The Plan
Sean Moore
Avoid the travel guides; the best way to have an adventure is to have nothing more than a good map.
I’ve never been a great planner. If you look at my calendar, apart from a list of my classes (which, truly, I mostly keep to remind myself what room the lecture is being held in on the days I do decide to show up), there’s very little structure to my day.
Structure has always worried me. Regularity, habits, any of it: I’ve done as best I can to avoid keeping a regular schedule. Why? It’s not only because I want to throw off the Chinese spies that are undoubtedly plotting my kidnapping. I want to preserve, as best as possible, my spontaneity.
Am I a spontaneous guy? Well, no. Apart from occasionally deciding to spend a whole night on a deep dive through Wikipedia’s maritime warfare section, or writing a web app from scratch, I typically don’t out of the blue decide to do crazy spur of the moment things.
What I do try to do though is keep my opportunities open. An open schedule means a last-minute call or text can be answered in the affirmative, a suggestion to start a cool project can be acted on.
There are drawbacks, of course, because every decision has a compromise. Lack of structure is a terrible thing. When you don’t know where you are, or where you are going, for the next hour, day, week, it’s easy to get lost.
Worse, perhaps, are the big gaps of time during the day. When there is nothing to tell you what you should be doing, it’s easy to make the wrong decision. You know, the one where you avoid all your commitments, all your homework, all your projects and plans and go on the aforementioned all-night Wikipedia binge.
Oops.
Perhaps the worst part of it all is the fear. When there is no piece of paper dictating what and where you’ll be spending your time, when your parents haven’t scheduled every activity for you from now until whenever you graduate magna cum laude from their alma mater, it can be scary. It can even be as simple as making a choice for lunch – when you suddenly are free to choose what you want to eat, rather than abide by a shool schedule, you suddenly are far more concerned that you’ll make the wrong decision.
That fear can paralyze you. Every decision you make could be one that sends you down a wrong path, and what’s worse, you may not even realize it until it’s far too late to turn back. You become a reactive machine, unable to deal with anything in the future because you need to make all these decisions that are happening right now, and you don’t have time for that.
Extremes are scary. Luckily, there’s usually a compromise when two ends of a spectrum are untenable. And sitting in between a regimented schedule and spontaneous wreckage is the plan: a description of the what how and why of what you want to get done, rather then the when. Maybe the distinction is subtle, but the ability to dissociate the work you do from a particular time you assign to do it is incredibly freeing: you can work on what you have the energy to do, or the tools at hand, and still maintain the flexibility to do your spur of the moment adventures.
The plan can be as detailed or as flimsy and high-level as you like; something as simple as where you want to be in three years, for example, probably doesn’t need to have a whole lot of detail becuse there is a whole lot of space between the you of today and the three-years-from-now self that you’re trying to tell who to be (he probably wouldn’t appreciate you telling what to do; after all, the you from m=now certainly doesn’t). If you are working on updating a design, the more detail is better – you’re walking the coastline after all, so you might as well give yourself as many roadmarkers as you can so you stay on track on time, and don’t lose sight of what you need to finish.
My personal favorite are the plans I make during a two-week design sprint. It starts as a major feature, one or two words. Over the next day, that gets broken down into the components that make it up, and then as those are implemented, those each get broken down into five or six tasks, and a similar number of associated subtasks, and before you know it, you’ve got a nice fractallized plan and more than enough to fill up your plate for two weeks, and you can work on what you’re in the mood for, rather than what’s sitting on your calendar for any given day.