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Michael Gardon

  • Writer's pictureMichael Gardon

To Overcome Career Fear, Do This - The Break Issue 65

Updated: Apr 30

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#65 The stupid simple concept that took me from risk averse 20 year old to risk seeking middle aged dad even with three kids:

Hello Unbreakables!

FUD = Fear. Uncertainty. Doubt.

The triad that keeps us from betting on ourselves.

And keeps us on the incremental path to nowhere.

I used to be a FUD.

I grew up in a very fiscally conservative household.

My parents are well off, but massive penny pinchers.

This isn’t bad, in fact it’s noble.

However, saying no to even the slightest risk of losing isn’t great for personal growth.

So naturally I was extremely risk averse for the first 20 years of my life.

Until I learned about the BARBELL strategy.

Here it is, and how it can help you take more bold action (that seems risky) to go after what you want in life.

I learned Barbell from author Nassim Taleb in his amazing book ​Skin In The Game​.

The concept appealed to me as a young finance trader, and

I adapted it to personal development and decision making.

Here are the principles:

Uncertainty exists on a spectrum.

We can think of it like a normal distribution.

We take actions every single day, some are extremely safe like walking (for most of us)

and some are incredibly risky like driving a motorcycle without a helmet.

When it comes to careers, that spectrum spans

get a job (safe)


rage quitting in your 40’s with no plan (risky)


starting a restaurant (possibly insane!)

The extremes of the spectrum are easy to understand

But the middle gets very messy, and is full of hidden risks we are not equipped to predict.

Like how far off course will I be in 5 years if I keep chasing promotions?

We don’t want to play this game.

And that’s where the Barbell comes in.

In a barbell strategy, instead of taking a bunch of incremental actions in the middle (you know the ones where everyone tells you to be responsible), we cut all those out to make room for very safe, and very bold.

Like: keep my safe income as long as I can while building my entrepreneurial escape.


Middle risks are harder to understand.

This is the space where you’re pursuing incremental growth for hard to define risk.

Think: we lower our goals to be realistic, but don’t realize small goals take the same effort as big ones (same risk, less payoff = middle).

That’s a recipe for:

  • Procrastination

  • Self doubt

  • Overthinking

  • Late starts

  • and imposter syndrome

Instead think barbell

With barbell, you’re in binary mode all the time:

Either safety or all out

Either offense or defense

Exerting or recovering

Safety balances the risk taking.

The more safe you feel, the bolder you’ll be taking chances.

Here’s an example from my own life:

  • I hold a ton of cash (safety)

  • I used my job (safe) to fund my side business (risky), but rejected the ladder climb rat race politics (middle)

  • I don’t spend much except on personal development (I drive a beautiful, paid off 2014 Toyota Highlander with 103,457 miles on it)

  • I don’t own many stocks (middle, incremental risk)

  • But I did spend a bunch of cash to buy 100% of my business back this year (gulp!)

  • I’m default aggressive with creative pursuits (risky), and relentless with being attentive with my family (safe) rejecting the “meetups,” “conferences,” “networking events,” and other box checking activities with very little upside, and hidden downsides of eating my time.

Questions to ask to identify the messy middle risks:

  • Is this path incremental (middle) or transformational for me?

  • Could this make a 2X change for me (middle) or a 10X change?

  • Does this action get me toward my future vision of myself?

  • Does my logical brain find it reasonable (middle)? Or does it scare the shit out of me?

Key Takeaways:

  • Everything in life is risky

  • Risk exists on a spectrum, with most of our mental activity spun up on assessing middle risks (the kind that are incremental in nature)

  • Instead, choose a barbell strategy by oscilating between super safe and scared shitless risky

  • Over time, you build the capacity to take bolder action by knowing even if you fail, you are safe.

P.S. I just did a masterclass on using the Barbell Strategy on your career and personal growth journeys in the Unbreakable community.

Follow me and DM me “Unbreakable” and I’ll send you the video for free!!

Also, I’d love to see you as a member :)

If you're nodding along, and this all makes sense, I'd love to see you as a member of ​The Break Community​. It will be one of the best decisions you will make, and don't forget to use the code THEBREAK100OFF.

Wishing you boldness and clarity in the new year,



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The Latest Conversation on THE BREAK Pod

We're delving into the profound topic of reinvention, exploring how to pursue our passions, even when it means taking a leap of faith.

In today's interview, I had the privilege of sitting down with Roger Osorio, a remarkable individual who embodies the essence of reinvention. We unravel his personal journey from a corporate job to becoming a math tutor and eventually a teacher. Roger shares his insights into the transformative power of finding fulfillment and happiness in one's work, even if it means diverging from the conventional path of financial success.

He stresses the importance of taking small steps and running experiments in our lives to test different paths. Roger encourages us to discover what brings joy and fulfillment, emphasizing that it's okay to challenge societal norms and redefine success on our own terms.

Throughout the conversation, Roger advocates for considering our unique circumstances and values when making decisions about our careers and overall happiness. His wisdom resonates as a guide for anyone seeking a more meaningful and fulfilling life.

So, without further ado, let's dive into this enlightening conversation with Roger Osorio on reinvention and the pursuit of passion.

But before we do, make sure to learn more about Roger and his incredible journey by visiting his website at​. You can also connect with him on LinkedIn at​.

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.

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