How to make bad decisions correctly

Abinand Sivakumar
The Startup
Published in
5 min readJul 25, 2019

They come in different flavors.

Should I buy that car?
Do I really need new shoes?
Should I quit my job?
Should I break up with him?
Should I keep grinding?

Decisions need to be made to do something. Decisions need to be made to stop doing some other things. Decisions need to be made to even not make a decision right now.

Taking a few pointers from Daniel Kahneman’s stellar book “Thinking, Fast and Slow”, the easiest decisions are the one’s we already made several times over a period of time. “What route to take to work?” involved a lot of thinking and planning the first time around, but subsequent commutes involve barely any mental effort. It is already “in our gut”. The pattern that works is already soldered to our neural network.

Situations and realizations that are new, trigger the logical thinker within ourselves. We have to work with limited knowledge of the consequences of our actions — consequences that may be difficult to recover from. This post explores the faculties we have at our disposal to minimize regrets.

What is a bad decision?

Simply put, a bad decision is one that brings an outcome of regret.

Consider having to choose between two courses of action. A classical “two roads diverged in a yellow wood” kind of a problem. We don’t know the result of either choice but we need to decide one in order to proceed. Now, no matter what was chosen, there is a 1/2 = 50% chance that we are going to regret it and 1/2 = 50% chance that we are going to be satisfied with it.

Say there were more options. For a decision with three options, choosing one of them means we have 1/3 = 33% chance of being satisfied with it and 2/3= 66% chance of regretting it. Ouch! If we are presented with 10 options and have to choose one, well you get the idea — 90% chance of regretting it.

Does that mean having fewer options makes for a good decision? Yes and no, because in the real world, it is usually not obvious what options were available until after we choose one. That is why, even with meticulous planning and strategizing, the results would not exactly be what we wanted and we end up spewing a lot of “what ifs” after the fact.

So we need more choices to pick the one we would be more satisfied with, but having more choices means that we make a decision we are more likely to regret. This seems like a setup for failure.

A model for decision-making

The goal here is to be able to make bad decisions with confidence and use the experience of making those decisions to aid future decisions.

There are plenty of ways to aid logical decision making — read up on SWOT analysis, SCORE analysis, SOAR analysis, the Eisenhover matrix, etc and these are effective in various combinations for various personal or organizational needs but it is just one part of the decision making process. The strategies mentioned can be used to find what to choose but before this undertaking we need to refine the available options.

This is where we tap into our instinctive experiences and brainstorm all the possibilities. We are going to create an artificial “inspiration” from our automatic-action neural network.

The way we can do this is not very different from learning a new concept or skill. The active logical thinking brain can only hold a little bit of information at any given time. The information gets assimilated into the passive brain by deliberate repetition. A simple exercise to that effect can be done by writing down the desired and undesired outcomes like this:

By writing this down and reinforcing clearly what we want, what we don’t want and everything in between, the passive brain is facilitated to provide a decent set of options. The options that we “brainstorm” for ourselves would all be options that we can recover from even if it were bad ones. These options may not present themselves right away. It takes time to be processed. It may come as a form of inspiration when we are in the shower or while driving. They are subtle and fleeting so it is important to catch and pin thm when they appear. The clue for identifying such thoughts is that they appear to be triggered by an external cue, not very different from Archimedes’ eureka from the bath water, but they bear a shadow of our reinforced specifications.

At this point we end up with a set of choices. We could make a logical decision on those options with the resources available to us. The outcomes, even when they are not ideal, can be used to learn how to make the correct choice the next time.

This worked for me in situations where I felt “stuck” with no alternatives and where no amount of logical thinking or rationalization could manifest a solution. Scouring through endless online Q&A posts on what the right thing to do is bound to end up in frustration. Some guy on the internet cannot give situational advice tailored to a specific need no matter how good that generic advice might seem. Not that there is a lack of positive intent, it is just not possible to communicate internal fears and aspirations that way. There is usually more than one way to attack a problem so that no matter what choice we make, it is either the satisfactory one or something that can be learned from.

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