From Side Hustle To $200k : My Freelancing Story On Upwork

From boredom to $200,000 on Upwork - My Accidental Freelancing Journey

Back in 2019, I moved from Shanghai to Hong Kong for work. It was a new city, new culture, and I had no friends around. The first few months were spent figuring out the basics-transport, neighborhoods, and daily life. But soon after, boredom kicked in.

Weekdays after work and weekends felt especially long. My colleagues often invited me for hiking trips, but at that time, hiking sounded boring. I needed something else to fill my evenings.

My “Uber Walker” Phase

After exploring different options, I stumbled upon Uber Eats (Walker)-yes, delivering food without a bike or car. In my free time, I’d log in, accept orders, and start walking. It turned out to be fun!

I was discovering hidden cafés, high-end neighborhoods, and corners of Hong Kong I would have never visited otherwise. My family, however, was puzzled- “Why are you doing this? You don’t need the extra money.” But it wasn’t about money-it was about killing time and not feeling lonely.

One hilarious story - I once had to deliver to a residential estate at the top of a hill. I started walking up but gave up halfway. Not wanting to risk a bad rating, I booked a taxi to complete the delivery. End result? I lost money on that order-but got the 5-star rating. 😅

Uber Eats kept me busy for a few months. But like all things, I eventually got bored.

The Upwork Experiment

One day, a colleague mentioned freelancing and introduced me to Upwork. He even showed me his profile and earnings, which motivated me to give it a try.

I created my profile and started sending proposals. At first, it was rough-no responses, no jobs. I had no idea how to price my skills, so I underbid just to get started. Finally, I landed my first job for $7. Completed it, got a 4/5 rating, and felt unstoppable.

Soon, I did a $125 project, then another, and another. Each job taught me something new. Unlike Uber Eats, freelancing wasn’t just about time-pass-it was helping me learn, gain exposure, and build confidence in my skills.

From Side Hustle to Real Income

At first, Upwork was just a way to spend my free time. Then it became-

• Time pass + extra cash
• Covering monthly expenses (excluding rent)
• Covering rent itself
• Finally, saving 100% of my salary

That was a game-changer. Eventually, I started getting repeat clients. To my surprise, some clients would even wait for my availability instead of hiring someone else. That’s when I realized the value of doing quality work.

My Simple Upwork Strategy

I never wanted to sell a freelancing course, but here’s the strategy that worked for me-

• Apply only to clients from high-paying regions (US, Canada , Europe, Australia).
• Target jobs with less than 5 proposals.
• Log in and apply when competition is asleep (early mornings in my timezone).
• Avoid screen-share jobs on client systems (too frustrating).
• End jobs politely at the first red flag.
• Never juggle multiple jobs at once-quality over quantity.
• Always share best practices, even if clients don’t ask.

Following these simple rules, I made my $200,000 on Upwork.

Balancing Work, Hiking, and Life

Meanwhile, I finally gave in to my colleagues’ constant hiking invitations. Best decision ever! Hong Kong turned out to be a hiker’s paradise-trails starting in the city and ending on stunning beaches. Hiking became my weekend ritual.

With new friends and weekend hikes, I started spending less time on Upwork. Yet, clients began inviting me to jobs instead of me applying. That shift felt huge.

Later, I secured a long-term hourly engagement with a client. Eventually, I proposed a retainer model-getting paid for minimum hours whether or not there was work. The client agreed, and that became a stable income stream.

The Bigger Picture

Freelancing in my spare time, while saving my entire salary, accelerated my journey toward FIRE (Financial Independence, Retire Early). What started as boredom with Uber Eats evolved into a freelancing career that gave me freedom, money, confidence, and skills.

Looking back, I smile at the journey-from losing money on a food delivery to earning over $200,000 online.

And it all began because I was just… bored.