A Sad and Cautionary Freelancer’s Tale

Cautionary Freelancer's Tale

Over the years, I’ve been in and out of contact with a fellow writer who’s been trying to make a go out of freelancing. She started freelancing about seven years ago because she wanted to be a stay-at-home mother, yet still contribute to the family income. She started with the best of intentions, but things have not gone well. Unfortunately, she insists on clinging to a lot of bad advice and habits. Her unwillingness to move past these things killed her career. She’s looking for a regular job again.

It didn’t have to be this way. She’s a good writer, capable of producing quality content on a variety of subjects. She could have succeeded with a little more effort and a willingness to learn. Here’s her sad tale. After the story, I’ll tell you the problems and fixes that might have saved her career.

Seven years ago, “Sally” decided she wanted to quit her job and stay at home with her kids. She also wanted to contribute to her family’s income so she decided to try freelance writing. She wasn’t a writer by trade, but people always told her she had a way with words. Sally didn’t have a network of contacts or any clips, but she heard that content mills could give you a start, even without clips or contacts. 

So Sally signed up with two content mills and got ready to work. Things weren’t too bad at first. She got some paying gigs, moved up the rankings, and made a little money. Unfortunately, work on the mills comes and goes, so she ended up with some very lean times where she couldn’t cover her bills. 

Desperation had her searching and applying for random jobs advertised online. Most of these turned out to either be ridiculously low-paying gigs, outright scams, or run by people who needed legitimate work but who weren’t willing to pay and found ways to skip out once the work was done. She thought she was protected from these people because she got everything “in writing” via emails and chats. That turned out not to be the case.

Things got worse as the content mills continued to pay less and less. She took on more and more jobs to cover the bills and ended up working horrific hours for well below minimum wage. One content mill folded and she wasn’t paid for many articles.

At this point, discouraged and exhausted, Sally decided to quit freelancing and look for a real job. She’s giving up her dream of staying home because, “Freelancing is a sucky business and it’s impossible to make a living.” (Her words, not mine.)

There are a ton of red flags in this story that led to Sally’s ultimate career implosion. Most, if not all of them could have been dealt with or avoided in the first place, had Sally been willing to change her approach to the world of freelancing. Here’s where she went wrong.

Relying on content mills is a terrible strategy.

Content mills are nothing but a race to the bottom. They pay less and less every year while the hassles only grow. The mills are looking for people to work for super-cheap, or even free. There’s almost no way to make a living with these sites. Maybe there was once, before everyone and their brother started “freelancing,” but now there’s nothing to be gained but a headache. Unfortunately, there’s a lot of advice out there that says, “Begin your career with a mill, get the clips, and build to bigger things!” This is the advice Sally bought into and it locked her into a vicious circle.

The vicious circle is real and requires strength and sacrifice to break.

The content mills pay so poorly that if they are your only source of income, you have to take on more and more jobs just to make any money. That leaves you drowning in poor-paying work and gives you no time to search for better work. You’re exhausted from working so hard and every available moment is sucked up by yet another assignment. It’s a terrible vortex that sucks most people under. The best solution is to not get caught on the event horizon at all. Avoid the mills and begin your career with solid volunteer assignments (if you’re unable to secure any paid work). Or, if you can’t do that, write spec articles for reputable publications until you gain a few acceptances.

You can’t rely on one or two places/clients for income.

Freelancing is an up and down gig. There will be times when you have more work than you can handle and times with very little. These lean times are why it’s important to diversify your client base. If you rely on one mill or employer for work, what happens if they fold, or stop giving you work? Exactly. Even writers who do corporate work need a variety of clients, preferably in different industries. That way if, for example, the computer industry starts cutting back, you can pick up work from your clients in the pharmaceutical industry.

You’re competing where there’s too much competition.

If you want to make money, you have to go where there isn’t as much competition. And that isn’t the content mills. The content mills are drowning in people who want to work for them (all as a result of the “easy money” myth). They can afford to pay peanuts because another writer is always available. The web in general isn’t the best place for work because too many people are sitting at home in their PJ’s chasing every online lead. There’s stiff competition for every spot and online magazine/blogs have way more submissions than they could ever print. You’ve got to go where there aren’t as many competitors and that means…

You have to get out into the real world.

