Writing Lessons: 10 Things I've Learned Helping 16,000+ Writers - Make a Living Writing

Writing Lessons: 10 Things I’ve Learned Helping 16,000+ Writers

Carol Tice | 17 Comments

Have you ever wondered if someone can predict whether freelance writers will be successful or not? Well, at this point, I can after the writing lessons I’ve learned helping freelancers.

How? Well, this week marks the 10th anniversary for me of helping writers launch and level-up through my Freelance Writers Den learning and support community. (Note: We’re celebrating by admitting new members, this week only!)

Since the community launched, the Den has served over 16,000 freelance writers. That number absolutely staggers me. I learned a lot of writing lessons and business lessons along the way.

If you’d told me I could impact so many writers’ lives, I would never have believed it, back when I started. And what a crazy time that was. I’ve learned so much from the Den members — certainly, as much as they learned from me.

Before I tell you what business, entrepreneurship, and writing lessons I’ve learned about freelance success that will help you in your own efforts, though, I want to take you back to the beginning. I think it’ll make more sense if you know where I started, and why the Den became one of the most successful freelance communities online.

So many questions

In 2011, I was a six-figure freelance writer and mom of three kids ages 8, 9, and 18. My husband had developed a seizure disorder, and I was the sole breadwinner. I’d also been writing a blog about how to earn well as a freelance writer for three years — this one.

I was wondering what to do about all the frantic emails I was getting, with questions like:

“I have a first client meeting tomorrow — can you tell me what to bid, what to say?”

“Is this website a scam?”

“Where are all the good clients hiding, and how do you convince them to hire you?”

I knew that I couldn’t be the world’s free, 24/7 Dear Abby of freelance writing. But writers clearly needed customized, realtime advice about their particular situation. This writing-lesson realization made me start think about ways to help other writers.

I’d seen online communities for bloggers, and fiction writers’ groups. But there didn’t seem to be a community where freelance writers could gather, learn, get help from pros, and support each others’ journeys. I wondered if an affordable community could be the answer.

Enter market research

The next step was to survey my blog audience and see if they’d be interested in paid community — and if so, what member services they’d like to see.

Writers were definitely interested. There was only one catch. Creating a membership community platform online was completely beyond my technological skills. Far more complex than a WordPress blog.

How would I make it happen? And if I did, would anyone join?

Taking the plunge

Next, I did something that seemed pretty crazy at the time: I charged $3,000 of tech help I couldn’t really afford and opened the doors to Freelance Writers Den. A few dozen brave Den Pioneers got in for $17 a month, instead of the $25 a month rate it’s been ever since Month Two.

A few of my early coaching students got in free, to ‘warm up the room.’ We filled the library with a few PDFs and course recordings I had on hand. It was a start.

We started holding live events, and creating month-long training bootcamps. From our tiny initial library, we’ve now grown our archive to over 800 recordings, with experts including Ed Gandia, Steve Slaunwhite, Casey Hibbard, Jennifer Goforth Gregory, Heather Lloyd-Martin, Claudia Suzanne, and many more.

Word spread about the Den and soon, there were 100 members. Fairly quickly, there were 500 — which was my target for the most I thought there could possibly be. And then 1,000. (If you want the full details on how the Den went from zero to 1,000 members, there’s about 200 pages of info here.) These days, there are about 1,500 members.

Every day, all day, writers tap the Den resources and forums to learn what they need to know about freelance writing, to get a virtual hug, a check-in, or a hand up. Whatever they need.

The life-changing magic of helping writers earn more

In my Jewish tradition, helping another person find employment is one of the highest forms of good deed. In the old days, back in the shtetl, when someone lost their job, they’d tell the rabbi. And he’d get up from studying Torah and start knocking on doors, to help that congregant find a new job. Because securing employment for another is more important than even studying the holy book.

The Den enables me to do what I consider holy work. To answer all those frantic, individual questions in a way that lets thousands learn from the conversation.

The excitement of opening my email each morning or reading the Den ‘Share Your Success’ forum to see that members have found their first client, gotten a raise, finally quit their day job to write full time…well… it’s hard to describe the satisfaction I feel.

Hearing members’ success stories as they found first gigs, got raises, and landed better clients, every single week, has been the most deeply gratifying thing in my entire professional career.

It also gave me insights into how freelance writers sabotage their own careers. Into who is likely to do well at freelance writing, and who really needs a full-time job.

I love freelance writing — so much so that I never stopped freelancing. Right now, I’m working on three book-ghostwriting contracts. So I’m not one of those people who got into mentoring and coaching because I was tired of writing and preferred to teach it instead. I love my clients… it’s just that nothing beats the high of knowing I’ve been able to transform thousands of other writers’ lives.

