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Michael Gardon

  • Writer's pictureMichael Gardon

How To Decide What You Want Using Inversion - The Break Issue 24

Updated: Mar 15

Welcome to the new members of The Break since last week!

If you like what you’ve been reading follow along on Twitter ( @mngardon ) and Linkedin for more community and conversations about breaking work.

Today's Issue

In today’s issue, we’re going to explore the most underrated approach to solving a career decision:


I'll show you how looking at a problem backwards is often more effective than trying to solve it forwards, and I'll show you how I used inversion to define my Break path. You’ll be able to immediately apply it to whatever you do.

Let’s dive in.​

Looking for a great Holiday Gift?

Check out my kids' side hustle, Quotebook . Quotebook is a great gift for a young couple or family with young kids to start building the daily habit of being (and capturing) funny(ness). The kids and I built Quotebook out of our tradition of capturing all the funny things we say in our family, and reliving them whenever we want to laugh.

Invert To Align Your Career

Millions of people are daydreaming about breaking their careers. Less than 10% are taking action.

We’re told to “find our passion” but most of us don’t start with a passion.

Others think they have a passion, but find they are pursuing a path for the wrong reasons. That was me. I was a trader fresh out of college, why? Because I wanted to make a lot of money.

I left the trading world tired, depressed, and physically sick.

As Richard Feynman once said:

The first principle is that you must not fool yourself and you are the easiest person to fool.”

Shame on me.

The Problem with “What do you want?”

When we use the question "what do you want?" we are thinking about things we haven't experienced by definition.

This creates many problems, but there are mainly two big ones that throw us off the right track.

  1. There are literally infinite possibilities of what you could want to do with your life, so we don’t choose.

  2. Our brains overcorrect to cope with too many possibilities. We shut down good ideas as “impractical” or us other labels.

Our brains are not set up to deal well with the uncertainty of infinite possibility.

It looks like this with our careers (Taken from a talk I gave recently).

So how can we figure out what we want more quickly, so we can make faster progress towards aligning who we are with what we do?

We start by flipping the question on its head.

What Is Inversion

Inversion is a powerful mental model for decision making and problem solving where you think about a question or a problem backwards to get to a better answer.

Charlie Munger is famous for saying, “all I want to know is where I’m going to die so I’ll never go there.” This is classic inversion.

Inversion often forces you to uncover hidden beliefs about the problem you are trying to solve. Like, why do I want money? or is there another way I can achieve the same feeling?

Why Inversion Works

To put some math terms behind it, lets say thinking forward is additive (ie we must do something), while thinking backwards is subtractive (ie what should I not do).

Activity (addition) without proper grounding can actually increase the odds of a bad outcome. This is the concept of iatrogenics in medicine where treatment actually causes harm. Iatrogenics has applications to the fragility of systems and governmental interventions, but I won’t go into all of that.

Subtraction on the other hand (thinking backwards) is more robust. We remove complexity from a system, get down to the essence of the problem and weigh the factors more correctly.

Think about it this way, avoiding stupidity (fooling yourself into a bad career move) is more important than seeking brilliance.

As a corollary:

it’s easier to be happy by avoiding unhappiness, than seeking happiness.

Obviously this framework doesn’t work for every action - but for thinking about problems, and more importantly, framing the problem correctly, inversion is a power tool.

Inversion Applied To Career Choices

This is my story that seems to resonate.

I had been through a few ups and downs and career changes, failed companies and false starts early in my career. I was burned out and I had wasted countless years of progress trying to find the “right next opportunity”.

Frustrated with my corporate consulting role back in 2017-18 I sat down to figure out “what I want”. I even wrote it up on a sheet of paper. I had read enough about inversion, so I decided to try it.

I thought to myself:

“I can basically do anything. I’m at a point where I need to seriously **design** my life. I’ve spent years asking myself what I want and that hasn’t worked, so what do I NOT want? Let’s start there.”

While I didn’t know what I wanted, other than abstract concepts of success, wealth, freedom that were hard to define, I was pretty sure I knew what I didn’t want. I could concretely think about what frustrates me, what I don’t want to do, what I’m not good at.

So I made a list:

  • No raising investor money

  • No travel

  • Not too many employees

  • No office

  • No boss

  • No vacation policies

  • No bureaucracy

  • No deadlines

  • No emergency meetings

  • Nothing that prevents me from seeing my kids

Executing that list was a tall order, but I was pretty sure I’d be happy if I hit a bunch of them.

Now the universe of possibilities was constrained to a narrow set of ways I could achieve that list.

Putting all my focus into how to hit that list became my path. I could block everything else out.

I started with some side hustle experiments, gave myself enough time and eventually was able to leave my job to run and The Break full time.

Next time you’re faced with a hard problem, or you feel overwhelmed, give inversion a try and let me know how it goes.

Finally, if you’d like to help me develop more ideas around my Advantage Mapping System (for free) please let me know - I’d love to work with you 1 on 1. Just message me on Linkedin .


See you again next week.

P.S. I'd love to hear from you.

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What’s happening on the pod?

I'm taking a little break from interviews on the podcast, but I'll be back next year with a ton of great conversation.

Till then, here's another interview I did on The Business of You podcast with BrandID.

You made it to the end! Hopefully you learned something about breaking your career today! If so, please share this with someone you care about.

P.S. What did you think of today's email? Click one of the ratings below to send us your feedback. We'd love to know what you think!

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