Mental Models for Planning

The burden of decision! The difficulty of planning! Responsibility for the outcomes! These are a few problems we all face in our professional & personal lives. Thanks to the amazing network of founders who make similar decisions on a day-to-day basis, I have a pool of people whom I can rely on getting answers to such impossible questions. But the suggestions and advice I usually get are very subjective & contextual.

How do you choose which projects/strategies your team should work on? Cost of implementing your strategies, cost of not implementing them, there is no apple to apple comparison when you have to prioritize one team task over other, protecting downside risk vs building new functionality, budget constraints, etc.

Radically open-minded people know that coming up with the right questions and asking other smart people what they think is as important as having all the answers

-Ray Dalio

Each founder tackles problems in a very unique way and most of the time the idea gets lost in articulation. This weekend I was reading a lot on 'planning' from the first principles. What I found was that planning is more about knowing than doing, more about predicting about yourself than about predicting your future, more about iteration than about commitment.

Writing is the best way I learn and Below are my learnings Summarized-

• Planning is about predicting your future by choosing actions/options from the various alternatives you have at any given time.
• To choose the right option you need to have the right information and cognitive ability to calculate all the permutations and combinations of your choices and how each combination of options changes the outcome for you.

Any planner’s ability is going to be capped by their epistemic skill.

Epistemic Skill - Potential sources of your knowledge and justified belief, such as perception, reason, memory, and testimony.

Belief - Snow is white.

Justified true belief- when you see for yourself, that snow is white.

But not all justified true beliefs constitute knowledge.

At times your perception, reason, or memory may deceive you into believing that you have knowledge about things, but you may not be having the right information or the truth.

Planning is not about doing, its about knowing

• Knowing about your options, consequences of those options, knowing about how much you know, knowing about how much you don't know, and keeping a margin for things you don't know that you don't know.

[Ex: Most people lack scientific information about how the human body operates, how much nutritional requirement needs to be met to keep the metabolism high. If you do the right exercise which builds muscles (strength training) your metabolism increases which in turn helps you become lean, instead of just burning calories (cardio/walking/running). Most people would have lost muscles by eating very less and burning the calories by just walking, which in turn decreases their metabolism and never help them to get fit again. ]

• Most important of all in any planning will be knowing yourself. How will you behave when executing your plans, how much motivation and drive you to have to complete what you set out to do, and to understand, in which emotions you are making the plans. Is it what you really want to do in the first place or are you a person who rushes into a plan with inadequate information because you dislike being in a state of indecision and are likely choosing a worse plan because you are unable to handle the unpleasant emotions. 

One of the most important things to be able to predict is yourself.

While emotions serve multiple purposes, one of the things they do is carry an important signal of information from your subconscious mind. If you feel anxious about something or having a niggling doubt or whatever, that’s because there’s a part of your mind that has been processing raw data and finding it significant. The skilled planner and predictor will be someone who can extract that valuable information from their emotions.

Emotional mastery is more important to planning than having all the information and options.

• Tools for predicting yourself - Introspective methods such as meditation, Focusing, Internal Family Systems, etc. are helpful for having a better knowledge of which outcomes you actually want.
• Tools for emotional mastery - Schools of thought which help with emotional mastery such as ACT, CBT, and DBT have a place among the training materials for great planners.
• Planning can be Iterative or Recursive - An Iterative algorithm will use looping statements such as for loop, while loop or do-while loop to repeat the same steps while in a Recursive algorithm, a module (function) calls itself again and again till the base condition(stopping condition) is satisfied. If you are clear with the path and outcome, you simply execute till you reach the expected outcome. But if there is an element of uncertainty in the options available and their effectiveness, you can iterate by trying different options and getting information from them to make your next steps more effective.
• Once you turn planning into a multi-person activity, you also need to factor in uncertainty about others' plans, which complicates the model quite a bit. The physicist-founder might have been very good at reducing uncertainty in the laboratory with experiments, but the feedback loop for iterating on sales strategy might be completely different, even if in both cases you’re trying to reduce uncertainty.
• Many of our default intuitions about how to pursue uncertain ideas are counterproductive: We often try easier tasks first, when instead we should try the most informative tasks first. We are often too slow to try to disprove our own ideas.

Resources -you can read in more detail below,

1. https://www.lesswrong.com/posts/ZJzSxo6nCNvod67Xs/why-planning-is-hard-a-multifaceted-model
2. https://cs.stanford.edu/~jsteinhardt/ResearchasaStochasticDecisionProcess.html