Writers Worth: Freelance Writing Career Do’s and Don’ts

When I asked my writer friends for guest posts, Ashley Festa was not only the first one to volunteer, but also the first one to offer two posts. That’s why I love her — she’s eager to give back to the profession and help beginning writers get a good start. What follows is a fantastic post that should be a freelance writer’s mantra. She’s learned a lot in her few years of freelancing, and it shows.

Ashley apologized for the length of this post, but there’s no need. Every point is worth committing to memory. Thank you, Ashley. Your insights are great, and much appreciated.

Dos and Don’ts of a Successful Freelance Writing Career

By Ashley Festa

Everyone has to begin somewhere. Without taking the first step—whether it’s a success or a failure—you’ll never achieve any goal you set for yourself.

My first step was fearful and cautious, but unstoppable. There were also many missteps before I found a solid foothold. When I made a mistake, I backtracked a bit to catch my balance. Then I stepped out again, sometimes in a new direction, sometimes in the same direction but on a different route.

That path has led me here, to this blog, to Writers Worth Month, to being able to say that I’m more successful today than I ever thought would be possible working for myself.

That’s because I learned to value myself, value my business and value my work as a service to help clients achieve their goals. If I didn’t realize my worth, I would have quit after the first mistake I made. There have been lots of mistakes since then, but I still move forward, learning lessons as I go.

That’s what I want to share with you—things I’ve (mostly) learned not to do, and what to do instead. Hopefully you can benefit from my trials and errors.

So, let’s get started.

Making the Leap

Don’t be afraid to ask questions. When I first started, I asked So. Many. Questions. I could string some sentences together well enough, but otherwise knew nothing. At all. Running a business, setting rates, finding clients, marketing—it was all new to me. I found a trustworthy group of writers right here at Words on the Page, who were kind enough to take me under their wings. (And I still ask lots of questions.)

Do research for yourself. Once, while working full-time in public relations, I received a phone call from someone who had just seen the business’s commercial on television. We were promoting an event and provided a number to call “for more information.” Would you believe that someone called me and said, “Can I have more information?” I had no idea what to say to her.

Moral of the story: While it’s perfectly OK to ask questions, make sure you have something specific in mind that you want to know. A little background research will let the other person know you’re willing to work and don’t just expect everything to be handed to you.

Don’t automatically choose the easy route. Sure, go after the low-hanging fruit if you don’t have published clips or if you’re just learning the basics of writing. But make sure it’s still fruit, not compost. Content-mill-type work that’s handed to you, along with the $1 paycheck, is not fruit.

Do spend time and effort to find the best markets for you. Researching markets is harder than signing up for some bidding site or content mill, but you’ll benefit in the long run. And you can still pick the low-hanging fruit like nonprofits or charities in the beginning. They might not pay well, but they’ll provide professional clips you can use to break into bigger markets later.

Don’t spread yourself too thin. When I first started, I had WAY too many marketing ideas bouncing around in my head. I wanted to try this, then that, now this other thing. I didn’t devote enough resources to any one marketing tactic to see whether it would work.

Do make a plan and stick with it. Focus on one thing. Do that thing enthusiastically for a month to see whether it will work. If it doesn’t, move to your next idea. But choose one, and work it until you’re certain it doesn’t work for you. When I finally chose one tactic and stuck with it, I finally started seeing results.

Don’t twiddle your thumbs waiting for replies. So you shared your business card at a networking event and sent an email introduction to an editor. Great! Now do it again. And again. And again. You could be waiting a long time to hear back from that potential client. Don’t let your work schedule hang in the balance.

Do remember to market regularly.To keep your schedule full and avoid the feast-or-famine cycle, set aside time for marketing. Keep plugging away at your favorite marketing tactic every day to keep the projects rolling in.

Knowing Your Worth

Don’t underestimate yourself. We’re always our own worst critics. If you feel insecure, get an honest appraisal of your writing ability. Ask a client for feedback, or get a coach to evaluate your work. You’ll discover you aren’t as bad as you thought.

Do charge what you’re worth. Writing well takes practice and work. Make sure you’re compensated accordingly. Not sure what to charge? Try this handy-dandy freelance project rate calculator to figure it out.

Don’t miss deadlines or turn in shoddy work. Not much to elaborate here. Just don’t do it. Even if it’s not a great paying client, you still accepted the assignment, so it’s your responsibility to do your best.

Do respect yourself and your clients. Submitting your best work not only reflects well on you and your business, it shows your clients that they’re important to you. That keeps them coming back.

Don’t take it personally. You won’t always see eye-to-eye with your clients. They might even disagree enough to fire you. Remember: It’s not you—it’s business. You aren’t a bad writer just because you weren’t a fit for that client.

Do learn from your mistakes. When (not if) you screw up, forgive yourself first, and then examine your error. Figure out what you did wrong, and resolve not to do it again. It’s not you, it’s business, so learn how to improve your business.

Learning and Growing

Don’t stagnate. No matter how much you know, you can always learn more.

Do grow professionally. To flourish as a writer, you must keep cultivating your craft. Whether you branch out into new areas or plant deeper roots in your own field of expertise, you have countless avenues for growth. (For a popular and free option, try Massive Open Online Courses aka MOOCs.)

Don’t believe everything you read. Bloggers and “gurus” have flooded the internet with advice about how to be a successful freelance writer. Some of it rocks—for every writer. Some of it works in particular situations. And some is flat-out bad advice. Learn to sort out what works in your situation.

Do follow the leaders. You can rely on some bloggers (including my Writers Worth Month host!) to provide excellent tips, lessons and guidance in every post. Find them, and follow them. And don’t just read these blogs—put the advice into action.

Don’t think sole proprietor has to mean “solo”. Even if you enjoy working alone, everyone needs to bounce ideas off others from time to time.

