Guest Post: Your decisions are not all the same, so why treat them the same?
Plus other actionable lessons to help you decide better
Hello, all!👋 On this week’s menu is a special. I’m hosting my friend Pritesh Jain.
Pritesh has worked with some of the most successful consumer internet companies (Zovi, Myntra and Cure.fit) in India. He’s a builder, operator, and independent thinker. We go way back. I’ve been picking Pritesh’s brains for a long time now and I’m excited to present this guest post from him to you all. Pritesh writes a weekly newsletter called Stay Curious. What I most look forward to in his writing is his range of sources, as I hope you’ll also see in his eclectic picks for this post. So, here it is…
When Seth Godin proposed the modern curriculum for the new world, he recommended including subjects like statistics, programming, decision-making, communication & real skills like honesty, empathy, curiosity and problem-solving.
He believes that these should cater well in service of learning to solve interesting problems and how to lead as well as follow.
Decision-making, as he suggests, is using the rest of the skills to make better choices. It’s the culmination of all that is learnt, an application layer of sorts.
When we are young, people around us dictate our choices. We’re rarely required to make decisions. Even when it’s needed, walled gardens protect us from the impact of any bad decisions. And so, we remain forever novices in the world of decision-making. There is no formal education except trial and error. To be fair, there is nothing wrong with ‘trial and error’. But, there have to be more concerted efforts to pass on these skills from expert practitioners to novices.
This post is a humble attempt to share what others have learnt & shared about the art & science of decision making.
We will focus on three fundamental lessons, top it up with a couple of related concepts. And finally, I will leave you with a fun game to practice your ‘decision making’ skills in the real world.
Without further ado, let’s get to these.
Three things you should know about decisions
All decisions are not the same. There are two types of decisions. And people who can identify which is which are able to do better than others.
Decisions are more temporary than we think. Make decisions early and often. You’re more likely to succeed.
One should learn to distinguish between quality of outcomes and quality of decision making. You can control only one of these.
Let’s expand these a bit more on the back of learning from the giants in their field.
1. Two types of decisions
In one of his Amazon shareholders letter, Jeff Bezos talked about two types of decisions:
Some decisions are consequential and irreversible or nearly irreversible — one-way doors — and these decisions must be made methodically, carefully, slowly, with great deliberation and consultation. If you walk through and don't like what you see on the other side, you can't get back to where you were before.
But most decisions aren't like that — they are changeable, reversible — they're two-way doors. If you've made a suboptimal Type 2 decision, you don't have to live with the consequences for that long. You can reopen the door and go back through.
Wearing merchandise of your favorite band is a two way decision, you can just not wear it when you don’t like them anymore. But, getting their names tattooed on your forehead is something you cannot reverse easily — a one-way door.
2-Way-Door rule can help make better and faster decisions. Farnam Street had a really insightful post on this topic, in case you are hungry for more.
But it’s not very easy to embrace this reality. The real challenge we face is to identify correctly if a decision is Type 1 or Type 2. There are no scientific methods for this, just a simple framework and intuition and tacit knowledge.
To get better at identifying your Type 1 decisions from your Type 2…
2. Make decisions early and often
In The Eleven Laws Of Showrunning, Javier Grillo-Marxuach (aka Javi) tells us why one should make decisions early and often.
Bezos’ 2-way-door approach can help make a quick assessment of reversibility & impact. That should aid in making these decisive choices faster.
But, that’s easier said than done. Not everyone is daring or smart enough to do this. We’re afraid of making decisions. Javi warns us against this cancer of decision aversion that’s highly prevalent.
…an aversion to making decisions is a massively common showrunning dysfunction. It comes out of an understandable insecurity: once you make a decision, the world knows where you stand. Once you say “This is what this is,” you have made your taste and opinion clear: the world will judge you. Decision aversion can also be a stalling tactic designed to let you have it your way without ruffling too many feathers on an interpersonal and creative level. Wanting to be seen as “a nice person” and a “good employer” are understandable desires.
While “nice” can mean “affable” and “pleasant,” a second definition of “nice” is also “precise and demanding careful attention.” In my experience, nice people - and good bosses - rip off the Band-Aid early, make the case for their decision, hear out any remaining arguments, then shut down the discussion and send everyone off to get on with their work.
Javi points to the role of ‘leaders’ in making this decision-making process quicker & iterative. Those who can do this effectively stand out of the crowd and move mountains. All others get stuck in a world where nothing moves and drag their feet waiting for the perfect decision and outcomes. Which, almost never happens.
So don’t wait up because decisions are not absolute—you’ll never have all the information or all the time to make just the perfect decision.
3. Decision-making is thinking in bets
Annie Duke says the biggest problem in decision making is “resulting” — equating the quality of a decision with its outcome.
