I’m taking a break from my normal grammar-related content to share a bit of my story. This is how I became a freelance proofreader and editor. I hope it inspires and motivates you. -Jon
COVID screwed up my life—in a good way.
In January 2021, I was a quality manager, 15 years into my career. I had spent most of those years working for a large aerospace company, but I had become disillusioned by the insane drive for profits over safety and quality. I left that big company for a small business, thinking that a change of pace would be good for me.
But that’s not what happened.
The small business had its own set of issues. While there was certainly a lot more care about the customer over profits, I did not feel any real autonomy or say regarding how things worked.
All that aside, it was my internal state that was still broken. I still dreaded Sunday night, because Monday morning was just one bittersweet slumber away. I still hoped and wished and prayed every day on the drive into work that today would be the day I could quit. I still came home exhausted and depressed by the Herculean efforts to do my best at a job and in a career I had lost passion for a very long time ago.
All that aside, my internal state was still broken. I still dreaded Sunday night, because Monday morning was just one bittersweet slumber away.
Then COVID hit.
The small business I worked for sold a very niche product, the kind that is nice to have but easy to eliminate from a budget when the money dries up. My company lost its major revenue stream almost overnight. The owner held on as long as he could, but eventually the layoffs started. I wasn’t the first to go, but on a cloudy Friday afternoon in January 2021, I was called into the conference room.
They told me that my performance had nothing to do with it—they literally couldn’t afford me anymore. Everyone was friendly and felt bad that it had come to this, but that didn’t change the fact that I had to pack up my boxes and leave the premises.
After the shock wore off, I found that I wasn’t sad about being laid off. In fact, I soon realized that other than the paycheck, I didn’t miss my job at all. Rather, I began to smile more. And laugh. After several months, the man I saw in the mirror each day looked about five years younger.
I began to smile more. And laugh. After several months, the man I saw in the mirror each day looked about five years younger.
I began to collect unemployment while I tried to figure out what to do next. Thankfully, with the massive amounts of government pandemic assistance, I had some time to rest and then really think about the future.
I knew that I did not want to go back to another job in Quality. And for that matter, I didn’t even want another corporate job. I was long since burned out on useless meetings, endless PowerPoint presentations, and daily commutes.
One day, I said to myself, “Hey, I like proofreading and I think I’m pretty good at it. I wonder if anyone would pay me to do it?”
I’m just old enough to remember life pre-internet. I can still hear the series of noises the dial-up modem made. I lived through the birth (and subsequent death) of services like Prodigy and AOL. Facebook wasn’t even a thing until after I graduated from college. I had literally grown up alongside the internet.
I thought, therefore, that I was pretty hip to everything it offered, but it turns out that while I was slowly dying on the inside each day at my traditional job, another group of people were busy figuring out how to monetize being online.
I started researching the idea of freelance proofreading. I quickly found out that it’s actually on virtually every list of online side hustles. This was a good sign, I figured, so I kept searching and eventually stumbled across a site called Upwork.
Upwork, if you don’t know, is an online platform that connects clients with freelancers. I had no idea something like this existed, but the more I looked into it, the more I thought, “I should give this a try.”
The more I looked into it, the more I thought, “I should give this a try.”
There are a lot of Upwork haters out there. If you don’t believe me, just google it. And it’s true that a number of people have had bad experiences on the platform. It’s also true that Upwork takes a cut of your pay for the services they provide.
But for a guy like me, Upwork is a Godsend. Here was the chance to do a 180 in my career. I could work from home with flexible hours, choose my clients and my rate, and do something I actually cared about and—dare I say it—enjoyed? Sign me up!
I quickly found out that starting over in a new career is like climbing a ladder—you have to start at the bottom rung.
I quickly found out that starting over in a new career is like climbing a ladder — you have to start at the bottom rung.
After setting up my profile, I began submitting for proofreading jobs. It took somewhere between 10 and 15 bids before I found work, but I did finally land my first paying gig. A company hired me to proofread user reviews for slightly more than minimum wage. Around the same time, a client hired me to edit their academic paper—and this student was a particularly bad writer, I found out. It took hours to get his paper into shape, all for a grand total of $10.
I kept the user-reviews gig but quickly decided against editing any more students’ papers. I managed to get another contract a month or two later proofreading SEO blog posts. This time the pay was a little better, but I still was far from raking in the money. For the first half of 2021, in fact, I was pulling in just a few hundred dollars each month.
But I kept at it, believing that I was slowly building inertia. And over time, I slowly added to my workload. In September I saw my first big jump in income, and in the last quarter of 2021 I managed to earn four figures monthly for the first time.
I slowly but steadily worked day in and day out, focusing on quality and professionalism while slowly upping my rates, and by February 2022 I had doubled my monthly income from Q4 2021, a new standard that held through May.
And then it happened.
I don’t know what it was about May. Maybe I had accrued enough hours on Upwork. Maybe my five-star client ratings finally started bearing fruit. Maybe it was just luck of the draw or a change to an algorithm.
Regardless, I began to see a dramatic increase in offers. Clients were now reaching out to me. I had so many offers for work, in fact, that I got to pick and choose the best ones while regretfully declining the rest.
I began to see a dramatic increase in offers. Clients were now reaching out to me.
My income from May to June more than doubled from its previous high-water mark. I went from just a few long-term clients to a half-dozen almost overnight. And for the first time, I could really consider myself a full-time freelancer making actual, real money.
I’m far from done, however. In the course of the past year and a half, I’ve realized that there are many more opportunities out there than I ever thought possible. I have future plans to scale the business, and all the while I’ve been slowly working on adding multiple other income streams.
My story is really an experiment where n=1. That being the case, it’s impossible for me to tell you what all the other internet voices say: “You can achieve unparalleled success just like me!”
But I can share with you my story in the hope that it inspires you. One thing I can tell you that I feel my story has undoubtedly proven is that results require action—and action requires faith.
I think my story also points to the fact that building a successful business often takes time. I took whatever small jobs I could get—for almost no money—for a year and a half before I was finally able to position myself in a good place. Today I can take on jobs I want while charging a rate that accurately reflects my value, but it took a long time and a lot of work to get there.
So if you’re like I was in early 2021, you have probably read dozens of stories of people leaving the corporate world for a freelancing or entrepreneurial career. But most of them are sensationalized and make it seem like the transition is an easy road to riches. It’s not. I’ve put in a lot of time and effort, and I still make considerably less than what I did as a quality manager.
Most of these types of stories are sensationalized and make it seem like transitioning to freelancing is an easy road to riches. It’s not.
But the transition can be a rewarding one nonetheless. I have complete control over my time. I can drop a bad client at a moment’s notice (although thankfully, I haven’t had to do that!). I have almost no meetings, and I get to do meaningful work. I can potentially grow my business (and therefore my income) over time in ways that I could never do in a traditional role. And I can do all of it while sitting on my couch in my pajamas if I so choose.
In the end, the last several years have certainly not been easy — for me or for anyone else —but I am thankful that COVID screwed up my life. If it hadn’t, I would have never found such an amazing opportunity.
If you need expert proofreading and editing, we can help. Book a call today and let’s have a conversation!


