The Unexpected Path to Becoming a Six-Figure Freelance Writer

Evan Jensen

Follow the Six-Figure Freelance Writer Path. Makealivingwriting.comEver wonder if there’s a well-trodden path to being a six-figure freelance writer?

You know…a step-by-step plan, without any twists and turns, that leads you straight to that sought-after income goal for a lot of freelance writers.

If you’re just starting out or you’ve been a freelance writer for some time, you’ve probably experienced the ups and downs of freelancing. It’s part of the gig.

So how do you get to be a six-figure freelance writer?

Here’s the thing. There’s more than one way to get there. Everybody’s path is a little different.

In fact, one freelancer almost gave up on writing for a living to teach English in Asia. And then unexpectedly found her way back.

At first it was a rough and winding road that included a stint on food stamps. But she hustled. She worked hard. She got some help along the way. Last year she broke the six-figure mark as a freelance writer. And so can you.

Want to be a six-figure freelance writer? Your path is this way…

Meet freelance writer Casey Hynes

Freelance Writer Casey Hynes

Freelance Writer Casey Hynes

Freelance writer Casey Hynes earned a master’s degree in journalism from Columbia University. From there, it didn’t take her long to get on the path to becoming a national political reporter. And then something happened.

She wasn’t sure political writing was her thing. She needed a change of scenery. So she moved to Asia to teach English.

And then almost unexpectedly, she found her way back to freelance writing about eight years ago.

She’s been writing for a living ever since. Last year, with the help of Carol Tice, fellow freelance writers in Den 2X, and plenty of hustle, Casey surpassed the six-figure income mark. Here’s how she did it:

Q: When you decided to get serious about freelance writing, what happened?

Hynes: I was in Beijing to teach English, and decided I’ll give writing a go again. And I ended up kind of being in the right place at the right time. There were tons of companies lots and lots of people and publishers in Beijing who needed someone who could write content for their English-speaking audience and their expat audience.

Q: What kind of freelance writing jobs did you get?

Hynes: It was kind of like a scattershot approach. I would just take anything that anyone would give me. I was editing translated work. I edited a guy’s fiction book. I mean, anything, writing, editing, whatever.

Q: How did it feel to start landing clients and making money as a freelance writer?

Hynes: I realized that I justloved working for myself. I was like,”This is what I want.” I liked the flexibility that came with it. I liked being able to choose different projects, and work on things that interested me, and just the whole aspect of being self-employed and having that kind of freedom in my life. I was like, “This is it. I don’t ever want to get a job again.”

Q: How did you find your niche as a freelance writer?

Hynes: I thought I was gonna do travel writing and that ended up not panning out. I just ended up getting different clients and doing different types of features. And then I started getting fintech assignments writing about start-ups and personal finance. I never in my life would have imagined that that’s what I would be writing about. But one thing kind of leads to another and doors start to open.

Q: How long did it take you to be a full-time freelancer?

Hynes: I was able to make a full-time income by my second year freelancing. My first year I actually had been working. I was still teaching, in addition to writing, and odd jobs here and there. I was actually able to sustain myself by the second year.

Q: What made you decide to join Den 2X?

Hynes: I was at a crossroads at the time an,d I really wanted to be making more money. I booked a call with Carol with my regular Den membership. And she was just so awesome and direct. She went over my website tore it apart (which it really needed), and told me what to do. She talked to me about SEO and mentioned Den 2X.

It was just the thing I needed to level up, gain confidence to drop bad clients and raise my rates, and connect with a cohort of other people at the same stage in their careers to energize me an exchange ideas.

Q: Did Den 2X help you double your income?

Hynes: I didn’t double my income, but I increased it significantly. In 2017, my gross income was about $65,000. In 2018, I made $108,500, which was more than I thought that I had done. And it was far more than I had ever made. A lot of that had to do with Den 2X.

Q: What was the biggest change that helped you earn a six-figure income?

Hynes: I started writing for a client through Contently, which is a content marketing agency that works with pretty big companies. I got a really good client through them that had lots of assignments. I was able to use those clips from a brand-name client to go other places, get more assignments, and command higher rates.

Q: What freelance marketing strategy worked best for you?

Hynes: LinkedIn marketing. I updated my LinkedIn profile and started posting updates every week or two. When I did that, I started getting leads from LinkedIn really, really quickly. And it made pitching a lot easier. For example, I messaged a girl I knew in Beijing to ask if she knew anyone who needed a freelance writer. She started assigning me articles right away at 500 bucks a pop.

You’d be surprised at how quickly people will respond on LinkedIn. It only takes five minutes, if that, to send someone a message like:

Hey, I’m a freelancewriter. Can I send you some clips? Are you guys working with somebody?

