Inversion Thinking: Flip It, Fix It, Fine-Tune It
Most people plan forward.
“How do I make this work?”
“How do I succeed?”
Inversion Thinking flips the question.
You ask, “How could this go wrong?”
Then you design your plan so it doesn’t.
same view…
…different perspectives
A Surprising Way to Make a Stronger Strategy
The phrase inversion thinking comes from Charlie Munger — Warren Buffett’s longtime business partner — who famously said, “Invert, always invert.”
More notably, he borrowed it from the world of mathematics, where working backward often reveals what’s hidden in a problem.
The Stoics used it too: Instead of just dreaming of success, they imagined loss and failure to build resilience and gratitude.
You may want to try inversion thinking when you have big goals to crush, dreams to manifest, and pitfalls to avoid.
Why Try Inversion?
Reveal blind spots: When you flip the question you often see what’s missing. As James Clear puts it, inversion “puts a spotlight on errors and roadblocks that are not obvious at first glance.”
Reduce risk: You build guardrails before the contents hit the floor.
Boost clarity: It clarifies what you refuse to become, and what you want to guard.
Shift from reactive to proactive: Instead of responding to failure after it happens, you design so you limit the chance of it happening at all.
It’s a deeply self-aware practice. And, as a life coach, I’m all about that. In using this technique, you’ll learn what your non-negotiables are, how you tend to sabotage yourself, and what structures help keeps you in integrity.
The 3 Steps: Flip It → Fix It → Fine-Tune It
1. Flip It
Start with your goal or question. Then ask the opposite.
“How do I make this project thrive?” → “How could this project fall apart?”
“How do we build trust?” → “What would destroy trust fastest?”
List three to five ways things could go sideways.
You’re not being negative — you’re being clear-eyed.
Some people call this step a premortem — imagining what could go wrong before it does.
When you look at your list, you’ll probably see patterns — the same traps you fall into again and again. That’s gold. It tells you where your growth edge lives.
Personal Example: The Raincoat That Failed the Test
The only way a raincoat purchase can 100% guarantee to fail is if:
it doesn’t repel water, and
it doesn’t fit over what you’re wearing.
If I had used inversion thinking in my raincoat decision-making process, I would not currently be stealing my partner’s oversized raincoat every time water falls from the sky.
When I bought my raincoat, it fit perfectly over a T-shirt. But the first time I tried to wear it over a chunky sweater — game over. Too uncomfortable. So I wore a puffy and became a soggy Oregonian.
A two-second inversion check — “How could this purchase go wrong?” — would’ve saved me from my current life of borrowed outerwear.
It’s funny, but it’s the same principle: think ahead. Anticipate what would make this fail and adjust accordingly. I would have sized up!
2. Fix It
Now, take each potential pitfall and turn it into a simple, protective rule — a guardrail.
Ask yourself:
Flip It: “If I wanted this to go off track, what would I do?”
Fix It: “So, what can I do differently to prevent that?”
Your “anti-goal” is the thing you refuse to become — the version of you that overcommits, stays silent, avoids conflict, or burns out.
For example:
I don’t want to get stuck in endless decisions.
→ Guardrail: “Every meeting ends with a clear decision-owner.”I don’t want resentment over invisible work.
→ Guardrail: “We check workload and wins every Friday.”I don’t want to lose my creativity to over-scheduling.
→ Guardrail: “At least one open block on my calendar every day.”
These small shifts prevent big messes.
They keep your goals alive without costing your sanity.
3. Fine-Tune It
This step turns inversion thinking into a lifelong habit.
Set a regular rhythm — weekly, monthly, or quarterly — to reflect and recalibrate.
Ask yourself:
What almost went off track?
Which guardrails helped?
Which need an update?
Reflection keeps your system alive.
It turns good intentions into real wisdom — the kind that grows through awareness, not accident.
[By the way, I offer The Monthly Reset Ritual to support people in doing this on a regular basis. It’s open to all that want to attend. I host it virtually every month. Register here: https://calendly.com/jen-otto/monthly-reset]
Work Example: Startup Founder Decides to Bring on a Co-Founder
I recently worked with a client that is a startup founder. He was wighing a big decision around a potential co-founder partnership. A big decision!
The excitement was real, but so were the risks. Rather than asking, “How do we make this partnership great?”, we used inversion thinking and asked, “How could this partnership fail?”
Step 1: Flip It
We brainstormed all the ways the partnership would fail…
lost of decision limbo
uneven effort
fuzzy ownership
unspoken tension
misaligned timelines
Step 2: Fix It
We built safeguards…
naming decision-owners in every meeting
weekly workload checks
clarifying who leads product/hiring/marketing/budget
a transparent conflict repair process
milestone-based equity/vesting
Step 3: Fine-Tune It
Build reflection into the “Operating System”…
Before agreeing to test out the partnership, they named upfront that they would do a 2 week sprint, then a retrospective before finalizing equity. They agreed to meet 2x per week for the first month to review what is working well and what needed adjusting.
When you have weekly syncs, monthly retrospectives, quarterly strategizing build into how you run your business (or your life!) you are more likely to stay on track and aligned.
It’s not about perfection—it is about anticipating challenges and designing for safety and efficacy, to the degree that we can. Knowing what we know now.
Try It This Week! Here’s how.
Pick one goal, endeavor, or intention you care about.
Flip it. Name what could go wrong. (Ask yourself “If this failed, what would the top 3-5 reasons be?”)
Fix it. Turn pitfalls into protective habits. (Write small, practical safeguards for each reason.)
Fine-tune it. Reflect, adjust, and grow. (Set a date and time now to revisit this in the future - what’s working? what’s wobbling?)
That’s inversion thinking — a unique, powerful way to set yourself up for resilience in the face of challenges. And to move yourself closer to the life you want.
Final Thoughts
Inversion thinking isn’t about pessimism or cynicism. It’s a brain exercise to think of things in reverse. So you can set more rigorous goals, feel solid in your execution plan, and be kind to your nervous system by anticipating challenges in advance (and planning for them).
By naming what could go wrong, you create strength in your plan before you hit turbulence. You protect not just your strategy—but your spirit.
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