Do find a community. Whether you head to your local coffee shop, join a forum or seek out a writers group, find a place that feels right to you.

Running a Business

Don’t waste your entire day with time sucks. First word: Facebook. It’s a black hole that drags me in doing “Which Disney Character Are You?” quizzes and other nonsense. Second word: Wikipedia. Once when I started doing “research” for a story about space physicists, I resurfaced an hour later with a migraine somewhere on the hypothetical dark matter/string theory/dark energy bunny trail.

Do know where your time goes. Use a time tracker. I log interviews, email writing, brainstorming sessions, even invoice writing—every working minute—to the appropriate project, even if it’s not billable time. This method gives me a good sense of how I’m spending my working hours.

Don’t forget you’re an independent contractor. You aren’t an employee, so don’t act like one. As a contractor, you set your own hours, routines and working location. If you’re required to be available during business hours or work on-site, you lose the “independent” nature of being a contractor.

Do take advantage of your flexible work schedule as much as you’d like. You need to meet your deadlines with quality work. That’s your job. When and how you do it is up to you. If you like working within the buzz of a coffee shop, snag a seat by an electrical outlet. If you need inspiration from your cat, grab Fluffy and some kitty treats. If you work best in the wee hours of the morning, burn that midnight oil.

Don’t be shortsighted. Sometimes we get caught up in the thrill of a new client. Don’t let a prospect make you forget about your future, and don’t take on a crummy gig for a quick buck.

Do plan for the future. Remember that question, “Where do you see yourself in five years?” from your corporate days? That still applies now. You need to know where you want to go so you can figure out a plan to get there. You also must consider insurance, self-employment taxes, investments, retirement and more. Think beyond your next invoice.

Moving Forward

Don’t be too hard on yourself. Everyone makes mistakes. Some people (like me) even occasionally make the same mistake many, many times before getting it right. But 99.99999 percent of the time, your mistake isn’t going to destroy your business. Acknowledge the mistake, figure out how you can do better next time, and then next time, do better.

Do congratulate yourself on a job well done. Writers, like many artists, often struggle with perfectionism. We focus on failures, not feats. We brush off our byline and move on to the next thing. Instead, soak up your achievements. Relish praise from your clients. Name yourself Employee of the Month. Whatever it takes, remember to celebrate your successes.

What have you learned from your trials, errors and missteps throughout your freelance writing career?

Ashley Festa is a higher education freelance writer based in San Antonio, Texas. Visit her online at www.ashleyfesta.com.

About the author




  • Anne Wayman May 22, 2015 at 12:05 pm

    Excellent advice Ashley and it's fun watching you follow your own advice.

  • Cathy Miller May 22, 2015 at 12:11 pm

    Excellent list, Ashley. Here's my bottom line ~ Do what's right for you. Only you know what's best for you.

  • Sharon Hurley Hall May 22, 2015 at 12:12 pm

    Amen, sister! Ashley, this should be required reading for new freelancers. I still believe in asking lots of questions: it saves time later.

  • Susan B. Bentley May 22, 2015 at 1:26 pm

    Yes to all of this, what a great post. I agree that one of the biggest things is to not beat yourself up, don't be too hard on yourself – see mistakes as learning opportunities. Cheers for this.

  • KeriLynn Engel May 22, 2015 at 2:13 pm

    Yes! I was nodding my head to everything on your list. Very uplifting & just what I needed to read at the end of a long week. THANKS Ashley & Lori 🙂

  • Lori Widmer May 22, 2015 at 2:14 pm

    Ashley, once again I thank you for a great post.

    Susan, isn't she good? 🙂

  • Ashley May 22, 2015 at 4:04 pm

    Thanks for the kind words, everyone. I'm glad this list is helpful, especially to newer freelancers. Stuff I learned the hard way, and some things I'm still working on.

    Cathy – YES to that. It's so simple, but still hard to accept sometimes!

    Thanks, Lori, for hosting me. I'm very glad to contribute to Writers Worth Month. 🙂

  • Paula May 22, 2015 at 4:18 pm

    What they said.

    Plus, "Fruit, not compost" should be a mantra for all new writers.

    Like you said, Ashley, sometimes it takes a couple low-hanging fruit assignments to garner respectable clips. Once you have two or three of solid clips, those markets can be retired to the compost heap while the clips help you grow your business.

    (Impressively heavy handed metaphor mixing on my part, huh?"

  • Ashley May 22, 2015 at 4:53 pm

    Paula — ha! I just love that you consider something I said could be a mantra for someone!

  • Melanie Kissell May 22, 2015 at 5:22 pm

    Fabbytastic read! Sharon Hurley Hall is RIGHT: This should be required reading. Nicely done!

    I'm a blogger and freelance copy editor, Ashley, not a freelance writer. BUT everything you've shared still applies. I can tell all your do's and don't's have evolved through personal experience — and maybe from temporarily attending the School of Hard Knocks. 😉

    Simply put …
    Stellar advice.

  • Ashley May 22, 2015 at 6:36 pm

    Thanks, Melanie! And yes about the School of Hard Knocks. Don't we all attend, at least a couple of times in our writing career? But I'll say, those are the lessons I'll NEVER forget. Hopefully this list will help some writers avoid at least a few of those hard lessons.

  • Alicia Rades May 26, 2015 at 12:29 pm

    Fantastic post. My favorite is probably, "Don’t forget you’re an independent contractor." Too many new writers don't understand that, and too many don't even know what it means. It took me three years to really understand how much control it meant I had.

  • Jahirul Islam September 27, 2015 at 6:50 pm

    Become a freelancer is not an easy job. First, you have to decide that which thing you going to learn. Then you have to learn that very well. Then you have to practice more and more. After practicing more more you will become a good freelancer as my opinion.

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