I know, it’s sacrilegious to suggest actually leaving the house to look for work. After all, isn’t everything done online these days? No. A lot of businesses, particularly local businesses, have work for you and they probably aren’t advertising online. Heck, they may not even know they need work until you show up one day offering to help them with their web site, catalogs, programs, or advertising materials. When you ride in, offering reasonable rates and great work, they may bow down before you and kiss your ring. Or not. No way to know unless you try. Even larger companies sometimes find themselves in this predicament, with someone who isn’t qualified and/or doesn’t have time writing content for their website or brochures. You don’t know unless you get off the computer and get out there and pitch.

You also have to network.

Sitting at home in isolation doesn’t lead to success. Leads for work come from all kinds of sources and you won’t find them if you cling to that mill. Get out and join hobby groups, make friends with other writers, go to some Meetups in your area. If you insist on not leaving your house, at least join some writer’s groups online, or look for groups in the industries in which you hope to work. Make some friends and see where it leads.

Starting from scratch is a recipe for disaster.

Sally went out on her own, needing money, but with no experience. This is a bad idea. If you’re going to start from scratch, you’d better have another source of income such as a partner with a well-paying job, or a part-time job somewhere. Or a nice trust fund. That takes the away pressure to make money now. Keep a paying job until you have some experience, whether that’s from your real job or from some work you do on the side. A network of contacts is also helpful.

You have to protect yourself from the deadbeats.

That means contracts. Not emails or chat transcripts. Those aren’t worth anything. You need enforceable, legal, binding contracts. No one likes them and hiring an attorney to create or vet them for you isn’t cheap. It’s also not cheap to hire an attorney to enforce the contract if your best efforts to deal with the client fail. However, contracts are the only protection you have against scams, deadbeats, disappearing clients, clients who lie about payment terms, and all the other riff-raff out there. Contracts are especially needed when you’re dealing with online job ads posted by random people or companies that pop up out of seemingly nowhere. The trouble is, many of these operations will never sign a contract because they don’t want to be tied to you legally. (It gets in the way of bad, scammy behavior, you know.)

If someone won’t sign a fair contract that protects your rights as well as theirs, that’s your first clue that they aren’t on the up and up and you need to run away. If you work for these people, do so with the expectation that you will never see a dime. Better yet, move on. Also, if you can’t afford an attorney to create a solid contract for you, and to chase those deadbeats when they crop up, you need to think about a different line of work. Legal fees are an unfortunate part of working for yourself without a corporate attorney to handle these things. Factor them into your startup budget.


You have to go where the crazies aren’t. 

Looking for work solely online leads to dealing with a lot of crazies and deadbeats. Many of the ads posted online are scams, or posted by people who will skip out without paying. (Not all ads are like this, but there are enough to make me feel like any work taken from an online post is a gamble. It might be legit, but it may not be. I don’t deal with anyone who posts a random ad online unless I’m willing to gamble. If I need that money, I steer clear.)  Again, deal with reputable companies that live in the real world. They’re far less likely to skip out or screw you over because it’s too easy for you to find them.

Desperation breeds poor decisions.

Freelancing when you’re desperate for money is never a good idea. Yes, desperation can make you work harder, but it can also make you stupid. It makes you take jobs you know you shouldn’t take. It makes you vulnerable to scammers and deadbeats. Desperation makes you go crawling to people who’ve treated you badly in the past. You sell yourself short and devalue your work. Have a backup source of income in the beginning and don’t go out on your own until you’re sure you can make money. That will keep the desperation at bay and allow you to make smart decisions that move your career forward instead of sucking you down into the vortex of penny work.

Freelancing is a tough business, but it isn’t impossible to succeed. The problem for Sally and many others is that they’ve bought into this idea that the online world will lead to success and riches. While online work can be a great way to supplement your income, it can’t be your whole income. The big money comes when you are working for reputable companies/publications who need legitimate, ongoing work. Fly by nights, “startups,” and random people you meet online are too often either looking for a freebie, or will skip out when payment comes due. (Or they fold before paying.) You need to build a network of solid clients and that means getting out into the real world and hustling and pitching. There just aren’t any shortcuts to success, despite what many “how to” sites want you to believe. 


(Photos courtesy of Unsplash, stevepbgreekfood-tamystika)

1 thought on “A Sad and Cautionary Freelancer’s Tale

  1. Pingback: Give Yourself a Better Job Description Than "Freelance Writer" | Jennifer Derrick

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