I Wrote 300 Words Every Day for 150 Days. Here’s What I Learned.

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I Used to Be a Writer…

At least, that’s how I put it for about seven years: from the time I decided to give up my writing career in order to pursue a career in music. And during all those seven years, I hadn’t ever looked back. There was no reason to. Music turned out to be a good career choice and I’d done well for myself. And I never missed writing for others. It was enough to write in my private journal each morning.

But that changed last summer. I had just moved to Portland, Oregon, and since I was so new to town, I had little work and few friends. It was one of the hottest and driest summers on record, and I spent my days of unemployment in my darkened living room, almost overwhelmed by the heat, picking through the many boxes and hard drives of old writings that I had carried from apartment to apartment for years, yet had somehow never really looked through or organized before, in all that time.

Oh yeah, I thought, as I turned over the journals, poems, essays, articles, short stories and novels to which I had devoted my 20s. I used to be a writer. And I could be one again.

But how to start?

I know: just write. But that was inadequate advice. I’d been “just writing” my whole life. What I needed was a supportive venue. I needed an audience who’d bear with me as I once again practiced the art of writing for strangers.

As a musician, I had conquered performance anxiety by busking. When you’re playing on the street for spare change, it doesn’t matter if you suck. Few people look at you twice, and half the passers-by have earbuds in anyway. I developed confidence performing literally on Valencia Street in San Francisco; a couple years later, I was playing shows in a popular bar on that same street.

I needed to find a similar path with my writing.

A Place to Write

Those drowsy, rootless summer days quickly gave way to an active professional and social life. And as my music work picked up that fall, it became that much harder to sustain a routine writing practice. In fact, once I decided to pursue writing again, it took me almost a year to find a rhythm with it.

It happened like this. In early May, a friend of mine posted on Facebook: “I kind of miss writing,” and she expanded on that thought by evoking the glory days of Xanga and LiveJournal — specifically, what it was like back then to practice writing just for the handful of her friends who themselves had blogs. I had been on those sites too in the early aughts and also missed that vibe. This started a discussion about how to “get back into writing,” and many ideas were proposed, from face-to-face writing groups to email lists to using Facebook Groups for the purpose.

All of those were good ideas, and I considered pursuing the latter. But that same day I did a little Googling and discovered something interesting.

Write Together

What I discovered was a tiny blogging platform called Write Together. It’s a paid site, launched on January 1st, whose object is to create a community around the goal of writing and posting 300 words every day. The primary feature is a stripped-down form for entering text. You can only hit the “publish” button once your text reaches 300 words. And if you post for two or more days in a row, the site tracks your streak and displays your icon on the site-wide leaderboard.

The site immediately resonated with me. For one thing, I liked the small user base. It reminded me strongly of my early days writing on LiveJournal for an audience of about half a dozen friends. Such a small group seemed likely to make for a supportive place.

For another thing, I liked the emphasis on daily minimum practice. For years I’ve been giving my piano students a directive, “touch the keys,” which I learned from a book by Kourosh Dini, MD — who is a wonderful improvising pianist in addition to his many other attainments. Every day, even if you don’t have time to really practice, always at least touch the keys of the piano and, ideally, play for the few minutes you have. This keeps you literally in touch with the instrument and your larger practice. The goal of 300 words a day reminded me of this — a way to “touch the keys” of my writing practice, the literary equivalent of improvising for five minutes before getting on with my responsibilities and obligations.

The membership fee of $8 a month was a drawback for everyone I mentioned it to, but to me it seemed like one of the most positive aspects. At the very least, it meant that everybody who was writing on there would necessarily be of serious intent. Nobody pays $8 a month in order to be an internet troll. I wanted to practice in a place where all my readers were similarly engaged. And in case I had any doubts, I could make all my posts “community-only” (as I ultimately did), meaning the outside world wouldn’t be able to see them.

I figured I may as well give it a shot. I signed up for an account, and on Saturday, May 11th, I made my first post introducing myself to the community.

