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Freelance Writing Pros on What They Wish They Knew When Launching Their Freelance Writing Careers

New freelance writers are full of questions.

  • “How do I get started?”
  • “Where are the high paying freelance writing gigs?”
  • “Should I sign up for freelance marketplaces or find my own clients?”

I hear questions like these every week. But are they the kinds of things beginner freelance writers really need to know?

To find out, I caught up with some more experienced freelancers — the type of people I’d personally trust for advice — and I asked them:

With all that you know now as a successful freelance writer, what one thing do you wish you had known when beginning your freelance writing career?

Here’s what they had to say.

I wish I'd known to focus on building relationships rather than chasing one story at a time." - Susan Johnston Taylor - On what she wishes she knew as a new freelance writer - All Freelance Writing

Susan Johnston Taylor

Freelance Journalist & Copywriter

I wish I’d known to focus on building relationships with editors rather than chasing one story at a time. Early in my career, I’d brainstorm an idea for a market, pitch that market, and then move onto another website or magazine because I didn’t have more ideas for the original market. That’s a lot of work to convince that editor, learn their style and invoicing process, then start fresh. Rather than getting a lot of one-off assignments for different markets, it’s much more time efficient to focus on markets that have a steady need for the kind stories you want to write. That’s my approach now.

Connect with Susan on social media:

Peter Bowerman

23-Year Veteran Commercial Writer

Don’t deify clients.

If I had it to do all over again as a commercial freelancer (a.k.a. marketing copywriter), I wouldn’t put clients on a pedestal, and assume they were, by definition, so much smarter and savvier than I was. Many are sharp people, but just as many are overextended, have a middling marketing sense, or are even way out of their depth.

Even the sharp ones, overwhelmingly, aren’t over-demanding hard-asses (second misconception I was laboring under). Sure, they have reasonably high expectations, given the prevailing wages for good writers in our field. But again, a large majority of them are good, decent people who sincerely want your help in solving their marketing challenges.

Bonus Point: How I view what we do as commercial writers is very different than what it was at the outset. And when I finally shifted my perspective (explained here), my concern over whether this field “was still a good opportunity”—a question I’ve gotten more times than I can count—vanished forever.

Connect with Peter on social media:

Francesca Nicasio

Professional Blogger & Web Content Writer

You need a lot of discipline, hustle, and self-motivation to make it as a freelance writer. This is one of the things I wish I knew when I first started out. While passion and writing talent are important, they’re not enough to sustain a thriving freelance writing business. If you want to be successful, you need to show up, market your services, and delivery quality content time and time again. Doing all that consistently can be a challenge, especially if you work from home and don’t have a formal “boss” to answer to.

Over the years I’ve cooked up ways to keep myself motivated and push myself to get work done even if I don’t feel like it. Some of the things that work well for me include reading old emails from happy clients and asking myself, “What would future me thank me for?” Had I known about these things when I first started out, I would have been much more productive, and I would’ve reached my goals sooner.

Bottom line: if you’re an aspiring freelance writer, don’t get blinded by the joys of working from home and being your own boss. Realize that freelance writing takes work, and you need more discipline and self-motivation than most if you want to succeed.

Connect with Francesca on social media:

Sharon Hurley Hall

Freelance Blogger

If I could have known one thing when I started that I know now it’s that as a freelancer you have to be in the driving seat for your writing business and writing career. Like many freelancers, at the start I let clients make the running on everything from deadlines to compensation, often having to pull all nighters to meet impossible delivery dates for low-paid work. Once I started to think more about what I needed, and to manage my time and value my work, my writing business blossomed. When you value yourself and your time, clients do too. I’d have had an easier and more lucrative first year of freelancing if I’d realized that at the start.

Connect with Sharon on social media:

Jake Poinier

Freelance Writer & Consultant

By nature, I enjoy taking risks and experimenting–but looking back, I’d take even more chances. Here’s what I would tell my younger self: Your career is durable. Short of doing something illegal or unethical, you’re not going to break it or damage it. Don’t content yourself with new opportunities, throw in the occasional lottery-ticket play just to see what might happen. On the flip side of that, be smarter and faster about ditching something (whether a client, client project, or personal project) when it becomes clear that it’s not going to work out. The sooner you get on to What Comes Next, the better off you’ll be.

Connect with Jake on social media:

Anne Wayman

Freelance Ghostwriter & Writing Coach

The one thing I wish I’d understood when I started was the whole marketing-money thing. We need to learn to keep marketing to bring money into the business and we need money to keep marketing. It turns out that marketing, which is what creates the money, and handling money well are critical to a well-lived life. My advice: Learn both early and well.

Connect with Anne on social media:

Lori Widmer

Lori Widmer

Freelance Insurance Writer

The one thing I think had the most impact on my career that I wish I’d known at the start was that I’m running a business. The moment I put my head into the business mindset, not the “freelancer” mindset, everything fell into place. I now had a business, not just a career. That meant every decision I made would impact the success of my business. It helped me shift my thought process from a personal, emotional one to a professional one. That mattered because now I was marketing a business, not schmoozing people into hiring me. I wasn’t pestering someone to pay a late invoice – I was following my business’ collection process. Nothing changed except my perspective, which colored everything differently for me.

