How to be a messy thinker

Crossposted from my blog: https://​​​​how-to-be-a-messy-thinker/​​

I love thinking about thinking. Give me a research paper on rationality, cognitive biases or mental models, and I’ll gobble it up. Given the amount of knowledge I’ve ingested on these topics, I had always assumed that I’m a clear thinker.

Recently, though, it hit me like a lightning strike that this belief is counter-productive. That’s because is you “know” that you’re a clear thinker, you’re less likely to suspect that you might be missing something big in your thought process. After all, if you are convinced that you think clearly by default, why would you put in any extra effort to scrutinize your thought process?

So, ironically, the belief that you’re a clear thinker creates a backdoor for cognitive biases to creep into your thinking because you’re less likely to suspect they might be there in the first place.

Once this realization dawned upon me, I resolved to lower the expectations from my thinking process. Instead of celebrating clever arguments and things making perfect sense, I now see clarity as signs of missing something. The real world is often nuanced and, hence, thinking about it should lead to messy details, not grand one-line aphorisms.

Clear thinking sets you up for unrealistic standards

As a clear thinker, you can make no mistakes. After all, you should have seen everything in advance, made perfect plans and thought of all contingencies. But that never happens – a moment of reflection is sufficient to convince anyone that such perfect foresight is impossible.

Clear thinking is perfectionism in disguise, and like all forms of perfectionism, it creates a persistent source of anxiety as you’re never good enough against your unrealistic standards.

So, abandoning the expectation of clear thinking is a huge relief because now you know you’ll always miss something. You are no longer in a state of persistent self-criticism because your standards are realistic.

Also, instead of beating yourself when inevitable surprises crop up, now you see them as a source of learning.

Abandon clear thinking, be a messy thinker instead

In nature, everything is continuous and interacts with one another. Unless you’re working with fundamental physics or mathematics, you shouldn’t expect simple, understandable models of reality that we crave so much.

A messy thinker acknowledges this incompatibility between the messy reality and our impulse to make sense of everything in neat, little boxes.

So, while a clear thinker asks: “am I right?”, a messy thinker asks: “what am I missing?”

This might seem like a simple re-arrangement of the same question, but the focus on what you’re missing defines messy thinking. It’s the humbling admission that, no matter how hard you try, you’ll always be missing something in your thinking.

However, it would be a mistake to think that because reality is messy and unpredictable, we should give up thinking altogether. Messy thinking is not nihilistic. Rather, it is pragmatic. It aims at doing the best job possible on a decision knowing the constraints of time, while simultaneously acknowledging that a perfection is impossible. So, instead of aiming for optimality like a clear thinker or giving up on thinking like a nihilist, a messy thinker simply aims for landing at a “good enough” outcome.

When you abandon the expectation of clear thinking, you redefine failure/​success as something that’s binary to something that falls on a continuum. Instead of aiming to be right and asking yourself later whether you were right or wrong, you now aim to land closely to one of the many good outcomes, while asking yourself what you did not see earlier that you should account for the next time.

Can you see how messy thinking is a much more forgiving and practical way to live, and why clear thinking is a delusion?

How to be a messy thinker

My beliefs in clear thinking were confronted after I spent two years chasing product-market fit at my startup (Nintee). After a few unsuccessful pivots, I was facing a decision of whether to continue with another pivot or whether to shut it down. This was a major decision because it impacted investors and my team. Given the importance of getting a good outcome for everyone, this pushed me into picking up a few books on decision-making.

I gained many fresh perspectives from these books, and finally ended up shutting my startup, returning the investor money and offering a job to my team at my second company. (Out of these 3 books, I recommend reading “How to Decide” and “The Scout Mindset”.)

I (obviously) can’t capture all the ideas contained in these books, but three big perspectives that helped me in deciding were the following:

1. You’re not as special as you assume

Everyone thinks they’re special (and, often, above-average). A couple getting married thinks they’ll remain married forever, and yet it is a fact that if you’re in the US, there’s a 50% chance that a marriage will end up in divorce or separation.

I know it’s very challenging to believe that you’re not special because from the inside everything looks special, but know that other people are also like you. People who constitute the population also believe they’re special, and yet add up to the statistics that you see. So, while deciding, look at population-level statistics.

(In my case, I looked at several statistics, and it became clear to me that the odds of success for a consumer startup is very low and that even if an initial product-market fit is found, the odds of getting stuck at a sub $10mn revenue zone is very high, which as a VC-funded company is probably worse that complete failure.)

2. Outside-view v/​s inside-view

Daniel Kahneman (who recently passed way, RIP!) has perhaps written more about cognitive biases than anyone else in the world. That makes the following story very interesting.

Early in his career, he was part of a group tasked with writing a new academic textbook. As a group, they debated how long it will take them to finish the book, and they converged on an estimate of two years. Guess how long this group actually took to finish it? Eight years. Guess how long does an average academic book takes to be finished? Six years! (And many never get finished at all due to abandonment).