It’s been my honor and privilege to spend an entire decade engaged in this deeply meaningful work. And there’s more ahead.

All that work helping writers earn more and listening to their challenges has also taught me much about the obstacles that hold writers back. And the attitudes, insights, and personality traits that high-earning freelance writers tend to have.

The traits you need for freelance writing success

When you interact with thousands of writers for a decade, you start to see patterns. You see common traits in who succeeds and who doesn’t, and why.

What do you need, to make it as a freelance writer?

Here’s are my top 10 traits that predict success:

1. Adopt a business attitude

Smart freelancers understand that they aren’t following their muse, writing whatever they want whenever they feel like it. They follow the money, find out what pays well — and then learn to write that.

They set healthy boundaries and have a businesslike attitude about what they charge, how they work with clients, ask for raises, and meet deadlines. They’re mindful of the tremendous value our craft brings to our clients’ businesses, audience, or readers. Business-minded writers don’t work for peanuts because they’re just so grateful that anyone is willing to pay anything for something they find enjoyable.

Writers who know they’re in business also take time to work on their business, not just in it. Once or twice a year at least, they analyze where income is coming from and map out an improvement plan.

2. Don’t buy into the myths

The freelance world is an incredible gossip mill, and a lot of urban legends make the rounds. You have the sense to reject blanket statements about the enormous freelance industry, like:

“It’s impossible to earn a living as a freelance writer.”

“X niche is oversaturated, so you should avoid it.”

Too many writers give up before they start, because of what they’ve heard online somewhere. Meanwhile, the number of people who freelance just keeps growing. That wouldn’t be happening if nobody could pay their bills with freelance writing. Right?

3. Focus

This trait applies to everything from how you niche and market your writing to what you choose to learn to improve your skills. Businesses have a focus, and business leaders have a mentor — not 20 of them. 

Too often, I hear from writers who are clearly subscribed to dozens of newsletters about freelance writing. As a result, they spend most of their time cross-comparing advice and then freaking out when they see everyone doesn’t agree. Then they email me to say:

“I see you say that letters of introduction are highly effective, but Y expert says they don’t work anymore. Now what do I do?”

This sort of problem stems from the belief that there is only one right, true, best lowest-cost way to pursue freelance writing. But that’s not how it is.

4. Engage the gut

Good businesspeople understand that they can get advice from smart mentors. But sooner or later, it’s time to look in the mirror and decide.

Does this fit into my plans? Does it feel like the right direction to me?

I meet many writers who don’t seem to be in touch with their gut feelings. I ask, ‘How do you feel? Which seems like the right decision for you?’ and they say, ‘I don’t know, please tell me the right answer!’

But I don’t wake up in the morning in your skin. I can tell you what I’ve seen reliably, repeatedly work for many writers before. But no one should be in charge of your business decisions but you.

5. Grow your skills

One thing’s for sure — the freelance marketplace is not standing still. There are new tools, markets (hello, legal cannabis!), social platforms and marketing approaches all the time.

Business-minded writers are constantly examining whether their skillset matches marketplace demands — and finding training to fill any gaps. They also know when to stop learning and get to work implementing their new info to earn more.

6. Take action

Many writers love to learn. They take class after class, read book after book. A lot of time is spent fantasy-planning your freelance career, safe and alone in your armchair. But often, there’s a problem.

Instead of learning something and then going out and doing it, so that your freelance writing career sees progress, many writers just keep learning. For years. I touch base with them five years later, and they still consider themselves ‘almost ready’ to go out and actually be a freelance writer. They’re always sure one more class will do it. But it won’t.

Stay out of the learn-learn-learn trap. Commit to learning a new skill and then taking action to use that skill, before you dive into another training. Otherwise, you’re not going to end up paying your bills with freelance writing — you’re just someone who enjoys taking classes.

7. Be bold

The act of running a business requires self-confidence and courage (or a willingness to act as if you have those traits, until you feel them). You have to be willing to put yourself out there. A lot. When I said ‘take action,’ I don’t mean once a year. Professional freelance writers get up and hustle, every work day.

Rather than letting yourself be paralyzed with terror as you pursue a career where in general, no lives are at risk, I recommend you lighten up and try to enjoy the process of discovery, the journey to your best clients.

This career works best if you imagine yourself in a 1920s jalopy careening through the countryside on a madcap adventure. You might crash, but oh, what fun in the meanwhile!

Or that you’re a scientist conducting experiments. “Hmm, if I send out 20 pitches to magazines about X topic, what happens? Let’s dispassionately examine the data…”

Life is short. If you want to be a freelance writer, don’t waste time feeling too scared to go after it. The worst thing that happens is… nothing. So why not give it a whirl?

