“I spent hours meticulously drawing an old castle, three levels of floor plans and carefully populating every room with Orcs, Trolls, Undeads and treasure. But even more hours was invested in planning how the players would approach the castle with their Role-Playing characters. The front doors would be unlocked and the characters would discover that, sneak inside, engage in a small fight with two filthy Orcs playing dice instead of guarding the castle, commence to the guard room, find a treasure, get surprised by a lutenant Orc walking into the room, etc. The plan was a masterpiece, but upon reaching the castle, I was taken completely off guard. They walked around to the back side, got out a grappling hook and climbed in through a small kitchen window on the second floor and… completely wrecked my plan! Dang! I hated unpredictable players.”

The purpose of planning is to increase predictability. Regardless of the name and the scope – strategy, plan, tactic, game-plan – the purpose is to avoid unpredictability. With the knowledge of Now, one seeks to make decisions into the future. The aim is to focus effort and to limit dispersement.

Sounds all good, perhaps. But there is a flip-side to this coin. When one focuses, one also limits and excludes.

In opting for predictability, you trade in intelligence, creativity and agility. By limiting future choices, you limit improvisation and potential genius. This is why most creative geniuses prefer not to work in large corporations or set structures, but rather in lean and mean startups or prefer to work on their own.

What you gain in focus and stability and predictability in the short run, you lose in attainment of long-term valuable skills.

To quote Ole Wiik, “one must practice what one wants to be good at”. As you focus your training in one area, you become less adept in other areas. Planning makes you better at planning. But it makes you less adept at improvising. By avoiding the unpredictable, you will never get good at tackling the unpredictable. Your mental dexterity will suffer proportionately with your increasing planning skills.

Another factor to consider is that decisions are always sharpest with the best and up-to-date data readily at hand. Thus, any decision made by planning, decisions into the future can never be potentially as good as a decision made in the Here and Now with fresh data and input. Limiting mental dexterity by planning and adding some blinders will make you less sharp mentally. Planning adds preferences, it adds filter that makes fresh input looks dimmer while you become dumber. In an interview with Chess.com, Magnus Carlsen said: “Having preferences means having weaknesses.”

Planning is a tool, a crutch. It enforces a view of the future based on today’s data. It stimulates preconceived ideas, adds a filter for new data, tend to help you avoid unpredictability and helps you never get good at tackling surprises. Tools and crutches are needed if you cannot cope with a situation without them. But right there it should make the alarm bells go off. Instead of getting addicted to the tool of planning, how about starting to practice tackling the unpredictable? Scary shit. I know. But it does add spice to life and skills to you.