This story is dedicated to the crazy ones; the creatives; the innovators; the entrepreneurs; the misfits; the artists; the warriors; the pioneers; the explorers; the revolutionaries; the renegades; the rule-breakers and risk-takers and trouble-makers and dream-chasers of the world.
This story is also dedicated to my dad. Sorry I missed Father’s Day, 2019. I hope it was worth it in the end.
Creator of Renegade OS
Over 90% of tech startups fail, but I never thought my baby, 99dresses, would be one of them.
If there is one thing that doing a startup has taught me, it’s that I am much more resilient than I could have ever imagined. Looking back, when I started 99dresses fresh out of high school, I was very naive and had zero idea what I was doing. In fact, I didn’t even know what a startup was! I just knew I wanted to solve a problem I personally experienced: having a closet full of clothes but nothing to wear.
Since then I’ve survived being stabbed in the back by cofounders, investment rounds falling through, massive technology fuckups that brought sales to a halt, visa problems, lack of money, lack of traction, lack of a team, hiring the wrong people, firing people I didn’t want to fire, lack of product-market fit, and everything else in between.
And yet I failed. I won many battles but I lost the war.
Published June 24, 2014 on Medium.com
It’s been over six years now since my startup failed. Since then, my painful and raw story has touched the lives of hundreds of thousands — if not, millions — of people around the world.
People read my story of failure and quit their job the next day, or took a step towards the dream they'd been putting off for years. Parents printed out my story and read it to their children around the dinner table. I've spent the past few years living as a nomad, and I still meet random people in different countries who say, "Oh! You're Nikki Durkin! I read your failure story. Thank you for that. It helped me in a hard time." It's so humbling to think my pain could be transformed into something positive for someone else.
But the story you're about to read is not a story about pain. Although you'll find plenty of pain and heartbreak in its pages, you'll come to realize it's all just part of the maze.
This is a different kind of story: a story about impeccable, breathtaking, beautiful order in the chaos of life. It's a story of love, of adventure, of learning and discovery and fun and tears and self-doubt and triumph. It's the story of what happens both after failure, and before it.
In some ways, it's a sequel to the narrative that was neatly set up and etched into an online record six years ago for all the world to witness. But in other ways, it's a prequel to that story. As you'll soon see, time's about to start collapsing in on itself from all directions.
In this story, you'll join me on a journey as I attempt to solve a riddle handed to me by my reality. If you make it to the end of this story, I doubt you'll see yourself or this universe in the same way again.
Eric Weinstein — mathematician, economist & managing director of Thiel Capital — has a podcast named The Portal.
The essence of his project is everything I love about life: the mystery, the call to adventure, the wandering and probing for undiscovered secrets…
When I was a kid I read all these stories that I thought were known to be the same story, but different versions of it. And I called it The Portal story, and it was always the same. Somebody is trapped in a humdrum existence, in an ordinary world, until some kind of magical portal either accidentally or on-purpose enters their life. And either they go through a wardrobe, they go through a rabbit hole, a looking glass, platform nine and three quarters.
And I came to believe that this story is actually an unkept promise for most people; that in their adult lives they don’t find these portals. If you look at a wall, how do you know that the wall doesn’t have a door? How do you know there isn’t a panic room behind the bookcase if you just pull out the right book?
We learn to stop looking for The Portal, and I think that what I do differently is that I became obsessed with exits. That there are other worlds, and that they’re real. That this mythology of the looking glass and the rabbit hole and the Matrix is a metaphor for a very real thing.
The Joe Rogan Experience, Episode #1320
I was twenty-two when I published my failure story. I haven’t returned to the keyboard since. I’m not really big into sharing. There’s this voice in the back of my head that says, “Nobody cares about what you have to say, Nikki.”
Except that six years ago, people did care about what I had to say — primarily because no one else was saying it.
In a social media world of “I’m killing it!” and “Look at my incredible life,” that piercing post about the truth — about what it actually feels like to go all in and chase your dreams and fail — cut through the entrepreneurial and creative communities like a red hot knife slicing through butter.
After sharing it on my personal Facebook, it instantly went viral, with over a quarter-million views in forty-eight hours. It was translated into multiple languages and syndicated in online publications all over the world, including the front page of my home country’s number one news site.
Over a million people must have read it. Thousands of them reached out to me, thanking me for articulating their secret; their hidden truth. What everyone was thinking and feeling, but no one was saying out loud.
To be honest, I can’t even remember writing the piece. I remember coming out of a meeting with my cofounder, having agreed to shut down the company that I’d started four years earlier when I was eighteen. I remember not knowing what to do with myself, wandering around our coworking space with wet, blistering eyes. I remember hiding away in a meeting room so no one could see me, and for some reason signing up for a writer’s account on Medium.com.
And then, seconds later, I remember staring at a several-thousand-word long post — my heart and soul poured onto a page.
What the fuck? Where did those words come from?
It was strange. It was so out of character. I don’t like sharing. I don’t want the world to see me fail.
Why did I write that?
Where did the time go? I couldn’t remember.
I checked the clock and several hours had flown by in seconds.
Very odd.
A few days later I pressed ‘Publish,’ and the whole world knew my secret.
***
The fanfare from that post was astounding: media interviews, job offers, invitations to speak at conferences. I even had an indie producer reach out about turning my bitter-sweet story into a movie.
I remember doing a podcast a few days after it blew up, and one viewer remarked that every second word out of my mouth was ‘umm.’
Thanks, Captain Obvious. My baby just died and I don’t want to be here and I’m sorry if I come across as inarticulate when being asked to talk about it for your benefit. This is hard.
But if I don’t tell the truth, who will? You? Sitting behind your keyboard, laughing at me?
I don’t think so.
