🐧 4 Portfolio Career Paths (+14 Real-World Examples)

Hey readers, I’m hosting a Singapore meetup on 13th November. 🙌 

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Today, in 10 minutes or less, you’ll learn:

• 🚀 WTF is a Portfolio Career and Why You Should Consider One
• 🧠 4 Portfolio Career Paths, Benefits, Trade-Offs, and Which Path is Right For You
• 💡 14 Real-World Case Studies of People Thriving in Each Model

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🎫 Singapore Meet-Up on 13th November: RSVP Now

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​30 tickets are available and we’re already 50% full, so sign up ASAP.

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📖 4 Portfolio Career Paths (+14 Real-World Examples)

Over the last 11 years, I worked as a full-time product leader and PM.

I’ve been fortunate to work with a $10B SaaS public company, $1B fintech unicorn, and several fast-growing startups.

Last year, I left my last full-time role.

Since then, I’ve been consulting for scaling startups, while building Money Abroad courses and content.

Over the past month, we’ve narrowed down our content to three pillars of the transition from “live to work” to “work to live”:

1. Money
2. Portfolio careers
3. Life design

Every month, I meet financially secure people who want to leave their corporate job, but feel stuck in figuring out what to do next.

That’s where portfolio careers come in.

In this edition, I deep dive into what are portfolio careers and why consider them, 4 portfolio career paths, and 14 real-world examples.

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WTF is a portfolio career and why are people talking about it?

Here is how I define portfolio careers:

• FT employment = working a single full-time (FT) role for one employer
• Portfolio career = having multiple income sources

Recently, both traditional media outlets and viral Tiktoks have featured portfolio careers.

Why?

Portfolio careers are becoming more common due to:

1. Employers are cutting costs - To save on labor expenses, employers are seeking greater efficiencies via fractional, part-time, and remote/hybrid work.
2. Employees are adopting alternative work - Since the Covid pandemic, workers have desired more flexibility. Over 50% of all US workers are projected to be doing some form of freelancing by 2027.
3. Rise of AI-enhanced productivity - An MIT study reported that genAI helped high-skilled workers increase productivity by 40%. Everyone in tech talks about the 10x engineer. In the future, I think we’ll see more 10x non-technical workers who can leverage AI and other technology to amplify their productivity.

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Is this a good thing?

Depends on who you are.

If you're ambitious and seek to work to LIVE:

• I believe this future will be golden for you.
• You can leverage productivity-enhancing tools to generate more value from per hour of your time than ever before.
• At the same time, you can do work you enjoy and have greater control of over your time.

If you’re an average worker:

• I’m less sure of the immediate benefits.
• This is because I believe economic rewards will follow a power law.
• Most rewards will accrue to the top 10% who can get the most leverage on their network, skills, and time.

If you’re reading this newsletter, it’s safe to say you’re amongst the 10%.

You’re a high-achiever looking to step off the hamster wheel.

And you might be wondering:

What type of portfolio career is right for you?

Here are 4 portfolio career paths (complete with real-life examples):

The Side Hustler

This one’s pretty obvious. Side hustlers have a full-time job while pursuing additional income streams.

Pros

• Financial security of a steady paycheck
• Opportunity to explore passions with less risk
• Good testing waters for full-time entrepreneurship

Cons

• Hard to manage time across full-time job and side hustle
• Potential to burnout from juggling too many balls in the air

Who is this a good fit for?

Full-time professionals who:

• Like their day job (don’t want to quit)
• Want to experiment with entrepreneurship
• Want to explore a new passion or income stream

Examples

• Janani Chandran (Singapore) coaches project managers while working as a Group Project Manager at a public tech company
• Chris Ming (Philadelphia, US) launched a Remote Job Search cohort program while working as a Growth Product Manager at a climate tech startup
• Elizabeth Schwartz (New York, US) grew her investing coaching business to $5k/month while she worked full-time at a social media giant
• Mark Soh & Ara Kyi (Singapore) became a 7-figure e-commerce distributor of a Taiwanese camera brand called Paper Shoot while working full-time tech jobs

🤓 Want more case studies? My team and I spent 50+ hours interviewing and researching real side income streams up to $10k/mo. Click here to download your Side Hustle Database.

The Expert

Experts leverage their deep expertise in a specific field across multiple roles.

They work as fractional C-levels, consultants, advisors, and speakers.

This requires specialized, unique knowledge (typically built on 10+ years of experience).

