How Failing Big Led to My Greatest Success

6 years ago, I was a 23-year-old under-experienced, over-confident bundle of bravado, hell-bent on success without understanding what it even meant.

Failure is rarely seen as progression although the two are one and the same. Success is deeply personal, making it impossible to find if you don’t know yourself.

I, just like so many others wanting to be successful, swore off losing in order to win. I wanted to construct the perfect life for myself but was blind to the giant obstacle lurking overhead — my crippling fear of failure.

This is the story of how I escaped from the hamster-wheel of superficiality by ignoring life’s peaks and embracing its valleys.

Chapter 1: Defining success

Motivation, drive, and perseverance are traits utterly supported in our culture. We view success as that that is tangible i.e. able to be shown off.

Satisfaction, joy, and happiness are impossible to measure and thus seen as less important than money, status, and notoriety.

Just like so many others, I fell into the trap of letting my ego dictate my self-worth. Social media followers, assets, and anything else brag-able made me feel successful. I chased these goals to the bitter end, no matter the consequences.

Upon reaching the summit of an egotistical mountain you will inevitably be faced with the base of an even taller one. Our egos are never satisfied and never-ending.

Chapter 2: Manifesting a peculiar goal

At the ripe age of 23, I had spent a lifetime using tangible goals to try to construct my perfect life. By age 25 I wanted to:

• Be making $100,000 a year
• Own a home
• Be universally recognized as cool

**If I'm being honest, I wanted to be the life of the party, host it, and welcome myself as the guest of honour.

I wanted a life partner that looked a certain way and to one day become a millionaire. It's embarrassing to admit, but I wanted these things to show the world how happy I was.

As you can imagine, after hitting each milestone I became less satisfied.

Each achievement came with a moment of euphoria followed by a lapse in direction. Like clockwork, I would plummet into a depression until the next shiny goal arose.

I realized these goals were merely an excuse to hide from not knowing who I was. It was at this point, at the age of 25, that I set out to achieve a very peculiar goal.

To fail until I discovered what success meant to me.

Chapter 3: Speaking my new goal into existence

Like any good manifestation, it must be first spoken aloud into existence.

I remember the scene like it was yesterday. The puzzled look on my mom’s face as I told her,

"Hey, I just wanted to let you know that I have a new goal. I'm going to fail for, like, two years. I can't be afraid of failing anymore."

I know now that she didn't quite understand what I meant but like any good mother she nodded and said, "Ok, honey". She was concerned, but I thank my younger self for never swaying, every day.

That one decision has shaped me into who and what I am today and pulled me away from a lifetime of pain and confusion.

Chapter 4: My first failure

Beginning in my awkward teenage years, I had developed a habit of overthinking and overanalyzing everything in my life. I had been caught off guard in the past and swore to never allow it to happen again.

If you think hard enough, there's a reason to not do anything.

Thinking of life like a battle saved me from social/romantic rejection, failures, and disappointment. If you don't show up, you can't lose.

Risk aversion was my trusty emotional shield.

Playing things safe gave me a super-suit self-confidence along with the insecurity of not knowing its weaknesses. Every superhero has a vulnerability and I had no idea what mine was.

But, with my newfound thirst for failure, I dove into the unknown headfirst. First on my list was giving in to a budding relationship that had been slowly developing over the past few weeks. I had previously deemed her out of my league but went for it anyway.

Ultimately, heartache was my future but it gave me the strength to love even if it meant losing. It also taught me that to learn is to win. With this, no experience is outright negative.

After a fall, you have two choices. Pick yourself up and realize you’re still alive or vow never to walk again. Understanding that you can face the worst possible outcome empowers you to move forward and experience the good in life.

Although I experienced my first bit of heartbreak, I was thankful for the experience.

For me, this was a giant milestone.

Chapter 5: Blissfuly failing, left and right

After wrapping up my first 5-year plan, I had achieved everything I had set out to accomplish one year early. I left my high-paying, totally brag-able job to pursue… well, I actually didn’t quite know what I was pursuing at the time.

I just knew I wasn’t happy where I was.

I gave up on pursuing sales targets and a lifetime of competitive work frenemies to, as cliché as it sounds, find myself. I put in my two weeks’ notice with a mortgage to pay and no financial backup plan.

From there, I embraced trying anything and everything I had always wanted to with no expectation of success. I joined a boxing gym, worked out like an athlete, drank wine with dinner, socialized, made YouTube videos, played around with stocks, started learning the piano, and attempted to teach myself French.

I was failing miserably and loving every minute of it.

Feeding my entrepreneurial spirit, I started buying and selling household items on eBay and Craigslist. Then, I fulfilled my childhood dream of bartending whilst pursuing an acting career.

Although I did not become the next Ryan Reynolds and most definitely did not make any of my childhood friends jealous with my success, I am still, to this day, mildly proud to say that I can be viewed on Netflix… way in the background of a sort of well-known movie with some actors you may have heard of.

Chapter 6: Failing at failing

There’s an old expression that goes, "Every ‘no’ is one step closer to a ‘yes’.

Life is just a matter of putting one foot in front of the other until you find what you’re looking for.

But, what happens when you run out of steps?

