Creating Thinking Exercise

1. Cognitive flexibility: Ability to switch between thinking mode/consider multiple perspective
2. Associative thinking: Ability to connect seemingly unrelated topics
3. Divergent thinking: Ability to generate multiple solutions to the same problem
4. Constraint breaking: Ability to identify and overcome hidden assumptions

Exercise 1: Perspective Shifting (Cognitive Flexibility)

1. Chose an object in the environment
2. For two minutes, rapidly adopt different perspectives on the object (how would an engineer look at it, a doctor? A child? Someone from middle age, what about an ant or a giant)

Shift rapidly.

Exercise 2: Random Word Fusion (Associative Thinking)

1. Pick 3 random words (from a book, a page, or generator)
2. For 2 minutes, create coherent content that use all three words (product, plot for a story, service, solution to a problem)

Exercise 3: Alternative Uses (Divergent Thinking)

1. Choose an object
2. For two minutes list as many possible uses for this object as you can (aiming for quantity over quality)

Exercise 4: Assumption Reversal (Constraint Breaking)

1. Chose any common service/product/process (a restaurant, a phone, food delivery...)
2. For 2 minutes, list all the assumptions and rules that typically apply to it (for restaurant you must pay for food etc)
3. for each assumption, ask yourself what if the opposite was true or how could we eliminate that requirement completely

Strategic Thinking

1. Second-Order Thinking: First order is focusing on immediate effect of action, second-order focuses on the "and then what". Practice asking yourself a set of questions of the form "if you do x what happens next, and after that what happens".
2. Probabilistic reasoning: Thinking in terms of likelihood rather than certainties. Practice asking yourself questions like "what is the likelihood this will work and under what conditions". To practice, write down decisions you make and measure outcome. Overtime review logs to calibrate your guts.
3. Opportunity cost assessment: Understand that every yes means say no to something else since resources are limited. Practice asking yourself questions like "If I pursue this what am I giving up." Whenever you are making a significant decision, force yourself to consider three opportunities you are giving up by pursuing your main option.
4. Inversion Thinking: Instead asking how to succeed, ask what could cause you to fail. This perspective reveals problems you may otherwise miss (also called pre-mortem).
5. Scenario Development: Envision multiple possible futures. Keep your eyes open for possible paths. Practice identifying major two or three uncertainties in a situation.
6. First principles analysis: Broke down complex situations to small fundamental truths.

Exercise 1: Pre-mortem

Take in inversion thinking and second order thinking. Before starting an important project imagine it has failed completely. Spend 10 minutes writing down all things that went wrong. After that spend some time thinking about how you could prevent those failures.

Exercise 2: 10-10-10

Take in second order thinking and opportunity cost assessment. When you make a decision ask yourself how you will feel about it 10 minutes, 10 months, 10 years from now.

Exercise 3: Future back planning

Scenario development + First principles analysis. Clearly design a desired future state. Then work backward to identify what would need to happen to reach it (also known as back-casting).

Exercise 4: Perspective shifting

Probabilistic reasoning + First principles analysis. When you are stuck on a problem try viewing it from drastically different perspectives. Ask how a competitor would see the situation, someone from a different industry and so on.

Exercise 5: Strategic questioning

Incorporate questions into your thinking routine. What am I missing. What info do I need to estimate likelihood. What would change my mind about this. What would make this decision look foolish in retrospective. What's the non obvious solution here. What am I giving up to do this. How will an outcome affect my future.