Why we make bad decisions (and how to avoid it) (Part 2)
Distilling Books - Number 28
Welcome to Mental Garden. The following letter is part of our “Distilling Books” collection, in which we extract the most revealing ideas from literature. For the complete library, click here.
🏷️ Categories: Decision making and biases.
Did you get here by chance?
If you haven’t read the first part of this journey through the book Decisive (by Chip and Dan Heath), do yourself a favor and start there—you don’t want to miss everything we covered.
👉 Click here to read the first chapter.
There we made the diagnosis: why even brilliant minds make bad decisions, how narrow framing creates false dilemmas, how confirmation bias makes us seek agreement rather than truth, how immediate emotion hijacks our long-term vision, and how overconfidence makes us risk everything without fear.
And here’s where things get really interesting: today we’re going to change the system.
Here is, step by step, how to decide—and get it right.
1. Expand your options
The biggest mistake in decision-making happens long before the decision itself.
It comes from considering too few options.
Most important decisions start with a question that seems sensible, but is already broken from the start.
“Do I take this job or not?”
“Do I stay here or leave?”
“Do I invest or wait?”
When you decide between A or B, you’ve almost always already lost before you begin.
Because the best option is almost never one of the first two you see. Narrow framing removes alternatives. You’re thinking on a board that’s too small—so before you think about making a move, widen the board.
Here are four techniques to do exactly that:
1.1. Reframe the question
The quality of your decisions depends on how you frame the initial question.
When you ask yourself “yes or no?” in a binary decision, you’re ignoring almost everything and jumping straight into evaluating and justifying one of the two options. If you change the question to “What options do I have to…?”, you gain an exploratory perspective.
You start combining existing options.
You begin exploring new ones.
You’re no longer trying to close the problem as A or B—you’re trying to understand it. This question completely changes the type of thinking that follows. It gives you a bigger board. Let’s look at an example.
Instead of asking yourself: “Do I take this job or not?”
Ask: “What options are there to improve my professional situation this year?”
Suddenly, paths appear that didn’t exist before: renegotiating conditions, changing roles, acquiring a key skill, waiting six months with a concrete plan, or even not moving yet and waiting for a better moment.
You haven’t decided anything.
But now you’re deciding from abundance, not from scarcity.
1.2. The vanishing options test
If you remove the dominant option, invisible alternatives appear.
One of the most powerful techniques in the book is called the Vanishing Options Test. The idea is simple: mentally eliminate the option that’s taking up all your mental space and ask yourself what you would do if it didn’t exist. This exercise breaks automatic attachment to the familiar. It forces your brain to move. To search. To create something.
Imagine you’re obsessed with a specific offer. Do the exercise:
“If this offer didn’t exist… what would I do?”
Suddenly, alternatives appear that you hadn’t considered: changing industries, starting a business, negotiating within your current company, training, waiting intentionally. This is the technique I usually call option suppression, and it’s also extremely powerful for boosting creativity.
It’s not that those options didn’t exist before.
It’s that your mind didn’t need them… until now.
1.3. Think in “AND,” not in “OR”
Many decisions are not mutually exclusive.
We just treat them as if they were because that’s the most obvious way to think. It’s easier to think in terms of “either this or that” than “this and that,” combining elements. But here’s the key: many stuck decisions unlock when you stop thinking in totally exclusive options and start designing hybrid solutions.
You don’t need to choose between two evils.
Sometimes you can build something good.
It’s not: “I want stability or I want growth”
It can be: “Stability in income and growth in skills”
It’s not: “I stay or I leave”
It can be: “I stay six months with a clear plan and prepare an exit”
The “AND” eliminates the false dichotomy.
1.4. Track your options
Comparing several options at the same time makes you clearer and less emotional.
When you analyze a single option in isolation, you grow attached to it. Evaluating options in parallel reduces emotional investment and helps you think more clearly. That’s why it’s recommended to consider multiple paths at once, even if they’re just rough drafts.
Everyday example: you’re thinking about changing jobs.
Instead of obsessing over a specific offer, consider at the same time:
Option A: accept that offer.
