I Made Over $125k Freelancing. Then I Started From Scratch.

There is a particular kind of fear that comes with starting over. It is not the fear of having nothing. It is the fear of having had something, and willingly walking away from it.

For four years, I built a freelance career that earned me over $125,000. Then I started from scratch. Not because I had to, but because I wanted to.

And a few years later, I found myself doing it again.

This is the story of why.

My First Career Was Almost Accidental

Before I became a freelancer, I was earning at most ₦15,000 a month as the manager of a printing house at Fajuyi Hall, Obafemi Awolowo University.

My journey to freelancing was not some carefully designed career plan. It was almost an accident.

A friend told me that someone wanted to give him a writing job. I needed money badly, so I told him I could do it too. That friend connected me to the client, Taiwo, whom I already knew.

I got the job.

At that point, I had probably written only two or three Facebook articles about politics. I had no serious background in professional writing.

But I did the job.

Taiwo submitted it to his client on Upwork. The client loved it. Then more work came.

Eventually, I created my own Upwork account before the end of 2019. I started earning in dollars, getting more clients, and eventually employing multiple writers to work with me.

Between 2019 and 2023, I earned over $125,000 from freelance writing.

From the outside, it looked like I had figured it out. But something else was happening. I was becoming increasingly interested in building things.

The Project That Changed My Career

In 2022, I had an idea.

I wanted to build something I jokingly called the "Upwork of Africa."

I had personally experienced the challenges of finding and working with freelancers. I also had friends who regularly needed content writers.

So I started building AfriWrites, a platform designed to connect African freelance writers with clients.

I hired software engineers to build it. They started well. Then they got busy. The project stalled. I had two choices.

I could find another developer to finish it. Or I could learn software engineering myself.

I chose the second option.

At first, I wasn't trying to become a software engineer. I was simply trying to finish my own project. So I started learning. And something unexpected happened.

I began enjoying the process. I was spending more time coding than applying for writing jobs. I was choosing debugging over pitching clients.

I could spend 10 hours a day coding. Sometimes 18 hours.

And I didn't hate it. In fact, I enjoyed it.

This was when I realized something important about myself:

I had not simply discovered a new skill. I had discovered a process I was willing to commit to.

So in 2023, I made the decision to leave freelance writing and fully transition into software engineering.

This was not an easy decision.

I was walking away from something that had already made me over $125,000.

I sold my SUV to create an emergency fund.

And because I knew I was serious about starting again, I decided to start from scratch publicly and honestly. I even made a public announcement about my transition.

I wanted to give myself no hiding place. I was going to learn software engineering. From the beginning.

Again.

Starting From Scratch is Humbling

The funny thing about starting over is that your past does not disappear. But it also doesn't immediately help you.

My years as a successful freelancer did not automatically make me a successful software engineer.

I was still a beginner. I still had to learn. I still had to struggle. I still had to build things that didn't work. I still had to figure out how to get clients.

The difference was that I wasn't actually the same person who had started freelancing in 2019.

I had experience. I had discipline. I had learned how to work with clients. I understood proposals. I understood deadlines. I understood how to deliver value. I understood what it felt like to build something from nothing. I had social capital. I had a track record. I had learned how to learn.

But I still had to start again.

And that distinction would become important later; because starting from scratch is not the same thing as starting from zero.

I Eventually Found My Footing

The transition into software engineering wasn't immediately smooth.

At one point, I was essentially jobless for months.

I worked on local projects, but payments were unreliable. My financial situation became difficult enough that I had to think seriously about what I was going to do next.

But then something happened that reminded me of why I had started in the first place.

In 2025, I had an unexpected opportunity to work with a German software development agency through Upwork. The relationship became the best client relationship of my career.

I started with a $500 milestone. Then the client converted me to an hourly contract at $20/hour. My weekly limit increased from 10 hours to 20. Then 30. Then eventually 40.

At one point, I delivered a prototype over a weekend for a pitch. The pitch succeeded. The client gave me a $500 bonus.

That relationship lasted from May 2025 until February 2026. And it reminded me that starting over doesn't mean you will never succeed again. Sometimes, it simply means you have to rebuild your confidence.

But then, in February 2026, the relationship ended. The client told me the business was struggling because of an economic downturn and needed to reduce costs to zero.

I had earned about $22,000 from that contract. I even offered to take a 50% discount for a few months. But the client still needed to cut the cost entirely.

So we wished each other well. He left me glowing reviews on Upwork.

And I was unemployed again.

The Second Time I Started From Scratch

This time, the feeling was different.

I had already done this before. I had already walked away from one successful career. I had already rebuilt myself once.

But this time, there was a new complication, Artificial Intelligence (AI).

I had started seriously using AI to code through Cursor in December 2025. Before then, I had used ChatGPT for coding questions.

I would copy and paste errors into ChatGPT. Copy and paste code. Ask questions. Get answers.

Repeat.

I thought life was already amazing. Then I started using Cursor seriously, and my perspective changed.

I suddenly saw how much software engineering was changing. And I had to ask myself a difficult question:

What exactly am I supposed to do now?

Should I get a traditional job? Should I go into finance? Should I return fully to Upwork? Should I continue building my own products? Should I combine several options?

I had already spent years building a new career. And now the industry itself was changing rapidly. But I realized something:

I did not want my entire career to depend on one platform again.

I Had Made Over $125k on Upwork. But I Didn't Own Upwork.

This was one of the biggest lessons from my freelancing career.

I had made over $125,000 freelancing. At one point, I had made tens of thousands of dollars in a single calendar year.

I was Top Rated Plus. I had a strong track record.

But I still didn't control my access to clients. I didn't control the algorithm. I didn't control Upwork's policies. I didn't control how much visibility my profile received. And I didn't like the fact that I increasingly had to spend money just to get people to see my profile.

So I decided that if I was going to start over again, I wanted to build something I could control. I needed a lead-generation channel that belonged to me.

That meant social media.

The problem? I had neglected it.

My LinkedIn had over 10,000 connections, but I had little traction. My Twitter wasn't doing much for business. My Instagram had become mostly wedding and family pictures.

I had built a large network. But I had not built an audience. That taught me another lesson:

You shouldn't wait until you need social media before you start building on it.

You cannot plant on the day you want to harvest.

I Gave Myself Six Weeks

By early May, I gave myself an ultimatum. Six weeks.

I would either:

Get a job with a company in Nigeria. Get another job through Upwork. Or launch my own software development agency.

My heart was already leaning toward the third option.

The world was changing. Companies were laying people off. AI was changing software development. And I had become increasingly convinced that I needed to own my own distribution.

But there was one major problem. How was I going to get clients?

I didn't have a proper portfolio website. So I built one. It wasn't beautiful. It wasn't perfect. But it contained my Upwork success stories and showed what I could do.

I also revamped my resume. Not because I was excited about getting a traditional job. I simply wanted to keep that door open.

Then I started thinking about social media. I knew clients could come from there. But I wasn't getting much traction.

So I prayed for direction.

And then I saw a tweet.

It was from "Einstein of Marketing."

The tweet was essentially saying that if you're offering services to businesses and can afford to spend money on social media advertising but aren't doing it, you're leaving money on the table.

Something clicked.

I had seen businesses run ads continuously. I knew they must be getting results.

But because I had made almost all my money through Upwork, I had never seriously considered advertising as part of my own client acquisition strategy.

Now, my situation was different.

I needed clients. I needed them quickly. And I needed a system that didn't depend entirely on Upwork.

So that night, I started working. Within a couple of days, I had created a video ad. My wife helped me shoot and edit it.

I cleaned up my Instagram account. I removed most of the old wedding pictures and moved them to a dedicated account. I kept some recent family posts because I wanted people to see me as a real person and a family man.

Then I launched the ad. Since I started running that ad, I haven't lacked clients.

Yes, plenty of unserious people messaged me. That's normal. But serious clients also came. People who paid well, building interesting ideas. People who had real projects.

Sometimes I pause the ads because I have more work than I want to take on at that moment. Then I turn them back on when I'm ready; and I'm now working on creating a system for scalability.

The ad is bringing clients and attracting more followers. And for the first time in a long time, I feel like I am building client acquisition channels that I could actually control.

And that was the point.

The goal was never to escape Upwork because Upwork was bad. The goal was to stop depending on one platform.

I Have Started From Scratch More Than Once

When I look back at my journey, I realize that the biggest advantage I have isn't that I made over $125,000 freelancing. It isn't even that I learned software engineering.

It is that I have learned how to start again.

I started freelancing from almost nothing. I went from earning ₦15,000 a month to earning over $125,000. Then I left it.

I started software engineering from scratch. I struggled. I learned. I eventually found my footing. Then I lost my biggest client. And I started again.

This time, I didn't simply look for another client. I started building an agency. I started building products. I started building an audience. I started building my own distribution. I started building systems.

And I think this is something we don't talk about enough.

Sometimes, the greatest asset you can build isn't money. It is the ability to rebuild. Because if you know how to start from scratch, you are never truly starting from zero. You carry your experience with you. You carry your lessons. You carry your relationships. You carry your reputation. You carry your scars. You carry your understanding of what didn't work. And most importantly, you carry the knowledge that you have done it before.

So yes, I made over $125,000 freelancing. And yes, I walked away from it. Then I started from scratch. And I would do it again.

Because I am beginning to understand that my life may not be about finding one thing that works and holding onto it forever. Maybe it is about becoming the kind of person who can build something valuable, lose it, learn from it, and build again.

Again. And again.

Until something sticks.

God is good.