Inversion — Solve Backwards to Avoid Regret
The Inversion Playbook
Use this whenever you’re trying to:
- Make a high-stakes decision
- Strengthen a plan
- Avoid regrets later
Step 1: Name Your Goal
What are you trying to achieve?
Examples:
- Launch a successful freelance career
- Choose the right college
- Grow a business
- Find the right partner
Step 2: Ask: “What Would Guarantee Failure?”
This is your inversion trigger.
Write 3–5 ways the whole thing could fall apart.
Examples:
- Freelance failure? → No clients, burnout, unclear niche
- College regret? → Wrong course, bad location, lack of support
- Business flop? → Poor cash flow, bad co-founder, market mismatch
Step 3: Flip Each Point Into an Avoidance Move
For each failure point, ask:
- “What would prevent this?”
- “How can I build safeguards?”
Examples:
- “Burnout?” → Set a work limit. Define off-hours.
- “Wrong co-founder?” → Work on a test project first.
- “Market mismatch?” → Run small experiments before scaling.
Step 4: Score Each Trap by Likelihood and Impact
You don’t need a spreadsheet — just use a 1–5 rating for:
- Likelihood: How likely is this to happen?
- Impact: How badly would it hurt?
Prioritize fixing the high-likelihood + high-impact traps.
Land it Well
Opening Hook
Everyone wants success.
But very few people ask: “What would failure look like — and how can I avoid it?”
That’s the power of inversion.
You flip the question — and suddenly, your blind spots light up.
The Big Shift
Most thinking starts with:
“What should I do to succeed?”
Inversion starts with:
“What would cause this to fail?”
Instead of only chasing the outcome, you study the obstacles.
Instead of focusing only on action, you zoom in on prevention.
Because sometimes, the fastest way to win — is to avoid the obvious losses.
Explain and Expand
Work Backwards from Failure
Inversion flips the frame.
- Want to stay healthy? → Ask: What would make me sick?
- Want a great career? → Ask: What would ruin my growth?
- Want a strong relationship? → Ask: What behaviors would destroy it?
Once you know what not to do — you become smarter about what to actually do.
This isn’t negative thinking.
It’s protective thinking.
It’s how elite performers bulletproof their plans.
Building a Bridge
Imagine building a bridge.
You don’t just design for the cars that will cross it.
You design for the weight that could collapse it.
Engineers don’t ask only:
“How do we build this?”
They ask:
“What would make this fall apart?”
You should do the same with your decisions.
Inversion Is Risk Design
In life, business, and relationships — most damage isn’t from big shocks.
It’s from ignored cracks.
Inversion helps you:
- Find the cracks early
- Reduce the odds of failure
- Design moves that age well
It doesn’t replace optimism.
It makes optimism safer.
Where People Go Wrong
- Chasing “best case” without planning for “worst case”
- Believing planning = perfection — instead of preparation
- Thinking “what could go wrong?” means pessimism (it doesn’t — it means strength)
Reflection Prompt
Try this before any bold move:
- “If this blows up… what will I wish I’d done differently?”
- “What am I assuming will not go wrong — but could?”
- “What tiny thing, if ignored, could become a disaster?”
You’re not jinxing the plan.
You’re de-risking it.
Closing Thought
Success often hides behind the one thing you didn’t check.
So flip the script.
Instead of chasing only the dream… study the nightmare.
That’s not fear. That’s foresight.
And it’s how the smartest people stay standing — while others fall.
Recap Box
🔑 Key Insight
Inversion flips the frame: Don’t just ask what to do — ask what to avoid.
Tool
The Inversion Playbook: Name your goal, imagine how it could fail, design safeguards.
📍 When to Use
Whenever the cost of failure is high — career bets, big decisions, emotional moves.
PART 6: MOVE SMARTER, PLAY BIGGER
Inversion Thinking
Inversion is a mental model popularized by Charlie Munger, investor and partner of Warren Buffett.
Munger’s rule:
“Tell me where I’m going to die — so I don’t go there.”
He meant:
Avoiding stupidity is often easier than chasing brilliance.
And often — more powerful.
Sanya’s Side Hustle
Sanya was launching a side hustle selling handmade candles online.
Her original plan?
- Spend ₹40K on materials
- Build an Instagram store
- Launch in 3 weeks
Before starting, she ran an inversion drill:
What could make this fail?
- No clear brand
- Poor delivery logistics
- Low repeat buyers
- Getting overwhelmed with orders
So she inverted the plan:
- Did a mini-launch to friends first
- Partnered with a local courier
- Created a brand story with a unique scent angle
- Set a 20-order monthly cap to stay sane
Result?
She didn’t just launch. She lasted.
That’s the power of inversion.