There Aren’t Any Maps for Where We’re Going

TL;DR: An unfamiliar pursuit involves a lot of variables. This makes a detailed plan likely to fail. Instead, start with a vision of what you wish to achieve. Then stay flexible and learn from the terrain.

I’m wrong about most things. This isn’t false modesty. It’s an actuality one learns to accept (if they have any sense) by middle-age. I simply don’t know that much about most subjects. Additionally, I work on projects that involve a lot of unknowns.

Today’s post is from the “that seems interesting, I wonder if it’s useful?” pile. This means that it could be bullshit. Or, it might be so generic that it doesn’t amount to anything at all. Still, it stuck in my head for the past week, so, I’ll give it a little more consideration.

Better insights through family game night

Unlike me, my kid enjoys playing games. Like others his age, he’s all over Minecraft. He’s also a fan of Poker, Chess, Uno, and a little gem called Blokus. I actually enjoy this game. Anyone can play it. It’s easy to learn and moves quickly. In Blokus, each player gets a set of pieces of varying shapes. You then try to occupy the board with more of your pieces than your opponents’.

In a recent family game of Blokus, I noticed something. Normally, I play without thinking ahead much. This time, I took more time to consider how I could best use my pieces. Around mid-game, I saw it! If it played out as planned, I’d win in a few moves. I played my next piece, and my son played his. In doing so he ruined my plan.

Now, I know this is silly. Of course, the other players’ choices affect the course of the game. Still, I felt befuddled. I could see my win so clearly. It bugged me that my plan didn’t even survive until my next move.

I looked at the board again, and tried to come up with a new plan. Sure, I could anticipate the probability of certain outcomes. That said, these were only guesses. The further ahead I looked, the less certain they were.

Places you haven’t traveled

I like planning. This is in part because planning involves fantasy. You can put anything in your plan—and doing so feels good. It’s easy to write out actions (that are typically waaaaaay harder to act on). It’s fun to imagine how a scenario will play out. This is because it’s all dopamine without any of the sweat.

Don’t get me wrong: I’m all for planning. But, I’m wary of how seductive it is. Good plans demand that you pay attention to what might go wrong, as much as (if not more than) what might go right. But, the less I know about a subject, the more likely I am to create a simplistic plan. This is because I lack the experience to know what’ll go wrong.

This is the problem for those of us working on startups: there’s no map. You can survey competitors, but their circumstances are different. You can ask prospects, but they’re only operating with what they can already see. You can ask advisors, but this advice is often flawed due to how situational it is. Your journey is your own.

Vision, agility, tests

The older I get, the less detailed my plans are.¹ This is because detailed plans are brittle—and hard to act on. Many of the products I work on are new to me and involve variables outside of my control. So, I keep my plans for these brief, reflect on them daily, and retool as circumstances change.

This might also relate to humility. As a young person, I thought I could control my environment. I am now painfully aware that I can’t. That said, I can respond to my environment. I can’t make it rain, but I can sell umbrellas when it does. Similarly, I can’t force you to use my SaaS product. I can build one that you’re asking for, though.

Again, this might sound like rambling. It probably is. There’s one thought that’s spun around in my head for the past week, though. It’s this: If I can’t see 7 moves ahead, should I even try to plan for it? I’m starting to think the answer is no.

Instead, I need to determine where I want to go. Then, I can try out some approaches. As I do, the environment will teach me what I need to know—so long as I keep paying attention.

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1. I’m referring to unfamiliar situations, here (like finding product/market fit for something new). If I’ve done something many times (e.g., building a website), it’s easier to draw up a detailed plan that’s apt to work out.

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