010 | The Future of Job Security

📓 The Rise of the Portfolio Career

Job security is now a myth.

At least, job security's definition has changed.

And it starts by thinking about our lives as multi-faceted human beings capable of holding many different roles in life.

When I think of a portfolio, I remember my days in elementary school in art class. Our “portfolio” was our collection of works, each very different from the rest.

In a way, we are all a portfolio: a collection of ideas and roles.

I believe artists—creators—stand to benefit the most from the Future of Work.

These are individuals who push away traditional “job security” in favor of representing the collection of pieces they continue to be and grow into.

Those who work in the creator economy already see this massive trend. Simply search “my sources of income” on YouTube to find a plethora of creators like this one:

Let's put myself on the block.

This week, I found myself juggling 3 different tasks, each for a different "job." One as a consultant, another as an events facilitator, and one as a newsletter writer (hello!).

This isn't unique to me—it's becoming the norm for many professionals in 2024.

🎨 What Is a Portfolio Career?

This term was originated by philosopher and organizational behavior expert Charles Handy in the 1990s, and is a shift away from a traditional career path, as considered by the former VP of Bloomberg quoted above.

Think of your career as an investment portfolio. Just as financial advisors recommend diversifying your investments, forward-thinking professionals are diversifying their income streams and skill sets.

A portfolio career might look like:

• A UX designer who consults part-time

• A marketing manager who runs a successful Etsy shop

• A software engineer who runs ads on coding tutorials on YouTube

• A PMO who writes books and teaches courses (the story of Hassan!)

The beauty? No two portfolio careers look exactly alike.

This is because we all have the choice to express our interests in unique ways and monetize our career potential.

🔄 Why the Shift?

The rise of portfolio careers isn't just a trend—it's a response to our changing work landscape:

1. WFH opens up global opportunities

2. The gig economy normalizes flexible work

3. Technology enables multiple income streams

4. Economic uncertainty pushes workers to diversify

5. Ai handles mundane tasks, freeing us for creative pursuits

6. The creator economy shows us diverse income streams are possible

👷🏽‍♂️ Building a Portfolio Career

Starting a portfolio career isn't about jumping ship from the 9-5. It's about strategically adding layers:

1. Look back at childhood interests

2. Identify core skills (ikigai?)

3. Look for opportunities within your network

4. Start small, test the waters

5. Build systems for efficiency

6. Know when to scale (or pause)

My friend Dexter just launched his 2nd full cohort for Remote Side Hustle Launchpad, helping professionals build their portfolio career! Sign up for the waitlist to learn how to build yours in 2025.

⚖️ The Balance Equation

Let's be real—juggling multiple roles isn't always easy.

The difficulties and necessities to understand are:

• Time management — Leveling up organizational skills

• Focus — Practicing meditation can hone in on this power

• Boundaries — Learning to say “no” frees up the mental load

• Income instability — Knowing the project won't take off ASAP

• Identity — How do you explain your career without judgment?

• Information overload — There are 1 million + 1 ways to start a biz

The beauty of all these challenges are potential opportunities for the portfolio careerist.

💭 Final Thoughts

A portfolio career isn't just about having multiple income streams—it's about creating a career that's as multifaceted as you are. It's about building resilience in an uncertain job market and finding fulfillment in diverse pursuits.

Some companies are also catching on, encouraging employees to pursue personal branding as a side project, recognizing the trend for the people behind the logo as a way to spread brand awareness of the company.

Are you building a portfolio career?

Reply to this email—I'd love to hear your story!

⚡️ Updates

I'm on a mission to connect 100 unique individuals in 1:1 breakout rooms through online, speed networking. I call them: Connection Power-Hours. So far, we're at 58 unique persons!

These events have become so popular that we have to limit the number of individuals! For now, every joiner in the next 5 sessions must be new and not have been to a previous session.

Learn more on our website and subscribe to our event list here. All times in EST.

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