After much experimentation and many years of failure, I've surfaced two rules of thumb for myself that seem to be working lately: (1) Write a monthly plan that

After much experimentation and many years of failure, I've surfaced two rules of thumb for myself that seem to be working lately: (1) Write a monthly plan that's broken down by weeks, and then review/iterate on it weekly. The weekly review alone risks having too small of a focus, so blending it with a monthly planning horizon has felt like a nice balance. (2) Yearly planning is surprisingly useful, but it's best done as a solitary thing. Most people view the whole "new year's resolution" thing as a cliché, and — separately — most people don't respond well to seeing someone else's ambition. Silicon Valley promises to be some sort of magical land where everyone's working on big things, but — same as everywhere else in the world — people largely respond negatively to seeing someone succeed (or even want to succeed) on a long timescale.