8. Don’t compare

There is an epidemic among freelance writers of making toxic comparisons between where you’re at and how other freelance writers are doing. There is nothing useful or productive here, people. Just stop it.

Remember, people who seem to be doing great often have a backstory you don’t know. Stop comparing your whole picture to a few surface facts you happen to know about another writer. That’s not their whole story.

Instead, compete with yourself. Just pitch a little more than you did last month, or last year. Raise your rates a hair, then a bit more. Keep moving the bar up. That’s all I ever did, and when I looked up I had cracked six figures.

9. Operate sustainably

Burnout is another freelance-writer epidemic, mainly because too many writers seem to work 18 hours a day, 7 days a week. They don’t sleep right, eat right, or get any exercise. Then, they need 3 months off to recover from a big project. That’s not a recipe for a full-time living.

If you want to pay bills with writing, it’s critical that you design a life plan where you can operate sustainably. If you think sitting and typing all day isn’t hard on your body, just try it. I’ve been freelancing for 25 years on a steady combination of biking, hiking, yoga, weightlifting, healthy food and a dead-serious attitude about getting enough sleep.

Can’t get the work/life balance together because your rates are so low that you must work 24/7 to stay afloat? Then it’s time to raise them. Otherwise, soon you’ll wipe out and have zero income.

10. Get support

Freelance writing is a solitary, often lonely pursuit. It can be hard to keep going, all alone.

There’s a lot to know, and doing this gig in a vacuum means you’re vulnerable — to scams, to undercharging because you don’t know market rates, to putting up with unprofessional treatment from clients because nobody there to say, “You deserve better.”

Our friends and family often have traditional jobs. They don’t understand what we’re going through, and can’t advise us.

The only sane way to build any sort of freelance business is with a support network. But many people live in places where freelancer camaraderie for in-person networking is nil.

That’s why I created the Den, and I think why it’s so popular. No matter where you are, you can connect with other freelance writers.

The single thing I find most predictive of freelance success is having an accountability buddy you meet with weekly to discuss goal progress, and a community you can bounce ideas off and ask questions. Period.

Do the points above describe your approach to freelance writing? If not, I know a place where you can work on your mindset, and acquire the killer instincts needed for running a kick-butt freelance writing biz that earns you serious money.

Got community?

After reading this, perhaps you’re wondering if Freelance Writers Den is for you. We’re celebrating our 10th anniversary this week and are open for new members (for the last time in 2021!) — so if you’re interested, this is a rare opportunity to jump in.

The Den can be a great, fairly low-cost way to get professional development and support as a freelancer. There’s something magical about hanging out with hundreds of people who are in a similar boat to yours. The group uplifts you, offers encouragement when you’re down, helps you shake off the comments from crappy clients who don’t appreciate you, or the leads who ghost you. Your community has your back.

Without that sounding board…well, I meet writers who’ve been earning $10 for 1000 words for years, without ever knowing there was anything better out there. Or they do jobs on Upwork or Fiverr they get stiffed for. So many sad stories, where they don’t know how to find real writing jobs.

There’s a reason hundreds of Denizens have been members for years. Support is powerful — and it helps you earn more. (Also, you save hundreds on Den courses by staying a member.)

Is it for you? Freelance Writers Den can be a massive game-changer for your career if you:

  • Need to launch your freelance writing biz
  • Are freelancing, but not earning well
  • Have questions you’d like to bounce off some writing pros
  • Want a shortcut to figuring out the freelance-writing game
  • Don’t want to pay thousands for each course you take
  • Worry about scams
  • Find fears are holding you back
  • Don’t know what to charge
  • Need contract templates and examples
  •  Aren’t getting enough client leads — or only get lowball offers
  • Have never marketed your writing and need to learn how
  • Have client problems you need help with

Those are some of the top issues we solve for members. Can I help you become my next success story? If so, I hope to see you in the Den.

What do you think are the most important traits for a successful freelance writer? Add to my list in the comments.

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17 comments on “Writing Lessons: 10 Things I’ve Learned Helping 16,000+ Writers

  1. Alan Thrush on

    This is an excellent article, written by someone who clearly knows her stuff. I’ve been writing freelance for more than thirty years, and every single piece of advice given here rings true. Well done, Carol! Keep up the good work!

