Why we make bad decisions (and how to avoid it) (Part 3)
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 yet read the second 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 second issue
There, we built the first two pillars of the system: expanding options and testing assumptions. We saw how to escape false binaries and how to avoid “researching” only to confirm what we already wanted to believe.
Today, we complete the full framework.
With two more unusual… and decisive elements: distance and preparation.
Let’s see how to decide—and get it right…
3. Create distance before deciding
Many decisions fail because we decide too close to the fire.
When you’re inside the problem, everything weighs more: urgency, fear, pride, sunk costs, social pressure. Emotions don’t cancel out your reason… but they do hijack the horizon from which you reason.
The result is predictable:
what hurts now feels “dangerous.”
what relieves you now feels “smart.”
and the future becomes abstract, almost irrelevant.
That’s why we need to step far enough away to see the whole map.
Here are 4 practical techniques to do just that:
3.1. The 10/10/10 rule
If you could use only one tool from the book to gain distance, this would be it.
Ask yourself:
How will I feel about this decision in 10 minutes?
And in 10 months?
And in 10 years?
Why it works: it forces you out of the immediate present (where emotion rules) and makes you simulate real consequences across horizons you normally ignore. To apply it, follow these steps:
Write your decision in one simple sentence (without justifying it).
Answer the three questions in 2–3 lines each.
Underline what changes from one moment to the next—truth usually lives there.
Then repeat the exercise for each option, not just your favorite.
When to use it:
When you feel urgency (“I have to decide now”).
When an option “relieves” or “appeals” to you too quickly.
When there’s a high emotional cost today but a possible long-term benefit.
The 10/10/10 rule gives back what emotion steals from you: temporal perspective.
3.2. “What would I tell a good friend?”
Your judgment works better when you’re not the protagonist.
In Decisive, brothers Chip and Dan Heath recommend a way to “depersonalize” the decision: become an advisor to someone you care about. Because when it’s about you, you dramatize, justify yourself, punish yourself, and only see A/B dilemmas. But when it’s about someone else, you see nuance, balance risks, and think more critically.
How to use it (step by step):
Imagine your best friend telling you exactly your situation.
Write (literally) the message you would send them with the steps you’d suggest.
Read it, underline the key points, and ask yourself: “Why don’t I allow myself this advice?”
This is especially effective when you feel trapped by guilt or fear of judgment, or when the decision is tied to identity (“If I do this, what does it say about me?”).
Examples:
“If this were happening to someone I love, what would I tell them?”
“Would I tell them to keep investing out of pride, or to cut their losses?”
“Would I tell them to wait for ‘perfect certainty,’ or to run a small test?”
Seeing it in the third person makes your analysis more neutral.
3.3. Change positions
This technique brings long-term clarity.
The book illustrates it with a simple idea: when you’re inside, you’re biased; when you step outside, you see the obvious. Ask yourself:
“If I were no longer here… what would my successor decide?”
“If my future self 10 years from now looked at this, what would they have decided for the future?”
How to use it:
Describe the situation as if it were a consulting case, in five lines.
Write: “My successor decides…”
Force yourself to justify that decision with three well-argued, data-based reasons.
Compare those reasons with the ones you initially thought of without looking so far ahead.
When to use it:
When you notice attachment to the status quo (“since I’m already here…”).
When quitting feels like “admitting a mistake.”
When you’ve been “holding on a bit longer” for months without a plan.
This question kills the sunk-cost bias.
And gives you back the ability to let go.
3.4. Remember your priorities
Many decisions hurt because you’re trying to maximize everything at once.
Security and freedom.
Growth and comfort.
Money and peace of mind.
The Heath brothers explain that as long as you don’t prioritize, every option will seem wrong—because you’re trying to protect incompatible priorities.
How to make it practical:
Write down your three priorities for this stage of your life. Not ideal ones—the real ones.
Rank them: 1, 2, and 3.
Review your options: which option maximizes each priority?
Choose the option that maximizes the highest priorities on the list.
When to use it:
When a decision turns into an endless internal debate.
When every option feels like a “betrayal” of yourself.
Good decisions sacrifice lesser priorities to protect crucial ones.
You can never win everything at once.
And now, let’s move to the final step: what to do even when things go wrong.
4. Prepare to be wrong
The future isn’t a straight line.
It’s a fan too wide to see in full. And the biggest mistake isn’t being wrong—it’s having the audacity not to be prepared for it. That’s why the Heath brothers repeat something uncomfortable to admit: even experts predict poorly, so the goal isn’t to always be right—it’s to design antifragile decisions.
