Today, in 5 minutes or less, you’ll learn:
- đź“Š Why the #1 Portfolio Career Type caught me by surprise
- đź’° How 67% of quiz respondents factor money into their portfolio career
- 🔑 The patterns behind what drives high-performers to pursue unconventional career paths
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💎 Last Week’s Gems
- 🔄 Public company CEO departures increased 24% YoY. The WSJ interviewed executive recruiter firms saying the pipeline for corporate leaders is shrinking.
- 🚀 Meanwhile, US new business formation increased 6% from Feb 2025 to March 2025. I’m personally expecting the continued growth of smaller firms that can do more with less with AI.
- 🧠 44% of executives say a lack of in-house expertise is slowing AI adoption (Bain). United States: 1 in 2 AI jobs could be left unfilled by 2027.
- 💯 Vanguard is famous for saving their investors $1 trillion in fees, being minimally extractive. But this is opposite of most career advice (“Maximize your value and then negotiate hard for your piece!”). Personally, being minimally extractive resonates with me as a powerful way to create lasting impact.
đź“Š The Surprising #1 Portfolio Career Type
171 readers have taken our Portfolio Career Type Quiz.
Can you guess which type is the most popular?
The answer caught me by surprise!
I love nerding out on data. So I naturally found myself going down the rabbit hole, crunching the numbers to surface personal finance and career insights that go beyond the conventional stuff you see online.
In this edition, I’m going to break down 8 money and career insights I learned from your responses to the Portfolio Career Type Quiz.
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Insight #1: Polymaths, followed by Side Hustlers, were the most common types
This one took me by surprise. I was expecting Side Hustlers to be #1 win a huge margin based on my conversations with readers.
I suppose the portfolio path attracts more generalists and multi-hyphenates than I expected!
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Insight #2: 37% of respondents desire a mix of creative and consulting projects, followed by 32% like having a main job + side projects
The reality is that many portfolio pathers still prefer to have a structured approach to how they manage their time.
Contrary to popular thinking, I believe the right structures can be freeing. It can help you create clarity and focus, reduce cognitive load, and build momentum towards the next step.
Insight #3: 34% of respondents seek multiple income streams, but 33% prefer building a new income stream without risking main income
This one surprised me a bit. While walking the portfolio path might appear “unhinged” to a traditional career climber, the responses here allude to portfolio pathers preferring structure with their personal finances.
Stable income source coming in from your main job is the starting line—which then gives you the flexibility to layer on new income streams outside of work.
Insight #4: 44% of respondents get excited about learning something new when evaluating professional opportunities
Even though we hear from readers about their desire for diversified income streams, this result indicates that ROI is not the main factor driving professional decisions. It’s learning and growth.
My take here: if we zoom out, we ultimately choose the portfolio path because we want to spend our time on meaningful work. Unfortunately, this is lacking for most workers. According to Gallop, 79% of employees globally are disengaged with their work.
Satisfying our curiosity is a big part of generating meaning and purpose IMO.
Insight #5: 67% of respondents seek independent and project variety or stable growth
This one also surprised me. Again we can see the dichotomy between independence and stability.Â
I suspect the reason for this even split is because our readers possess middle-of-the-road risk tolerance.
Our readers don’t represent the high-risk, high-reward end of the spectrum (otherwise, they’d be reading a VC newsletter not Portfolio Path). Instead they’re focused on steady growth and income diversification.
Insight #6: 50% of respondents said at the end of their career they’d want to be known for building something meaningful while building their ideal lifestyle
Most people didn’t choose the answers centered around Impact, Innovation, or Execution. They sought out a career goal that incorporated lifestyle.
While I don’t believe in work-life balance, I do believe in work-life integration. The high-performers I see adopt this approach tend to be more creative with how they structure their time and energy.
For example, my entrepreneur friend’s wife recently went on a business trip from the US to Egypt. He tagged along to build relevant relationships for his business while they got a once-in-a-lifetime chance to explore Egypt together.
Insight #7: Connecting the dots is the top career asset for 40% of respondents, followed by turning complex challenges into solutions (25%)
Here, I expected more people to choose solving complex problems or the track record + entrepreneurial mindset. Essentially, viewing themselves as specialists.
But I was wrong. Given our high proportion of Polymaths/generalists, I can now see why “seeing connections that others miss” is #1 by a long shot.
Insight #8: 77% of respondents preferred applying skills across different client problems or learning new fields
Diversification is the name of the game—whether it’s clients, income sources, or learning. Variety is at the crux of the portfolio path for many.
In Summary
Here is what I learned about our reader community:
- Polymaths and Side Hustlers who value both structure and flexibility
- Prefer a structured approach to your time (main job + side projects) and income (main income + new income streams)
- Prioritize learning over immediate ROI when choosing opportunities
- Balance stable growth + independence + variety in your work
- Define career success as incorporating lifestyle (not just achievement)
- Superpower is being a generalist that connects the dots (vs deep expertise)
- Main goal is diversification of clients, domains, and income streams
Thanks for reading.
What were your takeaways? Reply to this email and let me know your thoughts.
P.S. If you haven’t taken the Portfolio Career Type quiz, but would like to, you can take it here.
đź“š From Our Archives
Curious about the 4 portfolio career types?
I wrote a popular edition on this topic — sharing 14 real-world examples, pros, cons, and who is a good fit for each type.
Check it out here:
✨From Our Community
May Community Call (Wednesday, May 7th 5pm PST)
This month’s topic: Client Growth Engine. Only 15 seats available.
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Community Spotlight: Ivan McAdam O’Connell
Ivan is co-founder of VIVOS, a global mobility platform; former COO of HSBC; and has advised firms like McKinsey, Bain, BCG, and investment firms. He’s based in Singapore.
How would you describe what you do to someone outside of your industry?
I'm a freedom lifestyle designer. Through my portfolio of businesses and services I help people unlock new opportunities, go global, and cross the river from employee to entrepreneur.
What triggered your interest in exploring the portfolio path?
The simple question: "Is this all?". Approaching mid-life, I felt the weight of being a good son, husband, father and employee (and not feeling good enough in any of these roles). I started to ask "Isn't there a better way?"
What’s your current portfolio career mix?
- Business building (VIVOS - global mobility platform)
- Industry expert consulting & coaching
- Investing, board roles, and advisory
- My book - "Live Big. Break Free”
What advice would you give to someone starting a portfolio career?
Build some foundations first... and understand that anything worthwhile takes time. In time everything compounds - but you can choose if it compounds for you or your employer!
What’s a fun fact about you?
Once walked across hot coals in a Slovenian forest at night (it only hurt a little!)
What's one piece of media that impressed you lately?
The Surrender Experiment - Michael Singer
How can people connect with you?
LinkedIn
P.S. Did you enjoy this spotlight? Hit reply and let me know—or suggest another amazing portfolio pather we should feature next!
