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We just concluded our 1-month Europe trip!

I enjoyed it, but grateful to settle back in at home.

As I get older, my travel tastes have evolved. From backpacker hostels to 4-star hotels. From wandering the streets to hiring a photographer-guide. Has this happened for you?

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

• 🗺️ My journey from burned-out tech worker to semi-retired portfolio careerist

• 🤑 How to earn 2.5x-5x your hourly rate through your part-time work

• 🦺 1-2 Rule for safely transitioning to a portfolio career

• 🎢 Why loneliness and income volatility are hidden costs of solopreneurship

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💼 Q&A on Building Portfolio Careers

Growing up in a hard-working immigrant family in Michigan, I saw my parents struggle with financial insecurity.

This experience lit a fire in my belly to pursue what I thought was the pinnacle of success:

A high-paying tech job in Silicon Valley.

I achieved my version of the Silicon Valley dream:

• Working as a product manager for companies like Dropbox

• Tripling my income in 5 years

• Enjoying perks like free meals made by Michelin Star chefs

But despite this outward success, I felt empty and burned out.

The turning point came after Dropbox's IPO. While I was heavily recruited by top companies, I realized I was chasing others' dreams, not my own.

After doing some inner work (harder than it sounds!), that’s when I decided to align my life with my top values like freedom, curiosity, and adventure.

I quit my job to travel to 20 countries, worked for a fintech unicorn in Singapore, and built a portfolio career that has allowed me to:

• Earn 2.5x-5x my hourly rate from part-time consulting

• Launch the online education business I’ve wanted

• Be semi-retired by covering my expenses

• Learn Spanish in Mexico City

• Spend 6 months in Vietnam

In short, I “work to live” instead of “live to work.”

But my journey taught me that working and living on your own terms comes from pursuing your own definition of success.

I’m excited about helping others build their own portfolio career, so they can also align their life with their values like I did.

Recently, I received a few questions from readers about solopreneurship and portfolio careers. In this newsletter, I will share my answers to the most popular questions.

Q: What inspired you to try a portfolio career? What else did you consider, and why did you ultimately go with a portfolio career?

There were 2 factors related to my decision to start a portfolio career:

Career goals and personal finance.

Factor 1: Career Goals

As I wrote in this piece on quitting my 9-to-5 job, I had been dragging my heels on this decision for a while.

Since I started working in the internet industry, my goal was always to pick up the skills and knowledge to build a portfolio of my own profitable businesses.

For ~10 years, I worked for growth-stage startups and a public company.

As a marketer, product manager, and product leader.

By 2023, I felt like I had checked off what I set out to learn in my tech career.

It felt like a natural next step to leverage my skills, knowledge, network, and capital into ownership.

Hence, going from professional to business owner.

Factor 2: Personal Finance

After a decade of working, I had an asset at 33 that I didn’t have at 23:

Financial security.

More specifically, I had achieved my semi-retirement number.

I spent the last decade sufficiently funding my investing accounts.

Assuming a 5% real interest rate compounded over the next 3 decades (until I’m 63), they would cover my traditional retirement spending:

This level of financial security freed me up to take more risk and pursue work I enjoy.

And the work I currently enjoy is:

• Building the online education business I’ve talked about doing for forever

• Writing, teaching, and helping others on money and portfolio careers

• Advising fintech founders & execs on building great products

Other Potential Pathways

I considered a few other options to achieve greater ownership:

1. Start a VC-backed company

2. Join as a startup executive

3. Invest in startups or SMBs

4. Buy and operate a profitable business

5. Invest in real estate

Each option comes with its own trade-offs: