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How to Start a Freelance Writing Business in 2019: 3 Tips for Your First Year



Photo by Ross Findon on Unsplash

A friend emailed me yesterday to ask about breaking into freelance writing. He passed along a few questions about how to get started, set pricing, and find clients.

I had fun answering his questions and thought some of the material might also be helpful to others. I put together three points and some helpful resources that I wish I'd learned about earlier in my copywriting career.

Hopefully they help you get ahead.

Here's what I've learned from 3 years of full-time freelancing:

1. Play the long game

Freelancing snowballs. The early months can be very hard, which is good to know before you jump in. The get-rich-quick, click-bait advice you see all over the internet simply doesn't translate to reality for most people.

If you want to freelance, expect to play the long game.

In the early days, you'll seldom get to be choosy about who you work with or what projects you take on. You'll take whatever lands in your inbox.

But not much will land in your inbox. You'll have to get scrappy to earn every gig. (More on landing gigs below.)

There's a lot of thumb-twiddling as you wait for opportunities to come your way. But, if you can make it past that initial investment period, one day things get simpler, work gets busier, and everything becomes more fun.

The flip from arduous and boring to flexible and exhilarating felt very sudden to me — almost like the switch occurred overnight, though obviously it didn't. It took me about a year before I truly felt like I was earning a small living.

If you're willing to endure the early insecurities, fears, learning curves, and boring projects for a while, chances are high you'll eventually reap the reward of the most fulfilling job ever.

2. How to find your first clients

Look within your network

I found my first clients by asking within my network. I happened to have two friends who owned local creative agencies. When I told them I was freelancing, one friend sent me work directly and the other recommended me to one of their clients, who hired me for several small projects.

If you have friends in the PR, creative, or advertising space, contact them. Mention that you're starting to freelance and "if you happen to know anyone looking for a content writer..."

Past employers are another great opportunity. When my father started as a full time logistics consultant, he didn't just step into his boss's office and resign. Instead, he offered to make his employer a client. They accepted, which meant my dad could continue doing a lot of the work he enjoyed, while leaving behind the tedious stuff he didn't like about his previous role.

Plus, he negotiated to keep his office. All they did was change the plaque on my dad's door from his prior position title to "Audie Lewis Consulting."

Attend networking events

If you're going to network, I recommend avoiding PR, writing, or marketing events for finding work. They can be educational, yes. But your target clients won't be at those events. Only people working within these industries attend them.

Instead, find local small business events. Events requiring an entry fee are more valuable than free ones, even if it's just $10. People who only attend free events can't afford your services, so it's a waste of time to try. The entry fee for the event doubles as a barrier of entry for affording your writing services.

Networking best practices: Try to collect more business cards than you give out. That way, the power is in your hands to connect afterward. Always follow up.

Freelance sites

I joined freelance sites like Upwork and Thumbtack.

Freelance websites offer unique benefits and challenges. Some freelancers avoid them entirely, while others swear by their benefits.

The main benefit is that sites like Upwork aggregate projects for you. All you have to do is send a bid and proposal. Easy peasy.

However, because applying is so easy, a LOT of people apply to each gig. It's super competitive. And, as supply and demand would have it, people low-ball.

The average project you'll get on Upwork or Thumbtack will provide much lower earnings than the same opportunity through a different avenue. Also, Upwork charges a hefty fee: 20% for the first $500, 10% of $501-10,000, and 5% after $10,001+. To review: clients pay less AND Upwork takes a big cut.

But there are still reasons you may want to keep your Upwork profile. Upwork has great SEO and they are a hub for freelance projects. But I'll say this: Don't get addicted to a single channel for your work. Diversify where you spend your time prospecting and connecting with clients. It will pay off.

Use your writing

The best way I think for you to drum up business as a writer: show off your writing. Ever heard of guest posting?

Think about the clients you want to work with (are they in tech? retail? eCommerce?) and then research to find out where these people spend their attention online. Get published in those places. The byline will tell them who you are, and you may get some emails (plus you get the fun of seeing your name in a byline).

3. Pricing your services

Per project pricing

I strongly advise not charging by the word or by the hour, if you can avoid it (though sometimes you can't).

The reason: it puts you and your client on opposite ends of the bargaining table instead of positioning you both as team members trying to tackle the same goal. (I learned this idea from Ed Gandia's High-Income Freelance Writing Podcast, which is a great writing resource you should know about if you're just getting started.)

With word-count or hourly work, you're incentivized to rack up a higher quantity of billable units (more words or hours), while the client is on the opposing side, hoping you write a shorter, faster piece.

Instead say, "I'll write you an article for $X. It'll be between 800 and 1,000 words and I can deliver Wednesday next week." This way, there's zero space for worry or confusion. You get a paycheck that you find fair, and the client gets the product he's paying for.

Billing as a business

Another key to freelance pricing is to remember that you're charging as a business, not as a salaried employee.

Three years ago, moving from being paid as an hourly employee, I was petrified to charge the going freelance rates for my experience. It seemed absurd compared to the $8-16 per hour I'd known as an employee in my late teens and early twenties.

But a business earns more revenue for your talent and work than you are receiving in your paycheck, because the business has bills to pay and profit to accrue. So, working as an in-house writer, you may make $18-25 for your time. But the business also has to cover its cost of operations.

Between utilities, your computer, your office space, your insurance, etc., a business may easily be billing your work at 3x, 4x, or 10x the hourly you receive as a salaried employee.

Bonus: Recommended resources

Finally, I'm a huge believer in self-educating. If trial and error was the most important teacher in my freelance career, then reading has been the close second.

Here's 5 books* I found most helpful as I started out:

The Well-Fed Writer by Peter Bowerman


Secrets of a Freelance Writer: How to Make $100,000 a Year or More by Robert W. Bly


Everybody Writes by Ann Handley


Writer's Market 2019 (as a reference guide for pricing, best practices, etc.)


On Writing Well by William Zinsser


If you want to know what we've been reading lately, Sarabeth and I wrote an article about the 10 books that shaped our business in 2018.

Hope all this helps. If you have additional questions or want to zoom in on any of these topics, just let me know. I'm happy to be a resource: alexander.lcwriting@gmail.com.

Good luck!

*I am an Amazon affiliate. If you use any of the links above to make a purchase, I'll receive a small compensation.


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Lewis Commercial Writing is a full-service SaaS copywriting & UX writing duo providing B2B conversion copywriting based in Austin, Texas.