It’s often fairly easy to make a concrete list of small next steps, reachable from your current position. It’s somewhat harder to write high-level aspirations which might meaningfully guide your life over years. Long-term planning requires that you adopt a very different posture: different emotions, different analysis, different risk tolerance, etc.
Unsurprisingly, then, it’s much harder still to create and maintain plans which span many time horizons. The delusional ideal is to sit down and write your 5 year goal, then translate that into a 1 year goal, and so on, down to what you’re doing this afternoon. Unfortunately, all those levels are intertwined. You’ll need to draw on your best short-term ideas to create credible longer-term aspirations. As you get a sharper picture of that big-picture ideal, you’ll likely find a much better framing for the next quarter’s work, which in turn will generate better short-term ideas, and so on.
Creating this kind of aligned plan is one thing; maintaining it and keeping line of sight day-to-day is even harder. The tools we use aren’t helping: each level has its own toolset, and they don’t mesh well. For instance, you might naturally use task lists for daily plans, a Kanban board for weekly-to-monthly plans, and various types of prose for longer-term plans. If you’re going to ensure that each level remains in line with the others, or that you reconsider the higher-level framings when things aren’t going so well, you’ll have to supply the triggers and behaviors yourself.
Elon Musk is a classic example of someone who does this well: he has ridiculous, consistent long-term visions; he creates companies to pursue them on a multi-year timeframe; those companies have well-defined near-term goals (well, Tesla and SpaceX at least); Elon seems to have pretty clear top priorities for his week; etc. Brian Nosek is another—less extreme—example.
Related: Insight through making prefers bricolage to big design up front
Conversation with Michael Nielsen, 2019-12-04