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Michael Gardon

  • Writer's pictureMichael Gardon

Why Are The Greatest Investors In The World Talking About Personality? - The Break Issue 25

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 picking my Advantage Mapping System up again starting with the second source of advantage:

Your Personality.

Today I’ll show you:

  • The mistake I made early in my career

  • Why the greatest investors in the world are obsessed with personality

  • Why it is easier to align your career to your personality, instead of your personality to a career.

  • How to identify advantages within your personality that you can lever in new ways to CREATE

  • Tools to understand your personality better

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.

Mapping Personality

I spent a lot of time in my teens and twenties fighting my personality.

Pursuing paths that didn’t fit led to a lot of frustration.

I thought there were very few “successful” paths we could take in life, and I had to bang my square head into one of those round holes.

But as I’ve grown older, and studied some of the most successful investors and entrepreneurs on earth, I’ve found one simple truth:

They all attribute success NOT to being uniquely smart, but rather to aligning their natural strengths with a field that is uniquely suited to those strengths being able to find success.

My podcast episodes with career Breakers echo the same sentiment.

They all found success when they married up what they are good at with what they like and what drives their curiosity.

That’s a recipe for doing what you love.

They all advocate for knowing yourself, and using your unique personality to your advantage.

Some are even studying personality as their lives are sunsetting.


I can only surmise by looking at their actions and words that “knowing yourself” is about the most profound life lesson they can pass on to a new generation.

Why is personality such a meaningful subject for billionaire investors?


One of my personal heroes is Ray Dalio who founded and built the largest Hedge Fund in the world, Bridgewater .

It’s not because of his investing prowess, but rather his contribution to learning that has my attention.

He wrote a book, Principles , which has had a profound effect on my life. It’s an operating system.

I even read Principles when it was just a pdf on his site, well before it was a book. It sits behind me on my bookshelf, visible on every single podcast video I do.

Me and Ray like to hang out

Ray has made billions of dollars.

He can virtually do anything with the time he has left on this earth.

But at 73, he’s passing down his principles and creating sites and tools for younger people to get to know themselves and use their nature to find success and meaning.

Ray says:

Knowing yourself, so you can get what you want out of life.

In his Five Step Process for a successful life, he describes step one as: Know Your Goals and Run After Them.

But he also cautions:

what’s best for you depends on your nature, so you need to really know yourself and what you want to achieve in life.


Warren Buffett and his business partner, Charlie Munger BOTH credit their success with aligning their work with their natural abilities, and not straying outside of their Circle of Competence .

Instead of spouting investment advice (which they are regularly asked for), Buffett tends to talk about a personality trait, temperament:

Investing takes a certain temperament. If you don’t have the right temperament, you’re better off just putting your money in an index fund.

By adhering to this one tiny insight about personality, people who have indexed or outsourced their investment management have saved themselves an enormous amount of time, frustration and emotional see-sawing!

The key insight I missed in my 20’s

Your nature, is your PERSONALITY, and your personality is part of you Circle of Competence. It is easier to align your decisions to your personality, not the other way around.

I wasted time in a scarcity mindset, thinking I had to force myself into situations instead of working how I’m naturally inclined to work, and getting the most out of my creativity.

That cost me decades of progress.

This is why we need to listen to 90 year olds.

How to create advantage from understanding your personality

Here’s how we map personality with my students.

1. You’re not looking to fit in, you’re looking to find alignment

First we need a bit of a mini mindset shift. Why are we getting curious about personality? It ain’t to fit into predetermined buckets of professional organization. We aren’t trying to jam our square pegs into round holes.

We’re looking for alignment. We want to uncover the opportunities that we are uniquely suited for, and ignore everything else. This is how great marketers and salespeople operate. They’re looking for the people that want to say ‘yes.’

You’re looking for that opportunity that is a resounding “hell yes!” You’re going to ignore all the other opportunities that look great, but that are traps for you.

2. Take 3 different personality assessments

I recommend getting a broad perspective on how different assessments categorize your personality. While backed by science, these assessments are very much art, and your interpretation of the results depends on what opportunities you think you want.

There are tons of personality tests you could take (that link shows a breakdown of some of the most widely used. please note it needs to be updated).

Here are three that I recommend currently:

  1. The Predictive Index measures behavioral attributes and is used in millions of hiring decisions by major companies.

  2. Career quiz by - More job function focused. Good to map to specific careers and get ideas on career paths

  3. Principles of You - The Adam Grant and Ray Dalio collaboration is completely free and data driven.

3. Reflect

Reflect on what resonates with you and your experience.

This is important. You have many personality advantages. You get to decide which ones you want to highlight.

Use this time to journal about your results. Combine results from different assessments that resonate with you.

Prompts for your reflection:

  1. What attributes align with how you want to be in the future?

  2. What attributes align with your curiosity?

  3. What attributes do you want to use less of?

  4. What attributes are strengths, but you don’t want to use them as much going forward.


In PrinciplesYou assessment, I’m in the archetype of Seeker. I have a high need to follow my own path, but I’m also a Thinker - so I take a long time to make decisions and I need to understand the meaning of action and have that all align.

So, I have an entrepreneurial bent, but I need to do it at my own pace. This insight was invaluable, because it set me on a path to find a lifestyle business to build instead of another high growth, VC backed startup.

4. Create narrative

Outline and highlight these attributes in a narrative that gets you closer to describing how you will use your personality advantages to get what you want

Start by pulling out specific keyword from your reflection. If you think you want a new job you can use these keywords later to build a resume tailored to that experience. If you keywords are more about the feeling your future self wants to have that’s ok too. The idea here is to get a statement of what you are naturally good at when you’re at your best.

You can use this statement to re-program you self talk over and over to start using these hidden gems of advantage in your daily life.

My narrative

“I am a seeker, always looking for new ideas which fuels my curiosity, but I also need to guard against distraction. I’m a thinker. I need to know how things fit together. I’m at my best when I am spending most of my day alone and reading or writing. I’m a lateral thinker. I am at my best when I’m combining ideas from different fields.”

Keep this on a piece of paper in your pocket. Look at it every day. This is you at your best. Use it as fuel.

It can also be helpful to narrate and reflect on your disadvantages so you stay away from those or improve them if that investment makes sense.

5. Start to outline your options portfolio

Start to bullet out options of how you can use this new narrative or where it may potentially be a good fit.

What industries need your personality? What roles? What projects?

This list will likely change over time as you progress through Advantage Mapping, so I suggest using an editable document, white board or post-it notes.

6. Find your tribe

Your network is your biggest asset for finding a new opportunity, and Linkedin is the single easiest way to find like minded (literally) people to connect with and learn from.

Seek out like people on Linkedin (start with me!) to start building your network. Do this not based on job function, but personality, values and curiosity.

Take these 6 steps and you'll be well on your way to creating a lifelong advantage from understanding yourself, and aligning with your highest attributes!


See you again next week.

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

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