Q1 Planning

I took a break from the mistletoe chaos of the dead zone between Christmas and New Year's to do two things, both portrayed below:

  1. Triage Buttondown's roadmap from 325 items (at time of writing this; by the time this goes out, it'll likely be 330) to around half of that.
  2. Stack rank the top ten things I want to get done in Q1.

(Thank you, Haley, for cutting up all of these into tiny slivers for me.)

(I might not work at a big company any more, but I can't stop myself from over-stylizing my Google Sheets.)

This process came from a simple desire: focus. Seven things on that list of ten are the current thing, but better, and only three things are net new:

  1. RSS automation, which I've chatted about a little here, but feels like such an obvious and useful feature that I don't mind its expanding the surface area of what Buttondown does. (The more I work on Buttondown, the more confident I am that in many ways the ideal user, as odd as it sounds, is someone who never uses the writing interface. This is not to say I don't think the writing interface is useful, but that Buttondown's most obviously useful when it is a headless CMS — a "just add subscriptions!" to someone's existing set-up.)
  2. Social signin, which is just one of those obvious "here's how you increase conversion rate by ten percent" buttons that I think will take me less time to implement than to write a blog post about how I implemented it.
  3. Teams support, which is already 90% implemented and again falls into one of the bucket of "obvious and useful". (Here's an interesting heuristic for whether or not a feature is a good idea — if you feel embarrassed when you tell someone that you haven't shipped it yet, you should probably build it.)

It is...hard for me to take planning processes too seriously. Sometimes it feels sacrilegious to worry too much about event sequencing when I know I have more than enough high-urgency, high-importance items to tackle for the foreseeable future. As my old colleague @basta writes:

There’s obvious value in knowing what you want to be doing in a year. Having a vision is important. Laying out all of the individual steps to get there isn’t valuable or important. Besides the planning process for an extended roadmap being tedious and slow, it forces teams to sign up for a plan that is disrupted by any participant in the plan facing disruptions.

(By the way — you should subscribe to his newsletter. I do not think I am exaggerating when I say he was the single most interesting technical writer within the company and I am thrilled that he's taken his talents to the public domain, so to speak.)

The vision thing is good. I think I write every two months about struggling to translate tactics into strategy; this is one of those times where I am trying to be a bit more conscious about having a horizon larger than a month and an appetite larger than a pull request.

All of which is to say: the vision I'm carrying forward into 2023 is (and will be enshrined into some somewhat hackeneyed principles, I'm sure):

  1. Buttondown should be very easy to go from "learning about" to "using".
  2. Buttondown isn't perfect for every use case, but it's the best tool for its given use case.
  3. Buttondown (to steal some video game parlance) has a great endgame experience without sacrificing the gameplay for your first ten levels.
  4. Buttondown feels boring to use.

I don't think I will actually track these as KPIs; I'm not sure that's useful or interesting. But they will be a good compass, and a good forcing function to push me to say no to work that doesn't move any of these hypothetical needles.

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