1800 words about 500 words

where my friend Marc triggers a tectonic shift in my writing life, and then maybe does it again.

I was asked this morning how I should be introduced for a thing I’m doing. For a podcast interview¹. I thought about this for a minute: should it be author and illustrator, or illustrator and author, or should it include designer and educator, or what? The last several issues of this newsletter have been all about the visuals, and I do think of myself as an illustrator before everything else. But this year, so far, has been all about the writing, as far as my own creative development and learning. This issue, as well as at least the next issue of Random Orbit, will be about that.

my beloved 1958 Remington, of which I just recently replaced the crumbling dried and worn ribbon, though I don’t actually do my writing (or drawing) on this thing.

---

---

500 words before email

I’ve mentioned this phrase, 500 words before email, here a few times in the last month or so, mostly in Instagram posts or as *notes* here on Substack. I cannot stress how important these four words have become in me making progress with some work I’ve been struggling with. A lot of writers use something similar to this as a productivity prompt, but this is the one that sort of glommed on to me, and I to it. The idea is to give yourself a manageable chunk of work to do, that’s the “500 words” part, and get it done first thing, before the rest of your life so rudely, yet predictably, interrupts, which is the “before email” part of it.

For years, I have tried some of the variations on this. My wife pointed out just the other day that she has suggested this sort of thing to me in the past, and she’s right. I have found stretches where I regularly carve out some time in the morning, or the afternoon, or in this room of the house or that room, or maybe go to the library or a coffee shop, and I can get shit done. I can find the head-space and the energy to focus, and play, and write. I’ve never had a name for these various attempts², and I guess they haven’t been so perfectly concrete as to give me a proper, black-and-white objective goal on a regular basis. Five hundred words is that.

But also, five hundred words isn’t much. My writing app here (more about this in a moment) tells me that right now, this is the 347th word of this newsletter. I started writing ten minutes ago. At this rate, and I’ll tell you when I hit five hundred words, it will take me about fifteen minutes. Not bad.

But also, five hundred words is a lot! It adds up quickly. Five days of five hundred words is 2500 words. Two weeks of that and we’re at 5000. A picture book is typically 300-350 words. An early reader is in the 1200-1500 range. If you’re writing a novel, expect to aim for at least 60,000 words, which means at five hundred a day, you’ve got your terrible, messy first draft in …does math… 120 days of writing. That’s like six months if you take off weekends (which I usually do).

When I first read this phrase, 500 words before email, in an email (!) from my good friend Marc Weidenbaum, my brain did this math and a bell rang. (By the way, “rang” was word number five hundred. Ta-daa!) The concept made immediate sense to me. Enough work so that it’s meaningful, but not so much that actually getting it done is intimidating and overwhelming. I’d just spent five glorious weeks in France, failing at writing. I had great success in things like sleeping in, and going for bike rides, and cooking dinner with friends and family. But getting actual stuff done, drawing and writing, had proved difficult. In hindsight, this was because my goal was to “write a short story.” And every day I was overwhelmed with the idea of writing this stupid short story. With so much else going on and things to do, each day was not the day that I was going to write the story. And I couldn’t make sense of more variable goals like “just a little bit,” or “part of a chapter.” Had I been able to just think, “I need a half hour to sit down and manage five hundred words,” I feel like that month in France would have gone very differently, work wise.

I began writing with this five-hundred word goal around late July, and I have to be honest here — I do usually check email before writing. I also may check the New York Times headlines, and I definitely make coffee. Some writers get caught up, sometimes emotionally, in work emails or politics, and it just ends the creative flow. I find that if I actually wait, I am wondering what’s going on out there in the world and whether there is some email I need to respond to. So for me, it actually gets some of that distraction out of the way so I can focus. Your mileage may vary.

One important rule for the process that I do follow, is to be fairly religious about stopping after five hundred words. This concept can be attributed to many writers from Hemingway to Stephen King, but the idea is to stop when the going is good so that you have something to pick up the next day. This can be mid-sentence, mid-dialog, whatever. On its face it seems counter-productive. I know where this bit is going, the writing is going well, so I stop? What? YES! And all day I am looking forward to sitting down and getting back to it. This really works.

