How I Made My First $100K on Upwork From India
After failing in multiple startups and hitting rock bottom, I somehow found my way into freelancing. But the journey was far from smooth.
Around three years ago, I started my life as a freelancer.
At the time, it wasn’t exactly a glamorous choice for me. I was the proud CEO of two startups (which, by the way, weren’t making any money).
But somehow, I was still very proud of that title.
Looking back now, I realize my ego was doing most of the talking.
I still remember once when someone asked me,
“Are you a freelancer?”
My mind immediately reacted:
“How can you ask that? I’m a CEO.”
Funny how the universe works.
Today I don’t run any startups.
But according to Upwork, I’m now among the top 1% of freelancers in the world.
Discovering Upwork:
I first heard about Upwork when I was in college around 2015.
At that time, I didn’t really understand what freelancing was. I just knew that people around the world were making money online by building websites.
Back then, Upwork actually had tests and exams before you could join certain categories on the platform. Yes, it sounds strange today, but that was how it worked.
I remember trying to pass those exams — and honestly, I probably Googled half the answers just to get through them. 😂
I was excited about the idea of building websites for clients, but the competition was already intense. The web development category was crowded with freelancers from all over the world, and I ended up sitting on the waitlist for a while.
Eventually, life moved on.
I forgot about freelancing and focused on building startups instead.
Over the next five or six years, I tried to build companies. Unfortunately, none of them worked out the way I hoped. The startups failed, and I eventually found myself stuck — dealing with debt, pressure from family, and a lot of uncertainty about what to do next.
Years later, I came back to Upwork and created a fresh profile.
This time there were no exams, but there was far more competition than before.
Still, I decided to give it a real shot.
Three years later, things look very different.
I’ve crossed $160,000 in total earnings on Upwork, became a Top Rated Plus freelancer, and was eventually accepted into the Expert-Vetted program, which represents the top 1% of freelancers on the platform.
In the last 12 months alone, I made $65K+.
Sometimes I think about my younger self — the one dealing with debt, pressure, and uncertainty.
If I could go back and teach him everything I’ve learned about freelancing, I would.
In many ways, Freelancer Stories is my attempt to do exactly that.
I hope that by sharing these experiences, it helps someone else move forward in their freelancing journey.
The journey definitely didn’t look like this in the beginning.
Even though it has been about three and a half years now, my first year on Upwork was far from impressive.
If I remember correctly, I made around $8,000 in the entire first year.
Going from $8K a year to $65K a year didn’t happen overnight. It was a long process filled with self-doubt, uncertainty, and a lot of learning.
There were many nights where I stayed up late in front of my computer, trying to figure things out — watching tutorials, reading articles, and learning from whatever free resources I could find online.
But there was always one thought pushing me forward:
If you can make your first $1 online, you can make $100,000.
That belief kept me going.
Around that time, I would often see freelancers online branding themselves as “six-figure freelancers.” At first it felt distant, almost unrealistic.
But slowly it became a target in my mind.
Another milestone I dreamed about was making $5,000 per month. For someone living in India, that felt like a huge number.
Interestingly, I only crossed that milestone about two months ago.
Looking back, those early struggles — the late nights, the doubts, the slow progress — were actually the foundation that made everything else possible.