Any writer will tell you that the hardest part of what they do is writing every day, no matter what. Every famous author in history has shared the perseverance to sit down and do the work, day in and day out. It’s what separates those who talk about wanting to be a writer and those who are writers. All other writing tips and dogma are nothing more than the icing on the cake.

It’s easy to write when you feel inspired. It’s easy for the words to flow when you have a clear head and a healthy body. What matters is writing when you feel awful. When you feel empty and uninspired. When the words seem to carry so much weight that your fingers feel tired just hitting the keys. When you have a headache, a box of tissues, and a cough that won’t go away. When you feel like an imposter.

Those are the moments when it is so critical to sit down and write. That’s when you learn how deep your motivation is. How much willpower you have on tap. How cathartic writing is to you. How far you will go to train your writing muscles.

The more you practice writing when you least feel like, the amazing difference it makes when you do feel inspired. How fast you can fly and how effortless it is to write when deadlines approach or when the pressure to rise to the occasion presents itself.

Today marks the first day of a 31 day writing challenge, in which I’ll be taking on the wonderful and inspirational writer, Melissa Joy Kong. The premise is as simple as it is brutal: publish an original piece every day, no excuses. If either of us fails to do so, we owe the other $20 per day missed. That’s it. At any given time there are hundreds of these going on across the Internet.

For me, this writing challenge represents the chance to end my on-again off-again relationship with writing. My writing history is divided into cookie cutter chunks of time with huge gaps between. I will begin writing, do so prolifically for a period of six months and then hit a wall. In the past, rather than push through that wall, I collapse. Then each passing week of not writing brings shame, then anger, then hopelessness, and then abandonment. The final chapter being deleting all traces of my writing from the web, in the hopes that if I can pretend it never happened, maybe the shame of giving up once again will fade away.

The first was in 2001, my freshman year at Ohio State. I’d create a static html page full of notes and images and upload it to my Geocities site on a weekly basis, chronicling my life as a college kid. Even though Blogger already existed, I preferred my ugly and manual publishing style as it felt more organic. I was getting 200–300 visitors a day. I did this for about a year and then wiped it from the web. I didn’t like the kid I was portraying in those posts. Geocities Seth was far more interesting and popular than I was in real life, so it felt disingenuous for him to exist anymore.

My second writing spurt came in 2007. I wanted to do a “meta” style WordPress blog, where it was black text on a white background with no formatting, logo, colors, etc… I wanted it to be about my writing and nothing else. My first post was the classic “I’m going to be blogging! Yay!” type of post. The second post I wrote was about how massacre related domain names were being acquired during the Virginia Tech shooting, just minutes after the killing began. Dozens of domains like vtmassacre.com were being registered. Some domain names were already being put up on for sale on eBay while the victims were still lying on the ground. I was disgusted and wrote a reaction piece that was widely shared. 65,000 visitors in the first 24 hours and over 200,000 by the end of the week. The Washington Post and Wired picked it up. The Univ. of Missouri School of Journalism reached out to invite me to speak about “citizen investigative journalism” (I turned it down.) It was overwhelming. Instead of reveling in it, I had a “brain failure” and became consumed with an irrational fear of never being able to repeat this success again. I honestly believed that I had just peaked and it was all downhill from there. I forced myself to post another dozen times over the following six months, but they were empty angry posts about random subject matters (I though anger was going to be my “thing”). They were vapid attempts to recreate the moment of magic again. None came close. I felt like an imposter who had gotten lucky. By Nov 2007 I gave up on my blog, swearing off writing. I was done. The shame had consumed me.

The third writing spurt came in between 2009 and 2010 after my company had almost gone bankrupt and my wife had left me, so I was once again a peak moment of anger (mixed with depression, disappointment, loss, irrationality, mood swings, and the like). It made my writing more “interesting”, which to this day still disturbs me. I don’t want to have to be in the middle of a violent series of emotional issues to find the inspiration to write and to write with passion. But, in the moment I ran with it. I decided to write about entrepreneurship for the first time, in a 15 part series no less. My sixth post was once again an anger and reaction style piece. This time in response to an article I read that outlined 20 rules to be a real entrepreneur that I thought were both ignorant and childish. My response piece struck a nerve once again. It was syndicated by the Harvard Business Review, got shared widely, and drove over 100,000 visitors to my blog in the first few days. My first thought was, “fuck me… it’s happening again”. This time I stuck with the writing, finished my 15 part series and even tried to continue on for a full year with additional entrepreneur advice. It wouldn’t last, as I deleted my blog in 2011 after not publishing in months. Even though I had co-founded a company that soared to #24 on the Inc 500, I had also almost destroyed it. I had to lay off friends who trusted me to employ them. I had buried myself in debt and my outlook on entrepreneurship was the most jaded it had ever been. Who was I to advise any founder on best practices? Why should anyone ever take me seriously? Therefore, no entrepreneur blog should exist with my name attached to it and bye-bye it went.

Since 2011, I have sporadically posted one-off articles here and there. They are so far between, of such random topics, and scattered across so many different sites it’s bizarrely schizophrenic. It’s the behavior of someone who does not want to gain a following by coming across as reliable.

This writing challenge represents much more than a chance to start writing again, but a chance to this time stick with it. To fight the urge to give up, to write when I feel awful, and to publish when I feel like an imposter.

To once again believe that I deserve to have a voice.