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Michael Gardon

  • Writer's pictureMichael Gardon

Here's How You Get Good at Creating Options in Your Career - The Break Issue 67

Updated: Apr 30

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#67 The Options Portfolio

You can do anything, but you can’t do everything. You must choose your path with the best odds.

Look there's 2 places people start when creating options:

  1. "I have no options. I can't imagine what else I could do."

  2. "I can do anything! How do I choose?"

It's work to realize that neither starting point is reality, but once you do you begin to see that the path to creating options starts with thinking about our odds.

The Uncertainty Spectrum

Introducing the uncertainty spectrum. On one end we can't see our options, and we risk being stagnant, never growing and never experiencing the success or happiness we could.

On the other, we risk taking blind leaps and chasing shiny objects that we have no advantage in. We risk choice overload, overwhelm and procrastination.

In the middle however, when we get a proper view, we become unbreakable. We understand our advantages, which give us confidence to do something new, and we have proper filters for weeding out low odds choices.

Toward High Odds Options

It ain’t skills, education, money, credentials or any other traditional way people get ahead.

To get high odds, we need to know more about what to avoid and eliminate than what to actually do.

We need:

  • A strong foundation rooted in our advantages

  • Filters to remove false options

  • A reliable process for ideation

  • A mechanism to problem solve along a path of several options (Portfolio Operation)


You must know yourself and understand where you can compete. This is why the foundation of all I do with my clients is ​Advantage Mapping​.

This process ensures you know how you create advantage, and what you are here on this earth to do.

With that knowledge you set your course.


FILTERS are mechanisms that get rid of fake options and shiny objects that low odds of getting us to where we want to go.


  • deciding what you don’t want is often easier than what you do want

  • elimination is more robust because it frees up mental capacity

  • This is how I started my own career exploration. I didn’t want:

  • to travel

  • to raise capital

  • to work for anyone

  • to go to an office

  • to miss my kids school or sporting events

  • Read more on these topics:

  • Inversion: solving problems backwards

  • Charlie Munger “All i want to know is where I’ll die so I never go there”

Your future vision

  • You don’t need a goal

  • You need a big ideal or feeling that illuminates your pathway

  • Anything not aligned with this vision is a distraction

  • Idea is to envision who you want to be and take those actions now. Start living as that person

Your Advantages


Now that we know what lies outside of our Circle of focus, we can begin to ideate hard.

Here are the rules of ideation:

  1. Never ideate and edit in the same session. We must diverge to capture the full power of our brains.

  2. Then we converge, by combining, removing and adding around only the best ideas.

  3. After you converge, take your list and stack rank your options. Cross out everything that comes after y #3 and forget about them. We want a max of 3 options. Anything else is overload.

Here are several other brainstorming rules that I learned from World Class Design Firm IDEO:

Portfolio Management

Now we need a mechanism to make progress on several options at the same time.

Most people have learned to pick a path and plan out every step. We are going to do the opposite.

  • A good portfolio manager makes a few bets based on a hypothesis of the future

  • If they’re wrong, they cut exposure (stop doing what isn’t working)

  • If they’re right, they add exposure (do more of what works)

Here’s the plan:

  • GOAL: acquire information that either tells you to keep going, or stop. (Signal acquisition)

  • ANTI-GOAL: avoid any middle of the road feedback. This is our enemy. We want Hell yess’s or Hell no’s.

  • Actively seek out disconfirming information

  • Identify high leverage activities that that could move you along multiple pathways

  • Continuously update your view of next steps while avoiding thinking 5 steps in the future.

Hypothesis>Experiment>Learning>New Experiment

  • The quality of your learning and the speed of your progress depends on the boldness of your experiments

  • Timid with your outreach and questions, slow learning

  • Small with your asks, small with your progress

P.S. I just did a masterclass on Building Options your career and personal growth journeys in the Unbreakable community.

Follow me on ​LinkedIn​ and DM me “Options” and I’ll send you the video for free!! Or simply reply to this email with "Options" in the subject line.

If you're nodding along, and this all makes sense, I'd love to see you as a member of ​The Break Community​. Starting next week, I am personally walking the entire community through Advantage Mapping so you get the most out of the course. This will likely never happen again because of time constraints. So, if you're looking for more alignment in your life, join today and le'ts become UNBREAKABLE.

Wishing you boldness and clarity on your journey,



Whenever you're ready, there are 3 ways I can help you:

1. Join the ​Community​, or ​book an intro call​ with me!

2. Get in the conversation on Linkedin. Messages are open - anyone can say hi here.

3. Promote your brand/business to 14k+ subscribers by sponsoring our newsletter contact (Booked out 4 weeks)

Resources To Make Your BREAK

  • Curated Job Board: I teamed up with Pallet to create a tech focused, remote first board. I’d love it if you joined 20+ followers. Maybe, just maybe you’ll find your next big opportunity here.

  • Career Quiz: Take the Advantage Mapping step of learning how you're wired and for what roles!

  • Recommended Reading: My list of must reads to BREAK your view of the world and what's possible for you.

  • Side Hustle Database: Over 200+ ideas to bring out your creative side as you explore your path. Maybe it will end up being your BREAK!

The Latest Conversation on THE BREAK Pod

Welcome back to another episode of The Break podcast, the space where we unpack the remarkable stories of individuals who've faced life's challenges head-on. I'm your host, Mike, and today's conversation is one that you don't want to miss.

Our guest today is Danielle Cobo, a powerhouse in resilience, courage, and unwavering determination. Before we dive into the heart of her story, a little sneak peek caught my attention recently – Danielle's truck. It's not just a vehicle; it's a symbol. We'll unravel the story behind it in just a moment.

Now, for our audience, if you're seeking inspiration and insights into overcoming life's hurdles, you're in the right place. Connect with us on our social media platforms for more exclusive content, and don't forget to check out Danielle's podcast, the ​Unstoppable Grit Podcast​.

But back to Danielle's journey. The heart of today's conversation delves into her mission – helping people discover the power of resilience, courage, and determination. We'll explore her experiences, her mission, and the unexpected twists that make her story truly compelling.

So, buckle up!! We're about to embark on a conversation that goes beyond the surface, exploring the depths of grit and resilience with Danielle Cobo.

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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