Damn You, Checklist.

I have to admit something. It’s frightening, and I’ve known better, but I just haven’t done it.

I don’t use checklists for anything. I rarely refer back to notes I’ve taken, too.

This has been true for as long as I can remember. Even in school, I took notes and almost never studied from them. I didn’t really study much at all. I could always ‘wing it’ and do well enough at school.

By the time I got to crazy high-level math, I couldn’t wing it anymore, and it turned out that all of my classmates who had long before memorized a ton of esoteric facts and formulas were way ahead of me.

I should have known, then, that I needed to start paying attention. I didn’t.

Instead, I spent twenty years viewing most projects as a one-off. Twenty years of missing opportunities to synthesize knowledge and make things easy on myself.

The result? I kept making the same mistakes, over and over.

It wasn’t because I didn’t care, although I must not have cared all that much. It’s true that most of my life goals have involved skis and surfboards while somehow having an unlimited supply of money derived from something genius I did.

Well, it’s been twenty years. It’s been a few failed novels, dozens of investments, many consulting clients, a couple of start-ups, and a lot of time aimlessly climbing the corporate ladder simply because it was there in front of me. It’s been interesting, for sure.

But genius? Far from it.

I’ve gotten to the point where I now believe what everyone told me right from the outset — that getting where you want to go in life is about taking one small step after another.

Of course, you still need to know what direction you’re walking in. Just taking small steps haphazardly will make you walk in a circle if you’re not careful.

I haven’t been all that careful. I’ve probably been walking in a spiral, and it’s fair to say that I have no idea what direction I’m pointing in right now.

Literally every successful person I know lives their professional life by a series of checklists and notes. They just go down the list methodically and determine whether or not they’ve done everything they’re supposed to do.

I’ve always viewed this as too much process, or as something that limits creative thinking, or both.

I think I’ve been wrong. I think that, when used properly, checklists are actually the boundary conditions that make real creativity possible.

I’ve been realizing this slowly over the past three years as I’ve had to do more and more computer programming.

If you’ve never done computer programming, here are the basics:

1. You can Google almost anything you need to know, and for the rest, you can ask someone who has done it before, and they’re usually really nice about helping you. This means that the amount of knowledge you have to have when you start out is purely learning syntax, which is boring but otherwise not all that hard.
2. Computer programs are just giant checklists on top of other checklists on top of other checklists. All they do, millions of times per minute, is go through the various rules you’ve set up, sees which one applies, and then do that thing (which is often a thing that tells it to do another thing and then goes right down some other checklist). This is true of all computer programs that I’ve seen in every single language I’ve written programs in. The only differences are in how you apply these rules and how many things have been written for you by other people (e.g., either included in the language as a function or as a library).
3. Computers take everything you say literally and have no sense of humor about anything. So if the software you wrote doesn’t do what you expected it to do, it’s because you screwed up the checklist somewhere along the way.

I’m not the primary programmer on anything, but that doesn’t mean I don’t have my own list of what the programs should do. And I find — almost all the time — that no programmer goes through and checks the entire list, and so you have to have someone else who specializes in making sure that humans followed their instructions properly check everyone’s work. That person — the QA (Quality Assurance) person — becomes the most important person on the team, because she’s the one who knows what everything is supposed to do and when.

I’ve come to accept (grudgingly) that you need to live and die by these checklists when you’re building a software product.

The hard part of this process is to break everything down into tiny components that are doable, and knowing what is doable as a single step. When I step back, I can see that so many of my friends, mentors, bosses and co-workers figured this out years ago, and now have an intrinsic knowledge of what comprises a single step. The good ones do, anyway.

For me, I’m new to checklists. I’ve only been trying to work with them for three years in a compartmentalized area of my professional life.

I’ve been living off of post-it notes instead, which I use as massive to-do lists. Coincidentally, that’s also how I use email.

But a to-do list isn’t a checklist. For most of my life, I’ve been confusing the two.

A checklist tells you everything that you need to know before you move forward. A to-do list is a series of actions you need to take.

I’m not knocking taking action, but I am knocking taking action without thinking it all the way through. I’ve gone back and fixed my work more times than I care to admit, and every time I’ve done that, it’s because I didn’t think things through properly. A checklist, done properly, should solve that problem.

But… how? When you come from the to-do list mindset, a checklist quickly becomes just a list of to-dos. The first fifteen checklists I made were just lists of things I should do, and so I didn’t use them, because I already had that list in post-it notes and in email.

What I want is a list that helps me determine if the actions I want to take are the best path to get me from A to B, or if I’m just undertaking an action for the sake of doing something. That is a much taller order, as it requires that I know both where A and B are and it requires that I have knowledge of what an ideal path looks like.

I don’t know any of that information. Seriously. I know that, mathematically, I should be shooting for a straight line between those two points, but I don’t know if there’s a mountain in my way and whether or not I’d be better off going around it.

Heck, I don’t even know if my world is flat or not.

When you start going down this rabbit hole is when you really start perusing the Internet’s self-help section, and where you start finding all of the systems that people have designed and want to sell you that will supposedly help you figure all of this stuff out.

I’ve read more than my fair share of this slop (that’s what it is), and I feel like I’m talking to a psychic each time that’s using cheap psychological tricks to make me feel like I’m accomplishing something by simply reading. Sometimes, the cheap tricks work for a little while.

But what I really want is to be able to consistently get from A to B, and then to the next B, and so on.

So I’m going to try something different. I’m going to approach life the way I’d have to approach a computer program:

1. With a very specific and very narrow goal in mind; and
2. A checklist of choices I need to evaluate.

I’m using some weird language here — a checklist of ‘choices.’ I’m using that on purpose.

I don’t think I can jump full-in to evaluating whether or not I’m making the right decision with a checklist. What I think I can evaluate is an extension of my to-do list: I can take a basic set of knowledge (including economics, psychology, ecology and a few other areas of science and social science) and ask, “What would this action accomplish under this model?” I’m sure other checklists will grow out of this approach.

If you’re a fan of Charlie Munger, then you realize that I’m bastardizing his mental models approach. I’m certain that I’m going to be doing it more poorly than he does, especially since he reportedly uses about 100 of them.

Here’s an example of what I’m going to try as it applies to a new website I’m building to help sell books (an actual project of mine):

1. Does this page cause cognitive dissonance by introducing a new belief or value to a potential customer? If so, the potential customer is likely to leave this page. Examples of potential causes of cognitive dissonance could be filtering options that espouse a world-view, such as saying a certain set of books are only for teenagers to buy rather than saying that a set of books would make a good gift for teenagers.
2. Does this page encourage confirmation bias, in which the information provided on the page reinforces some beliefs already held by the potential customer? Those beliefs can be that these books will be helpful to the customer, or that these books are high quality, or something else.
3. Are we encouraging ease of recall of products on this page by including them in a narrative that is likely to be remembered by the potential customer? If not, is there a way to repackage what we show to make it easier to recall? What are we doing to help drive the customer to the right book?
4. Is there a critical mass of information on the page so that the potential customer feels as if there is enough information available to feel like they are making an informed decision? Are we overloading the customer with too much information? Are we not providing enough? And how do we measure this?

I’m not so happy with this checklist. I’ve got to work on it. It’s a start.

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.