Connect with Lori on social media:

Laura Spencer

Freelance Blogger & Copywriter

I’m sure I’ve been asked this question before and I’ve probably answered it differently. That’s because most people aren’t really prepared when they start freelancing. There’s so much a new freelancer needs to know.

I think one of the biggest things a new freelancer needs to realize is that freelancing is not a magic fix to life’s problems. So many freelancers get into freelancing because they feel it will solve all their problems. It won’t. It can’t.

Whatever problems you had before you started freelancing, you’ll probably still face them as a freelancer.

  • If you had trouble getting along with a boss or coworkers, you may have trouble dealing with clients.
  • If your budget was tight before freelancing, remember it takes most freelancers several months to earn a decent income.
  • If you need more free time, keep in mind that freelancing is a real job. To earn full-time money, you need to work full-time hours.

The best way to prepare yourself for freelancing is to expect to have to deal with problems–those problems you faced before you began freelancing as well as unexpected problems that crop up as a result of being in business for yourself. If you can handle the problems, you can handle freelancing.

Despite all this, freelancing is rewarding if you deal with the challenges. Speaking for myself, I would choose freelancing again if I had to make the decision over again.

Connect with Laura on social media:

Cathy Miller

Freelance Healthcare & Insurance Writer

I wish I had known what being a business owner meant in terms of the administrative side. I knew how to write. I knew how to network and market. What I wasn’t prepared for was the myriad of time-consuming tasks that could easily distract from my core business. Dealing with the “mechanics” of my business was a huge learning curve. I first had to understand them to better manage them. Issues like setting up a site sound simple until you look at all that entails.
  • Creating and purchasing domain names
  • Choosing a web host
  • Learning WordPress
  • Selecting plugins
  • Understanding SEO best practices
And then there is the fallout when things don’t work as planned. And, trust me, that will happen. Over and over again. And this is only one aspect. Other challenges like tax preparation and health insurance are huge considerations. If I knew then what I know now, I would have mapped a better strategy for incorporating administrative management into my business. Connect with Cathy on social media:

14 thoughts on “Freelance Writing Pros on What They Wish They Knew as Beginners”

  1. As a freelance writer who only just went full-time in September, these tips are invaluable! What a ride it’s been already. It’s great to see what the highly successful writers worried about when they first started…and what they eventually stopped worrying about. Gives me a lot to think about.

  2. Really love to read post like this, it saves someone form doing the same mistake, and know what to do better. Thanks for this

  3. Great list, and I’m honored to be part of it! Thanks, Jenn. 🙂

    There are so many lessons we learn as we’re finding our footing in freelancing. I’m happy to see that many of those lessons are repeated here. It’s invaluable advice!

    • Thank YOU for taking part Lori. Much appreciated as always. 🙂 I loved that this wasn’t all obvious. There were things here I don’t often hear writers say.

      I’ve told writers in the past to remember that their clients are just people — nothing special, nothing better than them, so don’t get so nervous about pitching and negotiating (you’re the one with something they need after all). But Peter put it far better than I ever did with “don’t deify clients.” I think that’s so important to learn early on. Once you become a “yes man” type, giving in to a client’s every whim, you’re doomed until you learn the hard way.

      Also loved Susan’s emphasis on making the most of the editor / client relationships you build. It’s easier to keep a customer than replace them. Other businesses know this, but it’s not something we often think about on the freelance side of things.

      Loved all the tips of course, but those were two things I wish someone had said to me from the start.

  4. What an amazing list of experiences. I can relate to some of the examples here but I still learned a lot. Especially what Peter said about making the mistake of putting the client on a pedestal, and what Susan said about forming relationships with editors.

    Thank you for putting this together Jennifer. And thank you to all the experts who offered such great advice. I’m keeping this as a resource.

    This is very helpful and inspiring. 🙂

    • Thanks for stopping by Christine. I’m so happy you found the advice helpful. And I’ll echo what you said — thank you to those who helped out and offered their advice here. There was such a great mix touching on different areas of freelancing. I think there’s a lot of good info here for new freelancers to pull from.

  5. I just handed in my notice yesterday at my current job. In the next few weeks I plan to work on finding clients and not letting doubts sink in. If I could add some advice as a not-yet-brand-new freelancer, it would be to balance being confident and excited with doubts and a little fear.

    I’ve learned that I can use fear to move forward — it helps me create realistic plans and be realistic. But too much fear will keep me in the same place.

    This post was awesome! Have a feeling I will come back to it a few times in the next few months 🙂

    • I’m glad you enjoyed the post. 🙂 Good luck with your new freelance writing business! I hope to see you around here. 🙂

      And excellent advice. You have to know how fear affects you, and use it to drive you whenever possible instead of letting it hold you back. And if it hits, hang in there. It happens to all of us!


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