Is This Missing Piece Stalling Your Freelance Writing Career?

Carol Tice

missing puzzle pieceI get a lot of email from aspiring freelance writers as they set out on their journey.

“I am totally doing this freelance writing thing!” they tell me. “I’ve always wanted to be a writer. It’s time to quit the job and go for it.”

A year later, they write me again. And they have not gone for it.

They are still right where they started…lacking the nerve to put in their notice and leave that day job. Or earning peanuts writing for content mills, because it’s easy.

Loads of people want to be freelance writers. They read books, they read blogs, they take classes.

But when it’s time to actually get out there and market your freelance services and find clients, or time to do some writing…nothing happens.

Something is missing. To understand what it is, you first need to understand this:

Here’s what freelance writing really is

Writers love to dance around this and say it’s all about our creativity, our freedom, our muse, writing about what we want. To which I say, baloney.

That’s writing a novel. Being a freelance writer is something else.

Freelance writers are in business. Plain and simple.

Maybe you didn’t lease a storefront, but you are in business just the same. Your family’s ability to eat rides on your success.

And all business involves one key ingredient. If you don’t have this, your freelance business cannot succeed.

To circle back, why has that new writer not taken the plunge? They were so excited by the idea of freelance writing, after all.

It’s because they had an insight about what this path will entail — and it stopped them dead in their tracks.

Leaving the ‘secure’ world of corporate employment and starting their own business involves taking a risk.

So they make their plans, but then, when it comes right down to it, they balk.

Why? Because they don’t see themselves as risk-takers. Instead, they are risk-averse.

Without the willingness to take risks, you cannot make a go of this freelance writing thang. It will fizzle and die on you.

3 Ways to take the fear away

Fear of risk is the death knell for aspiring freelance writers. If you want to do this, you have to take risks. So you’ll need to build up your tolerance for risk.

Here are three tips on that:

1) Reframe the question

You’re thinking that embarking on a freelance career is a big risk. Now, flip the equation. How much of a risk is it to stay in your current job? Or if you are writing for content mills, how secure is that situation?

Corporations are increasingly fickle when it comes to their workforce. You could be out on the street in the next economic downturn, or just because a new boss doesn’t like you. Any random reason, really.

The content mill could close or change their rules. Happens all the time.

Yet most people think of having a steady job as the ‘safe’ option, and marketing their freelancing as the ‘risk.’

My experience coaching laid-off writers for nearly a decade now says that’s wrong.

Also, when you look five or ten years down the road, what do you want to see? How about at the end of your life?

You can look back and regret how you stayed stuck in a job you hated, or be reflecting with satisfaction on the fulfilling life you’ve had, living your dream career.

For those of us with kids, there’s also the question of what you’re modeling. Do you want to show them they should go for their dreams, and they can achieve whatever they set their minds to? Well, that message will be stronger if you’re doing that in your own life instead of punching a time clock.

When you think about it that way — with the long view of how you are spending the precious moments of your life — taking a ‘risk’ on freelancing seems less scary.

Writers who worry about the risk of putting their work out there are worrying about the wrong thing.

2) Understand inaction

Most risk-averse writers I know dither and procrastinate a lot. They keep trying to edge their way around their fears, to stay safe, to keep from doing the scary stuff that might fail.

And they are missing an important fact: Not taking action is also a risk.

It may feel safer, but it’s not. It’s just another form of risk.

While you are not moving forward, others are. Prospective clients who might have loved to work with you are finding someone else. New competitors are sharpening their skills, learning about industry changes from interacting with clients, and doing their marketing.

Each day you don’t act, you get older, and farther away from your goal. Because inaction breeds more fear.

In the vacuum of inactivity, you think up more reasons why it’s too risky. What will I do for healthcare? you think. How will I pay for my kids’ college?

Stop thinking you’re playing it safe by waiting and watching. In fact, you’re risking your chance to make freelance writing your career, every moment you wait.

3) Take calculated risks

As it happens, I am a fairly conservative person when it comes to risk-taking. So this third one is something that’s really worked for me.

You can do things to lessen your risk. For instance, finding the next, better-paying client before you drop the lower-paying one.

You can also find mentors, or join a writer community where you can learn more and avoid the freelance pitfalls. That knowledge reduces your risk that actions you take will flop or be a waste of time.

Like the writer I just heard from this week, who reported she’d wasted a year bidding on Elance gigs and only landed three of them. She wanted to know whether I thought bid sites were a waste of time! Only someone with no mentors or writer network could have wasted that much time without wising up.

With some savvy in your corner, you’re not taking foolish risks where you end up starving. You are taking considered, well-thought out risks.

