Reflections on (almost) two weeks of daily writing 

Donald Guy
9 min readJun 16, 2014

It has actually only been 13 days since I vowed to begin a daily writing habit, and in that time I have a) done so to a first approximation, but b) already had a surprising number of feelings and thoughts about it and how it seems to already be changing my thinking as a writer.

Shocking, I know.

The short version is:
1. It was surprisingly easy at first but its getting harder.
2. Trying not to worry about quality/topic is already ~backfiring.
3. I am already feeling constrained by the self-imposed time limits
but 4. It was probably a pretty good idea and I should probably keep doing it

But I am Donald Guy after all and when (if you ask my friends) have I ever stuck with just the short version? So on to the longer:

Making the Bed:
1. A reserve of clean sheets

I once, in passing, caught a clip of an interview with someone—I’m not sure who, but I actually think it was Girls’ creator Lena Dunham— in which they reflected on an interesting experience common among television creatives: that writing a first season is surprisingly easy, and it’s when you get renewed that the real creative fear sets in. I don’t have the source at hand so don’t take this as verbatim, but it was something like:

You’ve grown up with these characters in your head. You’ve thought about their lives and plotted out these stories and when you finally have the opportunity to tell them, they just flow right out, and it’s great… But then you run out. But people liked it and they want more and its like “Shit. I’ve created these people; people care about their lives and I have to make them keep happening!”

I haven’t been writing fiction and haven’t yet created any new logical people to keep up with—probably a good thing, since I seem to have trouble running even one life—but nevertheless this comment sticks in my head in a spotlight of sympathy.

When I first started writing recently I apparently had a creative backlog. I reached for what just seemed like “an idea” and out flowed words quite easily.

Not actually that useful

I didn’t really realize it, but I had been drafting at least a couple of those pieces in my head for a while:

  • I had talked to several people about my “fact” vs “opinion” theory of awareness and meditation;
  • I had tried on numerous occasions to explain to others (or even myself) what DevOps is.

I don’t really feel like I thought about these conversations explicitly when I was writing those pieces, but for better or worse, whether I realized it or not, I had rehearsed those ideas. I had some sense of how I wanted to express them. And now, despite a small list of vague descriptors for potential “topics” I have captured in OmniFocus, I kinda feel out of ideas. But I think I kind of only feel that way congruent to another idea captured in the “quote” above:

Lying in It:
2. Quality, quantity, coherence, and fear.

I set out on my writing adventure with several (meta)ideas behind it, but a major one was eliminating self-consciousness, lowering activation energy, and allowing quality to be an emergent behavior of quantity.

This idea seems kinda silly to me on some level, but I was inspired by Jonathan Mann’s video autobiography (left), which sets the probably still-high bar of 10% “awesome” to 70% “suck”; as well as some standup comedians’ reflections that it takes about 10 to 12 years of on-stage experience to find one’s comedic voice. I figured better to start sooner rather than later if I was looking for Gladwell’s (or better yet Macklemore’s) proverbial “ten thousand hours” on a path to proficiency.

And yet it seems oddly unfortunate that a mere 5 days into my experiment I hit something that—to my possibly too low for greatness standards— looked like a big success:

By a fortunate conflation of timing, hype, luck, and whatever my meager talents are, my DevOps piece has been making it around the twittersphere.

Now granted a) a 23% read rate probably reflects something negative about my execution, and b) a week later I haven’t had another hit so it’s hardly like I am even matching Mann’s .100 batting average, but LALALALA! I can’t hear you over the thunderous applause and the strange simultaneously ego-boosting and humbling experience of having your piece trying to explain a concept being tweeted by the referenced originator of the concept and complimented in-person by another thought leader you mentioned a day later. Also, I gained like 18 non-bot twitter followers including some I was already following for months.

These are difinitively cool things, and also pretty trivial things, but damn if they didn’t get me in my own head — it apparently really didn’t occur to me that shouting in a public square might gain an audience I felt a human need to cater to. Eight days ago, I didn’t actually realize Medium had a stats tab; now I’ve checked it a probably an embarrassing number of times. Suddenly I find myself feeling a weird, probably totally anticipatable, but to me totally unexpected confused set of feelings that, if in words, might sound like:

  • “People are coming to my Medium profile to read about DevOps! Now I can only ever write (on Medium) about DevOps!”
  • “I have to provide a cohesive narrative to acquire new readers!”
  • “Can I turn this into a way to pay my rent and have more time to write?! Is that even a thing I even want?”
  • “People expect my pieces to have at least one funny gif now! DON’T THEY!? OH GOD, WHERE WILL I FIND ALL THOSE GIFS!”
  • “F#@k! There are strangers! ON THE INTERNET! Anyone might read anything I say!”