Lies are dangerous, especially when we repeat them over and over again to ourselves. After a while, we don’t even start to question them. We just call them The Truth, and write about them as fact, and pass down our lies to our children in classrooms and over dinner tables. And the world enters a kind of collective delusion, where something’s not quite right but no one can say what. No one can find The Portal, so we all stop looking for it.
***
After the fanfare from the article died down, I went and hid away at my parent’s place in a small country town on the east coast of Australia. I wanted to get away from all the noise, all the busy-ness; all the humdrum of this and that, pushing pixels, talking to people, sending emails.
I just wanted to fade away and lick my wounds in private and figure out who I was and what the fuck I was going to do with the rest of my life, without the tyranny of high expectations breathing down my neck.
“Oh, you’re going to do amazing things in the future. This is just the beginning for you!”
“You didn’t fail. You just learned a lot. Can’t wait to see what you do next!”
“You’re an inspiration to me. I’ll be following your career closely!”
A few weeks after I arrived home from New York, my best friend asked if I could give a talk at her coworking space with two other well-known founders in the Australian startup community. I said yes, because she was my friend.
I got up on stage, flanked by two women who were everything I was not; two entrepreneurs who hadn’t led their team off a cliff and watched four years of hard work crumble before their eyes.
When it came my turn to speak, I looked out at the crowd, their smiling faces staring back expectantly. They’d come to hear me talk about failure. They’d come to hear me tell the truth.
And there I was, staring back at them, tears silently rolling down my cheeks, drowning in my own inferiority. I thought I was up for it, but I wasn’t. I was a mess. It was too soon. I completely choked.
You want to see the truth? This is what it looks like.
I went back home to my parent’s place, embarrassed. I remember sitting up in bed in the wee hours of the morning, thinking about how I ended up in this situation. Deep questions were starting to bubble up in the back of my mind, hardening and compressing into a sharp splinter that lodged itself somewhere in my consciousness.
You see, I hadn’t always had a rough journey. When I was just starting out as a naive eighteen-year-old, it was honestly like the Red Sea would part to deliver me every resource, every person, every opportunity, everything I needed to assemble the next part of my vision.
I was skipping through life, from one beautiful conversation to another lucky ‘coincidence’ like a happy little leprechaun. I had no idea what I was doing, so I just followed a trail of curiosity and took action on ideas that excited me with a sense of childlike wonder. I’d take a step into the unknown, and a golden path would magically materialize beneath my feet as fast as I could run.
And boy, was it an adventure!
I’d somehow find myself in a photoshoot for Vogue magazine, draped in expensive diamonds. Or on a phone call to the CEO of the biggest talent agency in the world, who met me for five minutes and wanted to make a reality show about my life. Or at the top of the Empire State Building at one a.m. with a handsome European stranger I’d met at the airport as we ran around Manhattan for one spontaneous night like a goddamn rom-com movie and then he kissed me in the hidden nook of a little bar on West 4th street — a temporary portal into a magical universe.
And I’d think to myself, how on earth did I end up here, having this experience? I was just a girl from a small country town in Australia with an overactive imagination, who spent her childhood mucking around with horses and having sword fights with her blue-haired best friend. How did all the stars line up to deliver me this?
Things just seemed to happen for me.
“So then why did I fail?” I asked myself.
My brain rattled off the usual culprits: I didn’t do X well; I executed Y poorly; I thought that idea was good, but it turned out to be terrible.
“Okay, but why did I feel so compelled to execute that terrible idea?”
Hmm… my brain ran through some compute cycles. Data? Intuition?
“Okay, but where do my ideas come from?”
Oh fuck, we’d entered philosophical territory. God, maybe? But I didn’t believe in a man in the sky. The religion taught to me in school always seemed completely nonsensical and reeked of man-made moral posturing and power plays — another type of collective delusion.
Hmm… let’s try another question.
How come I had a year-long stretch of green grass to sprint along when I started, but somehow found myself lost in the muddy, murky woods over and over and over again like a recurring nightmare?
The entropy in the adventure was suspiciously low. It felt like tossing a coin one hundred times and getting thirty heads in a row, then seventy tails. Wouldn’t that make you curious? Wouldn’t that make you suspicious of the coin? Something felt off.
I’d been told that life was disordered; random. But when I walked through the world and observed a seed growing into a sunflower, a child laughing with that sparkle in their eye, or the vast beauty of the cosmos — well, there was nothing disordered about any of that.
And when I considered the way reality would contort itself to deliver me another resource, another opportunity, another idea, another person that would be instrumental in my success — no, I just couldn’t pass it off as ‘random’ or ‘luck.’
My ego screamed, “Cognitive bias! You’re finding patterns where there are none! Stay in your lane like a good girl and move on with your life.”
But I’ve never really been a good girl.
That splinter in my mind was digging in, sharpening, twisting until I couldn’t take it any longer and my pent-up curiosity erupted in a flurry of action.
I needed to understand why I experienced what I experienced. It wasn’t enough to just tell myself, “better luck next time.” Fuck that! I used to be insanely lucky and then pretty darn unlucky, so what variable changed?
It almost felt like the past four years had been set up as some kind of game, some kind of mystery for me to unravel; an intellectual chew toy for me to gnaw on.
What variable changed, Nikki? Do what you do best and understand the problem. Think differently. Look beneath the surface. Experiment with it. Play with it. Solve it. Be creatively logical. Be logically creative. That’s what you’re good at.
I pulled my laptop from the bedside table, opened it under the covers, and typed three words into the search bar: What is reality?
I pressed ‘Enter.’
A portal appeared before my eyes, softly beckoning me to come explore its secrets and magic and mysteries.
I leaned forward, and tumbled down the rabbit hole.
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