Plan the Flight, Fly the Plan

My father-in-law apparently used to say this to my wife and her brothers and sister all the time when they were growing up. He had a small plane that he used to fly between factories, to client meetings, and, sometimes, on vacation.

The kids apparently always asked to go somewhere else — wouldn’t you? I mean, here you are in a plane that can travel hundreds of miles. Of course you should ask the pilot to take you for ice cream in Chicago even if you’re flying to Kentucky.

My father-in-law, practical as he is, said no. His response was, “Plan the flight, fly the plan.” There were those pesky FAA regulations about not changing course, and then there was the fact that planes are carefully calibrated machines and you’re better off doing the thing that you prepared to do in the first place rather than taking a silly risk and going off course.

As with much advice that you get as a kid (or get second-hand from people who were kids, as is the case here), it turns out to be truer than you want it to be.

I’d really, really like to go off course. I just finished making the first draft of my massive checklist of mental models (numbers 1, 2, 3 and 4) as part of an exercise in trying to make better decisions (the other part being recognition that everything takes a really long time and that I need to just take one small step at a time), and it’s already overwhelming. The idea that people actually follow checklists on a regular basis astounds me, and I haven’t even made it into a proper checklist yet. Heck, a lot of it probably repeats other stuff. It’s all just a draft right now.

In father-in-law parlance, all I’ve done is assemble some pieces I need to plan the flight. It’s more work than lots of other people have done, true, but it’s not yet in the category of useful work.

The problem is, I don’t think that there’s a way that I’ll actually go through this checklist every time I have a major decision. It’s like 100 items long. Each of those 100 items probably has 10–20 parts. That’s a lot of nuance to take into account. And I’m not even sure how to apply this checklist properly; there are some places where it’s obvious (e.g., I should get good at checking my own confirmation bias), but there are plenty of places where it’s not (e.g., how do I know the state of entropy in any business problem I have?).

So that seems like the next problem to address: how to actually use all those various bullet points I put together in a way that I might pay attention to. And the answer on how to do that seems kind of obvious — I need to be able to answer questions like, “how do you measure entropy in a business?” And also, “does measuring entropy here make sense?” And whatever other questions pop up for each of the approximately 100 items on my checklists.

That’s the plan, then: lets explode the checklist into a lot of tiny checklists that ask reasonable, answerable questions.

Jon has been published in Time, Inc., Forbes, The Huffington Post, and many, many other publications. He’s written novels, run a couple of start-ups, been a venture capitalist, a consultant, and has spent most of the last ten years climbing the corporate ladder. The Cold Shower Diet is a blog about finding motivation.