Updated: Mar 8
My freelance career started by complete accident. I resigned from my front desk job in March 2016, expecting to find my next full-time gig within a couple weeks.
I shopped my resume around Austin and attended a few job interviews. Nothing stuck. After several days, the panic began to set in. I needed some career advice.
One evening I got dinner with my friend Aaron and asked what sort of roles he thought I’d be good at. Aaron had an inspiring career. It was full of great roles doing interesting work. I figured he might know a good company that was hiring and be willing to refer me.
Instead, he didn't think I should pursue a full-time job at all.
He said, “You live in a tech city. All these developers know how to create great products but they don’t know how to tell anyone about what they’ve built. Why don’t you just start writing for all the local tech companies?”
I decided to give it a try.
That first year was hard. I leaned on my previous copywriting experience, but that’s where my advantages stopped. I was broke. I had no idea how to find clients. And I didn’t have a website or online portfolio. But I bought books and began reading everything I could find about freelancing and running a one-person business.
In the end, freelancing worked. I'm still doing it full-time more than five years later. But now that I’ve been in the business a few years, I know there are smarter and safer paths to becoming a professional freelance copywriter than the one I followed.
(Read the full story of how I went from earning minimum wage to becoming a six-figure freelance copywriter.)
Crossing your fingers and quitting your day job isn't much of a strategy. In this article, I’ll cover the three best paths to becoming a professional freelance copywriter, based on how most successful solopreneurs I know took the leap.
What does it mean to be a professional copywriter?
Let’s start with a simple definition. Professional copywriters are people who earn a living writing for businesses. Professional copywriters tend to work in one of three categories at any given time: freelance, in-house, and agency.
A freelance copywriter offers writing as a professional service. They are business owners, often working with several clients at once. Beyond simply writing, they also must navigate the challenges of running a business and finding clients.
Like freelancers, agency copywriters often work with multiple brands. But their work is performed under the umbrella of a larger organization, and alongside a team. Copywriters usually work at marketing and advertising agencies, helping clients produce creative copy.
And finally, in-house copywriters work for one brand. They get to focus on a single company, helping to hone and develop the voice of their organization across blogs, website copy, and much more. The benefit of in-house copywriting is focus. You get to work on the same challenge, alongside the same team, for years.
Out of these categories, freelancing is the one I have the most experience with. If you’re interested in becoming a professional freelance copywriter — and running a business on your own terms — here are the three most common paths.
Let’s dive in.
1. Start freelance copywriting as a side hustle
The best way to fund a freelance venture is through your current employer. Rather than taking the risk of quitting a job right away, many freelance copywriters begin their business as a side hustle.
You can find initial gigs through cold pitching, freelance sites like Upwork, or through your network. I found my first freelance projects by contacting agency owners in my network to see if they had work they'd like to outsource. (In my case, they did!) As you receive projects, you can slowly build a portfolio. Your reputation grows with each new client you serve.
Once you have your side hustle up and running, the new question becomes: How do you know when to go full time as a freelancer?
While there’s no clear-cut formula, most freelancers like to start by proving to themselves that they can earn a freelance income comparable to their full-time salary.
You might set up specific metrics for yourself. For example, once you earn 75 percent of your full-time salary for three consecutive months, it might be safe to take the leap. After all, if you can earn three quarters of your full-time salary working only nights and weekends, how much more could you earn freelancing full time?
Set your metrics based on your personal risk tolerance and situation.
2. Save money to give yourself a runway
Some jobs simply don’t provide the time necessary to successfully run a freelance business. Or you may be under a contractual agreement with your employer that prohibits you from taking freelance gigs.
Either way, if you can’t freelance as a side hustle, then maybe you can begin saving money with the intention of resigning by a specific date so that you can go full-time into the business. Your savings will serve as startup funds, a runway so you have time to learn this profession and find clients.
The big factor to consider here is your likelihood of success. Without building a freelance business on the side, you don’t have a way to prove to yourself that you have what it takes to find clients or maintain a small business.
This path is best for people who’ve experienced running a freelance business before. Copywriters often move from in-house to freelance to agency positions multiple times over their careers. If you’ve freelanced before, and know how to quickly win freelance clients, then simply saving for a startup runway is a great option that allows you to devote yourself full time to freelancing when you're ready.
3. Turn your boss into your first customer
This is perhaps my favorite version. It's the one my father used when he took the leap into consulting. If you’re already a copywriter at an agency or brand, you may be able to leverage your position and skills to turn your current employer into your first copywriting client.
First, perform an 80/20 analysis of your current workload. What are the 20 percent of tasks that offer 80 percent of the value to your employer? Write these tasks and responsibilities down and present them to your employer. Let them know that you’re building a freelance business and that you would like to turn them into your first client.
The obvious risk here is that they simply turn you down. Now what? If you don't already have clients lined up, then you don't have much leverage for making this arrangement work. Still, many employers will gladly take you up on the offer.
The easiest way to make this avenue work is by pairing it with the first path. By starting a freelance business as a side hustle, you give yourself an open door to freelancing full time. By the time you approach your boss, they likely already know about your freelance career and understand that you have real options outside of continuing to work for them.
This provides leverage which you can then use to (hopefully) convince your current employer to hire you on a freelance basis, eliminating the work you hate about your job, so that you can only work on the highest priority tasks.
The best path? Blend all three
The most realistic path to becoming a professional freelance copywriter is combining all three of these paths into one.
From your current job, begin freelancing as a side hustle. At the same time, intentionally save a startup fund for the day you finally go full time. And instead of resigning out right, negotiate with your boss to see if they're interested in working with you on a freelance basis.
By combining all three paths, you eliminate a lot of the risks and other downsides of freelancing. Before you know it, you'll be a professional freelance copywriter who earns a great living doing work you love for inspiring clients.
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