Embrace Failure to Discover What Makes You Successful
4 years ago, I took an oath of failure and it led to my greatest success
4 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.
I, just like so many others wanting to be viewed as ‘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.
It wasn’t until I embraced failure that I discovered what success really was, for me. Success is deeply personal, making it impossible to find, if you don’t know what you’re looking for.
This is the story of how I escaped from the hamster-wheel of false promises by ignoring life’s peaks and embracing the valleys.
Defining success
Motivation, drive, and perseverance are buzz-words utterly supported in our culture. We view success as that that can be quantified i.e. shown off.
Satisfaction, joy, and happiness are impossible to measure and thus seen as less important than things like money, status, and notoriety.
Just like so many others, I fell into the trap of chasing superficial goals to exhaustion: Instagram followers, financial freedom, assets, and anything else brag-able. I followed goals to the bitter end, no matter if it was healthy nor what it did to me.
Upon climbing to the top of the tallest mountain to scream, “I’m killing it!” you will inevitably be faced with the base of an even taller mountain — for me, it was my impossibly high standards.
Putting the wheels in motion
Until this point in my life, I had supplanted happiness with superficial goals. I held myself to exhaustingly high standards and made sure to achieve every single one of my KPI’s, even if it killed me.
By age 23, I wanted to be making $60,000 a year. By 25, $100,000 and to be a home-owner. I wanted to be recognized at corporate events and celebrated for my dedication. I wanted a partner in life that looked a certain way and to one day become a millionaire. I wanted to show everyone how “happy” I was.
But, after achieving every goal and hitting each milestone, I became less and less satisfied. The allure of shiny things eventually wore off and my achievements became mere ropes to a safety net. An excuse to hide from not knowing who I truly was.
It was at this point, in my early twenties, that I decided to fail until I discovered what brought me happiness. To find out what success meant, to me.
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, “I just wanted to let you know that I’m going to fail for like two years. I can’t be afraid of failing anymore”.
At the time, she didn’t quite understand what I meant and was concerned for me, but I stuck to my guns and thank my younger, bolder self for this flash of clarity, every day. This one decision has shaped me into who and what I am today and pulled me away from a lifetime of pain and regret.
My first failure
Since my painful teenage years, I began to over-think and over-analyze everything in my life. The things you don’t see coming always hurt the most, and certain aspects of life were just too painful for me to bear. Thinking away any risk saved me from social/romantic rejection, performance failures, and disappointment from my loved ones. Risk aversion became my handy emotional shield.
If you try hard enough, you can find a reason not to do anything, but the truth is, failure is scary for everyone. No one likes walking into a dark room for fear of falling on their face. Playing it safe helped me avoid losing but it also prevented me from living.
But, with my new thirst for failure, I dove into the unknown headfirst. And 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 and knew on some level she would hurt me, but went for it anyway.
Ultimately, heartache was my future but it gave me the strength to love even if it meant losing. If you can learn from your experiences, no experience can be outright negative and makes losing ultimately positive.
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 memories. For me, this was a monumental milestone.
Next, I continued to blissfully fail, left and right
After wrapping up my first 5-year plan and achieving everything I had set out to accomplish, at age 24, I left my high-paying and 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 competing with my 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 every day, 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 classmates 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.
But then, I started to fail and failing
There’s an old expression that goes: Every ‘no’ is one step closer to a ‘yes’.
Basically, it’s 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 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 life-line 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 lines 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 ways to make money as opposed to what would bring me 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.
Sometimes you can’t see the light until you stop looking
Life can be a lot like one of those pixelated pictures that after staring at it for long enough, it becomes a beautiful woman or a spaceship. You know the ones I’m talking about. In life, you often don’t find what you’re looking for until you stop searching.
It’s this concept that allowed me to fall back into love with writing — something that continues to bring joy and direction to my life, every single day. It has become my lifeline to happiness and North Star.
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 LA before and developed a friendship with a woman from Denmark named Sharin, a musician and 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 and moving on from 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.
Brushing the dust off of a lifetime of fulfillment
During this month of leisure, I started interacting more with Sharin and really listened to what she had to say. She would ask me how my life was going and was genuinely interested in how I felt each day.
I had mentioned that I used to write short stories and that the only aspect I really enjoyed about running my 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, and in the past, 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.
Starting out, 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 my thoughts were transcribed, I felt inspired and motivated for the first time in as long as I could remember.
This tiny sliver of passion grew quickly into kindling with every word and burst into flames. I started to experience the familiar trance-like state of losing myself in front of my keyboard, only to snap back to reality hours later with thousands of words written in front of 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 more, 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.
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 promoted work-life balance. It was a step-down in pay but a mountainous raise in clarity and contentment.
It has been over two years now since I decided to face my ultimate fear of failing.
Although the beast will never be slain, I’m proud to have started the fight. Failure will always be disappointing, but my willingness to face it despite any outcome truly is a superpower. No one can define you but yourself and success is only measurable 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.
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 or impressively as they once could the smile on my face and behind my eyes says it all.
My journey took me around the world, throughout many different industries and ultimately to rock bottom before finding what I was looking for. Everyone’s path is different and yours could be incomparable to mine but the destination is equally as fulfilling.
If you are trying to unlock the mystery of happiness and discover what truly makes you feel 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”.