You learn to go after clients you have the best chance of getting. You figure out the marketing method that works best for you, because you’re willing to risk trying out a few things and learning from the results.

This as sane, smart risk-taking. As you learn more, you build the confidence to bet on yourself.

Take little leaps

You can condition yourself to risk by starting small. Think of it as jumping over a puddle before you try to tightrope walk over the Grand Canyon.

Maybe it’s sending one query letter, or posting one blog comment. Writing a 300-word article for your local newspaper.

Make a list of small risks you could take to move your freelance writing business forward. Then, start checking them off.

You want to start exercising your risk muscle because as you build a freelance career, you’re going to need it.

Because take it from me — the risks only get bigger as you become more successful. As your portfolio builds, you have a reputation that could be damaged if you screw up.You end up with thousands of blog readers who stand ready to applaud — or trash you — each time you post.

You decide to invest money to produce an ebook – money you may or may not get back. But it’s good to invest in yourself to grow your writing business. It’s a smart risk you should take that could provide an ongoing income.

To sum up, it’s all risk. Every moment of life is, really.

Each stage of building a good freelance income will bring new risks.The more practice you get at taking risks, the better you get at developing your spidey-sense of what choices will pay off best for your freelance business.

So get used to risk now. Stretch your risk muscles and learn to tolerate that feeling of discomfort you get just before you jump. That’s the missing skill that takes your freelance writing career straight to the top.

What risks have you taken in your freelance writing business? Leave a comment and tell us about it.


  1. Williesha

    Focusing on building this business instead of traditional job hunting was a huge risk. But I understand now you can do both. That way I can earn even more to invest in my business (I didn’t have savings so I’m looking at working outside the home. Savings before taking the leap is a great way to take more risks in your career!)

    • Carol Tice

      It definitely helps to have a cushion when you’re freelancing, Willi — helps you avoid getting desperate and working for peanuts, which becomes a real trap.

  2. Mai Bantog

    This is so spot on! I love this, Carol. I’ve been putting off writing pitches and query letters for a month now in favor of the jobs I currently have from bidding sites. They’re pretty decent paying, but I want to earn more without writing 10 500-word posts per week. I want a better job, but I just can’t make that first step of actually sending a pitch. The most I’ve done was to make a LinkedIn profile, read up on marketing myself, and comment on blogs–anything but the actual writing. I really ought to set a deadline and take that leap of faith.

    • Carol Tice

      Take the risk, Mai — it’s the only way you move to the next level in business.

  3. hoongyee

    Hi Carol,
    So true about risk and how that fuels all creative pursuits.

    It is not only helpful, it is crucial to reframe your view on embracing risk in your life and to understand what swings in the balance – regret for not doing anything for your career, or reinvention of your mindset moving forward.

    what I would wholeheartedly add as an foolproof way to recreate risk into reward is to be unapologetically generous with your creative energy and your writing.

    Here’s what I mean:

    I published my first picture book with Little, Brown & Company many years ago and have not written anything since then. I had every excuse under the sun but the DNA running through all of them was fear. I was afraid to risk being a failure with my second book.

    When I finally could not stand being on line at the author’s table clutching a copy of their newly published picture book to be signed, I picked up my cell phone and called my biggest fan/ inquisitor/ demon on my shoulder/ critic / supporter.

    “Hi Mom. I am going to write a book. A 32 page, classic illustrated picture book, 1000 words. It is about the ghost dumplings you always made for the Hungry Ghost Festival.”

    I held my breath.

    She said, “That’s nice dear. Make sure you get it right or else I will look foolish and you don’t want that, do you.” Something inside of me perked up. Something like validation.

    “Besides, even if you don’t, you are just a speck in the universe so don’t go off thinking everyone is going to be upset with you. They probably won’t even notice.” My Mom, the Buddhist from Bayside, Queens, always had this way of putting everything into a somewhat enlightened and humbling perspective for me, her daughter the speck.

    I wrote my book, minus the angst over risk, and donated a reading and a set of thirteen limited prints of my illustrations to a fundraiser for art scholarships.

    Suddenly, I was an author & an illustrator. People talked about me as “that wonderful writer who also draws, and isn’t it incredibly generous of her to donate her time and pictures to our fundraiser? I can’t wait to buy her book!”

    Risk transformed into rewriting, revision, rehearsal and yes, reward.

    I sold 10 out of 13 illustrations, gained hundreds of new fans and most important of all, I stared risk down with a generosity of spirit.

    cheers, hoongyee

    • Carol Tice

      Good for you!

      I hear from too many writers who have an initial success, and then freeze.

