I recently posted about an issue I see as the critical flaw with planning – or at least one such flaw among many. In that post, I was focused largely on how major historical events ultimately turned on minor events that had massive impacts in ways that were unforeseeable and unknowable, not just to planners, but even to the people on the spot who carried out those actions at the time. But I also mentioned how this very uncertainty and uncontrollability can be found in our own lives, giving one example of such a butterfly effect moment in my own life. Does this mean that I am against the idea of people making plans for their life?

In a way, yes. Or more precisely, I think attempting to plan out one’s life path is a suboptimal way to approach things. When I tell people I’m not a fan of planning life in this way, they sometimes misunderstand that to mean that I’m against having goals. But having goals and having a plan are not quite the same thing. A goal is where you want to end up, whereas a plan is the specific means you intend to use to get there. You can have a goal, without needing to stake it all on having a plan.

In the Marines, we used to say “no battle plan survives first contact with the enemy.” This is because, rather annoyingly, the enemy isn’t interested in doing things in a way that goes according to our plan. Being well-trained to handle combat situations isn’t about having a step-by-step battle plan – such a plan would be useless because it would be obsolete by step two. But that doesn’t mean abandoning the goal of mission accomplishment either. Being well-trained is instead about having the kinds of skills, tools, and know-how to allow you to adapt to whatever the moment-to-moment circumstances are, in a way that still moves you to the goal of accomplishing your mission. That’s why the common saying in the Marines wasn’t “make sure you have a plan for that.” It was “improvise, adapt, and overcome.”

In the same way, when it comes to living one’s life, I’ve come to believe that having everything planned out is not just overrated, it can often be counterproductive in the same way that it would be counterproductive to try to go through a combat situation according to a step-by-step plan. One can still have goals they wish to pursue, but the focus should be less on planning how to achieve every step along the way, and more about making yourself into the kind of person who can adapt to the situation they face while also moving towards that goal. As I’m entering my middle age years, occasionally old friends and I will reflect on how our lives have turned out differently from what we were imagining ten or twenty years ago. And it’s very common to hear something along the lines of “I thought I had it all figured out how it was going to go, but then such and such unexpected thing happened, and that derailed everything I had planned from there.” Conversations like these expose the weakness of planning – in order for them to work, things need to go according to plan.

This isn’t true just at the individual level – it’s also true at the social level. While there is no coherent sense in which we can say “societies” have goals or plans in the way that individuals do, certain kinds of societies are arranged better to allow individuals to better achieve their goals. Free and decentralized societies give individuals the kind of elbow room they need to be adaptable in the pursuit of their separate aims in a way that just isn’t possible within centralized and planned systems. Even if every member of society were agreed on a particular end goal, having a centralized plan would be a terrible means to achieve that goal. Life is complicated, and reality is often messy and uncooperative, and the best means to deal with that is to prioritize being adaptable over making sure things go according to plan. Plans stifle innovation and discourage adaptability, but markets thrive on them – to the benefit of each of us, and all of us.