Option B: renegotiate conditions where you are.
Option C: look for a different role within the same sector.
Option D: hold on for six more months while improving a key skill.
When you have several routes already drawn on the map, you can see which one is optimal.
We’ve already seen how to avoid the first big mistake: binary thinking.
Let’s look at the second mistake—and how to annihilate it…
2. Test your assumptions
The worst enemy isn’t lack of information—it’s information that agrees with you.
Once you lean toward an option that aligns with your values, identity, or preferences, your mind stops exploring alternatives neutrally and starts defending that option because of the attachment you’ve built. Chip and Dan Heath make this clear in Decisive: many times we believe we’re researching when we’re actually seeking confirmation.
Here are four techniques to prevent that:
2.1. Look for disagreement before support
If no one contradicts you, you’re deciding blind.
Decision quality improves when friction enters the process. That’s why the best decision-makers don’t seek quick consensus—they seek disagreement. Making a mistake during the option-analysis phase and correcting it is cheaper than correcting it months later.
You need to be challenged. Here are some practical ways to do that:
Look for negative conditions: “What would have to happen for this option to fail?” Investigate what problems the discarded options have; dig deeply into everything that could go wrong in each one.
Assign a “devil’s advocate”: work with someone whose job is to dismantle the dominant option and systematically search for its weaknesses. What could happen that would make your option a mistake?
Talk to someone who’s already been there: find someone who has already lived the option you want.
Sometimes one uncomfortable conversation saves years of regret.
2.2. Ask questions that could dismantle your idea
Change the angle of your questions:
Instead of: “What advantages does this option have?”
Ask: “Where does this usually fail?”
Instead of: “Hey, does this seem like a good idea to you?”
Ask: “Why do you think an expert wouldn’t do this?”
In Decisive, they insist on asking disconfirming questions—this is the inversion technique. It’s key because these are the kinds of questions that expand real information. The others only reinforce a narrative you’ve already told yourself based on prior beliefs.
If an idea survives questions that go against it, that’s a good sign.
2.3. Look outside before looking inside
Your case isn’t as unique as you think.
The book introduces a key distinction we often ignore:
Inside view: your story, your reasons, your feelings.
Outside view: what usually happens in similar situations (patterns, statistics).
We’re great at using the outside view to choose restaurants. We’re terrible at using it to choose jobs, relationships, or projects, because we believe “our context is special.” Before thinking “in my case it’ll be different,” ask yourself:
What is the real success rate?
What usually happens in decisions like this?
What patterns repeat when others try?
External reality gives a massive advantage to those who know how to use it.
2.4. Sampling: test little by little before betting everything
Why predict something you can test?
Sampling is one of the most powerful concepts in the book. It means turning a big decision into small, reversible experiments. It replaces assumptions with real data from trials. Failing cheap before failing expensive.
Not all decisions allow sampling, but when they do, use it.
Everyday examples:
Before quitting your job → try a side project
Before launching something big → launch a small version
Before changing industries → talk to people who are already inside
The Heath brothers warn in Decisive: it’s not always applicable, but it’s the technique that reduces risk the most and replaces assumptions with real data. It’s ideal.
What you did today (even if you didn’t notice)
Today you didn’t learn “how to decide.”
You learned how to prepare better decisions before choosing.
You saw how to widen options to break false binary decisions.
You learned how to test reality before falling in love with an idea.
In the next and final edition, we’ll cover the last two parts of the system:
How to create emotional distance to decide with your head.
How to prepare for a future you can’t predict.
Here is the third part:
Want more? Here are three related ideas in the meantime:
Richard Feynman’s 7 principles for thinking clearly in a noisy world
The number that changes everything: how anchoring bias kills your decisions
✍️ Your turn: Lately, are you deciding from scarcity (“I have to choose now”) or from abundance (“I can design more options”)?
💭 Quote of the day: “Should I do this or that?” Instead, ask yourself: “Is there any way I can do this and that?” — Chip Heath & Dan Heath
See you in the next letter about Decisive! 👋
References 📚
Heath, C., & Heath, D. (2013). Decisive: How to Make Better Choices in Life and Work.