My First Website Paid Me $700. Here’s What Happened Next.
If you’re thinking about starting a freelance web design business, or you’re already in the early stages and wondering if it’s supposed to be this hard — this is for you. I started my Squarespace web design business in March 2020 with no portfolio, no clients, and a lot of doubt. What followed was three months of pitching into a void, getting ghosted on my first project, and then landing four clients in three weeks. Here’s what that actually looked like.
It was March 2020. COVID hit and I got furloughed.
For many people, this was their fear. For me, it pushed me to do something that had been on my mind for a while.
I was in a sales job that never really felt like me. I needed to ask myself: what’s next?
I knew I wanted to do something creative. I started exploring. Should I work as a freelance marketer? Around the same time, a friend started his own real estate agency. I offered to build their website. Something sparked. Through the years, I was always the person friends and clients called when they needed a website. Could this be it?
Then someone I knew said something that stopped me cold.
“There are so many web designers out there who are younger than you and willing to charge less. Do you really think this will work?”
That question stuck in my head.
So instead of going to people who knew me, where failing would have felt very public, I went somewhere no one knew me at all.
I got on Upwork.
The Safe Place to Start Over
Upwork felt right. It was a place where I could start fresh. No one knew my past. I just had to let the work speak for itself.
What I didn’t expect was how competitive it would be. Every job posted gets 30 to 50 proposals. You’re not just competing on skill. You’re competing on price, on speed, on whether the client even opens your message before they’ve already decided.
So I started low. My first website paid me $700. It wasn’t much. But it got me in the door.
Then I pitched. Every single day. Ten to fifteen proposals a day including weekends. An hour or so each morning. No results for three months.
I Got Ghosted on My First Project
My sales background helped a lot in those early months. I knew what rejection felt like. I had thick skin. I understood that most pitches don’t land. The ones that do are the ones you kept sending.
Three months in, I got my first project.
The client was great. We had a good start. But she got cold feet, paid half upfront, and then went quiet. No explanation. Just gone.
Three months of pitching. And the first one ended with me getting ghosted.
The doubt hit hard. I sat with it for a few days. I thought about going back to looking for a full-time job.
That voice from earlier came back. Maybe she was right.
But I had no other plan. And honestly, that was the best thing that could have happened. It forced me to keep going.
Four Projects in Three Weeks
Two months after getting ghosted, I landed four projects in three weeks.
I still don’t fully understand the timing. That’s just how Upwork works sometimes. Long dry spells, then a flood. But I was ready because I never stopped pitching.
I charged between $1,000 and $1,500 per project. Not a lot. But I treated each one like it was worth ten times that. I went above and beyond. I communicated more than expected. I stayed late. I revised until it was right.
All four clients left great reviews.
That was the moment things shifted. Those reviews became my portfolio. That portfolio opened more doors. I kept pitching, kept delivering, kept collecting reviews. And the business grew.
What Upwork Actually Is
I hear people say Upwork is too competitive. Rates are too low. Clients are difficult. Some of that is true.
But here’s what most people miss. Upwork is not a content platform. You are not posting and hoping someone notices. You are talking to real buyers. People who opened their laptop today to find someone who does exactly what you do.
For someone just starting out with no audience and no portfolio, that is one of the most direct paths you can take.
Today I am top rated on Upwork. Some of my best clients have come from there. Projects worth $5,000, $7,000, $8,000. It took time and consistency to get here. But it all started with one pitch at a time, from zero.
If you haven’t given Upwork a real try, I’m not saying it will be easy. I’m saying it is real. The buyers are there. You just have to keep showing up long enough to find them.
My first website paid me $700. That number embarrassed me for a long time. Now it just reminds me that every business starts somewhere. The only one that truly fails is the one you never start.
Shawn
Thinking About Starting a Freelance Business?
Starting from zero is the hardest part. No portfolio, no clients, no proof that it’s going to work. What I can tell you after six years is that the proof comes from doing the work, not from waiting until you feel ready.
I’m a Squarespace web designer based in New York, working with small business owners and first-time entrepreneurs across New York and beyond. If you’re looking for someone who’s built a business the hard way and brings that experience to every project, I’d love to connect. Reach out through the contact page to start the conversation.
