For the longest time I was obsessed with figuring out how to succeed.
Read all the books. Listened to the podcasts. Made a vision board once (felt stupid doing it). Studied successful people obsessively. Tried to reverse-engineer what they did right.
And I made progress, I guess. But it always felt like I was pushing a boulder uphill. Two steps forward, one step back. Sometimes two steps back.
Then I came across this idea from Charlie Munger, Warren Buffett's partner, the guy who's been quietly brilliant for like 60 years and it kind of broke my brain.
He said: "Invert, always invert."
The full quote, which he borrowed from a mathematician named Carl Jacobi, is something like: "Many hard problems are best solved when they are addressed backwards."
At first I thought it was just clever wordplay. The kind of thing smart people say that sounds profound but doesn't actually mean anything.
But the more I sat with it, the more I realized I'd been thinking about everything wrong.
The backwards approach
So here's the basic idea, and I'll try not to overcomplicate it because I think that's where most explanations go wrong.
Instead of asking "how do I succeed?" you ask "how would I guarantee failure?" Then you avoid those things.
Instead of asking "how do I build a great company?" you ask "what would definitely destroy this company?" Then you don't do that.
Instead of asking "how do I have a good relationship?" you ask "what would ruin this relationship for sure?" Then you stop doing those things.
It sounds almost too simple. But I think that's why it works.
Munger put it this way in one of his talks (I'm paraphrasing because I don't remember it exactly): "It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent."
That line stuck with me. Consistently not stupid. That's a very different goal than trying to be brilliant.
Why thinking forward is harder than it looks
I think the reason most people (myself included, until recently) default to forward thinking is because it feels more... productive? Like you're actually doing something.
"How do I get more customers?" feels like a real question with actionable answers. You can brainstorm tactics. Make lists. Feel busy.
But the problem is that success has a million possible paths. There's infinite ways to try to win. And most of them won't work for your specific situation. You end up spraying effort everywhere, chasing whatever seems promising this week.
Failure, on the other hand, is more predictable.
There's actually a pretty small number of things that reliably kill businesses. Or relationships. Or health. Or careers. And they're mostly the same things, over and over.
I read a Farnam Street article about Munger, that this is why inversion is so powerful. The paths to success are many and uncertain. The paths to failure are few and well-documented.
If you just avoid the obvious failure paths, you're already ahead of most people.
What would guarantee failure?
When I started actually doing this exercise, it was uncomfortable. Not because it was hard intellectually. Because it forced me to look at stuff I was actively doing.
Like, if I asked myself "what would guarantee that my business fails?" the answers were pretty obvious:
- Run out of money before finding something that works
- Build something nobody actually wants
- Hire people who don't give a shit
- Ignore clients when they tell me what's wrong
- Move so slow that someone else figures it out first
- Let my ego make decisions instead of data
- Fight with my co-founder about stupid stuff until we can't work together
None of this is revolutionary insight. Everyone "knows" these things. But when I looked at my actual behavior, I was doing like three of them. Not dramatically, but enough.
I was burning money on stuff that didn't matter because it felt like progress. I was building products I thought were cool instead of what clients asked for. I was avoiding hard conversations because they were uncomfortable.
The inversion exercise didn't give me some brilliant new strategy. It just showed me I was actively doing things that would predictably lead to failure.
That's the uncomfortable part. Forward thinking lets you dream about success. Backward thinking makes you confront your own stupidity.
Munger's mental models approach
This connects to something broader in how Munger thinks, which I find genuinely fascinating even though I'm probably not smart enough to fully grasp it.
He has this idea that you need a "latticework of mental models," basically, frameworks from different disciplines that help you see reality more clearly. And inversion is one of the most important ones.
He once said (and this is from Poor Charlie's Almanack, which is worth reading): "The way complex adaptive systems work and the way mental constructs work is that problems frequently get easier to solve if you turn them around in reverse."
I had to read that a few times to understand what he meant.
I think he's saying that our brains get stuck in certain patterns. We approach problems the same way every time. And sometimes just flipping the question around breaks the logjam.
It's not that the inverted question is smarter. It's that it uses a different part of your brain. Accesses different information. Lets you see angles you were missing.
Jeff Bezos does something similar with his "regret minimization framework": when making a big decision, he imagines himself at 80 years old looking back, and asks what he would regret. That's inversion applied to life choices. Instead of "what should I do?" it's "what would I regret not doing?"
Same principle, different application.
Pre-mortems and killing the company
There's this technique that's basically inversion applied to projects. It's called a pre-mortem, and I think Gary Klein developed it originally.
