Planning is essential. But, not too much. Mostly in the next 90-day window (with apologies to Michael Pollan).
Humans are, with few exceptions, awful at planning. It’s impossible to see the future. We rely on our previous experience over data too often. Or, not enough. Or, in the wrong combination for this scenario. Beyond a few days, the world we operate in is too complex, people too hard to predict, and all of it is interconnected in surprising ways.
Even worse, humans easily deceive themselves with plans. It’s so easy to look at basically any kind of ambition or outcome and say “yeah sure, given 6-18 months this seems totally feasible.” (With apologies to our ambition, it probably is not feasible.)
Yet when we account for those hazards, planning is essential (apologies to Dwight Eisenhower). Most things won’t go to plan, but making one forces us to think things through, ahead of time. Outcomes without a plan are worse than outcomes from a plan that has to change when reality punches us in the face (with apologies to Mike Tyson).
I find that periodically looking 90 days into the future to think about what I want to focus on and outcomes I hope to realize is a pretty dang good way of setting myself up for “luck favors the prepared”.
Planning the work is an essential part of doing the work. An ambitious but uncertain 6-month idea becomes an ambitious but plausible plan in steps. Make a 90-day plan by breaking it into chunks. Organize them into a coherent fraction of the 6-month idea. Make trade-offs to decide what’s most important or risky. Start on the first thing. Rinse and repeat.
Iteration is part of planning. Unknowns, predicted and unpredicted, rear their head. Risk turns into caution turns into incidence. Nothing goes exactly to plan. So, we take another swing at the plan, armed with new information.
We’re always smarter than we were last week or last month when we made the plan. Sticking to the plan is foolish. Updating or overhauling the plan makes much more sense than trying to argue with it.
Planning is like writing. They both focus our thinking. An idea that flops when we take it from our brains to the page probably needs more work, whether it’s writing or planning.