How a Mental Model Used by Billionaires, Stoics and Mathematicians Can Help You Avoid Failure… By Visualizing It

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You probably spend a lot of time trying to avoid failure.

You’re a business owner, after all. The whole point is to succeed, right? How many times have you been told to visualize yourself achieving your goals, doing the things you want to do, living the life you want, etc.?

Today, I’m going to advocate for the benefits of visualizing failure. Bear with me. I know it’s a little uncomfortable, but it’s highly useful, I promise.

The Inversion Technique — Used by Stoics, Mathematicians and Billionaires

The Inversion Technique is a mental model that’s been around, in some form or other, for centuries and has been used by great thinkers like Roman emperor Marcus Aurelius, German mathematician Carl Jacobi and billionaire Charlie Munger.

The Inversion Technique asks us to analyze the thing we usually avoid thinking about:

What would happen if everything went really, REALLY wrong?

Is this an uncomfortable question? Undoubtedly. But is it worth reflecting on? Absolutely. By thinking about what could go wrong before it happens (such as missing a big deadline), we can discover the likely behaviors that would lead to that outcome and avoid them (such as procrastinating).

How to Apply the Inversion Technique

The steps of Inversion Technique are pretty straightforward.

  1. Identify the “bad,” i.e. what you don’t want to happen.
  2. Think of the behaviors you can control that could make that bad outcome occur.
  3. Avoid those behaviors!

Let’s say you’re designing a new website for a client, and you really, really want it to go well. You want it so badly, in fact, that you’re willing to try this weird thing called the Inversion Technique that you read about on some marketing blog. 😀

Step 1: Envision what could go wrong.

Oh, so many things! But stick to what’s realistic. Most of the time, when clients are unhappy, it’s for one of the following reasons:

  • You don’t deliver the site by the launch deadline.
  • The client isn’t satisfied with the final result.
  • You promise something that you later realize you can’t deliver.

Step 2: Consider actions that could lead to those bad outcomes.

Now for the fun part. What actions could you take to really screw things up? Focus on what you can control. We aren’t talking about natural disasters or, ahem, pandemics, but about behaviors like procrastination and communication. So, what might you do if, for some reason, you really wanted to bomb this project?

Missing the Deadline:

  • You got distracted while working and just plain didn’t get the site done.
  • You took on too much other work, and this got lost in the shuffle.

Client Is Unhappy:

  • You didn’t ask for enough specifics from your client, so your final design is not what they expected or needed.
  • You didn’t work very hard, cut corners and delivered a poor quality product.

Promise You Can’t Deliver:

  • You didn’t scope the task appropriately when you first agreed to it, and it’s way more work than you realized.
  • As you worked on the site, issues popped up that you couldn’t handle. You didn’t communicate this to the client or seek the help you needed.

(Note: Step 2 is SO IMPORTANT! If you don’t move on quickly from identifying the bad to identifying controllable behaviors, the Inversion Technique is useless and can be harmful. We don’t want to feed our anxieties about failing. We want to use our awareness of failing to inspire us to accomplish more!)

Step 3: Avoid those actions!

It’s so elegant in its simplicity, isn’t it? Easier said than done, of course, but so are most things worth doing. I bet you can already think of a long list of things you know you shouldn’t do, but here are a few friendly reminders. In fact, if you consistently adopt just these behaviors, you’ll significantly increase your chances of success.

  • Easily Distracted? Put your phone on Do Not Disturb, or download a site blocker extension to keep you from mindlessly scrolling social media or saying, “Just one more video!” while you should be working.
  • Too Busy? Before you take on a new project, check your schedule to make sure you have room for it.
  • No Specifics? Be sure to establish great communication with your client. Use whatever form of communication works best for them, and never be afraid to ask questions.
  • Didn’t Work Hard Enough? Carve out enough time and space to complete every project well, and take care of yourself to help keep your motivation up.
  • Unexpected Issues? Never be afraid to admit you don’t know how to do something. Have a network of people you can reach out to for help, and be sure to inform your client ASAP if you’ve bitten off more than you can chew.

Thinking of the “bad” can help clarify the “good.”

The Inversion Technique isn’t just useful for business. You can apply it to relationships (what would a bad spouse do?), finance (what would I do if I wanted to make sure I could never retire?), decluttering (what my house look like if it was full of stuff that didn’t spark joy?)… you get the idea.

Once you get the hang of it, it can even be kind of fun to take these bad outcomes to their most outrageous end. More often than not, you’ll find there’s a lot you can control to avoid them.

Long story short, spend more time visualizing failure, and you just might see more success.

You’ve got this!

I write about radically ethical marketing, self-employment and non-sleazy self-promotion. Learn more at

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