Written 2021-08-07

Nassim Taleb’s Black Swan Theory teaches us that contact with reality leads to unknown unknowns, the “black swans” that surprise us. In my observations, people tend to take one of two approaches to this fact: they either become very good at Planning or Adapting. Planners spend energy now to anticipate future positive & negative black swans so they’re positioned to avoid or leverage them, while Adapters become very good at turning the realities of an unexpected situation right now to their advantage. We’ll visit each in turn, and see how the best navigators of chaos use both.

The Planner

The planner lives by the mantra, “Proper preparation prevents poor performance.” They recognize that forethought now can help them in the future, so they spend effort thinking about eventualities, caching supplies, and charting out possible if-then courses of action. A consummate Planner seems to be always one step ahead of the game, which can make him seem omniscient at times. In reality, these are the professions where forethought is rewarded - e.g. engineers, lawyers, and architects. In fiction, these characters are always one step ahead - e.g. Professor Moriarty, Petyr Baelish, and Hannibal Lecter.

Strengths

A good Planner uses forethought to discover potential black swans - unknown unknowns - before they happen, and prepare for them. This gives a Planner an edge over an otherwise-unprepared

Weaknesses

The space of possible eventualities is infinite, and a Planner only has so much time and energy. The pathological Planner spends endless time anxiously planning for as many eventualities as possible, afraid of any unknown (no matter how likely). Planning also requires a certain narrowing of the scope of events: in highly chaotic environments where even ten minutes in the future looks completely different from now, planning is a hindrance rather than a help.

The Adapter

The adapter believes no plan survives contact with reality, so they have become very good improvising. They process new information extremely rapidly, and they have a finely-tuned sense for good opportunities and danger that they’re prepared to act on at a moment’s notice. A consummate Adapter is calm in chaos, and seems to always turn the situation to their advantage. In reality, these are the professions where immediate action is required - e.g. air traffic controllers, soldiers, and policemen. In fiction, these are often the heroes - e.g. James Bond, Ethan Hunt, and Batman.

Strengths

An Adapter is very good at processing new information and improvising. They’ve a database of reference experiences of being thrown into the unknown without a plan and coming out on top, which means they can intentionally inject chaos to competitive situations to drive their enemies even further behind. In the terms of John Boyd, Adapters are exceptionally good at getting inside the enemy’s OODA loop.

Weaknesses

A pathological Adapter doesn’t recognize the value of forethought and never plans, meaning they get caught going down paths that looked good at the time but were longterm negative. They don’t have the caches of resources that a Planner does, and they can find themselves caught on the back foot by situations that could have been prevented (e.g. a gear failure while climbing that could have been prevented with proper maintenance).

Unification

The Planner and Adapter have complementary strengths and weaknesses, so the very best navigators of reality learn to channel both. Forethought is utilized in a constrained way to surface the most likely outcomes (even ones that might not be obvious), and action is taken now to prepare for those outcomes. When chaos inevitably arrives, the new information is synthesized, the plan is updated, and the pre-allocated resources are used to get back into action.

Natural Tendencies

In my observation, we each often have a strong tendency towards either Planning or Adapting as a result of our upbringing. Those who tend towards Planning have a childhood where the future was a scary but predictable place where surprises could be tamed with preparation. Those who tend towards Adaptability perceive the future have a childhood where the future was too unpredictable to be worth planning for, where opportunity was better created utilizing the information of the moment.

These natural tendencies seem to be self-reinforcing: a Planner scared of the chaos of the future will put ever more effort into Planning, ensuring that they never face any chaos (and thus, never exercise their Adaptability). An Adapter comfortable in improvising will continue to rely on their ability to improvise in the moment, thereby avoiding exercising their Planning ability.

Learning to Unify

To break these cycles, we need to build reference experiences of success using the opposite method. For a Planner, this means training his confidence in chaos: consciously stepping into the unknown without a plan, acknowledging that pain will arrive and be overcome. E.g.:

  • Talking to a neighbor about a disagreement without planning what to say
  • Going on a date without any idea of where to go
  • Choosing a restaurant with your friends without looking up the ratings
  • Going on a trip without a schedule in advance

For an Adapter, this means dedicating some time to thinking about & preparing for the future. E.g.:

  • Saving the locations and contact info of a hospital, police station, and embassy that you might need to visit if things go wrong in the foreign city that you’re visiting
  • Planning out an adventure day with your significant other
  • Writing down the milestones and likely snags you’ll hit in the project you’re working on
  • Spend 10 minutes brainstorming emergencies that could happen to your family (e.g. fire, break-in, kidnapping, frozen bank account, etc.), and then make a plan to guard against them

Notice any discomfort as you do these exercises. Where does it come from? Can you accept it and relax into it as a natural part of the learning process?


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