      They have an editor ask them to write an article…and they don’t. Months go by. They run away.

      Doing and having it flop will always be better than not trying to do anything.

  4. Steve Maurer

    Hi, Carol.

    Great article on learning to overcome the fear of risks. I agree that part of that fear comes from not looking at your freelancing as a business, as you intimated.

    Taking small steps helped me out immensely. Took training courses, read like a book demon and consumed copious amounts of information. Still seemed up against a road block. Even after spending quite a pile of money on it all.

    However, it was one small investment – about $15, in fact – take pulled the trigger. It was the fee for a business license in our hometown.

    Suddenly, I not only had a business – I WAS a business.

    Thanks for the great article on overcoming the fear of risk taking. Great ideas and counsel.


    • Carol Tice

      Thanks for spotlighting another great reason to not fly under the radar and register yourself as a business! It makes you realize, “I’m in business. I need to put it out there and find customers!”

  5. Darlene Strand

    I’ve written three short stories with MidLife Collage Writing Contests…Hoping one or all writings to win in their weekly contest entries. Continuing my visits to other writing sites, for gaining better perspective and understanding on possibly working for other sites for a little weekly or monthly income. Like your Writers Den and for Strong Whispers to write few articles. By summer, I hope to have a better uplifting experience in making a living in writing.

    • Carol Tice

      Hi Darlene —

      Freelance Writers Den doesn’t publish articles — it’s a learning community where we offer trainings and support forums for asking questions, among other things.

      Entering contests can be a way to get editors’ attention and earn a little money, but in general it’s not a major way to earn a living. Be sure to pitch paying publications and websites in addition to entering contests. Also, short stories are not the format that tends to be a reliable way to earn money…nonfiction articles and writing for business are the two mainstays of freelance writing income.

  6. Tom B.

    Thank you so much for your thoughtfully and well written kick-in-the-pants; I needed it badly. Truly inspirational. However, I believe many of us are put-off by the marketing dependence on the newest social-media such as Twitter, LinkedIn, Facebook etc. All these media apps take time to become savvy with, and monitor/attend to; thus taking time away from writing itself. Would you suggest building a large “Bank account” of sample writings, stories, blogs, etc, before even taking the first-step of diving into these types of media marketing?

    • Carol Tice

      Hi Tom —

      First off, we are not dependent on social media for marketing. I know very successful freelancers who don’t use it at all. All the old-school ways work, too — cold calling, in-person networking, sending letters of introduction, doing direct mail campaigns. It’s just my experience most freelance writers find these methods overwhelming and tend to not do them…where social media might be a more accessible and free way to put the word out about your freelance business.

      What social media has the power to do is connect you to people you might never form relationships with any other way, all over the world. Instantly. Which is why I recommend writers get involved in social media ASAP. No, do not wait and wonder if you’ve built a big enough portfolio. Get on NOW.

      I constantly hear from writers who’re intimidated because they feel everyone else already has 10,000 followers and how will they ever catch up? But this gap will not get narrower over time, only bigger. Jump on and get going.

      Big tip: You don’t have to be active in every form of social media there is! For instance, due to changes at Facebook, it’s stone dead as a business marketing platform these days, in my view. I’ve seen my views on my blog page there go from 600 for a typical update to 40.

      If you’re only going to be on one platform, make it LinkedIn, the only social media that is expressly about business networking rather than socializing. Twitter and increasingly Google+ can also be great for making amazing connections.

      As far as the timewasting — it’s up to you to be disciplined about your social media time. That’s the other reason I love LinkedIn — you can stay ‘active’ on there in about 10 minutes a week, once you’re set up. This post has more:

      For even more, I have a 4-week bootcamp on How to Use Social Media to Get Freelance Gigs in my Freelance Writers Den community, so you might want to check that out.

  7. Mare

    Carol, I am so glad I found you and your site! I have actually been writing for many years and finally formed “the company,” The Write Attitude, in 2004, but I kept up my full time career in the workplace, doing work on the side. Last September, with my youngest going off to college, I decided it was time to devote myself to The Writing Life full time and I have been doing so. I’ve had some success but it’s irregular and I really want to build a stronger foundation. This article–and other resources on your site–have really energized me. The best thing you note here is getting involved with other writers and surrounding yourself with people who will support your efforts and not turn up their nose.

    Thanks for the great advice and for your commitment to helping writers be successful! Happy Monday.

    • Carol Tice

      Thanks Mare — if you’re interested in writer community, be sure to check out Freelance Writers Den and get on the waitlist. Often, I only tell that list when we’re going to reopen for new members…like, say, is happening tomorrow. 😉

  8. Barbara Weddle

    I loved this article!

