Photo by Claudio Schwarz on Unsplash

This Is How I’ve Posted Every Day for the Last 100 Days

And here’s the price I’ve paid to do it.

This is number 100.

It’s an arbitrary number, but something about decimal conditioning of humans makes it appealing. It is a good time to take stock of where I am, how I got here, and what the future holds.

How I got here

The decision to write every day is due to two influences:

  • The #Ship30for30 program, which is more based around short-form and data-driven essay writing. But it taught me a lot about editing, about headlines, and also connected me with a writing community that was both supportive and demanding.
  • Khadejah’s article on her experience writing every day for a year:

There’s also the fact that I tend to enjoy numerically-bounded challenges. Can I do X, Y times? And what does that do? I am a stubborn person, which is not necessarily a positive trait; often it looks like too stupid to know when to quit.

I’m still trying to figure out if this is one of those times. Ask me again at 200 posts.

“I’d be interested to hear why you wouldn’t recommend this.” — Suzy Pope

Speaking of asking questions, I’ve had a couple pop up, particularly in relation to the article I wrote when I hit the 2-month mark of daily posts:

I mentioned in that article that I’d started out my journey on Medium by importing my long-running personal development blog Love. Life. Practice to the Medium platform — and that it had been a mistake.

It means I have over 900 articles posted on Medium — none of which were written for Medium, and some of which go back a decade.

That meant that when I posted those pieces, all at once, none of them had a chance to be curated — and worse, I ended up in “curation jail”, as @ZulieRane put it in her valuable piece that I read too late.

I managed to escape curation jail, and now almost all of my articles are “chosen for further distribution” as they say, but it was a hard lesson to learn.

It’s not a process, it’s a system.

“I’d love to hear how you break down the 2 hours for various tasks — writing, editing, formatting, publishing, and tips you have for making that time efficient.” — Anh Dao Pham

I have tried many writing processes, things like writing ten blog ideas every day (James Altucher), using an elaborate Notion content hub (Ev Chapman), and other kinds of creative pipelines. What I’ve found is that any rigid system of content creation does not work for me, because I am not rigid; my mood, energy, attention, and available time all ebb and flow. Any system that works one day is liable to not work the next.

What I’ve ended up with is a Frankenstein’s monster of a writing habit, made up of pieces of routines that I’ve picked up along the way. I think of it as a system rather than a process, because systems are made up of processes that interact and function according to the environment the system is in.

Here’s the basic outline:

  • My Writing Stack: simply for the gear nerds out there: I write most of my posts on my iPad using Ulysses app, which I then export to Medium as a draft for final layout and editing. I’ve also found that the Medium app on the iPad is useless for writing, so I stick to the online version.
  • Idea Generation: I do have a long list of potential topics to write about in my Notion database. The problem is that most of them seemed like good ideas at “idea generation” time, but when it comes to sitting down and writing them, I find them stale.
    Ideas have a shelf life. I find the best way to get slightly ahead of the game is to have two or three ideas in drafts on my iPad, migrated either from the notebook I carry to to capture ideas as they happen (Apple reminders and Siri also work well for this).
  • Content mining: On any given morning, even if I have something planned to write about, the actual post is far more a matter of what I feel like writing about. The best posts are personal and passionate, both in terms of how easy they are to write and how well they are received by readers — the data doesn’t lie. This, I believe, is the difference between a blogger and a journalist; I get to choose what I write about.
    On days that I don’t have as much time to write, I mine my own content (900+ stories, remember?) and will re-write a post from my past and put it up with shiny new formatting, fewer clichés, ruthless editing, and a better headline. That shortens the time it takes to write immensely.
  • The Act of Writing: My preferred way to write is early in the morning between 6–8am, sitting on the couch with my iPad on a lap desk and a cup of coffee. I listen to mixes of tango music, which I find has just the right mix of instrumental beats and melody to fuel my fingers.
    I use focus mode on the iPad to keep all but the most urgent messages or notifications from interrupting me, and you can ask my partner if it’s a good idea to try and talk with me when I’m in writing mode (sorry about that, hopefully the bite marks will fade soon).
  • Editing, Schmediting: I think my biggest weakness is that I don’t take the time to edit my posts as well as I could. Sometimes my posts go directly from draft to publishing without more than a cursory glance at the text.
    The thing is: I don’t see a huge difference between how well pieces perform on Medium whether or not I spend a lot of time editing them. And one of the lessons I learned from Ship30for30 is that you have to hit “publish” when your piece reaches the level of good enough, because it will never reach perfect.
    Also, I’ve learned to stop thinking my posts are precious. None of these are going to be manifestos that change the world — they are simply ideas that might help one or two people as they go through their day.

Right now I spend between one to two hours a day writing and publishing these posts. That in itself is a big reason why you might not want to do this; not everyone has that kind of time in their day.

What’s the goal for the next 100 days?

I can think of a few ways I’d like to change or adjust my writing process:

  • I plan to submit to publications: aside from one piece picked up by Forge, I haven’t done that during this daily practice.
  • I’d like to do more illustrations: sketchnoting is a passion, and I think it works well with this process, except for the time it takes; I’m still working on finding a way to make it a smooth part of the process.
  • I’d like to get more “emergency posts” set up: right now I’ve been very lucky, in that I’ve had 100 days with no unexpected events that would have kept me from posting. I don’t like living that dangerously; it means this is a fragile and easily ruined goal. In an ideal world, I’d have posts written a day or two in advance, maybe even edited (!) and then scheduled for publication later.
  • Working in some other channels: I have a lot of experience with podcasting and some video streaming chops as well; I have considered trying to re-purpose my content to Twitch, TikTok, or the like. Again, it means a time investment; but perhaps it would be worth it?
  • Reclaiming my personal habits: as lovely as this writing time is, it has replaced some core habits that used to occupy this time: morning yoga, daily pages, and meditation. After 100 days, I feel the effects of their absence, and it ain’t good. I need to find ways to fit those things back into my day.

The one thing I know is: I’m not ready to quit. Far from it — right now doing this for a year feels less like a chore than an inevitability. So the real answer to “what’s next?” is simply: Write. Publish. Repeat.




Gray is a former Marine dancer grandpa visualist who writes to help adults figure out what they want to be when they grow up.

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Gray Miller

Gray Miller

Gray is a former Marine dancer grandpa visualist who writes to help adults figure out what they want to be when they grow up.

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