Migrating My Freelance Business Off Upwork Was a Nightmare. I’d Do it Again in a Heartbeat.

Three lessons I learned that will save you some major headaches.

Image: Unsplash | Usman Yousaf

I, like many, got my freelance start on Upwork. It was easy to find jobs, connect with clients, and manage my earnings all in one place.

It was also a ticking time bomb.

Due to some shady business practices on Upwork’s part and my desire to stop losing 20 percent of each dollar I made, I decided to move my freelance business away from the platform. What came next was a nightmare that almost made me walk away from freelancing for good.

Today, we’re going to look at exactly what went wrong. Hopefully you’ll learn how to make the process smoother for yourself if you’re looking to go solo with your freelancing business.

That Fateful Day

I had been freelancing as a writer on Upwork for nearly two years before my eyes finally opened. I woke up one morning to find an email from customer service stating that payment from a client I worked with several weeks earlier never went through. Something about their credit card not working, blah, blah.

The next line sent my stomach into my throat.

“The balance of $428.10 will be collected from your Upwork account.”

The problem was, I had already been paid for that work, withdrawn the funds, and had them sitting in my bank account.

Somehow, Upwork expected me to cover the failed payment from the client even though I had already been paid through the platform and completed the job. The articles had long since been submitted and subsequently published on my client’s site. That left me out several hundred dollars and several hours of work.

For the next several days, I went back and forth with Upwork’s “support” team. I quickly learned that the company’s many promises surrounding payment protection and secure transactions were not only empty, but utterly false.

After being told that the $428 would be garnished from any additional income I earned through the site, I made a decision.

I was done with Upwork.

Without much of a plan or another source of income, I typed up a letter to my clients on Upwork. I explained the situation and told them that I’d no longer be conducting business on the platform. I offered to continue our relationship provided they paid me through Paypal or Stripe.

Then I waited.

Nightmare #1: Client Panic

One thing you pick up on as a freelancer is that clients crave stability. Pulling the rug out from under them isn’t usually a good idea.

Alas, that’s exactly what my naïve self had done.

Although I had also been taken off guard, spreading that to my clients made for a tumultuous few days.

One by one I started receiving responses to my letter. Most of the clients I had been working with for a few months or more were happy to move away from Upwork. It meant less fees for them in the long run. However, the majority of clients that I hadn’t established a long-term relationship with were hesitant.

Of course, that’s understandable. Some were forced to stay on the platform by the higher-ups at their company. Others didn’t want to step away from the escrow model that Upwork provides.

Ultimately, I was able to transition about 60 percent of my clients off the platform within the week. Although that number sounds good, imagine what your life would look like if 40 percent of your income disappeared overnight.

I didn’t know where to go next.

Cut off from a large portion of my income. Unsure of how to find new clients to replace it. Scrambling to put together a process for invoicing, emailing, and delivering content to the clients that moved with me.

That’s where I found myself.

It’s also the nightmare I lived through for the next several months as I worked to get my feet under me once more. I was now an independent freelancer, running my own show without any rehearsal.

The issue wasn’t my decision to move away from Upwork. It was the timing of it.

Had I been more rational, I could have been much more prepared for the transition. In turn, I would have invested more time into newer client relationships in hopes of swaying them. I believe more clients would have come with me had I taken this approach.

Although taking my time would have meant (unfairly) losing that $428 as new earnings rolled into my account, that figure looks tiny compared to the 40 percent of clients I lost in the transition.

Lesson: Don’t scare your clients away with a hasty transition. Take time to build a relationship and make a gradual transition.

Nighmare #2: A Dry Ocean

Have you ever been surrounded by opportunities yet unable to capitalize on any of them? As the dust settled in the first weeks following my leap away from Upwork, that’s where I found myself.

I knew there were plenty of clients looking for a writer. What I didn’t know was how to successfully connect with them.

I had become far too reliant on Upwork’s curated feed of job postings.

As a novice freelancer, I never had to work to find jobs. Upwork had brought them all to me. Although they were lower-paying than they should have been, they practically fell in my lap. Networking and making connections were foreign concepts. I hadn’t ever made a cold call.

Can you guess what happened next?

I learned how to make a cold call. Quickly.

