There’s an idea I got from a book (Poor Charlie’s Almanac) I read a while back. It’s an idea popularized by Charlie Munger, in which he says, “Invert, always invert.”
The idea of inverting is originally a math concept, but it applies to everyday life. I won’t touch the math aspect at all. I think it’ll take more than one newsletter to explain. However, in everyday life, the concept is simple.
The Concept
Inverting, applied to everyday life, simply means looking at things the opposite way, upside down, or in reverse.
Instead of asking, “How do I succeed?” ask instead, “What would guarantee that I fail?”
When you get the answer to the latter question, you simply have to avoid those things.
That simple concept is a major shift. It’s a shift from chasing the right answers all the time to eliminating the wrong ones. By eliminating the wrong answers as options, you increase your chances to succeed.
In Charlie Munger’s thought process, to achieve success people tend to add on more things to try, when they should be focused on subtracting stupidity.
“Success is often just what’s left over after you remove the obvious mistakes.”
To illustrate this idea I’m going to give a few clear examples. Examples from different aspects of our OG Millennial lives that this idea touches on and is imperative to add to your toolbox.
Example 1: Career / Business
The first thought here is, “How do I build a successful business?”
The inverted question is, “How would I guarantee that this business fails?”
Possible Answers:
Ignore customers
Overspend with no revenue plan
Partner with or rely on unreliable people
Quit too early
Now just focus on not doing those things, and that alone will put you ahead of most people in the game.
Example 2: Wealth Building
The first question usually is, “How do I get rich?”
The inverted question is, “How do people stay broke?”
Possible Answers:
Increasing lifestyle as soon as income increases
No investing
High-interest debt
Chasing quick money
Work on consistently avoiding those pitfalls, and you’ll naturally build wealth over time.
1,000+ Proven ChatGPT Prompts That Help You Work 10X Faster
ChatGPT is insanely powerful.
But most people waste 90% of its potential by using it like Google.
These 1,000+ proven ChatGPT prompts fix that and help you work 10X faster.
Sign up for Superhuman AI and get:
1,000+ ready-to-use prompts to solve problems in minutes instead of hours—tested & used by 1M+ professionals
Superhuman AI newsletter (3 min daily) so you keep learning new AI tools & tutorials to stay ahead in your career—the prompts are just the beginning
Example 3: Relationships
We all ask this question first: “How do I make sure I have a great relationship?”
The inversion of this question is, “What consistently ruins relationships?”
Possible Answers:
Lack of communication
Disrespect
Inconsistency
Taking the other person for granted
Eliminate those types of things, and the relationship improves almost by default.
Example 4: Productivity
This one hits close to home for us OG Millennials. In today’s day and age, with endless distractions, we probably ask ourselves all the time, “How do I become more productive?”
The inverted question would be, “What makes me unproductive?”
Possible Answers:
Constant distractions
No clear priorities
Multitasking everything
No structure
Figure out a way to eliminate those, and productivity rises without needing to implement any hacks.
Why This Works
Just like those four examples, there are four main reasons why this works:
Avoiding mistakes is much easier than chasing perfection.
Most of the paths that lead to failure are actually quite obvious. We just choose to ignore them.
Inverting simplifies decision-making. It gives you a filter and eliminates a lot of guesswork.
It compounds (one of our favorites). Small avoided mistakes lead to massive long-term gains.
The Bottom Line
The idea behind all this is simple:
We need to stop doing what clearly doesn’t work and stay consistent with what does.
Stop trying to win. Start eliminating what makes you lose.
That’s it.
Join the OGM Community
If this resonated, you’ll get a lot more like this every week.
The OG Millennial Newsletter delivers no-fluff insights on clarity, focus, and building real momentum—in business, money, and life.
Subscribe and lock in with us.


