5 of My Most Informative Failures in Life

Photo Credit: <a href=”https://www.flickr.com/photos/31969501@N05/6948989112/">Pete Labrozzi</a> Flickr via <a href=”http://compfight.com">Compfight</a> <a href=”https://creativecommons.org/licenses/by-nc-nd/2.0/">cc</a>
“Knowledge without experience hangs loosely and doubtfully”- @KyleEschenroeder

In my life I’ve failed far more than I’ve succeed. I’ve failed both personally and professionally over and over again. I’ve failed at jobs, as an entrepreneur and in relationships. Putting together a resume of my failures was actually easier than putting together a resume of my accomplishments. I’d love to to tell you that the failures didn’t hurt or fill me with almost paralyzing self doubt. But that would be a complete bullshit.

Failing at anything you care about sucks.

On the one hand we glorify failure, wear it as a badge of honor, and write articles like this one. But as a society we celebrate, admire, and look up to success. Everybody is in search of the next unicorn. And nobody puts your picture on the cover of a magazine because you’ve ran a startup into the ground.

Despite all this, I hold failure in high esteem, as failure remains one of our greatest teachers. The only way to not benefit from failure is to not learn from it. As one of my mentors told me over and over, your temporary circumstances don’t have to become your permanent reality.

1. Missing All-State band by One Chair

In the 7th grade, I switched instruments from the Trombone to the Tuba. The day I picked the instrument, my band director told me that I would be really good, and that I would make all-state band. From that day forward, my life was defined by that goal. For the next 3 years I practiced religiously. In the 7th grade I missed all region band by one chair. In 8th grade I was first chair in the region. By 9th grade I was being groomed by band directors and private lessons teachers to make all state. Even though there was an all region band that was specifically for freshmen, my private lessons teacher and band director were insistent that I not try out for that one.

I showed up at school an hour before school started, and I stayed almost 3 hours after school let out so I could practice. The band director left before I did. And after months of practice, my work had paid off. I was 2nd chair in my region and had advanced to auditions for all all-state band.

I was the first person at our high school to have done this in several years and I’d done it as a freshman. The odds that I would even get to this point were quite low. I remember thinking to myself “I don’t care if I make it, but if I miss it by one chair, it would be devastating.”

January 13, 1993 was a cold and rainy morning on the UT-Austin Campus, where All-State Band auditions were held. After arriving at the building, I got out my Tuba and started to warm up. A few hours later we were called into the audition room, and told what section to play. By about 1pm, the rankings were posted. As you’ve probably guessed by now, I missed all-state band by one chair. When my band director dropped me off at my parents house, he even told them they should be proud. But I was devastated. I’d failed at the one thing that had mattered to me more than anything.

For the rest of the year, my identity was wrapped up in the fact that I’d missed all-state band by one chair. I was even featured as a soloist at the spring concert. Even though I saw it as a massive failure, my teachers described it as “quite an accomplishment as a freshman.”

That failure taught me so many lessons that didn’t come to pass until almost 20 years later. It taught me to focus on the process, not the prize and how to show up and do something every single day. Above all, it taught me how to perform in front of an audience, which has been invaluable as a public speaker.

2. Getting Fired from my First Post-College Job

December 20, 2001 is another day that I’ll never forget. After a year of enduring a hellish commute from San Francisco to Milpitas, working 12 hour days, and struggling to make ends meet, I was called into the office of our VP of sales and told that I was being fired. Because we had just returned from a farewell lunch for our graphic designer, for years we joked that I stole his thunder by getting fired on the same day.

Getting fired when you’re that young is a formative experience. I have an almost inherent distrust of people in positions of authority and think that job security is largely an illusion.

But getting fired from that job taught me so much that became useful later on in my career. It taught me about what kind of work I hated doing, so that I could avoid it in the future. It taught me about the importance due diligence when choosing to work at a startup. And above all things, from watching the CEO, I learned what kind of leader I never wanted to be.

3. Getting Rejected by Every Business School I applied To

In 2006, with a dream of ultimately working in media and entertainment, I studied for the GMAT and started applying to business school. I put in countless hours of studying, paid an admissions counselor almost 5,000 dollars to help with my applications and applied to NYU, Columbia, UT Austin, and USC.

By February 2007, I’d been rejected by 3 and waitlisted by USC. I was humiliated because my parents had lent me the 5000 dollars and all of my efforts had ultimately led nowhere. But it’s because of this that I ultimately ended up at Pepperdine.

When the fall semester started at Pepperdine, I kept hope that my dream of working in entertainment would eventually come true. And for a few weeks I kept checking the waiting list at USC to see if perhaps I might finally be off of it.

