Lessons on Success from a Spectacular Failure

Dear Reader and Friend,

I think I might be the most optimistic disappointed person you’ll ever meet. For someone who is afraid of failure, I’ve fallen on my face with alarming frequency these past few years. I’ve gotten lost on a straight road. I’ve had eight jobs and moved four times in two years. I have tried to lose weight and only gained it. I have slept with, on average, one carefully-ish selected person every six months over the past three years, all of whom I have thought I was doing a favor, and none of whom agreed. My only claim to fame was when they put my picture next to “pratfall” in the dictionary. I am, for all intents and purposes, unsuccessful. It’s the only thing I’ve done consistently and with flair. My mother always told me to specialize, so perhaps this is a field where I have something to offer.

So, let me take the opportunity to share my expertise with you, my reader and my friend. Let’s take a look at the most recent humiliation I experienced over the past few days. Without going into too much detail, I developed the most inconvenient crush imaginable. There was nothing appropriate about the situation, it was fraught with personal risk at every level. And yet, despite being fully aware of the consequences, I lost the battle against every fiber of my being. I finally blurted out to this person that I thought he was the neatest thing since sliced bread and I’d like to hold his hand.

Let me be clear, I knew a huge rockslide of awkward was about to bury us both. I also knew that the combination of my terrible poker-face and flirtatious nature meant my admission wasn’t unexpected. We’d been dancing around the subject for weeks in a painfully obvious way. Conversations about our individual relationships or lack thereof had become more frequent. I suspected he harbored some feelings for me, and almost every interaction became an opportunity to test out that theory. I became flustered, noticeably quiet, and was losing the ability to look him in the eye. I knew once I opened my mouth that there would be no going back. I knew that, regardless of his feelings for me, he probably wouldn’t be on board because he is pragmatic to a fault. There was nothing simple or straightforward about what I was proposing. Every step forward would have brought a new complication. I’d have bet against myself if someone was offering me 10:1 on a spectacular defeat. But I was so attached to the potential that I saw in us. I was so content with the illusion that maybe, just maybe, we could make each other happy. I knew the minute our feelings were acknowledged, the dream would start to disintegrate.

Still I tried, as I have many times before, to bring the fantasy into the real world. And, like many times before, it floundered before it died. Our feelings for each other were aired, the complications were acknowledged. We kissed, and for a moment I thought that this might be the time that I got what I wanted. Maybe I’d met someone who was willing to be brave too, who would interrupt the quiet of their existence to try their hand at a life most people are too cautious to explore. Days passed, and I saw it all slip away. I could only state my position so many times, hoping that his ambition to create magical things would override his aversion to risk. I hoped that he would understand that there is a coldness in perfection, and that beauty comes from nuance. I tried to explain that nothing can be gained if nothing is risked. I tried to lead by example, and I failed. It hurt, I cried, and I seriously questioned how many more illusions I would let someone else shatter. This has happened more times than I can count, and to be honest, I wasn’t really expecting this to go any differently.

So why on earth would I get involved in something so risky when life was trundling along pleasantly enough? Am I a masochist? Am I trying to fail? No, I’m trying to succeed. When I say succeeded, I don’t mean materializing every tauntingly beautiful and intangible fantasy I imagined. I mean not tripping at the starting gun. I mean getting the chance to roll the dice and move past “Go.” After that, every step has to be reassessed. There are new risks to be considered. The result is never going to be how you imagined, but you’re suddenly given a whole new realm of possibility to work from.

You may be wondering why, with constant rejection and disappointment, I haven’t walked out the sixth story window yet. Probably because I’d hit my head on the glass because I forgot to open the damn thing. Also, every failure is a fantastic experience. Don’t get me wrong, being hopeful, then vulnerable, then getting flat out rejected is bruising. It’s humiliating to feel tears stream down your face and have to accept a consolation hug from the person you’re crying about. That being said, the weeks leading up to that confession were ones of tumultuous optimism. For a moment, in the middle of it all, I got to experience what success would have felt like. It was better than I imagined. And, while it was fleeting and the resolution was ultimately disappointing, it stiffened my resolve. I’m limping back to the drawing board, but with a clearer picture of what I want and how to get it.

When it comes to failing, it all comes down to what are you willing to sacrifice, what precious object you are willing to destroy in exchange for the chance of getting everything you ever wanted. I think my buddies on Mount Olympus would agree that I’ve given them some good stuff. I’ve sacrificed my ego and my dignity numerous times. I’ve laid out a future I’m attached to and said “Do what you will.” I’ll do it a thousand times. Nothing of value has ever been gained when nothing has been risked. Pragmatism is fear rationalized. Inaction guarantees a stifled existence. Humiliation is a small price to pay when you think about the reward.

