If I Don’t Publish 3 Pieces Of Writing By Midnight, I Have To Wire My Enemy $10,000

(On Creativity, Loss And Starting Over)

This summer I challenged myself to write one thousand words a day for ninety days.

I picked up the idea from a retreat I attended in the spring with Cheryl Strayed, my long-time literary hero. On the final morning of a three-day retreat - one where I had found myself infuriatingly blocked on writing anything - she off-handedly mentioned a challenge her friend Jami Attenberg ran each summer (Here us the link:)

The goal is to write one thousand words each day. That’s it. 

At the mention of the challenge, something unexpected inside me woke up. A ‘Yes’ rippled its way through my system. I wanted do this, for some reason. Something would surely come out of it. 

I will try not to bore you (too extensively) with the pitfalls of writing as a craft, but it is a well-worn adage that to get to the good stuff, you first have to clear out all of the garbage. I figured this would take me two to three days at most. Surely, I reasoned, there was not ninety thousand plus words of garbage inside of me. 

It turns out yes, there was. 

Every day of the summer, I sat down diligently in front of my laptop and put words to screen. I wrote about toxic shame, complex PTSD, attachment healing and relational wounds. I rehashed concepts I’d published videos about on Youtube and spoke with literary agents about the book that would best fit my brand. 

Some of the writing shifted things inside of my system. Most of it ostensibly did not. 

Sitting down in front of my computer on the average day felt like sifting through a pile of dead things: challenges and pains that had long since expired in my system, but could package themselves into digestible lessons if I asked them to.

I adhered, diligently, to these dead things, while my existing life fell apart around me. I wrote in the ER waiting room as my mother underwent open-heart surgery. I wrote from an empty apartment the night my closest friend moved out of the home we’d shared for years. I wrote through pounding hangovers as I processed the end of the first romantic relationship that I’d hoped, in good faith, would last the rest of my life. I wrote on airplanes, buses and trains as life shuffled me from one sudden emergency to the next. 

There were very few constants this past summer. But there was always one thousand words. 

Writing quickly become the most reliable thing I did each day but it was also a joyless pursuit. I knew how to put words to a page but nothing struck me as worth hitting ‘Publish’ on. The deep ‘Yes’ inside of me - the one that had swelled up that final day of Cheryl Strayed’s retreat - was demanding something more from me: it was asking me to find my beating heart inside the work.

This proved to be the harder thing to do. 

For years I have capitalized on my ability to package up pain and trauma neatly. On my very-public Youtube channel, I speak openly about how I’ve made sense of past confusions and found language for what was once incomprehensible pain. This  type of sharing is useful, and important to me. But it is also an invulnerable act. Teaching from a closed wound serves others. Writing from an open one serves me. 

And so I have come here today to serve myself. 

As I sit here writing this, I am surrounded by five of my closest friends. I have rented out a boardroom in a building I like to work out of and set up a challenge for each of us each to put our money where our mouth is when it comes to the projects we’d like to finish most. One friend has to finish a blog post, or lock himself out of his favourite phone game for a month. Another must complete a series of thoughtful LinkedIn posts, or shove his mouth full of blueberries and post that as his status instead. I have decided to wire a person who broke my heart ten thousand dollars by the end of the day if I do not publish three pieces of writing by midnight. 

The term ‘enemy’ in this title is written both in jest and from a place of deep pain. Enemy as in, the person who shares the majority of the memories that actually matter to me from the past fifteen years of my life. Enemy as in, the person whose laughter is the sound I miss more than anything on earth. Enemy as in, the person whose absence is likely pulling me towards the spiritual lesson I need to learn most next. 

And so this challenge is a spiritual pivot. 

Producing work, to me, has long-since been a way of earning money and teaching from a place of past wounds. Writing honestly is something else.

Writing is the act of revealing oneself to the world. Of deciding that what is inside of one’s mind at this exact moment is true enough, real enough, human enough, to be represented in actual words. This has been the hardest thing for me to accept during this season and so it is the thing I am forcing into my own awareness: now is not the time to give back. Now is the time to grieve. 

One of my long-time favourite adages about writing comes from Hemingway: “All you have to do is write one true sentence. Write the truest sentence you know.” 

And so, here is the truest sentence I have inside of me right now: This year has been a season of remarkable loss. 

Loss I don’t know quite how to make sense of or help myself through. Loss I want to avoid by claiming authority over and pretending I am above having to move through. Loss I cannot ignore or bargain or rage my way out of. But I can start by putting my attention on it. 

What is the shape of this loss, and the flavour? How do I live with it? How will I carry it around? These are the questions normal living shoves out of our awareness but writing demands from us ruthlessly. 

Through writing - the two pieces that follow this one and hopefully many more to come - I vow to keep my own attention where it matters. Not on what I want to dole out or give away but what I want to get deeply acquainted with inside myself.

My only condition for the work - for all of the work that follows - is that it has to be true. It cannot be work focused or goal-oriented or otherwise self-evasive. It has to be motivated by the desire to touch the sharpest edges of my life and give myself a safe place to bleed. 

And so, onward we go.

I could wax poetic for ages in an attempt to avoid publication. But I have spent a whole summer on this nonsense. Today I do not want to wire my enemy ten thousand dollars, so I’ll paste these words into a substack post. And I’ll call it an imperfect start.