The idea is simple: before you start a project, you imagine it's six months later and the project has completely failed. Total disaster. Then you ask: why did it fail?
Everyone on the team writes down reasons. And what comes out is usually stuff people were worried about but hadn't said out loud.
It's easier psychologically to explain why something failed (even hypothetically) than to raise concerns about a plan everyone's excited about. Pre-mortems give people permission to voice doubts.
I've started doing a version of this with bigger decisions. Before I commit to something, I imagine it went horribly wrong and try to figure out why. Sometimes the reasons are things I can mitigate. Sometimes they're reasons not to do it at all.
Amazon apparently does something called "working backwards" too, which is related but different. They write the press release for a product before they build it. Forces you to think about the end state first. What would make this worth announcing? If you can't write a compelling press release, maybe the product isn't worth building.
I haven't tried that one myself but I find the concept interesting.
The personal stuff
This is where it gets a little more real and I'm not sure I want to write about it, but whatever.
When I applied inversion to my own life not just business stuff it was kinda brutal.
Like, if I asked "what would guarantee that I'm miserable at 40?" the answers were:
- Stay in relationships that aren't working because leaving is scary
- Never exercise and eat like shit
- Spend all my time consuming instead of creating
- Avoid hard conversations until resentment builds up
- Compare myself to people on the internet constantly
- Never take risks because failure is embarrassing
- Let my work be the only thing that matters
- Ignore the people who actually care about me
Again, obvious stuff. But when I looked at my actual life, I was doing some of these. Not all of them, not dramatically, but enough to matter.
The inversion question doesn't just highlight abstract failure paths. It highlights the ones you're already walking down.
Shane Parrish from Farnam Street (who's written a lot about Munger's mental models) said something like: inversion helps you realize that success often comes from removing what doesn't work, not adding what might work.
I think that's right. Most of my progress in the last year or so has come from stopping dumb things, not starting smart things.
The avoiding stupidity thing
There's a concept in investing circles called "unforced errors" mistakes that aren't caused by your opponent or circumstances, but by you just screwing up.
In tennis, most amateur matches are decided by unforced errors. The winner isn't the person who hits the most brilliant shots. It's the person who makes the fewest dumb mistakes.
Munger thinks business is similar. And life, probably.
He said something in a speech once, I think it was the USC Law commencement address, about how most people try to be brilliant and end up doing stupid things. Whereas if you just consistently avoid stupidity, you'll do better than almost everyone.
"It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent."
I quoted that earlier but I think it's worth repeating because I still don't fully believe it. Part of me still wants to find the brilliant move, the hack, the insight that changes everything.
But when I look at the evidence both in my own life and in the people I've studied, the boring truth is that avoiding obvious mistakes beats chasing clever strategies almost every time.
How I actually use this now
I don't want to turn this into a listicle or whatever, but here's roughly how this shows up in my thinking now.
Before starting something big, I ask: what would make this definitely fail? Then I check if any of those things are already true or likely to become true. If they are, I either fix them first or don't start.
When something isn't working, instead of asking "what should I do?" I ask "what am I doing that's making this worse?" Usually there's something obvious I've been ignoring.
In relationships (business and personal), I think less about how to make them great and more about what would definitely ruin them. Then I try not to do those things. It's not romantic but it's effective.
When I'm stuck on a problem, I try flipping it around. Instead of "how do I get X?" I ask "what's preventing X?" Sometimes that surfaces an obstacle I can actually remove, which is easier than finding a path around it.
I don't do this perfectly. I still chase shiny strategies. I still make unforced errors. But I think I make fewer of them than I used to.
The limitation (because there is one)
I should probably say that inversion isn't everything. It's a tool, not a religion.
You can't only think in terms of avoiding failure. At some point you have to actually do something. Take a risk. Make a bet. Move forward without knowing if it'll work.
Inversion helps you clear the minefield. But you still have to walk across the field.
And there's a version of inversion that becomes paralysis. Where you're so focused on everything that could go wrong that you never do anything. I've fallen into that trap too.
The balance, I think, is using inversion to eliminate obvious stupidity, then having the courage to act anyway despite uncertainty.
Munger and Buffett aren't just careful. They're careful AND they make big bets when they see opportunities. The inversion clears the fog so they can see the real opportunities more clearly.
I don't really have a clean ending for this.
I guess I'd say: if you're stuck, try flipping the question around. Instead of asking how to get what you want, ask what would guarantee you don't get it.
The answers are usually obvious. And you're usually already doing some of them.
That's the uncomfortable part.
But at least now you know what to stop.