying if I said I didn’t still have doubts every single day.

I’m creating a new business.
A new story.
A total reinvention of myself.

It’s crazy scary.

Often, people ask, “What do you do?”  I find myself still saying media buying at times.

Who am I when I lose the identity of being Rob, the media buyer that travels all the time?

Whether Fail On succeeds or fails is indifferent.
I know that’s easy to say, but I truly feel that way.
I think.
I guess failing wouldn’t be ideal.
Like I said, it’s easy to say and hard to internalize.

What matters is that I’ve truly DECIDED on a new path.

As my friend & self-proclaimed etymology nerd, Fleming Talton says, “DECIDING implies the cutting of something. When you really decide to do something, there is a congruent sacrifice that is mutually exclusive to the path you’ve opted for.”

If I go broke pursuing this dream after quitting a profitable business that I wasn’t aligned with, so be it.

What’s the worst case scenario?
I can always get a job and rebuild.
I can always sell my car, drop my gym membership, find cheaper rent and eat Ramen noodles.
I’d obviously rather not.
But, I’ve done it before, I can do it again.

It’s a matter of ego.
Will I set my ego aside?

Can I truly internalize giving up such a heavy cash flow business with the potential of going back to nothing?

And truly, mentally be okay with that?

Or, will I hate myself for sabotaging a profitable business?
This is a terrifying subject for me.

I often wonder if I’m sabotaging myself.

Doug Brackmann mentioned that he wrote a lot on the subject.
@Doug, am I sabotaging myself? (By the way, Doug just quietly published an amazing book on Amazon. Check it.)

I’ve had two separate “friends/mentors” tell me that I won’t succeed at what I’m doing.
That I’m crazy for leaving a business doing so well financially.
One guy that’s worth $30M plus and another probably worth $10M plus.

I think they are wrong. Maybe they’re not. But, I think they are.

I’m okay taking that perceived risk.

I choose to have what AJ calls a “delusional belief” in myself.
That against all odds, I can overcome and powerfully create from scratch.

The path I have chosen is a unique circumstance that will result in an equally unique and powerful story that people will learn from, including myself.

In the first email that AJ sent me, he said jokingly (I think) that he hopes my podcast fails.

In a way, it fails everyday.

My download numbers are embarrassingly low.

My email list is nonexistent.
So nonexistent that I haven’t even bothered to write a weekly email newsletter yet.

I don’t have a product to sell.

I’ve created close to 50 hours of audio content in three months.
The amount of time and money it took to produce that content is actually staggering.
I’ve flown all over the US and Canada for interviews.
I’ve spent money on hotels, flights, dining and Uber.

Truth be told, and this might be glaringly obvious now, I haven’t really had a “strategy.”
What started as an experiment, is slowly taking shape.

I’m getting to know myself again.
I’m learning what I like and dislike.
How could I have gotten so disconnected to who I am at the core?
The allure of money?
The allure of traveling first class around the world at a moments notice?
The allure of flying in private jets?

None of those things are bad.
Never experiencing them before, they hypnotized me.

I’ve been committed to creating content.
I’ve had a lot of fun doing it.
I try to improve that content with each passing episode.

This is an honest glance into a new venture that I’m creating.

And all of the ugly self-doubt that comes with it.

And an honest glance at two warring sides of my internal dialogue.
On one side I have this delusional belief that I can create absolutely anything I focus on.
On the other side, I think I’m bat shit crazy for sabotaging a perfectly profitable, proven business.

Do I need to make money on this venture at some point in the near future?

Do I need to figure out how to grow and promote my podcast in a way that builds my platform?

Could I have done these things quicker?

But, sometimes it’s better to slow down and actually take the time to consider what we are building. And why?

And what we want our life and business to look like.

As Philip McKernan told me in Episode 007, “You might do one podcast episode, or it might be what you do for the rest of your life. It doesn’t really matter because what matters is that you are actually DOING it.”

People get paralyzed by fear. I do too.

My new story is about pushing through that fear and moving when I don’t necessarily want to move.

After each interview, I feel happy that I completed it.
A true sense of accomplishment.

There is power in the act of creating something that didn’t exist before.

I’m also horrified by my mistakes, my stuttering and often stupid questions.

As mentioned in my podcast intro, by having a brand about failure, it allows me to embrace the struggle and hardships without being consumed by the result.

If my podcast and business are failing, it’s okay because I’m embodying my brand by trying and learning.

And if others can learn from my mistakes, amazing.

If my podcast is a success, it’s because I have taken my failures and learned from them and gotten better at the craft.

As AJ says, “I think it’s important to give yourself permission to fail. Failing is good.”

AJ mentions approaching these experiments in two contrasting ways.

On one hand, you need an almost delusional belief in yourself that you will succeed and complete the experiment successfully.

On the other hand, you have to also be okay with the experiment not succeeding and looking at it as a lesson learned.

Sara Blakely is the founder of the billion dollar brand, Spanx.

Her father growing up would ask Sara what she failed at this week.

She’d tell him what she tried and failed at, and he would give her a high five and say, “Way to go!”

Embracing failure and pushing your limits cannot be overlooked.

I’m sure it’s a part of why she has succeeded to the tune of a three comma business.

She learned at an early age to consistently try new things without being consumed by the result.

Even during our podcast, AJ’s three boys got home from school and busted into the room.
Rather than getting frustrated or annoyed, he embraced the failure and kept rolling.

And AJ even told the boys the podcast was about failure and that it’s okay to fail.

I could try to edit everything and make my podcast perfect with no outside noise or I can just say screw it, this is life.
It’s never going to be perfect.
Let’s do the best I can with the circumstances I have.

Embracing failure and truly deciding to make a change matters a lot to me.

For anyone looking to make a change in their life, the concept of DECIDING is everything.

If not now, when?
What’s the cost of you not deciding to make a change?

I hope that when people see me publicly embracing failure that it will inspire them to try, fail and learn.

Maybe it will even change their life.
Maybe it will change your life.

You only have one and it’ll be gone in a flash.

The worst thing you can do is sit idly by and not try.

When asked about how she wants to be remembered, JK Rowling says, “I want to be remembered as a tryer.”

Will you DECIDE to be a tryer?


After letting my wife read this I could tell she was scared with my brutal honesty.

“Why are you posting this? And you’re right, we haven’t had income since January. You don’t have a product to sell. What is our plan? To just revel in failure?”

And she’s right.

Things are getting real.

It’s go time.

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