Aim for long-term resilience.
Here are 4 techniques to achieve it:
4.1. Switch from “What will happen?” to “What will I do if it happens?”
This is the mental hinge.
The question “What will happen?” fuels anxiety about an unknown future.
The question “What will I do if it happens?” creates plans that reduce anxiety.
How to use it:
Choose your decision.
Write three future scenarios in the short and long term: bad, average, good.
For each one, complete: “If X happens, I will do Y.”
Make sure Y is a concrete action with a plan—not a wish.
When to use it:
When you feel overly confident in your choice.
When there’s real risk and you need a plan B/C.
This eliminates the Irish error and prepares you for the unexpected.
4.2. Premortem: fail before you fail
The premortem is one of the most valuable tools in the system.
It consists of imagining that the decision has already happened… and it went badly. From there, you uncover why. This is a technique used by ancient Stoic philosophers to anticipate misfortune.
How to apply it:
“A year has passed, and this was a failure.”
Write 10 possible reasons why this could have happened.
Group them into categories: people, money, execution, market, energy, health…
For each category, define minimal prevention measures and possible actions.
When to use it:
When you feel overconfident.
When the decision is costly or hard to reverse.
The premortem lets you stay one step ahead of trouble.
4.3. Excess success: “What if it goes too well?”
The opposite error also exists: not being ready for success.
The Heath brothers call it preparade. It’s about imagining that everything goes amazingly well and asking what would break if you grew fast and things went too well.
How to do it:
“A year has passed, and this project I started exceeded my expectations.”
What new demand appears? (clients, workload, exposure, responsibilities)
What bottleneck breaks first? (time, support, money, health)
What decision will you have to make if this scales?
When to use it:
When an option has rapid growth potential.
When it depends on you (and your energy) as the bottleneck.
When success could bring new pressure you can’t manage.
Sometimes your plan doesn’t fail.
Your capacity to sustain it does.
4.4. Safety margins + tripwires
Here’s the combination that prevents a decision from rotting due to inertia.
4.4.1. Safety margins
The Heaths recommend adding an extra margin: more time, more money, more energy than you think you need. The real world is usually harsher than our plans. This is what I call a precautionary reserve.
How to apply it:
Time: if you think it’s 4 weeks, plan for 6.
Money: if you think it costs X, set aside X + 20–30%.
Energy: if you think you “can handle it all,” build rest into the plan.
Respect uncertainty.
4.4.2. Tripwires
A tripwire is a clear signal that forces you to review the decision before it’s too late. It pulls you out of autopilot when inertia takes over.
How to design one:
Define a measurable indicator (time, money, results, satisfaction).
Define a clear threshold beyond which you must stop—no exceptions.
Define the review action: “we stop and reassess,” “we walk away.”
Examples:
Work:
“If in 90 days I haven’t gained X real learning, I change course.”
“If the environment drains me for three consecutive weeks, I address it—or I leave.”
Project:
“If I spend more than X without more sales, I stop and rethink.”
“If I don’t get 10 customer conversations per month, we change strategy.”
Relationship:
“If we repeat the same conflict without progress for two months, we ask for help.”
Many decisions drag us into a black hole because we don’t know when to stop.
The tripwire cuts inertia before it costs you years.
And here ends our full journey through Decisive. It’s been great.
The book doesn’t promise perfect decisions, but it does give you something real that works: less self-deception, less regret afterward, more clarity when deciding under pressure, and more peace of mind—even when you’re wrong.
In the first part, we saw the villains.
In the second, we built the board and tested reality.
And today, we closed with distance and resilience.
We can’t control the future—but you’ve learned how to decide in an uncertain world.
And that’s a skill for life.
Want to go deeper? Here are 3 related ideas to explore:
✍️ Your turn: If you applied the 10/10/10 rule to your current dilemma, at which horizon does your answer really change? What are you overvaluing today that might be irrelevant tomorrow?
💭 Quote of the day: “Our decisions will never be perfect, but they can be better. Bolder. Wiser. The right process can guide us toward the right choice.” — Chip Heath and Dan Heath
See you next time! 👋
References 📚
Heath, C., & Heath, D. (2013). Decisive: How to Make Better Choices in Life and Work.
Wow this was an excellent series. Be sure to link #2 and especially this #3 to the first installment. I want to share this with my grandkids.