Thus far, I had been living my best life, failing blissfully and letting the universe do the rest. Things were going swimmingly, and I was slowly moving closer to discovering what brought me joy.

But then, reality set in. This self-discovery kick was great and all but I was not earning enough to pay my bills and my mortgage was slowly drowning me.

Owning a piece of property at such a young age had been my lifeline to self-confidence. It allowed me to chase my dreams without feeling like a loser.

In the deep depths of my mind, although I was failing, I was not a failure. I owned a piece of property, and failures don’t have sizeable investments… no way.

As I sank deeper and deeper into my line of credit and credit cards, I panicked and began putting monetary expectations on my passion projects. This took the “passion” right out of them, and they became work commitments. I started to resent them.

I began chasing money as opposed to fulfillment and my world spiralled out of control.

I wasn’t happy, I hadn’t found my true calling, and now I was treading water, slowly drowning in debt, with no lifeboat.

Chapter 7: Some things cannot be found whilst actively looking

Life can be a lot like one of those pixelated pictures that after staring at it for long enough, it becomes a beautiful landscape or a spaceship. You know the ones I’m talking about. They're called autostereograms.

In life, you often don’t find what you’re looking for until you stop looking.

Down on my luck, overdrawn, spread thin, and deeply saddened by my inability to discover what makes me happy, I decided to take one last stab at happiness.

I took a road trip down to Los Angeles before giving up and settling for a normal job again. It was very "Elizabethtown".

I had been to Los Angeles once before and developed a great relationship with my Airbnb host, Sharin. She was a musician, a beautiful soul.

At this point, I was running an e-commerce store from my laptop, lying to myself that it wasn’t about the money. Upon finally giving up on the world of Facebook ads and false promises, I felt that I had finally hit rock bottom.

With credit card debt nearing its maximum capacity and no real movement in finding my calling, I decided to give up trying to discover my passion and enjoy my last month of work freedom.

It was from this point forward that I started to uncover what I had so desperately been searching for.

Chapter 8: Brushing the dust off of a lifetime of fulfillment

During my last month of leisure, I started interacting with Sharin more and more and really listening to what she had to say. She would ask me how my life was going and I would answer, genuinely.

I mentioned that I used to write short stories and that the only aspect I enjoyed about the e-commerce business was writing blogs. She acknowledged that writing is a wonderful craft and that I should pursue it.

I appreciated her interest but had never thought of writing as financially viable. In the past, I would have given her advice no mind.

But the beauty of my month of leisure was that I didn’t need to earn money. I was already applying for jobs back home and had just enough money to spend the month doing whatever I wanted.

So, I started to write as I did when I was younger.

At the beginning, I wrote down jumbled ramblings, philosophies, and random thoughts about the world whenever I felt inspired… usually after late-night walks or my morning cup of coffee. I would sit out on the patio or near my bedroom window and write down whatever I felt.

As I transcribed my thoughts, I felt motivated for the first time in as long as I could remember.

With each word, tiny slivers of inspiration grew into kindling and quickly burst into flames. I would type away for hours in an inferno of creativity only to snap back to reality with thousands of words on my screen, staring back at me.

One day over breakfast, Sharin recommended a book called, “The Artist’s Way”. From it, I adopted the practice of “Morning Pages”, which I still carry out to this day — 200 words on the page every day no matter what. Even if they’re gibberish.

As I continued to write, I became more inspired and motivated than I had been in years. The passion I had been searching for flooded through my body and I felt a sense of purpose.

It was amazing that, in such a short time, I had found exactly what I had been searching for, for so long.

In a few short weeks, I was experiencing unadulterated joy doing something I love, and it translated into the simple things. Life became exciting again and fuel for my writing. Previously uninteresting people were now an opportunity for character study, and monotonous tasks such as the dishes led me into the wonderful realm of imagination.

Shortly after re-discovering my passion for writing I started outsourcing my services to various freelance websites and earning a small income. Ultimately, ghostwriting didn’t turn out to be my calling but I’ll save that story for another day.

Chapter 9: I traded in my sack of goals for a renewed sense of purpose

Returning home meant returning to reality as well. I found myself an honest job with good benefits and a work culture that supported work-life balance. It was a step-down in pay but a mountainous raise in clarity and contentment.

It has been over 4 years now since I decided to face my fear of failing.

Although the beast will never be slain, I’m proud to have started the fight.

Failure will always be disappointing, but the willingness to face it despite any outcome truly is a superpower. No one can define you but yourself and success can only be measured by how you feel.

Who you are, who you love, and what you love doing doesn’t have to make sense to others.

It only has to make sense to you.

Chapter 10: The endless road worth travelling

I am happy for the ups and grateful for the downs that have led me to where I am today. Although my successes can’t be measured as neatly nor impressively as they once could the glimmer of happiness in my eyes says it all.

Everyone’s path is different, yours may be incomparable to mine but discovering what makes you successful is worth the journey, for anyone.

If you are trying to solve the mystery of happiness by discovering what makes you truly successful, you must first stop thinking and start living.

Discover what you don’t love to find out what you do.

As Sherlock Holmes famously said,

“You must first eliminate the impossible, whatever remains, no matter how improbable, must be the truth”.