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Michael Gardon

  • Writer's pictureMichael Gardon

The Career Portfolio - The Break Issue 57

Updated: Mar 13

The Break is . . .

The moment that changes everything. We do stories and actionable tips to help you break your relationship with work so you can build the future you want.

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#57: The Career Portfolio

I was at a dinner party this weekend with a bunch of Neurologists.

These highly educated, and dedicated individuals have spent their life devoted to one cause.

And boy have they gone deep in one path.

Fortunately for them, neurology and medicine as a whole is an extremely stable profession that can lead to a lot of happiness.

They never had to look outside their blinders.

They started med school one day in their 20’s and now wake up each day in their 60’s looking back on a life serving patients.

These are amazing, hard working people.

To them, I am an total oddity.

  • 6 career changes

  • 3 business ventures

  • Every time they talk to me, I’m doing something different

I explained that while deep, one track careers are great for people who have a calling early, 95% of us can’t rely on their 18 year old selves making a great decision for the rest of their lives, and if we want to live a life of meaning and happiness, I argue that we need a system to adapt, change and learn on this journey we call life.

So I explained the concept of the career portfolio, and investment portfolio theory as not only a risk management strategy, but also an aggressive offensive strategy designed to find ‘winners’ in the game of life.

They left the conversation rather flabbergasted, and some even questioned what their lives would have been like if they explored more of their options.

The portfolio approach is a major underpinning of my ​Advantage Mapping Foundations​ course - it's how we create options to actualize our talents in the world.

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here’s why a portfolio approach to your career is necessary and how to do it.

A portfolio approach to your career is all about thriving in the uncertain future.

The truth is:

We don’t know.

We don’t know what’s going to change in the outside world.

We don’t know how we are going to change in our inside world.

A portfolio career is the antidote to uncertainty

To thrive in this uncertainty, three key elements come into play:

  1. Cross-functional Abilities: Create a versatile skill set. Specialization and narrow focus may work in a static environment, but they leave you vulnerable to long-term risks.

  2. Options (but not too many): Cultivate a diverse set of opportunities. However, avoid overwhelming yourself with too many choices.

  3. A Willingness to Change Your Mind: when circumstances dictate. Flexibility is your ally in an ever-changing landscape. This gets easier when you have #1 and #2 above.

Efficiency, specialization and narrowness are the enemy. Going deep only works in an unchanging world.

These things make your life easier in the short run, but expose you to more risk in the long run.

  • You dedicate your life to studying one microbe that turns out not to be real.

  • You become a freelance writer only to watch content teams turn to Chat GPT.

  • You work 20 years at one company that goes bankrupt, taking your retirement with it.

  • You go above and beyond for your employer, thinking that’s the way to get ahead, and then one day, poof, you’re gone.

So you need a portfolio of opportunities so you can leap from one to then next as circumstances change.

Your Life as a Funnel: Picture your journey as a dynamic funnel, guiding you through different phases and experiences. There is more opportunity than you could ever imagine. Your job is to filter out what won’t work for you and combine what will. It’s a delicate balance.

Here’s a step-by-step guide on how to build a portfolio approach to your career:

  1. Listen to Your Interests: Identify three areas that genuinely pique your curiosity and interest. These should be fields of study you could learn about for a long time

  2. Create Options: Generate ideas and opportunities within these chosen areas.

  3. Avoid Single-Path Optimization: Don’t chase after one path solely for the promise of more money, status, or responsibility. Instead, focus on foundational skills that transcend industries and roles.

  4. In the early stages: prioritize building meta skills that have broad applicability, such as sales, writing, leadership, and psychology.

  5. Adopt a Career Experimentation Mindset: Embrace a willingness to try new things and learn quickly.

  6. Prioritize Resilience Over Efficiency: Understand that you will encounter setbacks and mistakes along the way. The goal is long-term alignment, not just short-term efficiency.

  7. Leverage Your Advantages: Recognize and harness your unique strengths creatively.

  8. Never stop Networking: Your network is your gateway to opportunities. Only 20% of jobs are filled through the traditional application process. The rest get filled by networking and warm introductions.

  9. Always have a side project in your arsenal. At the very least, you’ll acquire new skills, and at best, you might stumble upon a lifelong passion.

  10. Practice Multiple Approaches to Problem-Solving: When faced with a challenge, tackle it from at least three different angles. You never know which approach will make the difference.

Incorporating these principles into your career strategy can help you navigate the unpredictable terrain of the professional world effectively, AND developing these skills will help you diversify your income streams as you get better at seeing the intersection of your unique abilities. Remember, your career is not a linear path; it’s a dynamic portfolio of opportunities waiting to be explored.

Here’s to breaking your old habits and becoming the best version of yourself!



P.S. My Advantage Mapping Program is all about systematically building a "high odds" path to your version of success. In order to build high odds we first need to break our low odds habits and scripts about work. This is hard work, but I personally guarantee you will find your path that aligns who you are with what you do. I'd love you to check it out ​


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

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

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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!

  • LinkedIn Headline Analyzer: See how your LinkedIn headline stacks up and how you can improve it to attract better opportunities.

The Latest Conversation on THE BREAK Pod

For those of us who have zig-zagged our careers, we often feel misplaced, misunderstood, and feel like we come across as scattered. But the truth is there’s magic in our intersections, and the key is excavating the unique value that comes from your intersection.

This has worked wonders for me as I now describe my own intersection as a coach who uses principles from human-centered design, investing, and entrepreneurship to help people unlock creative career paths that make them come alive.

My next guest says instead of shunning your disparate interests, embrace them and learn to live a Portfolio Life. HMMM, that portfolio phrase is something I very much ascribe to!

A self-described “human Venn diagram”, Christina Wallace has crafted a career at the intersection of business, technology, and the arts. She is currently a Senior Lecturer at Harvard Business School, where she teaches entrepreneurship and marketing. Her most recent book is The Portfolio Life: How to Future-Proof Your Career, Avoid Burnout, and Build a Life Bigger Than Your Business Card (Hachette, 2023).

A serial entrepreneur, Christina has built businesses in ecommerce, edtech, and media. She also co-authored New To Big: How Companies Can Create Like Entrepreneurs, Invest Like VCs, and Install a Permanent Operating System for Growth (Penguin Random House, 2019) and was the co-host of The Limit Does Not Exist, an iHeart podcast with millions of downloads over 3 seasons and 125 episodes.

In her free time, she sings with various chamber choirs, embarks on adventure travel, and is a mediocre endurance athlete. She lives in Cambridge with her husband and their two children.

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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