5 Lessons From This Rockstar Freelance Writer’s Last 5 Years

5 Lessons From This Rockstar Freelance Writer’s Last 5 Years

I’m in my fifth year as a full-time freelance writer, which means I’ve been freelancing longer than I’ve had any other job.

I’ve learned a lot since I started freelancing — how to pitch, how to negotiate, when to look for a new client — but my biggest lessons have been the large-scale ones. How to grow your income by tracking it. How to build relationships. The discovery that freelancing isn’t a solo gig; it’s a team sport.

So — because we’re all on the same team — I want to share my lessons learned with you.

Here are my five biggest takeaways, in five years of freelancing.

1. Track what you want to improve

If you’ve been following The Write Life for a while, you’ve probably seen me share my monthly income roundups as well as my future income goals. I’ve been tracking my freelance earnings here for over two years now — and although I know that information is beneficial to TWL readers, I’m actually tracking my income because it’s beneficial to me.

Knowing exactly how much money I’ll earn this month — as well as the money I’m projected to earn over the next few months — lets me know whether I’m earning enough money or whether I need to hustle for more work. (I track my expenses along with my income, and I want to make sure I earn enough to both meet my expenses and save for the future.)

It also lets me know whether my freelance career is growing.

Am I earning more money this month than I was six months ago? Am I getting higher rates for my work, or am I doing larger amounts of work at the same pay rate? Is it time to negotiate a raise or look for a new client?

“What gets measured gets managed” is a cliché, but it works. Tracking my earnings lets me manage both today’s money and tomorrow’s growth. Time-blocking my day helps me manage the hours I work and ensure I hit my deadlines.

Paying attention to the way I do my work helps me work better — which also helps me build my career.

2. You can earn a living on low-wage work — but figure out how to move up

You’ll often see freelancers arguing that “no one can earn a living” on the low pay rates given out by some publications and content sites. This isn’t necessarily true. I began my freelance career working for Crowdsource (now OneSpace) writing 600-word articles for around $11 each.

I wrote every $11 article I could. Five or six a day, Monday through Friday. Crowdsource had a leaderboard, and by the end of my tenure with them I was the fourth highest Crowdsource earner of all time.

You can earn a living on low-wage work, if you are able to write quickly and complete a large number of assignments.

But as you’re getting all of that work done, figure out how to move into higher-paying gigs. I set the goal of sending out one pitch per day. I didn’t meet the goal every day, but I met it enough times to get the higher-paying clients that helped me build my network — which is what helped me build my career to the point that clients started reaching out to me.

3. Everything changes when people start reaching out to you

Here’s how you know you’ve made it as a freelancer: people start asking you to write for them.

When that first started happening, I couldn’t believe it; clients were emailing me, offering to give me work? I didn’t have to pitch them or convince them that I was the best person for the job?

When clients reach out to you, they’re often offering you a job that isn’t advertised. These are the gigs that don’t make it to the freelance job boards because these clients don’t want to review dozens of pitches; they want to reach out to someone they know can get the job done. They’re also generally offering higher pay rates than what you might get from a pitched gig — and because they’re the ones reaching out to you, you’re the one with the power to negotiate. They want you. All you have to do is agree on the terms.

4. Get a CPA who understands freelancers

I’d advise all freelancers to get a CPA, but if you’re at the level where clients are reaching out to you with $10,000+ gigs, you absolutely need one. More importantly, you need a CPA who understands what freelance writers do.

My first CPA wasn’t a good fit for me — he didn’t understand what I did or how quickly I was increasing my earnings, which meant that he kept advising me to pay lower estimated taxes than I actually owed. I found a second CPA who was ready to talk to me not only about my taxes, but also about business licenses and other financial concerns.

Freelancing is not a solo career. You need good people on your team, and a CPA that understands freelancers is one of them. As for the rest of your team, well… that brings me to my final lesson.

5. Relationships are so important

“It’s all about who you know” is as much of a cliché as “what gets measured gets managed,” but it’s true.

Building relationships helps you build your career.

A good relationship with an editor means getting that email that ends with “please pitch us again soon — I’d love to see more of your work!” A good relationship with a client means landing recurring gigs, or being the first in line to claim a new project. It also means your editor or your client may recommend you to someone else, who will send you an email offering you a high-paying job.

Building relationships with other freelancers is also important. They know who’s paying well and who’s hard to work with. When their editor asks if they know anybody who might like an extra gig, they can recommend you — and if your work dries up, they’re the best people to ask for help.

So make your professional interactions good ones. Act like you’re on a team working towards a mutual goal, whether you’re recommending a friend to an editor or asking a client to consider a higher pay rate. Keep that team mentality going in your personal online presence as well; you don’t want to be known as the freelancer who complains about clients on Twitter.

Because the stronger your relationships are, the stronger your career becomes.

I’ve grown a lot as a freelancer over the past five years, and I look forward to seeing where my career goes in the next five years. I’d like to think these lessons will serve me well no matter what happens next — and I hope they serve you well too.