    Reply
  2. Kathy Hendricks on

    Thanks, I needed that this week. My writing is slowly, very slowly moving ahead. I am blogging for powersports now, it does not pay much but it pays. My old gigs that sustained me prior to Covid-19 are still not fully back, I will be dropping one of them when I get another writing job going. It has been a rough year and a half and I know I am not alone in this, but it does feel like it sometimes.
    I am glad you had the chance to make more money when your family needed it most. I also know I cannot give up and must keep plugging away, applying for work, honing my skills and getting the word out about my career path.
    Keep On Keeping On (from the 60’s for those of you who weren’t around then)

    Reply
    • Carol Tice on

      Like they say in the Marigold Hotel movie, if it’s not happy, it’s not the ending, Kathy! I definitely didn’t figure it all out instantly. Take a look at The Recession-Proof Freelancer ebook here on the blog, if you need more tips. Also check out the free Q&A I did yesterday — you can sign up to see the replay here (or check your email, if you enrolled to come live): https://freelancewritersden.com/ask-me-anything Gave a LOT of tips on how to recession-proof your biz, classic steps as well as things I’m seeing in this particular market, right now.

      PS – your Wix URL doesn’t seem to be working, just FYI.

      Reply
  3. Carl Isom on

    Under 1. Adopt a Business Attitude, I think you are right on target.
    You absolutely need to TREAT YOUR BUSINESS LIKE A BUSINESS, NOT A HOBBY. My father taught me that “Any goal worth setting is worth the work you need to do to accomplish that goal.

    Don’t just develop an action plan and think you’re done. Once you’ve come up with an action plan, then it’s time for you to figure out “Specifically, how am I going to IMPLEMENT my action plan? What steps do I need to take and what tools will help me succeed in this critical step?

    Reply
  4. Barry Desautels on

    Congratulations Carol.
    10 Years in any business is a worthy accomplishment.
    Although I don’t visit the Den as often as I should, its a comfort to
    know the training and support are always there.
    Thank you and all your staff.

    Reply
  5. Christine Osterwalder on

    Happy anniversary, Carol!

    Thanks for continuing to provide both resources and challenges to improve our skillsets and business practices. I loved this deeply personal piece and am grateful that you have found a way to do your own holy work everyday.

    Reply
  6. Williesha Morris on

    Carol, I think you’ve nailed all of them. I struggle with these often but your reminders have kept me going, even inching me along when I’ve fallen back into FT work over the years. Having chronic medical issues and living with my in-laws is always pulling me towards something “stable with benefits.” LOL I think for the umpteenth time, I’m moving away from the 9 to 5, because it has just not been a great experience overall. The freelance life is better for my mental health, even when I’m not making a lot of money.

    Your teachings and advice have been the foundation of my freelance writing business and I’m so grateful. I never tried the mills as a result, and I’ve gained a lot of confidence. Happy anniversary! No matter how successful I become, I can’t leave the Den! It is such an integral part of my life. Not sure exactly when I started following you, but it’s been at least 6 years (wow!) Thanks for being such a great mentor.

    Reply
    • Tanya Adams on

      Williesha, like you I struggle with a couple (okay maybe more than a couple) on this list from time-to-time. I’ve dipped my toes back into full-time work and get antsy for the freelance life for the same reasons that you mention. Except, I live alone and when I find that I don’t do all those things on this list my income drops and I get in a state of panic and I grab a full-time job for the benes (I say) and then find I’m miserable there. Hey, but that’s on me. By doing all on this list consistently, I know I’ll never put myself in the position of grabbing a full-time job I hate. Also, as an introvert, I’m one of those who likes the solitude of a writer’s life. It is so much better for my mental health as well. Thank goodness for the Freelance Writer’s Den. The support there and the resources have been a great help to me; especially the support.

      Reply
      • Carol Tice on

        Peer support is magical — I totally agree, Tanya! THAT is why many members never leave. It’s hard to get that support in our daily lives, friends and relatives don’t get what we do.

        Reply
    • Tracy Hume on

      Williesha — I totally agree with your comment, “No matter how successful I become, I can’t leave the Den!” I’ve been a FWD member for 10 years, and have been making my living as a freelance writer for about 15 years. Once in awhile I think, “Is it time to leave the Den?” and then Carol comes up with a new resource which turns out to be exactly what I need to keep moving forward. Most recently I completed the bootcamp for updating your LinkedIn profile, and it has absolutely increased my inbound leads. FWD is the best!

      Reply
      • Carol Tice on

        I use the resources myself sometimes, too! I don’t know every single thing, and we’ve had amazing presenters over the years. As a book ghostwriter, I go back and review Claudia Suzanne’s module on book structure now and then…!

        Reply
  7. Kristen Frisa on

    Carol, without your help I dont think I could have made a business of freelance writing. It would have remained an unfulfilled dream, because I had no idea how to start. Your guidance has helped me get started, and then 2x my income and I can’t thank you enough. I think I would add to this list the need for writers to constantly revisit their limiting beliefs and continually retrain their brains for success. Each time I have a bout of success I fear my business will all just dry up and go away, and sure enough a slump follows. I know that by going back through the training modules and employing your advice I can back on track again.

    Reply

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