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. 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.

  2. 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.

  3. 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.

  4. 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.

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