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

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