    Ok. As for risks I’ve taken: I sent an essay to an Ohio magazine (where I once lived) not knowing whether or not they published essays. (This was before Internet and I had no money to mail away for a sample mag.) The editor bought it and several others until the magazine folded. After querying other magazines and getting nowhere, I sent them completed articles. This worked, and, as w/the Ohio magazine, they (TRAVEL SMART and FUNDS FOR WRITERS and others) purchased other articles from me. The biggest risk, however, was taking out a personal loan one year of $2,500 to travel around the country and see my sons and their families and just see some country, and promising my husband I could pay the loan back w/money I earned freelancing. (I paid it back.)

    • Carol Tice

      That’s awesome Barbara!

      Sometimes making a commitment to spend money gets us to risk more in our business because we know we *need* the money!

      I know when I paid a $1,000 to attend my first SOBCon, it was completely crazy. I totally couldn’t afford that!

      And I came home SO fired up to take my business to the next level…and did.

  9. Nadia McDonald

    I absolutely love this article today Carol. Yes, life is about risks. The greatest tragedy in life is to go the grave and not achieve one’s goal. Life is about purpose and vision. Too many writers gave into fear and live mediocre lives. I want to leap and take that risks. There are articles I want to write, novels and books I want to publish, lives I want to influence. Nothing is wrong with being on a regular job.
    However, life is about living and not existing. While I am breathing God’s breathe in my body, I want to seize opportunities and achieve my goals.

  10. Halona Black

    Having a freelance writing business was the biggest risk of my life. I had been jobless for well over a year and had only done a few short term gigs here and there to pay the bills. I stumbled on some information from Yuwanda Black on SEO writing and decided to give it a go. I had no savings, but had enough initial freelance work to move to Florida. Life is way cheaper here than it was for me in NY/NJ. Now I am planning self publishing health books as well as teaching other health professionals how to self publish.

    • Carol Tice

      Great story, Halona! Look at all the changes you made to make this happen, making a move, learning SEO — great example of how taking a bet on yourself can pay off.

  11. Stan Scott

    Back in the 1990s I started an electronics business. The first year was spent cold calling without any clients. People kept telling me to “Get a job”. I persisted. Almost a year to the day I got a phone call. It was my first client and I made over $100,000 my second year.

    I know persistence is what it takes. While I only had a couple of copywriting clients last year, I know the potential of this copywriting business. It’s a matter of figuring out how to connect with the prospects and not giving up. The risks are worth the reward.

    • Carol Tice

      Wow, great story there…and hopefully one that keeps you moving forward.

      The one thing we know for sure is if we don’t risk building our own freelance business, it will definitely never happen.

  12. Mike Johnson

    Other great benefits of creating your own writing business are the legal tax deductions. For most people, taxes are your #1 or #2 expense. Paying fewer taxes is the same as getting a pay raise. Employees are taxed at the highest tax rates — far higher than businesses.

    For example, when you have a business, any business-related driving lets you deduct 56 cents per mile from your taxable income. Think of all the trips to the post office, bank, office supply store or nearby big city. Trips to research a topic or article or book are deductible. This can amount to thousands of dollars per year.

    The home office deduction is also another huge way to reduce taxes. You establish a specific area of your home or apartment and use it exclusively for business. Measure the square feet to determine the percentage of business space. Say it’s 20 percent of your living area. You now get to deduct 20% of your mortgage or rent, utilities, dwelling improvements and repairs. You can also deduct 100% of office furniture, business-related periodicals and books and business-related travel including plane tickets, hotels and 50% of your meals. The home office deduction gets a bad rap because some say it attracts audits. My accountant says this isn’t true. Just follow the rules and you legally save thousands in taxes that you are not legally obligated to pay. Fear combined with ignorance creates its own tax that many unknowingly pay!

    Even better, if you are a sole proprietor and file a schedule C on your personal return, you can take these business deductions for a few years even if your writing business doesn’t make money. You get to take business loss deductions from your other, active employee income that you’re getting from your job. This reduces your taxable income which reduces what you pay in taxes. So you get the tax savings, even though your writing business earned no money. See your accountant for details as I am not an accountant but have paid one for more than a decade to gain advice and tax savings.

    Everyone should investigate the big tax savings available (a pay raise!) by starting a side business, and writing is one of the best, low-cost side businesses available.

    Good Luck,

    • Carol Tice

      I don’t know if I agree, Mike, because of the fact that self-employed people pay double the employment tax you pay as an employee. Nobody should get into freelance writing for the tax breaks, I’d say.