(Wondering if this is you? Here’s how I think about it: “expert” isn’t a label you give to yourself, but clients are seeking out your advice.)

Pros

• High demand & compensation for specialized skills
• Opportunities to become a thought leader
• Continue to grow and learn in your field

Cons

• Risk of your skills becoming outdated (especially in fast-moving industries)
• Pressure to stay at the cutting edge (e.g. AI in tech)
• Limited flexibility to explore other fields

Who is this a good fit for?

Senior professionals looking to monetize their expertise across multiple roles and platforms.

Examples

• Aki Taha (Singapore/US) went from a senior talent leader at Netflix, Uber, and Google to building TalentStories, a talent advisory and content company
• Mark Mullinex (Singapore) went from 20+ years working on loyalty programs for airlines/hotels/banks to becoming a Fractional Head of Growth/Strategy
• Karina Mikhli (New York, US) went from publishing executive with nearly a decade of experience building, optimizing, and scaling SMBs to Fractional COO
• Gabriel Tudela (Mexico City, Mexico) went from working on operational/product launches for 4 unicorns to Fractional Executive for Startups (a) soft-landing in Mexico/LATAM and (b) identifying their ICP.

The Polymath

Polymaths combine multiple, disparate skills into a diverse portfolio.

Think Ben Franklin—a writer, publisher, scientist, inventor politician, and diplomat.

Pros

• Enjoys tapping diverse skills set across many domains
• Opportunity to leverage creativity and quick learning
• Ability to connect ideas across disciplines/industries

Cons

• Harder to market a multidisciplinary skillset
• Difficulty in overcoming a “jack of all trades” stigma
• Challenge in establishing credibility across multiple fields

Who is this a good fit for?

Curious individuals who get bored easily and LOVE exploring new skills/fields.

Examples

Here are few better-known modern-day polymaths I follow:

• Scott Young - polyglot, programmer, author
  • Wrote 1,000+ articles as a blogger, then published his 2019 WSJ Bestseller, Ultralearning
  • Led incredible self-designed learning projects: MIT Challenge (completing MIT's 4-year Computer Science curriculum in one year) and The Year Without English (learning four languages through immersion in one year)
• Derek Sivers - musician, entrepreneur, author
  • Started as a musician, attending Berklee College of Music, touring with bands, and even joining a circus
  • Founded and sold CD Baby in 2008 for $22M
  • Authored several books, including Anything You Want about his CD Baby experience and How to Live

The Freelancer

Works independently for multiple clients in a broader field (e.g. graphic design or copywriting).

Synonymous with consultants and agency owners.

Here is how I differentiate Freelancers and Experts:

• Freelancers/Consultants provide multiple services in a broad field (e.g., graphic design, writing, web development), typically works mainly on execution deliverables, has shorter or project-based engagements, and grows their portfolio by working with diverse clients and industries
• Experts provide services in a specialized area of expertise, handles both strategic and execution deliverables, typically longer-term engagements, and grows by deepening their specialized niche and becoming a trusted authority for it

Pros

• Ability to choose your projects and clients
• Flexible work schedule and location
• Potential for earning more than traditional employment

Cons

• Volatile income and workload
• Responsible for all parts of the business
• Industry thought leadership is not as common

Examples

• Xin Er (Singapore) founded Studio Hey Osh, a UX design agency after working as a Head of Design at a fintech unicorn
• Enzo Carasso (France) founded C17 Lab, a RevOps agency to help companies with lead generation and scaling revenue after working on GTM for companies like Square, Sixt, Booking.com
• Stephen Mostrom (Phoenix, US) started a copywriting agency for B2B Tech and Finance clients like Comerica Bank and Clari
• Michael Lim (Australia) started Modern Leverage, a content agency for solopreneurs after growing his own content to over 80k followers

So there you have it.

That’s 14 real-world examples of 4 portfolio career paths.

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In Summary

Portfolio careers are rising due to:

• Employers cutting costs
• Employees seeking flexibility
• Leveraging AI-based productivity

Four portfolio career paths:

• Side Hustler: Full-time job plus additional income stream(s)
• Expert: Leverages deep expertise across multiple roles
• Polymath: Combines diverse skills into a unique portfolio
• Freelancer: Works for multiple clients in broad field

Which one of these paths resonate with you?

Reply to this email with your thoughts and stories. I’d love to hear them!

And if this edition was helpful, give us a 5-penguin rating or leave your feedback at the bottom.

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