2020 — Tim Casasola — Tim Casasola

I often get messages from friends about my writing process. I figured I’d share it here!

This may not work for you. This is just what currently works for me.

This will also change and simplify over time.

tl;dr

I capture ideas on the go and write every Saturday. I write in Bear, mainly because it’s so clean. But the tool doesn’t matter. What matters is getting into the habit of capturing ideas and fleshing them out on a regular basis.

Writing Inbox

In terms of my writing workflow, I capture literally any thought that’s remotely interesting as a note in Bear. I capture the idea as the note’s headline and tag it #inbox.

This is inspired by Andy Matuschak’s writing inbox workflow. Anything that’s tagged as #inbox is fair game for me to write about.

Make coffee/tea

I’ll prep a coffee or tea before my writing session, depending on the time of day. For some reason I’m motivated to write when I make a coffee/tea. I think I’ve trained my brain to associate hot beverage with typing words on a screen. Find your trigger that gets you to type.

Write every week

Then, every Saturday/Sunday morning, I’ll pick one of those ideas and write more about it. I work a full-time job, so I find it easier to write on a day I’m not working.

The biggest driver of my publishing output was writing every Saturday/Sunday morning for at least one hour. I used to struggle with publishing not as frequently as I liked — I wasn’t able to publish monthly on The Jump, which was what I set out to do. Then I told myself “alright, no matter what, every Saturday you will sit at your desk (or at a coffeeshop, pre-Covid) and write for at least one hour.”

That worked.

Every writing session ends up being about 2-4 hours. Every session. However, if I tell myself “I’m going to write for four hours on Saturday at 9am”, I’m not going to write. I’m going to dread Saturday morning. So I tell myself that I’m going to write for one hour on Saturday at 9am. This makes me dread Saturday less: one hour feels less committal than four. Naturally, one hour writing sessions end up being four.

So find the right cadence for you. And do what it takes to get your ass in a chair in front of a computer. For me, that was committing to write every Saturday/Sunday at 9am for at least one hour. Every blog post and newsletter I’ve written in 2020 came from a Saturday/Sunday writing session.

Current experiment: Roam to outline my essays

I’ve recently been messing around with Roam to outline my essays.

Outline of this essay started from notes I took in Roam on a course I took.

Ideally, writing would happen in just one app. It is nuts that I am using both Roam and Bear. But because Roam imports highlights from my Instapaper and Kindle (via Readwise), I can easily pull out points from books and articles I’m reading into an essay outline.

So, specifically:

I pick a topic from my Bear #inbox
I find highlights that relate to that topic in Roam
I summarize those highlights into points
I expand on those points and turn them into paragraphs
These paragraphs make up the first draft

It’s not like this every time, but it’s like this most times.

Tfw your Instapaper and Kindle highlights auto-import to your @RoamResearch pic.twitter.com/u9isvBs5md
— Tim Casasola (@timcasasola) November 5, 2020

Minimize the distance from idea to output

The hardest part for me: writing the first draft. Always. Once I have a draft, it’s easy(ish) for me to edit, proofread, and publish. I think it’s because my brain says the essay is “80% done” once I have a first draft done. If I don’t have a first draft, my brain says I’m 0% done with my essay.

So I try to get through the first draft as quickly as possible. I try not to care about how good the first draft is. All I care about is writing a first draft, no matter how bad it is. Because once I have a first draft, I am 80% done, and my work ahead is easy(ish).

Separate drafting from editing

Each essay is split into two sessions:

Drafting
Editing & Publishing

First session: Draft

Pick idea in #inbox
Outline in Roam
Flesh out outline into first draft in Bear
End writing session

Give at least a night in between drafting and editing.

Second session: Edit & publish

Edit in Bear for content
- Am I missing any points I want to make?
Edit in Bear for clarity
- What could be more clear?
- What sentences are too long?
- What could be cut?
Use Grammarly keyboard
Read essay in Safari Reader View / Instapaper. This helps me catch typos
Pick thumbnail image (through are.na!)
Edit alttext in each image
Make sure punctuation is not hyperlinked
Double check links
Publish/Schedule a Publish
Share on Twitter, Discords, Slacks, and… maybe… LinkedIn. Maybe.

Sometimes I’ll use Figma to design any images for the post.

Sometimes the essay will still have typos. Whatever. I try not to feel bad about that. I appreciate when readers email/DM me to let me know. So definitely let me know if you spot a typo!

Sometimes an essay takes two six hour sessions. This is probably because I’m overly concerned with how perfect it is. I’m still working on this.

Sometimes I can write an essay (like this one) in thirty-minutes because I already have a note written about it. These essays tend to be better received than my twelve hour essays.

Sometimes I’ll share a draft via Google doc to trusted friends. I don’t do this as much as I should.

Quantity over quality

I’ve learned to prioritize quantity over quality when it comes to writing. Don’t worry about how good your essay is. Just write. A lot. The more consistent you are, the better your essays will get.

Just start

Don’t try to optimize your workflow on your first essay. Just start. You’ll know what works for you once you practice of doing it.

What would it take for you to start?

Why does writing matter in remote work?

Evergreen notes permit smooth incremental progress in writing

My current writing workflow