I hope you will all learn from my failures and find the courage to make your own.

Love Lili


To The New Year

Dear New Year,

If I could tell you all the pickles I’ve found myself in this year you’d laugh. I would too. Scraped knees, bruised ego, broken heart, and a few professional bumps. The thing is, I knew what I was risking every time. Every day. I’m not afraid of being humiliated. I’m not scared that I’ll be disappointed a million times. I should be so lucky. Do you know why? Because a million disappointments means I’ve had a million hopes and imagined a million ways to get everything I’ve ever wanted. Maybe I walked away with a red face or red eyes, but when I walked in I knew what I wanted and said “to hell with the risk, it’s worth it.” And it is. I  t’s worth every minute of squirming, every dollar mistakenly spent, every hour that I’ll never get back.  I wouldn’t change a thing. It’s not ego, or bravery, or naivety, it’s blind optimism. I don’t want to learn from my mistakes. I don’t see them that way. Do you know why? Because you get to leap before you fall, and I’d rather fall a thousand times than stop believing I can fly.

So let’s do it again. You and me. We’ll take on the world and make it laugh with us.

Love Lili

To The Bus Driver

Dear Bus Driver,

When I was small I had a recurring dream about an evil witch who, in no uncertain terms, was trying to kill me. It comes around, bizarrely, every four years and tends to last two nights. The first night I usually wake up moments before she vanquishes me. The next night, now familiar with her new tactics, I have the upper hand. When I was younger, I would be terrified of going to sleep the second night, I was already familiar with the world I was about to enter and scared that this time, this year, I might not wake up.

I remember one encounter in particular that I want to share with you. I was eight, and about half way through what would be four years of persistent bullying by the majority of my classmates. The witch , who was a terrifyingly familiar face, was chasing me through the forest which had various school-ground play structures scattered amongst the trees, and blackberry bushes. The blackberry bushes were significant for two reasons. Firstly, my ex-best friend/worst bully and I used to hunt for blackberries in the bushes near her house. Secondly, the blackberry bushes with their piercing thorns and wild branches were the only place I could hide without the witch being able to follow me. I was small enough to slip under them, she was not. It was the second night, and I was in hiding under the blackberry bushes, and the witch had me cornered when she dropped her magic wand and it rolled towards where I was hiding. I grabbed it, seeing it as my chance to defeat her, and waved it sending dark sparks shooting towards her. The dark sparks, as you may guess, were destructive black magic. Instead of weakening her, being hit by the powers of her own wand made her stronger. She laughed and grew more powerful as I continued to hurl black magic at her. I was petrified, and she had become so strong that she was able to push through the blackberry bush towards me. Suddenly, I understood where I had gone wrong. Even as an eight year old I had a small grasp on the concept of love’s power and opposing forces, so I kissed her wand and waved it towards her, sending out an entirely different shade of sparks. These hit her with the force I intended, and I continued to kiss the wand and wave it over her with a shower of white and gold light until it consumed her and she vanished, and I emerged from my refuge under the blackberry bushes exhausted and relieved. I had some moments to sit in the forest and reflect on what I had accomplished before morning took me back to the world you and I share. Unlike so many of my other dreams, every vivid detail of this one is burned into my memory.

I share this story with you because you were being an asshole today. You drove past another rider and I who were sheltered from the rain four feet away from the bus stop, and walked towards it as we saw you approach. You purposely zoomed past, forcing us to run after you. You stopped around the corner, but I am positive it wasn’t out of kindness. I think you wanted a confrontation. I hotheadedly engaged, and both of us were riled up once I sat down. I ran through all the things I could say to you once we had gotten over the bridge, the ways that I could embarrass you in front of the other passengers, or how I could make you feel guilty by showing false compassion and asking you what was wrong because clearly you were looking to spread your anger to others. As a bus driver, you’re in the unique position of being able to collect and distribute bad moods along the same route as you collect and distribute passengers. I wanted you throw it back in your face, but then something switched. I realized if I retuned all that darkness to you, with the passengers as my audience, it would just fuel your burning resentment against lord knows what. You were angry before I got on the bus. You were angry before you knew I existed. Your actions weren’t personal. You don’t know me. You don’t have anything to hold against me. My standing a few feet from the bus stop was just an opportunity for you to be hateful, and if it hadn’t been me it would have been someone else. You just feel like shit, and you wanted to pass it along. You wanted a reason to be angry so that you could release what ever funk you’ve bottled up elsewhere. That’s really selfish of you. Lucky for you, me, and the other passengers I’m not eight years old anymore and I control my temper. So, I’m not even going to blow you a damn kiss. I’m just going to vanquish you with the power of my mind, bitch.

Love Lili