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Michael Gardon

  • Writer's pictureMichael Gardon

How to Take Better Risks: Your Future Self Depends on It. - The Break Issue 30

Updated: Mar 19

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Today's Issue

In today’s issue, you'll learn:

  • To grow, you need to take better risks

  • The 3 phases of becoming a better risk taker

  • How to set the right conditions for more risk taking

Let’s dive in.

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Your Growth (and Confidence) Depends On Your Ability To Take Risks

I was not born a risk taker.

I still don’t consider myself one.

But I’ve made A LOT of progress -

That progress is probably the single achievement that I am most proud of in my life.

Being in a position to take risks is vitally important to your growth.

Because all of your dreams and desires are on the other side of a series of unknowns.

  • What will people think?

  • What if they say no?

  • What if I lose money?

There is no growth in certainty - we must leave certainty behind to become someone we are proud of.

Thankfully, even the most risk averse (like me) can teach themselves to take risks.

Taking risks is a habit. Formed like any other habit - by starting small.

There are 3 phases to becoming a better risk taker:

The 3 Phases Of Becoming A Better Risk Taker


Early on, for whatever reason, I understood no risk/no reward.

I recognized that to become whoever I wanted to become, I would need to try things I might fail at.

No risk/no reward is as certain a statement as there ever could be.

Internalize it as fact.

You will not grow in a fulfilling way without taking some risks.


You have to become someone who makes decisions in the face of uncertainty instead of being paralyzed by it.

Your peers are paralyzed. You want to pass them, so get out of your own way.

You can’t think your way, you have to believe .

Acting in the face of uncertainty is heroic.

Be a hero to yourself.

So how do we change our mindset around risk?

1. View every choice you make as an investment

Every decision you make involves some element of uncertainty. You are choosing to do one thing in place of another thing. That is a tradeoff that has risk. So you are placing a ‘bet’ or making an investment with your time and attention in every single decision you make. Great investors know that some investments work and some do not. They measure themselves by the long term quality of their decisions, not individual outcomes.

2. Learn to estimate probabilities

Fear clouds our ability to accurately understand true probability. We make all sorts of errors of judgement by overweighting recent events, history, certainty, and we tend to not give ourselves enough credit for our abilities.

We can make good probabilistic decisions and lose. We can make bad probabilistic decisions and win, but over time, if we estimate more correctly, we will win in the long run.

3. Take the long term view

Life is a long series of decisions. Any single outcome doesn’t matter as long as we keep going. This mindset is freeing. It takes the pressure off and allows us as people to detach from any one outcome. This builds resilience and allows probability to take over.

Do. Fail. Win. Learn. Update.

4. Fear Set

Author Tim Ferriss uses a technique called Fear Setting when he is afraid to take a risk. With fear setting, you literally ask yourself to envision the worst possible outcome. Then ask yourself if you could live with that outcome. Hint: most of our fears, we can actually live with.

Here’s a link to Tim’s Ted Talk on the subject.

Set the right conditions

The final phase of becoming a better risk taker is where we use our logical brains. Risk can be managed. The best investors set conditions that minimize their risk and maximize their upside. This is called skew. Here’s how to skew your risk down

Build a foundation

Rule #1 of risk taking is survive. This means we can’t let any single outcome knock us out. To survive, we need a strong foundation.

I’m talking about:

  • Have a cushion (cash, time, youth, energy)

  • Have a strong support system

  • Build meta skills you can take anywhere

You need a rock solid way to bounce back if things don’t go your way. This is how you build resilience.

Check out my barbell investing philosophy and see how I keep a huge portion of my net worth in boring safe stuff so I can take bigger risk with a small portion.

Size your bets

The size of the risk you take should be proportional to to your confidence and your real ability to estimate real probabilities (see mindset section).

Not confident? Figure out how to take the smallest risk you can.

Thinking you might like a different career? Don’t quit your job right away. Figure out how to put yourself out there and gain the information you need to make a bigger bet.

Can you:

  • Reach out to one person that works in that field?

  • Ask to shadow them?

  • Take a course?

  • Learn a skill?

The smallest bet you can make, is your ante. It’s how you stay in the game and gain information so you can build confidence to bet bigger when the time is right.


The best risk takers are always thinking about how to minimize the downside of every risk they take, and you can too.

Here are some examples:

  • Keep your job - it’s the cash flow to fuel your next move

  • Build on the side

  • Network and talk to people in your field

  • Barter/lease/rent before buying

  • Know your out

  • Always have other options (especially when you feel comfortable)

Cycle speed and recovery

Putting this all together, success is about discovery of what works. To discover, you have to take risks. Putting these phases together will help you take risks AND AT THE SAME TIME you are building the muscles of resilience.

Don’t stop! Life is not one play. It is a series over and over and over.

The key to success in the long run is cycle speed - your ability to take many risks, learn and update. Key to cycle speed and resilience is how you recover between setbacks. Developing a long term mindset and viewing every decision as an investment will help you build an unstoppable attitude to persevere, take risks and find success.


I’m not a natural born risk taker, but I’ve learned to become a better risk taker by following these steps:

  • Recognize to grow, you must take risks

  • Becoming a better risk taker starts with mindset shifts

    • long term vs short term

    • Small vs big

    • Decisions as investments

    • Putting fear in its place

  • Create conditions for risk taking

    • Build a solid foundation

    • Size your bets

    • Mitigate unacceptable factors

  • Take lots of shots

See you again next week!

3 ways I can help you:

1. Book a free Intro To Advantage Mapping coaching call . In this 30 minute, no obligation call, we'll get you executing on a high odds career path by leveraging your natural advantages and Circle of Competence.

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What’s happening on the pod?

Brian Gallagher is a Corporate American turned Global Citizen. Brian did what many bright and talented people do right out of college. He went into finance. But a few years in he had his BREAK moment where he realized the money, the status, the “dream” wasn’t all it was cracked up to be.

He got out. He owned a fitness studio for a while and then did something even more drastic. He gave away 99% of his belongings and left the traditional path to see the world and live life on his own terms.

In this episode, Brian and I talk about his Break moment. How he got over what other people think, and how the key to building your own future is about prioritization.

You’ll take away some great tips and examples from Brian’s story on how to choose yourself, and how you can really do just about anything if you’re willing to say no to traditional advice that often ends up being a trap.

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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