The Four Stages of a Freelance Writing Career

Father writing on laptop with baby's hands on top of his

When I started my freelance business back in 2011, I was wide-eyed and eager to learn. I’d been part of the AWAI community for a while at that point and read everything I could about copywriting and building a business. Yet, there was so much I had to learn.

In fact, I was an aspiring freelancer for three or four years until a layoff provided the incentive to move forward.

Maybe you can relate.

Now, nearly a decade later, I’ve learned a lot. One thing is that there are distinct phases to building a freelance writing business, and we all go through them. Those stages include aspirational, fledgling, growth, and established.

Each stage is necessary for the next. How long you stay in each stage depends on your skills, motivation, and focus. For example, some remain in the aspirational stage for years (like me). Others move through that within a few weeks.

One thing I’ve found helpful is being able to assess your current stage accurately. That way, you can choose the resources that best fit you right now. When you’re a brand-new freelancer, you have a different perspective and different concerns than someone who’s been at it for seven or eight years.

When you identify your current stage — give it a name — then you can focus on your next steps in a logical way.

Otherwise, it’s kind of like planning a road trip, but instead of having a destination, you drive aimlessly about, checking out curious side roads.

It’s interesting, but it doesn’t get you to where you want to go, does it?

It’s okay to start out that way. Most of us do. But you want to find a structure quickly, so you’ll make progress. By knowing where you are and taking action to keep moving forward, you’ll better enjoy your success at each level.

So, let’s dive in.

4 Stages of a Freelance Writing Business

1. The Aspiring Writer

You’re in research mode, reading everything and excited to learn. You feel motivated, and yet, you don’t know how to start, and you’re looking for guidance.

If this sounds like you, here are some other free resources you may find useful:

Watch for other test-drive and beginner webinars that allow you to learn more about copywriting while you are getting your feet wet.

If you’re not yet subscribing to Barefoot Writer, check it out. You’ll discover more about the direct-response industry and paying opportunities.

You should also check out The Writer’s Starter Kit. It’ll help you figure out what to do first (and second), so you can stop dreaming and get your first paying client.

Taking concrete action is the best way to move beyond this aspirational stage. Choose one direction to try and just start.

2. Fledgling Business

You’ve taken the first steps. Congratulations! You’ve started some training and announced your business intentions to the world. You are ready to get moving.

The best thing you can do for yourself at this stage is to set up the foundation of your business (choosing your niche, setting up your website and LinkedIn profile, creating your Information Kit, setting your fees, for example). With all of those pieces intact, you can stop any procrastinating you may be doing (consciously or subconsciously) and move forward with marketing your business.

Your primary goals are gaining experience, developing confidence, and getting your first checks. You’re eager to make your first $1,000 freelance writing.

You’re ready to take on any possible work just for the sake of experience, so you’re reaching out to your network and letting them know what you can offer. You can also reach out to local agencies and let them do the marketing while you focus on doing the work. Learn more about how to land freelance writing projects with agencies and other firms in this free Inside AWAI webinar.

Here are some other helpful free resources:

One more thing … When you’re in this stage as a freelance writer, talking to clients may seem a little nerve-wracking, so watch this free webinar to discover how handle your first client conversations with ease.

3. Growing Your Writing Business

In this phase, you’re beginning to recognize the type of client or project you like best. You’re choosing a focus because you realize it’s easier to find clients when you can be specific. (“I write blog posts for the real estate industry” is more effective than “I can write anything you need writing.”)

You’re putting parameters for yourself around what you will and won’t do and establishing templates and systems for yourself. You’ll even find yourself saying “no, thanks” to something that isn’t a good fit for you. This is a tremendous moment!

This is the phase where the most profitable freelancers build business skills and a vision going forward. You’ll want to create an intentional path for yourself and ways to check in to make sure you’re building the type of business you want.

I’ve found that having a supportive freelance community also helps. Not only can you develop alliances, but you can also share resources and experiences to help one another. One such freelance group is The Writer’s Life group on Facebook. Introduce yourself and start interacting with others. My AWAI colleagues are a wealth of knowledge and generosity.

Here are some free resources for this stage:

For secrets on how to move on to the next stage, check out 7 Top Success Secrets of Six-Figure Copywriters.

4. Established

This is where most beginners want to be on day one, and that is totally understandable. When you’re starting, “being established” can look like the pinnacle of the mountaintop.

Established freelancers have regular clients and make a good income. They’re in control of their businesses. That doesn’t mean they’re “done,” though. Most established freelancers want to know what’s “next.” They’re looking for ways to grow their income or expand their skill sets. Some want to consult, coach, or write a book.

Established writers should also take advantage of this: The Government “Perk” That Can Hand Copywriters (Like You) a $2.52 Million Windfall.

Additional income opportunities may be of interest:

As you can see, these four stages are distinctive, and everyone starts out at the beginning.

Also, there’s no “rule” as to how long each of these phases will last. It’s up to you. Some people spend years in the aspiring stage (like me!), while others spend only a week or a month. In the fledgling business stage, you might find yourself feeling confident within a few months. For others, it can take a year or so.

There’s no “one path” to success. It depends on your skills, motivation, and the amount of time you devote to your business. However, knowing (and expecting) these four stages can give you a framework for your expectations. That way, you know which resources you need and when. The tools you need for freelance writing success are well within your reach.

What about you? Which phase are you in? Share with us in the comments so we can help point you to more resources to keep moving forward.

The Professional Writers’ Alliance

The Professional Writers’ Alliance

At last, a professional organization that caters to the needs of direct-response industry writers. Find out how membership can change the course of your career. Learn More »


Click to Rate:
Average: 5.0
Published: June 25, 2020

1 Response to “The Four Stages of a Freelance Writing Career”

  1. Thanks for the write-up, I immediately recognized that after 6 months of studying, I'm at the fledging stage of my career. Looking for just about any type of work just to get my foot in the door...I've updated my LinkedIn profile and am currently working on my blog to go live in July 2020. The hardest thing for me at this stage is being patient with myself in trying to land my first client.
    So, if u are in need of a copywriter with HR experience, then I'm your man

    KupheeJune 28, 2020 at 9:47 am


Guest, Add a Comment
Please Note: Your comments will be seen by all visitors.

You are commenting as a guest. If you’re an AWAI Member, Login to myAWAI for easier commenting, email alerts, and more!

(If you don’t yet have an AWAI Member account, you can create one for free.)


This name will appear next to your comment.


Your email is required but will not be displayed.


Text only. Your comment may be trimmed if it exceeds 500 characters.

Type the Shadowed Word
Too hard to read? See a new image | Listen to the letters


Hint: The letters above appear as shadows and spell a real word. If you have trouble reading it, you can use the links to view a new image or listen to the letters being spoken.

(*all fields required)