If you struggle with how to overcome fear of failure, let me tell you a story.

I remember it like it was yesterday. Tom Petty’s “Learning to Fly” was turned up as loud as the radio would go, the windows were rolled all the way down and the wind was whipping my hair all around as we flew down the highway somewhere outside of Albuquerque, New Mexico.

The sun was shining and with every 100 miles we passed, the temperature seemed to raise several degrees. I was happy.

We were on an adventure… a cross-country adventure. It was March 1st, 2009 and Ryan and I were en route, moving from the suburbs of Detroit, Michigan to Southern California. One word to describe it?



I brought books to read in the car that I never even cracked open because there was something new to see and be excited about around every bend.

Mountains and giant windmills in Kansas, huge rock formations in Colorado, the twisty, windy road leading from Flagstaff into Sedona, what fun restaurant we were going to eat dinner at, at our next destination… we were buzzin’ on life.

This trip was definitely in the top 3 experiences of my life.

And when I stop and think about those top 3 experience, or even the top 5, one thing is true for all of them. I was buzzin’ on life because I chose to be.

You see, this adventure was a huge leap of faith for us. Let me say it again—WE WERE MOVING ACROSS THE COUNTRY.

Just the two of us. With nothing but what fit in our car and a few boxes we mailed before we left. No family in Southern California, just a “landing spot” with friends. No jobs even, just a couple possibilities. Oh yeah, and we were in the process of building a business.

We had some savings, but only a few thousand dollars. In fact, a week before we left, our accountant told us that we were going to have to pay $2,000 in taxes.

We decided to move forward with our plan anyway, and it turned out that he had made an error and we ended up getting about $4,000 back instead. Phew.

Outside Looking in Syndrome

It’s easy to look at someone else’s life and think, “Wow, they’ve got it all figured out. Their life must be so easy.” But that’s called the “outside looking in syndrome.”

We don’t know what challenges anyone else is ever facing. The truth is, no matter how good it looks from the outside, we all have stuff that we’re going through.

We all have fear and the seemingly never-ending debate is how do we overcome fear of failure so we can live that truly fabulous life we want for ourselves?

The answer lies in what Byron Katie calls doing “The Work.” Hindsight is 20/20, and I can now see that we were doing The Work, without even knowing we were doing The Work.

How To Overcome Fear

The Work is basically four questions that you ask yourself about any troubling thought:

  1. Is this true? (like absolute)

  2. Can I absolutely know it is true? (are you REALLY sure it’s true)

  3. How do I react when I think that thought? (how does it make you feel)

  4. Who would I be without the thought?

For sure we were scared of not knowing if things would work out or how and for sure we were afraid of not having enough money.

At that time in our lives, we didn’t have much certainty, which for me was big, because I like being in control and having a plan.

I don’t know why or how, but for some reason, we didn’t let those fears take over our attention. We kept our focus on the possibility—who we were without those fears.

The fear would creep up and I would sooth it away and tell it that everything was going to be okay.

I would focus on the parts of the plan that I did know – where we were headed, the cities we were going to stop in along the way – and I gave myself permission to get illogically excited about those tiny pieces.

And I trusted that we’d figure it out.


That’s an emotion that I come back to time and time again. Our cross-country adventure is one of my greatest examples in life of what it feels like to truly trust.

Sometimes I fall out of whack and forget what that feels like. I’m not perfect and I still get wrapped up in worrying and trying to make things happen instead of trusting and allowing things to flow.

But in this experience, when I trusted wholeheartedly—maybe more than I ever had before—that everything was going to be okay… it was.

In fact, it worked out more perfectly that I ever could have planned it, in ways beyond what I could have even known at the time. It all just came together with ease.


Ease and trust. This is what I want my life to be about.

I don’t need to eradicate fear, resentment, anger, or any other uncomfortable emotion. I’m practicing simply leaning into the ease and it feels a whole lot better than trying to dig deep and get rid of stuff.

I’ve learned that the more attention I put on trying to rid myself of the bad stuff, the more I end up engulfed in the bad stuff. I’d rather just let go of trying to fix myself and instead lean into the good stuff.

I know now that I can’t overcome fear. But I can lean into the ease.

I can enjoy the adventure.

I can have the time of my life even when “normal” standards would tell me that’s the last thing I should do.

I can stop listening to normal standards and instead create my own standards.

And I can stop worrying about worrying and fearing fear.

I can just trust. And be.