Desperate to find a way to repair my shattered income stream, I worked tirelessly on the soft skills I neglected for so long. I made countless calls to local businesses offering to write their blog posts or revamp their web copy. I became active on social media, connecting with fellow writers and potential clients alike.

Unsurprisingly, I wasn’t the best at this. Over time, though, I started to see results. A one-off press release here. A two-week blog post contract there. Soon I found myself with multiple repeat clients that I had never interacted with on Upwork.

Of course, that opened the door for a new challenge — negotiating.

On Upwork, your clients come to you with a budget that’s out in the open and often rather rigid. In the independent world, things are never that clear.

I was forced to learn my way around a negotiation on the spot. For those in a similar situation, I highly recommend Carol Tice’s article on Make a Living Writing, which I’ll link here.

The first few jobs I got on my own, I seriously undervalued my writing. Those clients got an incredible deal because I didn’t know how to negotiate.

The first time I countered a client’s offer with a higher figure, my heart nearly exploded. To my surprise, most clients were agreeable with the higher figure — even if it exceeded their original budget. That knowledge has since become a fundamental part of my business strategy when I’m discussing a project with a new client.

I’ve since learned my worth as a freelancer and know how to negotiate the terms of a job to reflect that.

Of course, had I done so sooner, my transition away from Upwork would have been a lot smoother (and profitable).

Lesson: Before migrating away from Upwork, make sure you’re prepared with the right tools. Practice things like networking, cold calling, and negotiating.

Nightmare #3: Logistical Lunacy

How does a platform like Upwork get away with charging freelancers a 20 percent fee on almost all earnings? By making life easier. Or at least they say so.

For new freelancers, it’s incredibly easy to fall into this trap. When you don’t know what you’re doing, a platform that makes it easy to manage everything in one place seems perfect. Upwork lets you communicate, bill, and negotiate in one “safe” place.

Though it’s clear the company puts its bottom line over the success of its freelancers, the platform itself is pretty solid. From a logistics standpoint, it does make life easy.

I found that out when I stepped away from the platform. As I briefly touched on, I needed to figure out how to do everything that Upwork facilitated on my own. To ensure I didn’t leave my clients hanging, that meant a lot of emailing in those initial weeks.

Of course, that took a lot of time. Time that I could have better spent writing.

I also struggled to keep track of what projects I had due. On Upwork, there was a tab just for that. Eventually, I found a handy tool called Trello that helped me keep track of my deliverables for all my clients. Until then, however, I had a wall of sticky notes and far too many pens rolling around on my desk.

Once I got something delivered, along came the invoicing.

Again, Upwork did that at the push of the button. Now, I had to come up with a standard format for my invoices, remember to send them on time, and (most importantly) remember to verify if they’d been paid. I’ll share some tips on how I manage this process in a later article.

Developing that process took me several months before I felt comfortable. Until then, I constantly worried that I would miss something or bill a client incorrectly. Perhaps that’s the perfectionism talking, but at the time, it was yet another thing on my plate.

Lesson: Work out the logistics of managing your business away from Upwork before you actually leave it. You’ll have much more time to focus on the work at hand and finding new clients.

Wrap-Up

Phew.

Is anyone else stressed after that?

As you may have gathered, transitioning my freelance writing business away from Upwork was a nightmare. That being said, doing so was one of the best decisions I’ve made.

Becoming independent has allowed my career to blossom into something truly special. Instead of grinding out content for faceless companies on Upwork, I now work with a roster of clients that I’m proud to have relationships with.

Likewise, I’ve built a system to manage my business that works for me. In fact, I’d wager it’s even more efficient than Upwork’s all-in-one solution.

Of course, the best part is that I have yet to be screwed over by my business platform because, well, I am my business platform.

With all this said, I do wish I would have done things slightly differently. By taking the time to plan, prepare, and organize, I could have made the transition a lot easier.

If you’re in the position of wanting to move away from Upwork, I envy you. Not only are you about to embark on the most exciting part of your freelance journey, you get to do it the easy way.

Go chase those dreams, fellow freelancers! Don’t be afraid to do you.

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🍻 Cheers! 🍻

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Cody DeBos

Cody DeBos

Freelance Writer | RN-BSN | YA author | MTG Player | LoTR geek | Meme Connoisseur | Owner of Bolt the Bird | Business inquiries to: cody@codydeboswriting.com