Making software and software development teams. Mostly the people parts.

My Writing System For 2023

When COVID hit in 2020, my desire to write went out the window. Except, that's not true. I've been writing as prolifically as ever these last three years. Several thousand words a day, at a minimum. What went out the window is my desire to publish anything publicly. I've been here in my tower, doing the work (remotely), and then using the back and forth of conversations or the timelines of the workplace as my forcing functions to ship. In private. Private spaces like slack, emails and group texts have gotten the best of my words and wisdom for the last three years. And I'm curious why.

I'm not sure why. Fatigue? I'd made a point of either giving a talk or publishing something longform every year since 2014. After seven years of consistently shipping in public, maybe I just needed a break.

Maybe the why will come to me. Or maybe it won't. Water under the bridge, either way. It's 2023, and I'm feeling the urge to start shipping in public again.

One thing I know for sure after nearly 46 years of living with me: If I'm going to do a thing, I need a system of doing to wrap the doing of the thing in. Otherwise the thing happens in fits and spurts and at the whim of my moods. Which means it's probably not going to happen.

Here's the system I've come up with to start 2023 with. A lot of it is stolen from Jerry Seinfeld (you know, the comedian), and specifically from this interview he did with Tim Ferriss. If it changes at all during the course of the year, I'lll come back here and edit this post.

1) Cultivate space for having ideas. I do this naturally at this point in my life. One trick that I've found recently is going on walks either first thing in the morning or after a couple hours of intense focus. This is a case where one thing you're trying to do - get 10,000 steps a day because that seems to correlate with me having better days - feeds into something else. It feels like that happens more and more in my life. Anyway. There's something about walking through the neighborhood at a medium pace that makes it perfect for having ideas.

Besides walks, I find long drives and conversations with old friends to be other great idea hatchers. Both can be challenging though with regards to the next step:

2) Capture those ideas. This sounds obvious, but it's not. You have to capture the idea in the moment when you're on a walk, or it might run down your pantleg and into the sewer when your phone rings, or an important text comes in, or you get back and there's a situation at home or work. Lots of people use pocket notebooks. I use Evernote on my phone, mostly because I've been using Evernote for ~15 years now. If I was starting today, I would start with Notion.

The best best situation for me is going for a walk with my laptop in my backpack. I live in a neighborhood with lots of coffee shops, I'm never not within four or five blocks. Fifteen or twenty minutes is usually all it takes to get a really good draft of something.

In the worst case, I might wait until I get home, and then it's a race: Can I get into a quiet spot that's not my office and doesn't have anything that needs my attention for the five minutes I need to scribble down some bullet points.

And that's it for divergence: Having a lot of ideas, capturing most of those ideas, and maybe somewhere in there organizing the ideas to some extent with folders or tags or whatever. Or not. Organizing can be overdone. Anyway and either way, it's time to converge. This is where it gets hard...

3) Edit. Editing is painful. When I taught creative writing, I tried to focus my units on the editing process. Opinion: Having the ideas and writing them down is the easy part. It makes you feel like a writer. You can look at your notebook or your files on your devices and think, wow, look at all these words. What are those words worth? Maybe a lot, if what you're trying to do is create an identity as a writer for yourself. On the other hand, if you want to be read and make an impact with your words? Not a whole lot, at least until you edit them.

My editing process for 2023: Schedule it. On a calendar. This is the part that I really stole from the Jerry Seinfeld interview. This is also really painful for me. My work week as an engineering leader is largely calendared. And then there's all the chores and appointments and such in my personal life, and those are calendared as well. Why do I want to take one of the few things that I enjoy for the sake of doing it - writing - and put it on the calendar as well?

A: So it gets done.

Editing is so painful that if I don't put it on a calendar and make myself do it, it will not get done.

What happens during editing? There's a reason Jerry Seinfeld's new book is called Is This Anything?, it's because that's one of the primary goals of editing: questioning whether these raw ideas that you have are in your grasp, in your target zone and valuable enough to share. The answer to all three of these have to be yes, otherwise the answer to the question is this anything is No. And when the answer is no, the thing gets thrown out, or rather it gets left in its embryonic state in Evernote. Full stop. And that's painful: letting go of your precious ideas.

Other painful things that happen during the editing process: Even if the idea is good, the original words usually need reworking, refactoring, or just a good rewrite. You have to think about ways of saying things, and whether those ways are clear, concise, and adding up to Your Voice. Finally, you have to polish the thing: Remove typos, forgotten words (my bugaboo), repetitive sentences, anything in the way of The Thing being the gem you want it to be.

4) Ship it. Once The Thing is polished and cleaned up, it's time to publish. Publishing should be dead simple: Take the finished piece, convert it to a blog post, push Publish. And that's it. Publishing is a step because publishing is 10% doing that, and 90% celebrating. Yay! I did the thing. All that pain has paid off.

5) Point people at it. The last step is the one that, sadly, I'm the worst at. It's talking about and referencing what I've written such that other people find it and read it. I'm just lousy at it. If editing is painful, then this thing that I guess is called marketing is torturous. I love scaling products massively, but when it comes to sharing my wisdom and experiences, I seem to prefer a smaller audience by nature.

I share the above as a warning. May you not share my weakness! Go forth and share with the world. And steal the rest of this guide, while you're at it. Or at least go listen to the Jerry Seinfeld interview.

posted in Writing