My dream was to choose what went on the air at television networks. But after countless conversations with people who worked in the industry, I realized nobody hired MBA’s for creative jobs in the industry. My dream was over- or so I thought.

Years later when I looked what I get to do at Unmistakable Creative, and as an author, I realized I’m working in media and entertainment. I not only get to choose what goes on the air, I get to create it, which is what I wanted to do deep down. If I learned one thing from this, it’s that dreams come true in this most unexpected of ways.

4. Not getting a Job Offer at the End of my Summer Internship

The summer between my first and second year of business school I worked as the social media intern in the Turbotax division of Intuit. But at the end of the summer, my boss called into his office and told me that general consensus was that they shouldn’t make me an offer. He also made the wise observation that he’d be doing me a great disservice by hiring me. I was pissed off, upset, and it was a huge blow to my self esteem.

However, if it hadn’t been for that job, I would have never started tinkering around with blogs and content creation. I didn’t realize it at the time, but with that job I planted the very first seeds for who I eventually wanted to become. Above all things, what that job taught me was that no experience in your life should be thought of as wasted.

5. Having No Job Upon Finishing Graduate School

There was probably no worse time in history to have graduated from any kind of educational institution than the spring of 2009. The global economy had collapsed and hardly anybody was hiring.

But it was because of this that I discovered two things that would transform my life in ways far beyond what I had ever imagined: surfing and writing. 7 years later, surfing would end up being the organizing principle and central metaphor for my first traditionally published book Unmistakable: Why Only is Better than Best.

Considering I don’t particularly enjoy paying taxes, I suppose not having to work at Turbotax for a living was a massive blessing in disguise. At this point I’m quite convinced the value I’ve added to people’s lives is far more significant than anything I might have done at Turbotax.

Sometimes the greatest work of your life emerges when your life doesn’t go according to plan.

When we experience any kind of failure or loss there’s usually a void of some sort that’s left by it. What we choose to fill that that void with can become one of the most life altering choices we’ll ever make.

Failing at something that you’ve attempted to create with your own two hands is particularly devastating because creative work often feels like an extension of who you are as a person.

When we had to pull the plug on our second attempt at planning a conference, I’d not only failed, but done so in a very public way. I had to tell all of our speakers that the event was canceled and refund money to all of the participants who had paid.

One of the most important things I learned from this was the difference between ego and grit. My mentor gave a piece of advice that I never forgot: “it’s going to be a lot harder to recover from being 50,000 dollars in the hole than it is to have a few burnt bridges.” To persist on something that was destined to fail would have been completely ego driven.

I also learned that momentum is the lifeblood of any startup or creative endeavor. When you’ve lost momentum, it’s hard to pull off daring and ambitious projects. Also, out of this failure my most ambitious project to date was born, a conference where everybody in the room (speakers and attendees) is somebody that I’ve interviewed on Unmistakable Creative. This is currently a work in progress. Our most spectacular failures can often be the driving force behind our most innovative ideas.

Spiritual Growth

When we go through a drastic transformation of sorts, we will invite chaos into our lives. What’s certain becomes uncertain. What’s predictable becomes unpredictable. But these are often necessary conditions are spiritual growth. Joseph Campbell spoke about the hero with a thousand faces, not the hero with two faces. We change throughout any hero’s journey.

Naturally, we will try to fight the chaos, we will try to control the uncontrollable. If we don’t resist for fight the chaos, it will flow through our lives like water. This is what allows us to go from operating at a smaller percentage of our capacity to a larger percentage of our capacity. This is how we become a newer version of ourselves.

Failure is a profound tool for spiritual and personal growth.

Failure tends to reveal.

It reveals the relationship that we have with ourselves and the one that we have with others. If we beat ourselves up, it becomes clear that we have to work on our relationship with ourselves. As Don Miguel Ruiz says, “You have to accept yourself and love yourself just the way you are. Only by loving and accepting yourself the way you are can you truly be and express what you are.”

If there’s one thing that all of my failures combined taught me, it’s this: I had a lot of work to do on the relationship I had with myself.

Failure will also test our relationship with others. Some bridges will burn. Some people will turn their backs on you. Others will stay beside you, and walk through the storm with you.

We always think that we would go back and do certain things differently if we knew what we knew today. But we wouldn’t know what we do today if we had done things differently.

If you’re in the midst of a devastating failure, I hope that reading this provided you some light in what might be a dark chapter. I won’t pretend to understand that I know what you’re going through. Our failures and the lessons we are meant to take from them are uniquely designed for each of us. As a friend told me, it probably feels like the worst thing in the world because it’s happening to you.

If there’s one upside to massive failure, it’s that you reach a point where you quite literally have nothing left to lose. At that moment, you have a blank canvas with infinite possibilities for what could become your next masterpiece.


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