10 Things I learned when I Became a Freelance Copywriter

This was written the week of the fourth anniversary of my leaving the bounds of employment and becoming a freelance copywriter. Well, it’s the fourth anniversary of telling my boss how I felt about her, with great enthusiasm, honesty and volume! So I set out on the freelance copywriter path four years ago this week – luckily I rocked it and now Talk About Creative is a thriving business that’s happily taking on the world.

Becoming a freelancer, or any self-employee, brings all those rewards that motivated you to take the leap in the first place but they come packaged in some pretty huge surprises. Here are ten things you might not see coming when you go solo.

Freelance Copywriter Credentials - Elance test results

Freelance freedom can be oppressive

The freedom and flexibility to work on your own terms when you want can actually make you feel trapped. If your business is a success, chances are the work is never done. So, choosing to have a day off can make you feel guilty and stressed, like you’re choosing to neglect your responsibilities.

You’ll miss having your boss

Remember having someone who could give you final say on a tough decision, who could cover your work load when you were sick or on holidays, who could tell you you’re doing a good job or what you’re doing wrong…..bosses suck (especially some of the ones I’ve had) but they also take care of the big stuff. That’s on you now.

You’ll get fat

OK you may not but I did. You may get….OCD. You may get addicted to video games or Facebook. You may double the number of cigarettes you smoke. Why? Working from home, nobody is keeping you in check. There’s no one to stop/judge you for having cake for breakfast and everyone knows it’s easier to think in front of an open fridge door (or while smoking a cigarette or while scrubbing scum out of the cracks between the tiles on your patio – they’re all addictions).

You’ll miss your annoying workmates

Well, maybe not all of them but you’ll find that absence makes the heart grow fonder and isolation makes it more so. Luckily, Facebook will help a little with this, and meeting other freelancers helps too…. but there’s no sadness like the sadness of knowing your former workmates, good and bad, are at the staff Christmas Party while you’re at home writing cheesy scripts about Christmas specials all wrapped up for your freelance clients.

Your family will NOT appreciate it

OK so I married the man of EVERY woman’s dreams. If he was any more supportive, he’d be holding me up while I type. My child however, sees me working away in the office and thinks that I work because he’s naughty (he actually said that to me once). He resents me working because he can see me doing it. More than the kids who get dropped off at daycare every morning at 6.30 – they don’t connect the two…. Your children will. Your parents may not respect what you do. And if you’re not married to Mr Perfect (very few people are) your husband (or wife) may make life harder, not easier.

Freelancers lack social skills

So, I’ve been known to work a room, to have meaningful friendships with colleagues and clients, to be able to answer simple questions and once upon a time, I was rather articulate. These were all handy in my former life as a media copywriter! Going freelance means that you interact more and more by email and you may spend days where you only talk to your children and dog. This is a massive problem for freelance copywriters, let me tell you. It’s not just talking, it’s standards of personal presentation (I am fan of No Bra Wednesday) and care.

You may turn into a tightarse

$8 for photocopying! I can get it for $5 if I wait 45 minutes at the local office superstore! When you start putting every little cost into “how long will I have to work to earn that” context, you get weird.

Success = earn less!

It’s a horrible, horrible truth. When you start out, you charge at the low end of the industry standard because you’ve got nothing in your portfolio. As you get good, you push your prices up. At some point you hit the sweet spot. Then, you’re so good, you need to say good-bye to your sweet freelance status and go pro. This means taking on an extra copywriter, an admin person, bookkeeper… these people all need managing and that takes time. Sure you make a cut of the freelancer’s work but you’re doing less of your premium writing and more “unbillable hours” while paying out for all these helpers. Bam. You’ve got twice the clients, paying twice as much, and a team to support you but you’re doing twice the hours at half the rate. This is where freelancers need to stop and think. Grow a business or choose that work life balance you signed up for. It’s a biggggg decision!

Managing freelance contractors can be harder than just doing the work yourself

As you get busy and take on contractors, you’ll notice how much they’re like….staff. Some are golden and awesome and you wish you could clone them. Some suck and you have to….terminate the contract. To get a freelancer up to speed, you have to teach them your system, your expectations, your time frames, sometimes even your trade. You need to work around their family commitments, their salary expectations, their lives. Each job needs to be briefed and checked for quality and compliance with your standards, it’s your brand on the line afterall. If they’re freelance writers, you need to pay an extra freelancer to proofread too. It’s all a lot of admin and a lot of considerations and it’s hard to find a percentage mark up that makes it all worthwhile! There’s one thing that drives you on to help them get up to speed: Sacking freelancers will make you feel like a total arsehole.

Success is harder to judge than you think

If you only had a vague idea of what you wanted when you went freelance, you may not know when you’re successful. Success may be an ongoing and vague notion of something you’re striving for, rather than something you’ve achieved. Spending more time with family, riches beyond your wildest dreams, freedom to spend your life on your own terms or just knowing that you don’t play well with bosses so you want to be a better one can all be marks of your success. If you don’t know what you want then you may be failing without realising or successful beyond your wildest dreams but still feel like you’re struggling.

Good-bye Freelance Copywriter, hello business ownership!

I have moved on from my ‘freelance copywriter” status now and I’m a fully fledged and totally legit business owner (we even have the good insurance) but the remnants of my freelance writing days remain. I still can’t put a sentence together when in a party situation. And don’t even look at my ever expanding butt. If you choose to jump the employment ship and go freelance, heed these warnings but know that it’s also a million kinds of awesome and I’d never go back to my old job….not that they’d have me if I wanted to.




  1. Going freelance was one of the best things I ever did. But in my industry, as a freelance journalist and editor, you are only ever as good as your best story. Every time you have a break – whether it’s to take a contract job, to work overseas or work on a book – you are often faced with starting again. You have new editors to prove yourself to. It gets exhausting after a while, which is when a ‘real’ job starts looking good. It’s certainly not for everyone and it’s changed a lot in recent years. And after all this time I still have trouble convincing others that I don’t have time to work for free for everyone.

  2. Love this Dana – I’m just about to take the leap, so will keep these in mind! I’m all for No Bra Wednesdays, that sounds awesome ;)


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