The people there turned out to be exactly what I had hoped for. And for the next 152 days, I wrote and posted at least 300 words, and often quite a bit more than that. No matter what else was happening in my life.

What I Learned

You can always draft one page.

The daily goal of 300 words is trivial — just a single page — and the Write Together leaderboard reminded me every day that I was trying to keep my place on it. Keeping the streak was a minor challenge, but achieving it each day was fun, and it gave me a small sense of accomplishment. And I badly needed that feeling for a few months. So of course I kept at it.

This combination of factors kept me practicing my writing, on days I likely wouldn’t have otherwise — the weekends — and through times I definitely would not have, such as when I was slightly intoxicated, recovering from surgery, sick with a cold, or close to falling asleep. (Fortunately, never all four at once.) However, this experience reminded me of a lesson I first learned in my twenties:

How I feel is (mostly) irrelevant to how the first draft comes out.

For most of my twenties, merely supporting myself took up most of my time. I’d go from one minimum-wage job to the other during the day, and would write in the little scraps of time left over, before work, after work, on the bus, on my lunches and five-minute breaks. I got into the habit of writing whenever the opportunity arose, no matter how I felt, always carrying a pen and half a dozen sheets of paper folded up in a back pocket.

Over the course of several years of this, I learned that I can draft complete garbage while fully rested first thing in the morning, and I can draft great material at the end of an exhausting day. Within certain obvious limits, it just doesn’t seem to matter what condition I’m in when I show up to write a first draft.

It helps a lot to write for well-intentioned strangers.

On Write Together, I got to know my audience through their own posts, and after a while I started trying to write specifically to their interests. Having an audience is key to my own motivation in both writing and music; knowing what my audience is interested in helps me select projects.

In those early days it was also really important for me to feel like I was writing for supportive readers. The first time around, I had writing groups and sympathetic editors, whose presence in my life offset the impact of nasty responses — or worse, total indifference. This time, the people on Write Together served that function. And after a while I felt secure enough to expand my ambition. I started wanting to write pieces that would require more than one session, aimed at a wider readership.

Which brings me to the next lesson I learned.

Just because you write every day, doesn’t mean those writings will add up to anything.

This seems obvious, but at several points in this run of posts, I convinced myself that whenever I posted for several days in a row on the same topic, I was “really” working on a larger project.

The thing is, I never did gather those posts together for revision, so, no, I wasn’t really working on a larger project. Regular drafting is an essential part of a writing practice, but for the work to amount to anything more than that, you must devote quite a bit of separate work to shaping, arranging, and revising what you have drafted. And that requires a lot more time and concentration than the initial drafting does; perhaps ten times as much.

And at the very end, I learned something surprising:

Once my daily habit was firmly established, the daily post started to become an obstacle to further development of my writing.

The effort of writing and posting every single day very clearly began to draw energy and attention away from projects that would take more than one session to complete.

I hadn’t anticipated this at all. Towards the end of my 150 days, I thought I could write up a few notes in my private journal, go on to do a quick Write Together post, and then work on a longer-term project. But I found myself repeatedly picking ideas I could complete in one sitting, and putting off the more-ambitious efforts. It had started to amount to virtuous procrastination.

So I decided to commit to a goal and schedule that would better serve my new ambitions. Instead of daily posts, I would write on weekdays only, and aim to publish a longer piece each week on Medium and my blog. This essay is the first product of that effort.

Final Thoughts

I really enjoyed the 150+ days that I was writing and posting daily on Write Together, enough that I have decided to remain a member for the time being. I’m enjoying the posts from the friends I’ve made there, and I’ve been posting there sporadically since I changed my goal. I definitely recommend the site to anyone who’s interested in starting a daily writing habit, because it was a fun and supportive place to practice for half a year. And it worked! It absolutely got me back into the habit of writing, and back into the mindset of writing for an audience. But in the end, I needed to move on in order to have time for more ambitious projects. And I’d call that a success for both Write Together and myself.