I find this story illuminating because Daniel Kahneman (of all people) should have known better. But he himself told this story as an example of how inside-view misleads by making everything looks rosy. In our head, everything makes perfect sense. When we sign up for the gym, it is as clear as day-light that all we have to do is to get up and go to the gym every day. What we’re unable to incorporate is the messy reality, the thousand little obstacles, distractions or new opportunities that crop up along the way (extra work from the office, laziness, a new hobby, or a health crisis).

The right way to counter-act biases of such inside-view is to take an outside-view by looking at the population out there and seeing what happens to them when they make the decision you’re about to make. Note that the book that Daniel Kahneman was co-writing took almost as long as the average book. Particular cases tend to converge to population outcomes. No matter how much in love you’re in during the wedding day, half of marriages do end up in divorce, so plan accordingly.

But, of course, it’ll be foolish to ignore that you’re a little bit special. So, after you’ve taken the outside-view, ask if there’s anything that makes you special pertinent to this decision. Perhaps you’ve known your spouse for much longer? Perhaps divorce rates in your community are lower? Account for all that uniqueness in your situation.

The right sequence, however, is to first take an outside-view and then do appropriate adjustments according to your particular situation. You won’t make perfect adjustments, and that’s ok. The idea is to get to the right ballpark. However, beware of assuming you’re too special and negating the outside-view altogether. Remember: the population where statistics come from is entirely made of people like you.

(In my case, I talked to many consumer app founders, and they all told me how crazy-difficult it is for them to grow. Moreover, I realized even second time consumer founders don’t have an edge these days).

3. Adopt the 3Ps of thinking: Possibilities, Payoffs and Probabilities

While deciding, we have a natural tendency to think in binary: either an outcome is good or bad. But the real world can accommodate many different possibilities, and it makes sense to explore as many of them as time or energy constraints permit.

Let’s say you’re deciding whether to buy a house or not. The natural impulse is to decide between two options: a) buy a house, or b) not buy a house. But forcing oneself to explore more possibilities will reveal new options that won’t come naturally to you. For example: you could c) take up a long-term lease, d) ask friends to co-purchase a larger building, or e) buy land and build a new own house on it.

Forcing yourself to explore possibilities beyond the obvious ones pushes you to be creative. Taking the outside-view and asking multiple people what they did in situations that you’re encountering also expands the list (perhaps you end up talking to someone who f) bought an RV instead of a house).

Once you have the possibilities, realize that they’re not just plain good or bad. Each one of them has some upside, and some downside. Perhaps buying an RV seems like a bad idea at first, but realize that it comes with an upside of being extremely mobile. Force yourself to think of both upside and downside. Then, against each possibility, write an expected payoff, which is simply upside measured against downside.

Of course, the upside or downside will be as per your preferences, so write what you like and dislike first. Remember: you want to optimize for what’s good for you (and not what’s good in the abstract). Perhaps what’s a downside for others (being surrounded by many houses) is an upside for you (being part of an intimate community).

(As a short detour: beware of the pros/​cons list. I had assumed they were a great way to think, but the inside-view suggests that you almost always end up writing a biased pros/​cons list. By the time you start writing a pros/​cons list, you likely have already made up your mind, and all you will write on the paper is justifications for your pre-decided decision.)

Finally, against each possibility and its payoff, write an estimated probability of its happening. You estimate the likelihood of something happening by first taking the outside-view and then integrating the inside-view. This estimate will be very rough, and that’s ok. As long as you’re in the ballpark, that’s fine. The point is to not be accurate, but get a feel for what’s more likely to happen. For example, buying land and building a house might seem like having a big payoff for you, but if it is less probable (because of complex laws of land buying), you should spend less energy and enthusiasm on it.

(In my case, I explored many other possibilities, including pivoting to B2B startup. But my preferences weren’t aligned to this possibility. My other company, Wingify is a B2B company and I have already done a 10+ year journey with it, so even though the odds of success objectively are higher for a B2B company, for me, it didn’t appeal. I should note that the 3Ps process specifically helped me get this insight.)

It’s a lot of work to be a messy thinker

Yep, I know all of this sounds like a lot of work, and it is. So, you should invest effort proportionally to how important the consequences of a decision could be on your life. You don’t need to do all this to decide what to eat for dinner, but when it comes to which job to take or which product to launch, a few days going through the messy decision-making process is worth it.

To help you, I’ve put together all that I have learned from the books in a Google Sheet. It has many other ideas that I haven’t talked about it in the essay, but hopefully, they’ll be clear from their descriptions

Download the Google Sheet to help you work through your decisions

How to use this Google Sheet? Simply copy it for each new decision you’re about to make and fill in all the sheets.

A nice side-benefit of keeping a log of your decisions (in such a sheet) is that it helps you learn effectively from your failures and successes. Long after you’ve made a decision and observed what actually happens, you can always go back and read what assumptions were you operating with and whether they turned out to be true or false. Over time, a collection of decision-logs like this becomes an invaluable tool for reflection and self-improvement.

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