3 Frustrating Freelance Writing Challenges: Overcome Them NOW

Anyone with a freelance writing business has challenges. Your challenges may be huge, or trivial, but either way, they take up mind space and ruin your creativity.

Common challenges in a freelance writing business

Freelance writing comes with lots of challenges. The most common is feast or famine syndrome: you either have too much work, or too little.

Challenges you can overcome:

  • Underemployment: not enough work coming in;
  • Too many low-paying gigs: you’re on a hamster wheel spinning faster and faster;
  • A lack of confidence: you know you should promote your writing business, but you don’t.

1. “I need more gigs!”

Under-employment is a worrying challenge for your freelance writing business. When the “famine” portion of freelancing hits, you realize you need more gigs FAST.

Many freelancers find the roller-coaster ride of freelancing too frustrating and rush back into employment. That’s perfectly OK. Sometimes conditions aren’t right. There’s no shame in freelancing as a side hustle.

“More gigs” solution: diversify

You need to do more marketing. See “I know I should promote my services…” below. Also, consider diversifying.

Luckily, professional writing offers many opportunities to diversify.

Often you’ll diversify for a change of pace, or because someone makes you an offer you can’t refuse. I started my career as a romance writer. I diversified into copywriting and ghostwriting because people offered me gigs.

Ideas to diversify your freelance writing business:

  • Write fiction and self-publish your novels.
  • Develop a specialty from any insider knowledge you have. For example, perhaps you’re a fashion and beauty blogger. Gigs have dried up, but you’ve worked in finance, or health. Research companies in these areas. If you get a couple of gigs in the finance writing area, look for more. Then suddenly, you’re a specialist.
  • Think local. Take a wander around your local business park; make a list of companies. Check the companies’ websites and marketing efforts. Could you help?
  • Got a blog? Monetize it. Chances are you’ll need to write fresh content, but that’s OK, you’re developing another income stream.

2. “I’ve got too many low-paying gigs…”

3 Frustrating Freelance Writing Challenges

Too much work, too little income. This means that your positioning isn’t working.

A student told me: “I’m working 14 hours a day but I’m not making much. I’m too scared to give up my low-paying gigs to look for new clients…”

Low-paying gigs’ solution: charge more and reposition

New freelancers take any and every gig that’s offered and that’s fine, because you need the experience. Sooner or later, you suddenly realize you’re writing 12 hours a day, but your income’s dismal.

You know you should get higher-paying clients, but you don’t have the time to market your services. Nor do you have the confidence. (See promotions, below.)

The solutions:

  • Charge more. Raise your rates by 10% across the board, today. Most of your clients won’t even notice.
  • Raise your rates when quoting on projects. Find out what other freelancers in your city are charging. Tip: if web developers and graphic designers are charging ten times more than you do, it may be time to raise your rates.

Repositioning your freelance writing business

Repositioning takes time, but you can do it. “Repositioning” means targeting a different market.

When you start writing, you take any gig which comes along. You fall into a rut. Then you realize that you need to attract higher-paying clients.

Big tip: it’s often much easier to write for clients who will pay you more. Not only do they give you better briefs, because they know what they want, but they’re also experienced in working with freelancers.

So how do you reposition your business? 

When repositioning:

  1. Think about your ideal client. “Clients who pay more” is too broad. Generally B2B (business to business) companies pay more than B2C (business to consumer) companies.
  2. Consider that your clients pay for value. In other words, they pay for what they can’t do themselves, because of time or knowledge constraints.
  3. Pitch. Make time to research companies every day, even if it’s only 20 minutes. Once you find prospects you can help, send a pitch.
  4. Keep pitching. Look at it this way. You may have to pitch 20 companies to get hired by one, but what if that one new client pays you more than all your current clients put together?

Repositioning is the one big secret to making a top income as a freelance writer.

3. “I know I should promote my services, but…”

I managed to avoid marketing my freelance writing services for years. Book contracts and magazine writing took all my time.

Then the tech wreck of 2000 happened. Book contracts dried up overnight, so did magazine writing gigs.

Although I was happy enough writing marketing material for copywriting clients, I hated to do it for myself. But… I learned. And so can you.

Promotions’ solutions: do what works for you

You won’t know what works for you, until you try.

Marketing comes in two forms: inbound and outbound. “Inbound” marketing means clients approach you, because they’ve heard your name. Perhaps they found your website or someone referred them to you.

“Outbound” marketing means you go hunting for clients using direct approaches (calls and emails) and/ or advertising.


  • Pitching for new business. (We mentioned pitching when we talked about repositioning above.) Pitching works. Send proposals and you’ll get hired.
  • Making cold calls and sending cold emails to companies with which you’d like to work. This is a numbers game. You’ll need to make a lot of calls to get gigs, but you’ll get them, so keep calling.

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