The problem
The hardest part of writing a newsletter isn’t the writing.
It’s everything around the writing.
The Indy Hall weekly newsletter used to take upwards of four hours every week.
Four hours for something with no direct sales call to action is bad business math.
Pulling events from three different calendar systems. Copying descriptions. Hunting down links. Double-checking dates. Formatting. Proofreading. Pushing to ConvertKit.
That’s 10% of a work week spent on logistics with no direct revenue attached.
I knew the newsletter mattered. It keeps our community informed, shows signs of life to the outside world, builds trust over time. But the math doesn’t work forever when most of those four hours aren’t even the creative work.
What I tried
Templates helped with consistency but didn’t touch the actual time sink, which was assembling the raw material before I could even start writing.
My business partner handled the newsletter for years. Same four hours, regardless of who sat in the chair. The problem wasn’t the person. It was the process.
I looked at tools that auto-generate newsletters from links and RSS feeds. That’s not what we do. We don’t ship content made by robots. Our newsletter is written by a person, for people. I wasn’t willing to trade quality for speed.
How Andy handles it
I type /newsletter and Andy does everything that isn’t the actual writing.
It pulls events from our multiple calendar systems, filters them by our criteria, and drops them into the draft with dates, descriptions, and links already formatted. If something’s ambiguous or below a 90% confidence level, it stops and asks instead of guessing. That alone used to take me 30 minutes of tabbing between calendars and copy-pasting.
For recurring events, Andy maintains a library of descriptions from the last time we ran them. When a monthly meetup shows up on the calendar for the second time, the proven description gets dropped in automatically. No rewriting, no digging through old emails to find “what did we say last time?”
For the essay, I’ll sometimes talk it through in voice mode. I describe what I want to say, why it matters, what I’m not sure about. Andy structures my thoughts into an outline or rough draft that I then rewrite in my own words. It’s not writing for me. It’s helping me figure out what I want to say before I start saying it. The first draft is basically never what ships. Instead of writing that throwaway draft myself, I have Andy write it based on my words and ideas, then I rewrite essentially everything.
After I write, Andy catches typos, flags unclear references, spots things like “you mentioned this event but never included the link.” The kind of stuff that’s easy to miss when reviewing your own writing.
Then it formats everything into our template, spins up a preview I can check, and pushes the final version into ConvertKit through their API. After it sends, it automatically publishes the essay to our blog so it’s indexed by search engines.
Here’s the part that makes this a compounding investment: when something goes wrong, I fix it and tell Andy not to repeat it. Every issue solved once stays solved. The workflow improves every time I run it.
The result
We went from one newsletter a week, struggling, to two a week in maybe a tenth of the total time. The actual writing takes about 25 minutes. The rest, maybe another 5 to 10 minutes of reviewing what Andy assembled and approving the send.
The quality went up because I’m spending my time on the part that actually matters: the writing. Not wrestling with calendars and email formatting.
The thing I didn’t expect: because the barrier dropped so far, I actually enjoy writing the newsletter now. When the hard part isn’t hard anymore, you do more of it.