How Trying to Fail Once Every Day Changed My Life

My goal was my way of trying to keep myself aware, and awake, and alive. My goal was my way of dunking my head in cold water every single morning and every single evening. My goal was to set myself up for a failure every single day.
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When I think about how to live my life, and what I want to do, I'm stunned by how often it can change. I'm stunned by how often, and how drastically I've changed. No matter how sudden it's seemed, I know my life has never changed in a single huge, life defining moment. It's changed a little, every day, and a lot in the quiet seconds that tick by unmarked and unnoticed, but I've never experienced a moment of clarity on a mountain top.

A year ago today, I set a goal for myself. I decided that I wanted to improve, in 365 ways. I wanted to change my life, daily, in 365 different ways, in 365 different 24-hour blocks. It sounded like a good goal, a tough goal, something that could make me get out of bed and try to be more than I was.

I don't believe that a life lived unconsciously, on auto-pilot, without a thought to the wider picture, is a life lived well. Call me judgmental, but I think being a human being is about gaining a certain level of self awareness -- not just acting on animal instinct, or out of reaction the people and the world around us.

My goal was my way of trying to keep myself aware, and awake, and alive. My goal was my way of dunking my head in cold water every single morning and every single evening.

My goal was to set myself up for a failure every single day.

I kept a diary of sorts, a small scratchpad. I've written about it before. It was simple, and it wasn't anything detailed. Every day, I wrote down what I tried. And whether I won or lost, succeeded or failed. I wanted to share a few with you, and give you a glimpse into the world I made my own, and explain my reasons. I've added some notes to these.

Day one. I tried to write my first long form poem. I failed. It was unfinished.
This one was something raw, and emotional for me. I walk a fine line, as an investor, a founder and a person who loves to create art, and write. Pushing myself to create a long form poem, a piece of work that entwined my heart and soul with my words, that was difficult for me. It's not at a point where I'd ever be ready to share it...but you never know. Doing it made my examine why and how I write, and the version of me that's reborn every time I hit publish.

Day two. I tried to eat Escargot. I succeeded. It was unexpected.
I know this seems a little ludicrous. It's not that big a deal. But you don't know me, and you don't know how set in my ways I can be with my diet. If I had my way, I'd subsist solely on bottles of Soylent, with little else to nourish me. Making myself eat something completely out of my usual range was an attempt to re-imagine what I eat, and why. Turns out I don't hate Escargot. But I don't love it.

Day three. I tried to do a drop-in on my skateboard, the way I did when I was younger. I failed. Skinned knees and a sprained wrist.
When I was a kid, when I was a teenager, I was a skater and a punk kid. That's a version of me that I regret losing, over the years. I still break out my Black Flag records, from time to time, and I still give them a spin -- but the rebel who was ready to fight the world isn't around so much. I wanted to get back in touch with him, and I tried to see if I could still skate the way I used to. I'm sure it's no surprise that I fucked that one up. It hurt a lot. Still, it was the catalyst that made me pick up my board again. I've been practicing a little, every week, ever since. I haven't gotten much better, but I will. That's a failure I call a win.

Day four. I tried to find and close a deal in a single day. I succeeded. I found a startup, and pitched them a service, and closed the entire deal. It was a whirlwind.
This was pretty much driven by a blind panic. From time to time, I freak out about being relevant and useful. That particular freakout was largely because of an email I got mocking me for working with startups instead of founding another one. It was a cruel note, and I get a lot of them...largely, from founders who look down their noses at any business model that isn't hugely scalable. These emails don't usually bite me, but this was from a man I personally respected, and it hurt a little. I needed to prove to myself that there was value in what I did. I guess it kind of worked, but the larger lesson -- nobody can define your value but yourself -- that's only sunk in now, in retrospect.

Day five. I tried to make the perfect burger. I can't speak objectively, but I don't think I failed. I cooked Labneh into the meat. No regrets.
  • Beef mince, formed into patties with flour, onion, garlic and olive oil
  • Labneh folded into the patties
  • Each pattie cooked and pressed into a mound of onions
  • A slice of Monterey Jack cheese melted over the top
  • Brioche buns brushed with mustard and olive oil

...I made a note of the recipe to remember. I think this was a challenge from my girlfriend. She says I met the challenge. I don't know, I think it could have been better.

Day six. I tried to gain an overseas speaking engagement. I failed, but I found some good leads...
...Which ultimately turned into a speaking engagement in the Netherlands. I'd been out of speaking professionally for about six months while I worked on developing some tech products. I've struggled with a speech therapy issue for years, and I was starting to panic that I'd lose the progress I made, so getting back into it before I lost the skill and momentum was a priority.


There's obviously 359 more entries (I didn't miss a single day) but I'm not about to transcribe them all yet. I think you get the picture.

What was I actually trying to do? I was trying to make a bold attempt at something new every single day, for an entire year. An attempt at something that I would run the risk of failing at, privately or publicly. If you're one of my readers, you'll know I love risk, and I believe it's the only thing that can drive innovation and success.

When I started my goal, I had a vague idea that I would turn myself into a real-life YES man, like Jim Carrey in the movie of the same name, or Ben Stiller in the Secret Life of Walter Mitty. I was picturing myself in far off lands, in a helicopter, driven by the power of just-fucking-trying.
Looking back, I'm able to say that it was a little like that. And a little like living on the edge. And a little like becoming vulnerable and scared, for an entire year. But if I could go back and do it all over again, I don't think it'd be any different. I wouldn't want it to be.

The truth is, trying to fail once a day for the last year has changed my life. I know the few days I've shared with you don't look like much, but for me they were a driving force, something that pushed me every single day to break the confines of my comfort zone and be in the world, in the game, in the running.

I'm working on the story of this challenge now, and I hope to turn it into a longer piece that could inspire other people to follow my lead. It's a raw story, and it's personal, with more than a little of my soul written into every word. I can't wait to share it with you.