You really don’t need an elaborate marketing plan or invest hours and hours into writing the perfect pitch. Just use LinkedIn to make easy connections and ask for referrals, and you probably won’t be scrambling for work again.

Q: What advice do you have for other freelancers on the path to a six-figure income?

Hynes: It’s absolutely possible. Wherever you are and however much you’re making today, you’d be amazed at how quickly you can ramp up your income and just achieve so much stability in your freelance life. Just start by taking a few steps, like improving your marketing efforts, create a foundation for yourself. Things have a way of gaining momentum when you do that.
Are you on the path to becoming a six-figure freelance writer? Let’s discuss in the comment section below.
Evan Jensen is a contributing writer for Make a Living Writing. When he’s not on a writing deadline or catching up on emails, he’s training to run another 100-mile ultra-marathon.

Get the best freelance clients - join Freelance Writers Den 2X Income Accelerator


  1. Linda H.

    Casey you encouraged me. I’m currently on food stamps and recovering from a two-year health issue that left me hospitalized for most of that time. I’m changing my focus now and working to overcome some bad experiences from my previous writing career that spanned 32 years. I’ve been with Carol since 2010 and love her training and encouragement. I’m looking for new work and will definitely rebuild my LinkedIn profile, my website and see what happens. Thanks for sharing your story. It’s a boost I needed.

  2. Judith Norris

    Hi Casey,

    Awe-inspiring! Your message encouraged me with its possibilities. Your ex-pat teaching experience reminded me so much of my own in Sydney, although mine included advanced music theory. Your path to freelance writing happened at a good time for you.

    Do you suggest a retired English, Reading, and Music teacher who has recently discovered freelace writing continue or seek another trail? I’m not ready for retirement (whatever that means.) Six figure income sounds great if it’s within the realm of likelihood for an older newby.

    Thank you.

    • Casey Hynes

      Hi Judith, thank you for reading and for your kind words! I’m really glad to hear this was helpful. It sounds like you had an interesting teaching experience as well!

      As for whether you should pursue freelance writing, I can’t really say – I think it’s a personal decision based on your goals, interests, and financial circumstances. But I think you can determine the best path by considering those factors. Do you want to write because you enjoy it, or simply as a means to earn money? Freelancing is a joy but it’s also hard work, and it requires a lot of hustle in terms of finding clients, managing those clients, figuring out your invoices and tax obligations, etc. In my experience, the love of writing and the love of the freelance lifestyle have to outweigh the stresses if it’s going to be sustainable.

      The financial side can be a challenge, and I always suggest that, if possible, new freelancers have several months of savings set aside because the early days can be slow going. You might find a couple of clients or get a couple of pitches accepted, and that’s great for your portfolio. But it may not be enough to cover your expenses, and being stressed about money seriously impedes your ability to work clearly and efficiently (at least that’s the case for me). So, having some savings or a part-time job to fall back on can really alleviate stress in those early days.

      Having savings or a part-time job is also useful if you’re still figuring out whether freelancing is right for you. Sometimes you may find that you need to take assignments that pay well but don’t spark your creative fire (to put it mildly), and that’s not always an easy thing to do. You may find that that’s not a trade-off you’re willing to make and that you want the freedom to write whatever you want, on your terms, without worrying about compensation. That is a totally valid position, but it’s an easier one to take if you have another source of income and haven’t thrown yourself into freelancing before knowing whether it suits you.

      Personally, I love both writing and freelancing. There have been many dark nights of the soul in the eight years I’ve been doing this, because of money and because of time spent on client work vs. the creative writing I love most. But on the whole, I have found that I enjoy the freedom and autonomy enough to keep going with freelancing, because they have allowed me to explore new opportunities and to work in such a way that I can also travel with my partner, take extended time off to visit friends and family, and structure my time in a way that fulfills me. There are always challenges, but whenever I question whether it’s time to stop freelancing and get a full-time job, the clear answer for me is always to continue freelancing.

      I think the answer depends on what is important to you, and there is no right or wrong. I wish you the best in your decision and writing career, and please feel free to contact me at if you want to talk more.

Submit a Comment

Your email address will not be published. Required fields are marked *

Related Posts

WordGigs Review — Is It Worth It? (2022)

When it comes to finding writing gigs, there are a million places to choose from. You might be looking for a WordGigs review and trying to figure out whether you should go through the application process to become a freelance writer for their site. This WordGigs...

How to Get Into Gonzo Journalism

If you wanted to learn about how to get into gonzo journalism or the history behind it, you've come to the right place. Originally credited to Hunter S. Thompson, gonzo journalism is the style of writing where you're covering a topic or event, but you're mixing your...