I really ought to have learned the last by now — e.g. it was almost exactly four years ago that I discovered the not large, but not trivial popularity of my college essays on a back corner of the internet—not to mention that I just, you know, live here. But nevertheless, it seems hardly a coincidence that I wrote only DevOps for a few days, managed only private writing for the few days between then & now, and suddenly find the need to use grawlixes when titular expletives for dramatic effect seemed perfectly cool 13 days ago.

Similarly, ask some of my friends and they’ll tell you I’ve been an obnoxiously outspoken proponent of effusive, privacy-skeptical social networking use for going on 3 years now (coinciding, probably not coincidentally, with my FB internship), but suddenly I am feeling weirdly and perhaps hypocritically exposed. I turned on the passcode feature of Day One on my laptop a couple days ago. I tell myself that I haven’t taken the “respond to a prompt” option yet in this writing exercise because I feel apathetic about and can’t think of a response, or at least not a “good” response, to the prompts I’ve found. But it seems also possible that I’m simply just afraid. That I’m worried what people will think of me for my thoughts about something arbitrary—about the content itself, but also about the quality of the writing.

What Dreams May Come:
3. Rising skepticism on the daily artifact

The point of this exercise was to get me writing more. It’s working there. A sub-point was to get me writing more freely and eagerly. As I addressed above thats proving an uneven struggle. I thought I could get myself to focus on churning out a haystack and let the thresher of the internet worry about finding the needles — but now I am getting caught up, already, with a concern for delivering a consistently high quality product. I remain at an impasse of whether thats a good concern at this point or a mere impediment to creativity.

One particular thing I am wondering about is whether it it is smart to think of a habit of daily writing as a habit of one piece a day. I have never been one much for the process of drafting, despite abstractly knowing its wisdom-qua-necessity. But its creeping up on me. Some of my concern for quality comes from self-consciousness, some of it comes from perfectionism, but some of it is coming from the simple logical question “can I actually expect to (regularly) write anything good in a single seating?”

I resolved to write daily; I did not resolve to publish daily, but I was thinking largely in terms of dichotomous expression of publishability — public or private; as dumb as it is, I really didn’t account for the idea of works in progress. I am unclear on to what extent I think revision “counts” as writing for a given day: should only material addition count? or so too should rewording, restructuring, and correction? I really don’t know. Nor do I have a sense, if I allow things to expand over time, how to split attention: how often to make myself publish, or how much to parallelize. It seems like a pretty big can of worms, but already in these couple weeks I feel some amount of reservation with my initial approach.

Rolling over:
4. Creative Inertia

Obviously, I have some things to figure out about how to practically, and to good effect, keep doing this. But it seems pretty clear, despite momentary doubts here and there (sometimes for up to a few hours at a time), that it seems worth keeping on. In the last couple weeks I haven’t been free of fatigue or angst, I haven’t even always been 100% sure I shouldn’t still worry about being maybe burnt out, but on the whole, I think I have felt more engaged in life.

The latter part of last week, I felt, for the first time in a while, that I can remember, “positively busy”. That is “ positive” in the emotional valence sense, not (just) the certainty sense. I felt like I maybe had more to do in the immediate future than I had time for, but that I was like excited to get at least some of it done. I felt not so much an overabundance of obligation (negatively busy) as an overabundance of opportunity. And while I know that feeling can also be stressful, in that moment it was nice.

One thing I noticed was that it wasn’t just easier to write words; it was easier to write some code that I needed to. And counterintuitively, both of these things were actually maybe easier still when there was also a talk at DevOpsSummit I was aware I was missing, or had to run to get to soon. I thought of what Arnold Schwarzenegger said in his (pretty motivational) appearance on the Nerdist podcast — again not verbatim, but it was something like—“I’ve learned that really the more you do, the more you can do”. He was pretty sure in his claim there, as others also have often said, that outright rest is rarely the cure for (creative / motivational) exhaustion.

I thought of it, somewhat reflecting on the theory of paradoxical optimism, as akin to the other half (and the whole) of Newton’s first law of motion:

A mind at rest will tend to stay at rest unless acted upon by an external inspirational or motivational force
A mind in creative motion will tend to stay in creative motion until acted upon by an external distracting or demotivating force (e.g. physical exhaustion)

And yeah its hand-wavy and overgeneralized, and also probably “obvious”, but I think there is some sublime experiential truth here. Research about morning rituals, daily habits, and burnout all apply to some extent and its a good rule of thumb.

Thus, though I am finding topics harder to come by and select, the act of publishing slightly more unnerving, and the logistics of how to scope writing confusing, I think I am onto something here. And I should keep at it. ☺

Thanks for reading!