We have a natural tendency to judge a decision based on its outcome rather than only its quality. It’s all too common to believe - If a decision leads to a good outcome, it must have been a good decision. Likewise, if it leads to a bad outcome, it must have been a bad decision.
But, this approach ignores a critical element of decision-making — all decisions are actually a bet taken based on our best assessment of available information & time. There are probabilities at play here and any outcome is a slave to those probability. One cannot ensure a certain outcome against its odds.
If you think in system terms, we can only ensure that our inputs to decision-making are fair. But, the outputs are governed by forces beyond our control. By putting in rigorous effort in information seeking, assessment & evaluating all possible bets, we can improve our odds but we cannot make them absolutely certain.
Once you are able to subscribe to this philosophy, you will embrace uncertainty to make better decisions and not get blindsided by resulting.
If you’re reading this, congratulations. You’ve shown a remarkable curiosity to discover something new & become better.
Let us jump to some related ideas that you are bound to encounter in your journey of decision-making. Knowing these can help you be better prepared for what lies ahead.
4. Decisions are made in a specific context & their rationale is highly driven by that context
Chesterton’s Fence is the best mental model on this. It says - “Do not remove a fence until you know why it was put up in the first place”. Here’s a snapshot from the Farnam Street post on this topic.
Chesterton went on to explain why this principle holds true, writing that fences don’t grow out of the ground, nor do people build them in their sleep or during a fit of madness. He explained that fences are built by people who carefully planned them out and “had some reason for thinking [the fence] would be a good thing for somebody.” Until we establish that reason, we have no business taking an ax to it. The reason might not be a good or relevant one; we just need to be aware of what the reason is. Otherwise, we may end up with unintended consequences: second- and third-order effects we don’t want, spreading like ripples on a pond and causing damage for years.
In no way does the principle discourage change. It just encourages understanding the rationale behind previous decisions. If we don’t understand how we got “here,” we run the risk of making things much worse.
Unless we know why someone made a decision, we can’t safely change it or conclude that they were wrong.
The first step before modifying an aspect of a system is to understand it. Observe it in full. Note how it interconnects with other aspects, including ones that might not be linked to you personally. Learn how it works, and then propose your change.
Understanding the rationale is critical for ensuring progress. But they cannot be cast in stone. The earlier decisions were made in a certain context and the rationale represents our best judgment in that context. If we don’t account for changes in context, we run the risk of making a poor decision.
Seth Godin warns about this in “Bad systems get replaced by bad systems,” where he explains it beautifully using a metaphor of parking meters.
When a system is new, few are watching, so a handful of people with intent can design it and optimize it. As it gains in scale and impact, it calcifies at the same time that new tech arrives to codify the decisions that were made when the conditions were very different.
The next time you pose for a photo, keep in mind that we pose for photos because the speed of an exposure used to be so long that if you didn’t pose, the photo was blurred. We changed the tech, but baked in the cultural expectation.
Sometimes, we need to take a deep breath and go for better instead of more.
In any case, even though we come to expect rational thinking and risk taking through iteration, it doesn’t happen naturally. We’re biologically designed to be risk averse.
5. You need to prepare an environment for iterative decision-making
It involves the ability to get feedback, tolerance to failure & resilience to do things over. It’s an environment of ‘high agency’. No external force can drive it. It needs to be driven from the core. The following snippet from a conversation between programmers Ward Cunningham and Bill Venners alludes to similar advice. In Cunningham’s words…
I can't tell you how much time is spent worrying about decisions that don't matter. To just be able to make a decision and see what happens is tremendously empowering, but that means you have to set up the situation such that when something does go wrong, you can fix it. When something does go wrong, it doesn't cost you or your customer an exorbitant amount. It isn't ridiculously expensive. When you get in situations where you cannot afford to make a mistake, it's very hard to do the right thing. So if you're trying to do the right thing, the right thing might be to eliminate the cost of making a mistake rather than try to guess what's right.
If you’ve come this far, I commend you.
And here’s a little bonus read with some practical advice for the young professional in you.
6. Bonus read
Brian Armstrong’s post around the decision-making process at Coinbase is a good overview of a functioning system that enables high-quality decision-making. It encapsulates good frameworks on thinking, communications and org workflow that makes it all possible.
Finally, if you’re up to playing a game, give Absurd Trolley Problems a shot. This one is going to challenge you a lot! And possibly, there are no right answers at all.
It’s been great fun curating this post for you. I hope you learned something new & useful, because I surely did .
I send across a weekly mail covering lessons from varied fields such as product building, storytelling, leadership, design, content & communities. “Stay Curious” is your window to the world of new ideas. Come, explore new things and find something useful every week at 8priteshj.substack.com
See you there!