What have you learned since you started freelancing? Share your biggest lessons — or your thoughts on Nicole’s lessons — in the comments.

Filed Under: Freelancing


  • Tom says:

    I’m confused, you say you are a “rock star” free-lancer, but I never heard of you until today and that’s solely because your headline convinced me to open the Website to determine if you are telling the truth. Apparently, the headline would not qualify as an accurate statement.

    • To be fair, Tom, the editors of The Write Life write the headlines for the pieces you read here, and we think Nicole is a rockstar! Just read her posts here and you’ll see her success over the years. -Jessica, Editor

  • Jimoh Ibrahim says:

    True, experience pays. Great tips here Nicole. I believe beyond dishing out great content to clients, it is paramount to maintain a sound relationship with them.

    With good relationships you’d definitely be differentiated from the other guy that sucks. You’d always be ahead.

    More success, Nicole.

  • Lynne D says:

    Thanks so much for that Nicole! That was so informative and helpful and ultimately inspiring!

  • Great thoughts. My biggest learning curve has been knowing when to sack a client. I got burned so many times by sticking with someone that messed me around, paid late, paid low, or etc. Having a one-strike rule has been scary to implement, but so much better for me in the long run.

  • Wendy says:

    Y’know, I’ve been trying to track my typing-time on a book I’m working on–mainly to get a benchmark on how long it actually takes me to write a book, but I’m finding that “clocking in” is actually discouraging me from writing (if the document’s open, I might peck at a paragraph or two between other tasks, but if I “clock in,” I feel like I have to put a decent chunk of time into it, and if I don’t want to put a lot of time in, I don’t put any at all). Anybody else experience this?

    • Wendy, some of it is finding the method of tracking time that feels least obtrusive to you. For example, you could set up a “time log” spreadsheet and save it as a template so that you could easily create a new one for each project. It could have columns for starting and ending time (with a row for each writing session) and then calculate how much time was between them, while keeping a running total at the bottom to tell you how much time you’ve spent on the project so far. Leave your spreadsheet open along with the project itself, so that clocking in and out takes just a moment.

      If even this feels a bit obtrusive, check to see if your cell phone (or perhaps an old cell phone you may have around the house) has a stopwatch function that you can pause and restart easily at various times of the day. Start it running with the first writing session of the day, and get used to clicking “pause” if you stop for a phone call or some other task, or just because you’re done writing for the time being. At the end of the day, you can put the total time into your spreadsheet.

      If you still can’t find a strategy that works, then writing the book is a higher priority than timing how long it takes you to do it, but I do encourage you to try to find a way to do both.

      I wish you success with the project!

      Trish O’Connor
      Epiclesis Consulting LLC
      Editorial Services and Writer’s Resources

  • Mark Kaplan says:

    Great points. There are never too many good tips.

  • Mike says:

    Congratulations on your success. I really appreciate you sharing this info with us- I’m a beginning freelance writer and I’ll be visiting this website often.

  • Megan Sharma says:

    Congratulations on 5 years of freelance writing success!

    These are great points to keep in mind. It’s so easy to get caught up in the day to day without adding strategy to the mix.

  • Timely and inspiring!

  • Nicole:

    Congratulations! It’s wonderful to read your great news! It inspires everyone else.

    Best wishes,
    M. Latela

  • Nicole says:

    Yes! I often refer to my work as a small business, because that’s exactly what it is.

  • One suggestion I would make is to make a habit of saying “I own a business,” rather than always saying “I’m a freelance writer.” If you are like me, you will find that this opens your mind to opportunities that may not have fit easily within the individual self-image you had at the start.

    Several years ago, I thought of myself as “becoming a freelance editor,” but I also thought of myself as “starting a small business.” It made a difference! It made me open to diversifying my revenue streams.

    Yes, the biggest jobs I do still involve editing book manuscripts, and I still love doing it, but I also do other things, such as publishing my own collections of prompts for creative writing exercises and spiritual journals in digital format. I ghostwrite About pages for other businesses’s websites. (Both of these have forced me to remind myself from time to time that, like my editing clients, I, too, am a professional writer.)

    I am also able to put my work as a retreat presenter under the same broader business as my editing. I am currently working on a couple of programs for churches. (Before I started my business, I worked in ministry.) I am open to the possibility that my business may someday publish ebooks and programs from others rather than simply my own, making me more of a full-fledged electronic publisher.

    Who knows what opportunity may present itself next? It is my hope that I will be open to it when it comes.

    Trish O’Connor
    Epiclesis Consulting LLC

    • Great point, Trish! I’m currently planning my transition into full-time freelance writing and have been exploring the idea of branding myself as a small business.

      One unanswered question I have so far: do I need a business license as a freelance writer? And, if so, what type is recommended? I’m still very new to this and would love to hear from some more experienced freelancers on the topic.

      • It depends on your state, Erika. I suggest you go to your state’s website and see what information they have for business owners. Also, you may want to visit and

        Best of luck to you!

        Trish O’Connor
        Epiclesis Consulting LLC

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