      You might have more writeoffs — depends on what you do in your business and what deductions you decide to take. The home office deduction isn’t for everybody — especially if it’s a side business and you have another workplace, IRS may take a dim view of that. I was Entrepreneur’s tax columnist for many years, so I’ve spent some time on this issue. These days, many freelancers do about zero travel for work-related reasons, too. I personally did not take any mileage deduction last year — wasn’t worth calculating as it was so little business miles driven.

      The idea of running your freelance biz at a declared loss while continuing to take deductions can also be a red flag for IRS to disallow your business as a ‘hobby.’ It’s often wiser to simply take fewer deductions and continue showing a profit. What you’re proposing is essentially a bald tax dodge, and IRS may figure that out.

      Being in business for yourself is worth it for many other reasons, beyond possible tax advantages.

      Personally, I love being able to write off all my newspaper, magazine, and cable TV subscriptions, as they’re all places I find ideas. 😉

      • Mike Johnson

        Hi Carol,

        Of course you would not enter a business with the idea of making it a tax dodge. But the laws allow you to lose money for several years and deduct it from your other income as long as you are truly trying to make it a profitable enterprise rather than just a hobby. So that is a benefit of starting a business — it can increase the amount of money you keep during those early years where generating sales is the toughest.

        And employees are taxed at the highest rates because their taxable income has so few legal deductions that it pushes employee’s income higher up the tax tables where the rates are the highest. Businesses that pay the extra 6% social security and medicare tax is quickly overcome that with other legal deductions. Having owned many other non-writing businesses, I have direct experience with that.

        Taking legal tax deductions is yet another example of people perceiving a higher risk where it is unnecessary. The less people know about taxes and the tax code, the “riskier” any deduction looks. I suspect US citizens pay far more than required in taxes because of fear and ignorance than are ever uncollected due to tax evaders. If no other reason than there are so many millions of the former and many fewer of the latter.

        So once again, self-education and making yourself an authority on topics that matter to you (or accessing people who are already authorities), makes a huge difference in the quality of your life. Knowledge reduces risk. Less risk = less fear. Less fear = more action. More action = more results. There is always valuable information hidden much deeper than the mainstream “experts” discuss. As writers, we have the power to find and use this information to make our lives better.

        Outside this blog, there are millions of people who think writing as a career is ‘risky.” We know better because we’ve become authorities (and have experience) on the topic. This is true for every topic. If something looks “risky” it’s only because we haven’t dug deep enough to learn more about it.


        • Carol Tice

          Well, I’m certainly a big fan of learning more!

          Having done nearly everything the hard way in my freelance writing career — mostly because the Internet didn’t exist yet — it’s so easy to learn a writing niche or skill now, like the Freelance Writers Den bootcamp we did on PR writing, for instance. Writers are lucky to have those shortcuts to take advantage of. And those are risk-reducers.

  13. Robin Cromer

    Carol, I can’t thank you enough for this post, I so needed and need it – your timing is perfect. I appreciate both what you said and the boldness with which you said it; your honesty and passion are much appreciated.

    I never made the connection to fear and being risk averse, nor saw inaction as risk before. I know first-hand the risk of betting on a steady corporate job. I’m also guilty of worrying about the wrong thing.

    Recently however, I got tired of wanting without action and started doing. In addition to this post, I’m lucky enough to be one of your Article Writing Master Class students; I can’t thank you enough for that as well.

    Thank you for your willingness to provide support, to share your experience, expertise, wisdom, spirit, resources, connections, and having the boldness to take up your mission to help writers, including wannabes like me. You are priceless. Though I’m newly aware of the tremendous amount of work that lies ahead, my transformation is well underway.

    • Carol Tice

      Glad you’re enjoying Article Writing Masterclass, Robin!

      I have had the luck of having a formative experience with my mother-in-law, who is a big waiter. I’ve known her over 30 years now, and met her when I was still a teenager.

      I discovered that life happens to her. She does not act in her life.

      She’s always waiting to hear what the doctor says, the judge says, the lawyer says, her friend says, before she can take any action. She’s in her 80s now, and has spent the bulk of her life avoiding making decisions and taking actions.

      I can tell you, it doesn’t end well, the inaction strategy. Her inaction risked it all, and she lost big. She is a sad, lonely woman who never pursued her dreams.

  14. Inderpreet

    Hi Carol, As usual this post hits the spot. I too have been neglecting sending queries and looking for more work due to a busy personal schedule as well as getting so involved into personal blogging.
    I lost sight of my goal of turning it into a profitable career by year end; but I am back on track now.

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