Thought experiments to make better choices

New perspectives for free

Yo girlz and boyz, and welcome to another issue of the ProtoNewsletter, where I share not only ideas, ravings, insights, and tips of dubious usefulness but also grammatical mistakes and odd phrasing.

Let’s start!

As good human beings, we usually live immersed in the realities we belong to: the world around us and the one inside our heads.

We sail the ocean of immediate matters — worries, chores, meetings, thoughts — and we observe everything from the first person. Well, it’d be odd if it wasn’t so (unless you suffer from depersonalization).

This perspective, even though it’s reasonable and necessary, is limited. If we base solely on it when we reason, make choices, or deal with problems, we will have a partial view of the possibilities available to us.

A simple way to get out of this “operating mode” is through thought experiments.

A thought experiment is a hypothetical situation in which a hypothesis, theory, or principle is laid out for the purpose of thinking through its consequences. — from Wikipedia

In a nutshell: imagine a scenario and reason on its implications. This forces you to look at things from other perspectives.

The core of a thought experiment is the question: What if…?

  • What if I moved abroad?
  • What if the truth was the opposite of what I believe?
  • What if I changed career?
  • What if I quit social media?
  • What if I started that blog I’ve been thinking about?

Many techniques were built around this core. Below, three that I liked and that are all variations on the Stoic Premeditatio Malorum, i.e., “negative visualization.”


The inversion technique involves looking at the problem you are dealing with from the opposite perspective. Let’s say I have a goal. I will ask myself how to achieve it (regular thinking) and how to achieve its opposite (inversion).

  • If I want to attract more readers to my blog, I will ask myself how to push them away.
  • If I want to be more focused, I will ask myself how to be continuously distracted.
  • If I want to be healthier, I will ask myself how to destroy my body.
  • If I want to save more money, I will ask myself how to drown in debt.

Imagining the opposite makes you find out things you wouldn’t have thought of otherwise. (This is also mentioned in The First 20 Hours, which applies this idea to learning.)


Murphyjitsu helps to reduce a plan’s odds of failure. After applying it, you get to a point where failure appears shocking because it’s highly improbable.

The steps:

  1. Make a plan.
  2. Imagine that you’ve passed the deadline and find out that the plan failed.
  3. If you’re shocked in this scenario, you’re done.
  4. Otherwise, simulate the most likely failure mode, defend against it, and repeat.

Suggestion: when you’re simulating the failure mode, pretend you’re evaluating a friend’s plan. It’s easier to imagine roadblocks and failures if they concern someone else. 👀

Fear setting

This last strategy, popularized by Tim Ferriss, is designed to deal with fears.

Apart from the unpleasant feeling it causes, the practical issue with fear is its paralyzing effect. Being afraid of something means trying to avoid it.

For example, I might be unsatisfied with the job market in Italy and yet be afraid to move to a different country.

The framework in three steps:

  1. What if…?
    E.g., What if I moved abroad?
    • Define: list the worst-case scenarios that could happen if you did what you’re considering.
      E.g., feeling lost because I don’t know the language and I can’t communicate.
    • Prevent: how could I prevent or decrease the likelihood that they happen?
      E.g., taking a language course before moving.
    • Repair: if they do happen, how could I repair the damage, or whom could I ask for help?
      E.g., pay a translator; move back to my country.
  2. What are the benefits of action?
    E.g., new life experiences, finding a better job, learning a new language.
  3. What would be the cost of inaction in 6 months, 1 year, and 3 years?
    E.g., it would cost me at least tens of thousands of euros because of the lower salary; I would be less satisfied with my life; I would’ve wasted time; I would regret not trying.

This process helps you clear your head and pushes you to find solutions to your fears, thus making them manageable.

Thought experiments are an easy way to improve the quality of your choices. They take you outside of your usual mode of thinking and widen the range of opportunities you can see. Moreover, they don’t require any particular tool nor external help.

You can’t ask for more!

Things I liked

Episode Party

If you are used to listening to podcasts like me, you’ll share the same pain I feel when I want to listen to something new. I’m sure that out there is full of beautiful podcasts that will blow my mind, but how do I find them?!

I have no definitive solution, but I found a new “tool” some days ago: I discovered a podcast to discover podcasts. #meta

I could build this during the weekend

Some days ago, a colleague of mine linked this blog post. It’s aimed at software developers, but the underlying idea could be extended to everyone.

When looking from the outside, many things seem simple and straightforward. Instead, it’s more likely that we have no idea about the context behind them.

A bit Dunning–Kruger effect, a bit planning fallacy. It’s a product of the human brain’s limitation in its ability to deal with the world’s complexity.


I started using Mailbrew, a service that allows you to create a personalized newsletter by setting the sources you care about and the frequency.

The daily digest I set up became one of my favorite newsletters.


My daily digest

The latest content from yours truly

🗞 I don’t keep up with the news. It’s boring, useless, and harmful. I tried starting more than once, but it never lasted.

There are good reasons for you to stop too.

Why I don’t keep up with the news (and why you should stop too)

📓 I also published my summary & notes from this little book that teaches the benefits of sharing your work online.

Show Your Work! — Austin Kleon