how to run a creative business
Writer Management

Guide to Running a Creative Business: Managing Freelance Writers Without Tears

There’s no one-and-done guide to managing freelance writers or running a creative business. But, you can get a good start with these DO’s and DON’T’s from the owner of an online writing agency.

Perhaps you’re one of those SEO companies finding themselves in a scaling dilemma: With more clients, the demand for content is growing beyond your present capacity. Now that you need more and more SEO articles each month, which is best for your company: managing freelance writers, running a creative business by employing in-house writers, or outsourcing to a content writing agency?

DO’s and DON’T’s of Running a Creative Business with Freelance Writers

9 years into:

  • Article writing for businesses big and small (25,000 articles to date!)
  • Managing dozens and dozens of freelance staff (50 gemstone-writers!)
  • Working with over 200 clients
  • Running this crazy outfit 100% online

…We’ve gleaned (read: hard-earned) a trick or two. When it comes to starting a small online business, a lot of the HOW TO’s out there don’t apply. Often geared towards larger outfits, many how-to guides blanket-prescribe tactics that just don’t make sense for a smaller enterprise. Narrow that again if you’re running a creative venture. So how do you get started? What should your employee model look like? Training? Fixed costs? To office or not to office?

I asked Chirene Hughes, creative create-her behind the white label article writing agency Two Red Crows Brand Storytelling, for her DO’s and DON’T’s for starting and running an online business.

*Know that there is no one-size-fits-all guide, not even this one, but it’s a good place to start.



1. Start Where You’re At

When you start an online business you can feel like you’ve got nothing: no website; no social media; no logo. But — and remember this — you aren’t nowhere. You’re at Point A.

It’s simple: Start here. Start now.

It’s easy to procrastinate by spending weeks making a website, or designing your logo. Yes, marketing is vital; but it’s also important to not get bogged down in the details. If you worry about having the perfect presence on every social media platform at the beginning, you’ll roadblock yourself before you start.

You have to start to build. You can always come back and tweak your logo or redo your website  — in fact, you are expected to go back and rewrite content if your marketing is going to be successful. See: Google loves fresh and relevant (updated) content.


2. Choose a Name to Remember

This one is as much for you as it is for others. When it comes to your name, have fun with it! Choose something that stands out (and stands the test of time). Vanilla Ice-Ice-Ice Cream, for example, might have been a hit in the 90’s, but fall flat today.

Or would it…?

For example:

Our online business is called Two Red Crows Brand Storytelling. People are forever asking, why? Especially as our logo is a single black crow. This name does 2 positive things: it is memorable, and it creates engagement.


3. Spread the Love

Two things: don’t hire without due diligence; but don’t overextend yourself financially either. There is a lot of talent out there that might lack the experience, the time, or the training to dedicate to this full-time. If you’re ready to invest in feedback and training, try out some rising talent that other companies might not give the chance. Start with small projects, giving them feedback and opportunities to grow in the trade.

A good team is a mix of veterans and fledglings.

Who knows? You might just find someone you want to add to your team full time.

That said, working with budding freelance writers is a time investment. If you don’t have the time for this give and take, consider outsourcing the task to a trusted professional article writing service. But remember that due diligence still applies–there are lots of blog writing services out there. Be sure to make sure they’re the real deal.


4. Stand Up for Your Staff

As the head of your company, you’re responsible for whatever anyone on your team does. You vetted your team, you hired them, you okay-ed them. So when it comes to unruly customers (and you’ll have a few), stand up for your team.


I’m not the most diplomatic person on the planet. But, I’ve learnt that if I’m kind, I can protect my team without offending our client.

Why this is important:

  • Acquiring a new customer can cost 5x times more than retaining an existing customer
  • 65% of business comes from existing customers
  • The probability of selling to an existing customer is 60-70%

However, never be frightened to fire a client who is draining your will to live.

Be respectful, be kind. But, stand up for your team.


5. Make Space for Staff Walkabouts

Speaking specifically to our experience working with writers, the consensus is: space is good for everybody. When it comes to output, writers have a finite period where their content is up-to-snuff. Then they need to recharge.

At first, I was horrified that writers just vanished mid-project. And confused when they came back a few weeks or months later, without explanation. But, now that we know that this is A Thing, we’ve built it into our process and timelines.

Part of managing freelance writers is knowing when to back off. Giving them space to stretch their legs allows them to come back rearing to go (and it prevents creative burnout).

Look: We appreciate that not every online business relies on creatives. However, the point is that, when you’re working online, it’s easy to forget the people that are doing the work.


Infographic of DOs when it comes to running a creative online business


1. Try to Be Like the Big Guys From the Get-Go

You’re not going to have the time or the resources to have all the bells and whistles at the beginning. You might want to have a team training system in place, but that’s something you’ll grow into. So revel in the learning process of your new business and give the rest time to fall into place. 


2. Give Free Trials

Don’t defeat yourself before you begin. Many people are audacious: they will just take the free thing and never place an order. And yet, real prospects may be reluctant to order before they know what they’re getting in terms of quality.

To bridge the trust gap, we offer one free if you order a bunch.

Don’t underestimate your product. Price is important, but a customers’ perception of value is even more so. When people get a product for free, they are less likely to value it. So, stick to your guns, but create a win-win solution.

3. Work Without a Deposit

This one is pretty self-explanatory. It might be tempting, especially at the beginning, to be so excited that you trust your shiny new client to hold up their end of the bargain. Don’t. Trust is earned: ask for at least 50% before you start.


4. Promise What You Can’t Deliver

In our case, we can deliver consistent quality, but coming in on deadline is tricky. And yet, that’s what our clients pay for: a reliable writing agency. Never, ever, ever have a last minute deadline.

We write bespoke SEO articles to order. This means that we can’t keep a bunch in stock. Every one of our blog articles is individually written — are you starting to see the challenge?

Always build in a buffer before a deadline.

This is even relevant if you’re selling a product not a service. The pandemic has messed with supply chains. There are stock shortages. What buffers will you build in so that you protect your reputation?


5. Get an Office

Starting your venture online gives you freedom to work with talented individuals from all over the world! But this doesn’t mean you should get a head office. (Of course, this is more of a reality with the pandemic but back-in-the-day it was a bit odd.)

At the beginning, I used to suggest getting an office for local staff, with a large screen for Zooming or Skyping, and a nice fire for the winter. You know, with an inspiring view of the Knysna Lagoon or the Outeniqua Mountains– the pictaresque setting for a blog writing service. But each time I’m reminded that our writers work to the beat of their own hearts, and may not wear anything but pyjamas for days.

Keep your team inspired and connected and inspired (again).

So: schedule regular virtual team meetings. Keep up with your staff, create a relaxed work environment. Just don’t worry about an IRL office.


Infographic with 5 DON'Ts when it comes to running a creative business online!


Let’s face it: you can’t start your online business without clients or customers. How will you generate leads? The best solution is a combination of free online marketing (content marketing) and PPC (pay per click) advertising. With marketing and advertising being so important, you’re likely to be a bit confused when we say:  forget about online marketing results. But that’s a story for another time.

Once you’ve got your hens in a row, and you’re ready to expand your online presence, get in touch with Claire. We’d love to help you with your digital marketing content!


Thanks for reading.








About Emily Kim

Emily Kim is a writer by day, and an English teacher, also by day. When not pulling inedible things out of her dog's mouth, she manages the Give Me Articles blog.

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