After two weeks of this, after just ten mornings of writing about this beetle musician, I had 5260 words written, the last two being THE and END, and it felt like a miracle. It’s a terrible and messy first draft full of holes and typos, but it has a beginning, a middle, and an end. It is my story, and it now exists (and now for editing and rewriting and sketches and… stay tuned!).

So try it. Just five hundred words. Give it a few days and let me know how it goes. (1043 words, by the way.)

Product Placement

This issue of Random Orbit is being written on an app called Ulysses. Up to this week I’d been writing my newsletters either directly in Substack or in Apple’s Pages, or, even, at times, in my Notes app. The common feature I liked about all three of these was that I could write on my laptop or my iPad, and I could even start posts or jot down ideas with my phone, which would then lead to an actual newsletter. A process that led to things being pretty scattered. Bits and pieces in one app or another, sometimes in my iCloud folder so that they could sync, sometimes somewhere else. It was a mess.

The novel that I’ve been writing here and there since 2018 lives in an app called Scrivener. I first learned about Scrivener from Peter Brown’s blog post about writing The Wild Robot, and at the time it was revelatory. I loved the idea of being able to focus and write in small chunks — chapters or scenes or even paragraphs — no matter how big or small, that I could easily rearrange and move around, something like index cards³. But Scrivener is also a big and arguably bloated piece of software and it’s customizable beyond belief. Customizing is sometimes good, but it leads to option paralysis and procrastination. Color coding, custom icons, special templates… When you start a new chapter you can name the chapter, write a synopsis of the chapter, write a note about the chapter, and then you have a research file for the chapter, all before actually writing the chapter. All of this is searchable, and it all just got to me too much. If you want to write at times on one device and other times another, it syncs via Dropbox, and while the problems I ran into this were fairly small⁴, I know writers who have suffered some real losses.

My writing writing, like the insect stories, has been in Apple’s Pages as well. Not because I like Pages, but because it’s just easier than using Scrivener. It just seemed more manageable, without all the extraneous stuff that Scrivener does. But Pages has a lot of some things, like layout stuff, and very little of other things, like no typewriter mode⁵. It’s basically a simple hybrid of a word processor and a page layout application, and it’s not really great at either.

My friend Marc, the same Marc that first mentioned the 500 words, told me he was using Ulysses, and it piqued my interest. I don’t like the learning curve of new software as I once did, so I decided that if I can’t figure out how it works after an hour, it’s not for me. I opened it up while watching baseball the other night, and within fifteen minutes I saw the potential. By the next morning I’d transferred the insect stories into Ulysses, started a folder called “Random Orbit,” for these newsletter entries, and even imported the entirety of the novel. (this was no small feat, and will be an ongoing adventure. I had to export the entire project — notes and outlines and the body of the story itself — as MS Word files, and then bring all of that into Ulysses. Nicely, Scrivener saved the folder and file structure that I’d created within the application, and Ulysses recognized that as well. There is a lot of extraneous stuff that Scrivener makes that Ulysses has no use for. But this is actually good: Since I’ve not written anything toward this novel since 2022, I look forward to going in and literally reading the content of every single file. Some of the stuff is in the form of notes from twenty years ago, when I thought the story was going to be a picture book! It’s changed!)

I’m on day four of my one-week trial, and I’m liking it. I’m not here to sell Ulysses, but it’s working well for me.

Thanks Marc for both of these suggestions, and thanks everyone for reading.

---

Because I know you’re really here for the pretty pictures, here are two astronauts I made this week. One is collage, 12x18 inches, and the other a teensy drawing I made with a pen in a sketchbook, scanned with my phone and colored on the iPad. Same, yet different.

1. More about this later, I’m kinda nervous about it.

2. seven paragraphs and a footnote after breakfast isn’t memorable

3. which Scrivener actually uses as a skeumorph — little index cards that you can move around on a virtual bulletin board

4. I trashed an old version of a chapter, which somehow tagged that file as the latest version which replaced the actual good version. I only saved it, the best chapter I’d written, by finding a MS Word export of the chapter from six months earlier, and copy/pasting.

5. Oh man. If you’ve never used typewriter mode in a writing app, give it a try.