7 Lessons I’ve Learned in 7 Months of Freelancing

Courtesy of Quino Al via Unsplash

Five years ago, my boss told me I had become too expensive to employ. The economy where his niche business operated was taking too long to right itself after the recession, so to make it work something had to go.

That something was me.

A woman pushing 50 is not in a superb position to command a high wage these days, so after two years of unsuccessful job hunting, and a move across the country to curb expenses, I decided to try my hand at freelancing (if no one else would hire me I could at least hire myself, right?). Everything I’d read suggested I could be successful in less than a year.

I didn’t think I’d make a $100k in my first year, or even $50k. But I thought I’d make something. In 7 months of full-time freelancing — pitching, researching, and learning the trade for nearly 16 hours a day — I’ve made…well, a lot less than I’d hoped.

Here’s what I’ve learned so far:

The market is crowded. Everyone’s trying their hand at freelancing. In fact, according to Freelancer’s Union, there are 57 million freelancers in America, including 47% of the powerhouse millennial generation. A huge percentage of that group is willing to work for next to nothing. That doesn’t mean it’s impossible to find success as a freelancer, but it does mean that competition is tough and it’s going to take some resilience, business savvy, and a big savings account to make it work.

Niching isn’t everything. There’s a lot of advice out there about finding a niche. “You can’t be successful as a generalist; it just can’t happen.” The ubiquity of the message is staggering.

A few months ago, I joined a writer’s group. They suggested I drop the “VA” side my Copywriter/VA business and rebrand myself solely as a freelance writer. I had picked up my first two clients within 30 days of becoming a VA, but the argument was that writers earn a lot more. Since writing was mostly what I was doing anyway, I bought in. I moved my website to a new writer-focused domain, changed my logo and email address, and began an aggressive marketing campaign targeted exclusively to writing clients in the real estate industry.

I haven’t picked up a new client since.

Update: I have since reversed my branding decision, opening my field of prospects to include all small businesses, not just the real estate market. Almost immediately, I picked up two wonderful new clients and am in talks with two very promising prospects — further evidence that niching isn’t always the right answer.

Everything’s an opinion. While I strived to be the best I could at what I did, I heard a lot of conflicting advice from people who thought I was doing it wrong. It didn’t really matter what I was doing, someone was always there telling me to do it differently. When I followed their advice, someone else would come along and tell me that was wrong, too.

All most of those people were really saying is this: “You’re doing things differently than I do (or would do if I were brave enough to freelance).” So I’ve learned to take advice with a grain of salt and realize that just because something worked well (or didn’t work at all) for someone else doesn’t necessarily mean I will have the same outcome. It’s OK to carve my own path.

History is written by the winners. The internet is full of freelance success stories. Read too many of them, and it’s hard not to feel invincible — like freelancing is a silver bullet — and for some, it certainly seems to be.

Harder to find are the stories of the thousands of freelancers making less than $10,000 per year. I found this rare and very brave post by Alysa Salzberg who tells the other side of the story. I caught up with Alysa to find out where her business is now.

“Since writing that Medium post in 2016, I’ve had some ups and downs, some really great gigs, and even netted a very well-paying occasional client. I was even hired by a small publishing company to write a nonfiction book that apparently sold pretty well (relatively speaking — again, this is a small publishing house). But none of that has made my freelance writing income skyrocket or remotely approach the enthusiastic, sure-thing high earnings so many writing websites seem to promise.

“I also continue to experience the usual reversals that I know freelancers in all fields deal with: clients who can’t fulfill their promises of regular work or a certain rate, due to their own business or personal issues. So, to sum it up, although my earnings will be a bit higher this year (yay!), I’m not earning anything close to what those promising websites and maybe the general public would think.”

Alysa is not in the minority. According to Freelancewriting.com, 65% of the writing community is made up of writers earning less than $10,000 a year. Contently and Venngage agree, showing similar stats going back to 2015.

It’s easy to get mired in information overload. Like most new freelancers, I Googled a lot of questions. I went down a lot of rabbit holes filled with conflicting answers and shades of grey. I often felt like I was lost in a hall of mirrors: I saw myself reflected in every scenario and had a hard time recognizing the right way out.

I decided I had two options:

· Try everything and see what works best. I did this for awhile. It was time-consuming and I hit a lot of dead ends, but I learned a lot and stumbled onto a few ideas I wouldn’t have thought of on my own.

· Recognize my strengths. It seems obvious now, but striking out as a freelancer after decades in an office had me convinced my current skillset had no value. My advice to new freelancers: solving an expensive problem for someone is the surest way to get paid for what you do, regardless of your prior work history.

It’s cheap to get in, but the mistakes are expensive. I owned a shop once. It was a cute little thing — a pet boutique. I brought years of experience to that project so when problems arose, they were of the $15 and $20 variety. Since lessons were quick and cheap, it was easy to course correct and move on. As a freelance writer, it’s a different game. A mistake here can — and often does — result in the loss of an entire project. There’s no “sorry, ma’am, let me reorder that for you” in freelancing. When you blow it, the client moves on.

Case in point: I have a client who throws me work every month. They’re not big jobs, but they’re super fun and I love doing them. Last month, the client contacted me to work on a much bigger job: a 30-page high-visibility, high impact sales project. I jumped at the opportunity! The client gave me all the details but wouldn’t tell me his budget, so I went to my writer’s group for advice. They recommended I charge $1 to $2 per word, which are top-of-the-line pro rates. I thought about it for a while, then pitched the lower price, which felt right for the value of the product and the effort I would put into it, though it was a lot more expensive than any project I had done for them up to that point.

The result? Not only did the client gasp and go silent, but he gave the project to someone else without even attempting to negotiate.

A lot of projects don’t pay all that much. When Google changed the landscape with Panda and Penguin, it became more difficult to throw $0.03 words on a page and call it writing. Producing cleaner, more valuable information drives the cost of content creation higher because it takes more time and research to create quality, useable work.

Unfortunately, the average business owner doesn’t realize the real cost of a freelancer’s time. Asking for $0.36 per word — let alone $1 — can feel like demanding a pot of gold, even though it’s barely a minimum living wage for someone with a project-based income. Unfortunately, there’s always someone right around the corner willing to do the job for pennies.


Freelancing is not for everyone. Being successful requires a lot of networking and writing a lot of great pitches. It takes almost as much effort to put together a series of $100 blog pitches as it does to apply for a traditional $50,000 job with medical benefits and PTO. And to remain successful, you have to do it every single day.

These are the lessons I’ve learned in my first seven months of freelancing. How has your journey been so far?

If you need a copywriter, I’m available for hire. Find me here: https://roxannewritescopy.com.