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Stop Making Dumb Life Choices

The Road Less Stupid: Advice from a Legendary 94-Year-Old Investor

by Shane Parrish

Business

TL;DR

This book is all about leveling up your brain game so you stop making rookie mistakes. It teaches you to slow down your thinking before you YOLO into a bad decision, how to spot your own brain's BS (aka cognitive biases), and pre-game your screw-ups by thinking about what could go wrong before it does. Basically, it's a manual for not being a walking L by applying some ancient wisdom to modern problems, helping you make smarter moves in everything from your side hustle to your dating life.

Action Items

Pre-Gaming Your F*ck-Ups
1.

Before your next big decision (even what to eat for dinner), spend 5 minutes imagining the worst possible outcome. List 3 reasons why it went bad.

Follow the Money
2.

Next time someone tries to convince you of something, ask yourself: 'What's in it for them?' Don't be naive.

Just F*cking Wait
3.

For the next 'urgent' email or message you get, force yourself to wait 30 minutes before responding. See if the urgency changes or if a better reply comes to mind.

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Key Chapter

Chapter - Chill TF Out: Your Brain Ain't a TikTok Feed

Ever feel like you gotta react to everything right now? This chapter drops the truth bomb: most of your dumbest decisions come from rushing. It's like your brain's a broken vending machine, spitting out bad ideas because you keep hitting the button too fast. The real flex is hitting pause, letting things marinate, and not letting your FOMO or instant gratification monkey run the show. Seriously, just take a beat, breathe, and watch how many problems solve themselves or how much clearer the right path becomes. It's not about being slow, it's about being deliberate and not impulsive.

Key Methods and Approaches

Pre-Gaming Your F*ck-Ups

(AKA: The Pre-Mortem)

Description:

Before you do something, imagine it's already gone horribly wrong. What happened?

Explanation:

Your brain's a hype beast, always thinking everything's gonna be lit. But this method is like being that one friend who's always like, 'Yeah, but what if the cops show up?' You literally fast-forward to the future where your brilliant plan has crashed and burned. Then, you work backward to figure out all the ways it could've gone sideways. It's like getting a spoiler alert for your own life, so you can avoid the plot twists.

Examples:
  • Before launching that sketchy crypto investment, imagine you lost all your money. How did that happen? (Probably because it was sketchy, duh).

  • Before asking out that person you barely know, imagine they ghost you hard. What did you do wrong? (Maybe don't open with 'hey big head').

  • Before starting that 'easy' side hustle, imagine it failed spectacularly. What were the hidden costs or time sinks?

Today's Action:

Before your next big decision (even what to eat for dinner), spend 5 minutes imagining the worst possible outcome. List 3 reasons why it went bad.

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