I’ve been waking up at 5:30am recently.

Mornings were never my thing. Yet 33 does funny things to your brain.

Are you a morning person? DM me your tips.

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

• 🏃‍♂️ How I Decided to Quit My Job (It’s Not What You Think)

• ✅ My 8-Question Readiness Checklist & 1-2 Rule

• 📖 An Entrepreneur Case Study & Financial Runway Calculator

Subscribe | Advertise

FROM OUR LABS

🚨 Refer 3 Friends to Get 23+ Side Hustle Case Studies

Great news — we’ve revamped our Referral Program, so you can unlock access to our Side Hustle Database (valued at $97) for free.

You’ll get 23+ case studies, including consultants, fractional executives, content creators, digital product creators, course instructors, coaches, and e-commerce owners.

Share this newsletter with your friends:

🌱 When I Decided To Quit My Job & Start My Portfolio Career

In December 2022, I quit my 6-figure tech job.

For about a decade, I had worked for growth-stage startups as a product leader, product manager, and even marketer in the early days.

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 businesses.

After taking my time, I finally felt ready.

In this edition, I’m going to breakdown when I decided to transition from full-time tech worker to portfolio career. Included is a practical readiness checklist, case study, and runway calculator.

I’ll first explain why the timing felt right:

Why now?

Honestly, I had been dragging my heels on this life decision.

Here’s why things changed:

• Satisfied with my career learnings - I checked off what I set out to learn in my career 10 years ago: launch 0-to-1 products, grow products, build a high-performing team, get exposure to various industries (edtech, fintech, and SaaS), and work in international markets.

• Had a practice run in 2018 - I quit my job at Dropbox in 2018 to go on a 1-year travel sabbatical. I started a side hustle, then found a job in Singapore in 2020. Things turned out okay. I gained more confidence in myself to navigate the unknown.

• Experimented with side hustles - For 5 years, I had been running side hustles like career coaching, consulting, and even tea e-commerce. I knew I enjoyed having control over my schedule and gained more confidence in my skills.

• Funded a 12-month runway - Throughout Covid, I saved a nest egg amounting to 12 months of runway to give myself more flexibility. More on the finances later.

Yet, I was still torn. I had several reservations, including:

• Went against reasonable advice - More conservative advice says to grow your business to replace your salary before you quit. I had side hustle income, but it only covered partial living expenses. This gave me a bit of anxiety.

• Major upcoming personal expenses - I was proposing to my now-wife right after quitting my job. So if it all went smoothly, I’d have wedding expenses (we celebrated with family in Singapore, Sydney, and Shanghai).

• Fear of running out of money - This was probably my biggest fear, given I wasn’t planning on raising money. I was self-funding my business operations.

Hence, I was feeling 50/50.

Here’s what pushed me over the edge:

How I decided to pull the trigger

If you read career advice on social media, it tends to fall into 2 camps:

1. Burn the bridge and don’t look back. YOLO.

2. Start on the side and don’t quit until you’ve replaced your salary. Or you’ll regret it!

I chose a 3rd option: