I Just Made $700,000 on Upwork—and Wrote a Book About It

I just hit a wild milestone, one I never thought I’d achieve: I’ve officially earned over $700,000 on Upwork. To celebrate, I decided to do something big—I wrote a book about my journey. It’s called The 10-Day Upwork Jumpstart Guide and Workbook— now available on both Freelancer Files and Amazon—and (biased as I am), I think it’s the best Upwork book out there.

How I Got Started in Freelancing

Freelancing has been a part of my life for as long as I can remember.

My first gig came out of nowhere in 2005 when I was just 19. I had just left my part-time job in the Copy and Print department at OfficeMax. One of my regular clients, who had grown accustomed to working with me, tracked me down through my college and offered me a freelance gig.

Back then, freelancing wasn’t a career—it was something I did on the side for extra cash. I wasn’t trying to build a business; I was busy chasing a full-time corporate career while picking up small freelance jobs when time allowed.

Most of my early gigs came from word-of-mouth referrals, and I charged peanuts—$20 here, $50 there—for quick tasks.

Over time, my client base grew organically, and I started raising my rates.

Things slowly progressed over the years, like an untended but resilient fruit-bearing garden.

By 2017, there were some months in which my freelance income doubled that of my corporate salary. That’s when my husband staged what I like to call an “intervention.”

Making the Leap to Full-Time Freelance

My husband, an entrepreneur at heart, had been telling me I should go all-in on freelancing for years. I, on the other hand, was terrified of losing the stability of a full-time job.

We argued about it for months after that intervention at dinner.

Sure, the money seemed great. But the risks were just far too high.

That is, until the day my boss made the decision for me, and I ended up quitting on the spot in a blind fit of sudden rage.

I remember that day well.

I had just finished working nine days straight, including a holiday double shift. I was exhausted. My boss called me into her office and handed me a manila folder with something she called an “improvement plan.” The plan required me to spend even more time at work—without a penny of extra pay.

In that moment, I realized I was done. I stopped her mid-sentence and said, “I’m sorry, my heart just isn’t in this anymore,” and walked out.

I went home, invited my husband out for margaritas, and told him I was finally ready to give full-time freelance a shot.

Why Upwork Worked for Me

At the time, I had enough clients to get by, but I knew I needed more work to make freelancing sustainable long-term. So I took two big steps:

1. I emailed every client I’d ever worked with to let them know I was going full-time freelance and was available for work.
2. I signed up for every freelance platform I could find: Fiverr, Thumbtack, Freelancer.com—and, of course, Upwork.

For me, Upwork quickly became the game-changer. While other platforms seemed to rely on clients finding me, Upwork let me take control by applying for gigs myself.

It wasn’t an easy start. I applied for dozens of jobs before landing my first gig—a $10 vector tweak. But that tiny job, and the five-star review it earned me, became the foundation for everything that followed. Over time, those little jobs turned into big ones, and eventually, I hit the $700,000 mark.

Why I Wrote a Book

First, let me start by saying, I receive no compensation from Upwork for promoting their business on this website, encouraging freelance signups, or writing my book—though I certainly wish I did (Upwork, please sponsor me!).

Nor do I make a ton of money off this blog, nor do I expect to make a ton of money off the book.

So why do I do it?

Over the years, I’ve been fortunate enough to have my story featured in publications like Business Insider and Refinery29. These articles brought a lot of attention my way, and people started reaching out with questions about how they could replicate my success.

To help, I started a blog in 2021 (originally MorganOverholt.com, now FreelancerFiles.com). It was a great way to share tips and save myself from answering the same questions over and over.

While the blog has earned me a little money over the years—money that pales in comparison to my freelance income—the real reward has been the joy of helping others.

When I hit the $700,000 milestone, I realized it was time to take things to the next level. That’s why I wrote The 10-Day Upwork Jumpstart Guide and Workbook.

What’s in the Book?

The book is a step-by-step guide for freelancers who want to succeed on Upwork. It covers everything you need to know, including:

• Optimizing your Upwork profile and portfolio
• Writing winning proposals
• Pricing yourself competitively
• Landing your first job
• Scaling your freelance business

I also share the mistakes I’ve made so you can avoid them, and the exact strategies that helped me win big contracts—including the proposal I used to land a $158,000 gig (my biggest to date).

The workbook component helps readers set goals, track their progress, and stay motivated.

Get Your Copy

The 10-Day Upwork Jumpstart Guide and Workbook is available now on Amazon and FreelancerFiles.com. Whether you’re brand new to freelancing or looking to level up, I hope it helps you reach your own crazy milestones.

PS: Here’s a present for making it all the way to the end of this article–enjoy 15% off your copy of The 10-Day Upwork Jumpstart Guide and Workbook only on FreelancerFiles.com with promo code ARTICLE15.

Here’s to your freelance success!