It’s so easy to write a newsletter!

I'm in a cozy upstate New York cabin in the dead of winter. It's snowing outside, and I'm sitting on the couch with a glass of orange wine. It’s zen, the perfect environment to write my first newsletter. Here we go!

Hmm. I can tap my fingers rhythmically, but no words are being typed. Something’s off.

I realize something: it’s much more instinctive to think about the look of the final product than the content of the words. What color will the text be to contrast well with what color of background? Which font, and what line-spacing, will be most pleasing to the eye? When the user hovers over certain words, wouldn’t it be cool to show a popup with some tangential content, such as the definition of some labyrinthineDefinition:
1. Of or relating to a labyrinth.
2. Having or requiring great skill or knowledge; intricate or difficult. word?

I’m procrastinating. It turns out visualizing a product is easy, coming up with a subject for an essay is hard.

It’s so hard to write a newsletter.

Throughout my life, I’ve never found it easy to write for other people. Back in 11th-grade literature class, I didn’t enjoy analyzing the classics, and I’m sure Mrs. Thurston didn’t enjoy my dubious blunders of wordy spaghetti all that much either. Then in undergrad, I finally “did well” in a technical writing course. My final paper was a case study on the “Practicality of swarm robotics”The study of how groups of small, simple agents can collectively solve complex problems. The most common example is a swarm of drones, but it can be applied to anything from a school of fish to a flock of birds.. That class hammered in the idea of cutting fluff, sticking to the facts, writing beautifully predictable sentence structures. In short, I had found the glorious “technical writing style” i.e. an engineer’s perverted idea of communication.

Creative writing is now an engineering problem.

Rose Technical-tinted lenses

Adam Savage’s book Every Tool’s a Hammer talks about his strategies for solving a complex problem:

Define the problem clearly; know the “why” you are doing it. Research relevant techniques and past works. Roughly plan a solution; break it down into its smallest parts. Document your progress & any new ideas. Prototype, iterate, repeat. The takeaway: every failure is just another step towards success.

Here’s my complex problem: I don’t love writing, but I do love building.

Can we apply our engineer’s lens towards the writing process?

• Define the problem: every week, I want to improve on my writing skills and make something I think brings some value for my friends, and maybe even someone else in the world one day. Why? Peer-pressure from my friends’ newsletters mostly. And what’s wrong with a little external motivation to kick things off?
• Research: I think this may be the most natural part of the process. In my job as a wear-many-hats engineer, I tend to learn a new technology/technique every week, which involves researching until I understand the fundamentals, then practically applying what I learn to make a solution.
  • For example: A few weeks ago I found out about a powerful new CSS feature: anchors! They power the popup you’re seeing right now👋.
• The plan: As of now, I’m thinking of noodling about engineering challenges, meta-problems e.g. motivation, random thing I learned that day, and we shall see what else!
• Documenting progress: I took some notes yesterday, does that count? — In all seriousness, writing my thoughts throughout the writing process is not one of my habits. For now, my goal is to take more random notes on things I learn throughout the week.
• Prototyping: this is my 3rd stab at writing this dang thing. Iteration achieved 🙌

The last important piece that Adam Savage mentions to solve a complex problem: you do have to actually complete the project. Your definition of complete may change as you go, but push through the challenges to get to some end-state.

I know this will be the hardest part.

For those of us that have the perfectionism disease, it can be hard to balance:

• making something we are proud of
• making something at all

So, for these first few newsletters, I want to avoid burning out. I will try to get something out there, even if subpar. I know a few people who followed Julia Cameron’s The Artist’s Way—Sid, I'm impressed you were writing 3 pages every day—I like one of her quotes:

We deny that in order to do something well we must first be willing to do it badly.

So let’s do it badly for now. And if you’re reading along, feel free to call me out if I start obsessing over fonts again. For now, just ship it 🚀