Every four months (on the same cadence as The Ready's internal retreats) I take myself through a process of retrospection and planning that borrows a lot of the ideas we use with teams. I have found it to be a very helpful practice (this is my second iteration on it) so I wanted to share the template/process with you in hopes that you may find it useful as well. Please feel free to leave questions or comments in the document or in Slack and I will be happy to go into more detail or explain my thinking around anything. I'm also very open to feedback and would love to hear what you change if you adopt this practice for yourself!
A couple general thoughts: I usually let this take an entire week to finish. I work on it in the mornings before Retreat and sometimes in the evening. I like to take a couple days for the retro, a couple days for some initial planning, a day or so to just sit with what I planned, and then make final tweaks at the end of the week.
My other key moments in my personal operating rhythm, which this feeds into, is my Weekly Review (template available) and my Monthly Review (template available). I use Things as my basic task manager and a physical Kanban board to keep me focused on a day-to-day basis.
The first time you do this process it takes longer because you need to develop an initial Purpose and Essential Intent. Subsequent versions of this process go faster because you aren't re-deriving Purpose and EI — just tweaking them. I mostly use the same process we teach teams during a Strategy Meeting. I could obviously write up a ton of stuff on how to do this, and maybe I will eventually, but for now just dig into the stuff we use with client teams.
Y'all know what a retrospective is. Mine is a combination of reflecting on the questions we all know and love and just pulling together a bunch of different data on myself that I mostly passively track. Feel free to skip that part. Here's a list of my retrospective activities to give you a sense of the possibilities. As I do each of these activities I'm generally taking notes on things I want to remember, knowing that I'm going to be tweaking my Purpose/Essential Intent and setting new Outcomes later.