Chapter 29: Challenge Your Assumptions — Before They Quietly Shape the Wrong Move
Chapter 29

Challenge Your Assumptions — Before They Quietly Shape the Wrong Move

Decision Tool

The Assumption Finder Framework

Use this anytime you’re making a plan, launching something, or betting on a decision that feels “obvious.”

Step 1: Write Down Your Move

What’s the decision you’re about to make?

Example:
“I’m quitting my job to launch a startup.”

Step 2: Ask: “What am I assuming?”

Make a fast list. Be honest, not clever.

Example:

  • I’ll find a co-founder easily
  • My savings will last 12 months
  • I’ll get funding within 6 months
  • I’ll still want this lifestyle after quitting

Step 3: Test Each One With 2 Questions

  1. What if this isn’t true?
  2. What else could be true instead?

These two questions unlock clarity fast.
They also punch your ego — in a good way.

Example:

“What if I don’t get funding in 6 months?”
→ Do I have a backup plan?
→ Am I prepared for Plan B?

“What if I can’t find a co-founder?”
→ Am I willing to go solo?
→ Should I start with a smaller version?

Step 4: Adjust the Plan — or Reinforce It

You don’t have to kill the dream.
You just have to sharpen the strategy.

Some assumptions will pass the test. Great.
Some won’t. Even better.

Because now you’re making a stronger move — not a louder one.

Opening Hook

You’re not stuck because you’re weak.
You’re stuck because you’re building on something you didn’t question.

The Big Shift

Most bad decisions don’t start with bad thinking.
They start with hidden assumptions.

Assumptions that felt true.
Sounded smart.
And quietly shaped everything that came next.

Until it all cracked — because the foundation was false.

Assumptions Shape Reality — Whether You Notice or Not

Every plan, every dream, every strategy you’ve ever created… rests on something you think is true.

But what if that “truth” was just an old belief?
A guess you never questioned?
A past experience pretending to be a fact?

That’s the danger of unchecked assumptions.
They don’t ask for permission.
They just sit quietly — steering the ship.

Why This Is a Power Skill

Strategic thinkers aren’t just good at planning.
They’re good at pausing before committing.

They know that one bad assumption can:

  • Wreck a launch
  • Mislead a team
  • Waste six months of effort
  • Burn out their savings
  • Cost them credibility

But they also know that catching that assumption early?
That’s leverage. That’s wisdom. That’s power.

Where People Go Wrong

🙄 “This feels like overthinking.”
→ No. It’s thinking smart before running fast.

😤 “I’ve already committed.”
→ Great. Now check what’s fragile — before it breaks.

😎 “I’ve done this before. I know what I’m doing.”
→ Perfect. You’re exactly the kind of person who needs this. Assumptions hide best in confidence.

Land it Well

(When You’re In a Hurry)

Try these fast checks before acting on any big plan:

  • “What would need to be true for this to work?”
  • “What might I be assuming without realizing it?”
  • “If this fails — what assumption might be to blame?”

These questions don’t slow you down.
They protect your momentum.

Closing Thought

The riskiest part of any decision isn’t what you see.
It’s what you didn’t know you believed.

So before you double down on the plan…
Pause. Question the base.

Because strong ideas don’t fear scrutiny.
They get better from it.

Explain and Expand

Recap Box

🔑 Key Insight:
Assumptions shape your decisions — even when you don’t realize they’re there. Catch them early, and you catch the cracks before they spread.

Tool:
Assumption Finder Framework
→ What am I assuming?
→ What if it’s wrong?
→ What else could be true?

📍When to Use:
Any time you're making a plan, placing a bet, or feeling too confident in your next move.

This Is Not Doubt — It’s Discipline

You’re not being negative.
You’re being sharp.

Assumption testing doesn’t kill ambition.
It protects it.

It’s what turns enthusiasm into execution.

The Dream Job Myth

Neha landed a job at a fancy company she’d dreamed of.
On paper, it was perfect.

But she’d assumed:

  • The team would support her growth
  • The work-life balance would be sustainable
  • The “brand name” would make her happy

None of those turned out true.
She left in six months — feeling confused and deflated.

Looking back, she said:

“If I’d just paused to test those assumptions, I would’ve asked tougher questions during the interview — and saved myself months of frustration.”

Where Assumptions Hide (Watch These)

People — “They’ll understand / deliver / care.”
Time — “It’ll only take 3 weeks.”
Money — “This price is worth it.”
Motivation — “I’ll be consistent this time.”
Outcomes — “If I do X, Y will definitely happen.”

These aren’t facts.
They’re bets dressed as guarantees.

Make Personal

What Do You Think You Know?

Assumptions are sneaky.

You don’t write them down.
You don’t say them out loud.
But they’re there — built into how you decide.

  • “This client will definitely deliver.”
  • “This job will make me happy.”
  • “They’ll understand what I meant.”
  • “I can handle this later.”
  • “There’s no better option.”

Some are tiny.
Some are massive.
And some are silently wrecking your next big move.

Spot the Assumption Trap

Have you ever:

  • Overcommitted to a plan… then realized halfway through that a key part wasn’t true?
  • Trusted someone’s word… only to find they had different expectations?
  • Built a strategy… that fell apart because one piece didn’t behave the way you thought it would?

That’s not bad luck.
That’s an invisible assumption — crashing the party.