Ten Things I’ve Learned After Freelancing for 6753 Hours.

James Dunlop
Social Club
4 min readDec 6, 2017

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From inside the coddled womb of the agency creative department, earning a living as a freelance copywriter looked like it was about as steady as Angela Lansbury after mainlining dark roast espresso. Sure it can be a cold world out here. But, beyond the value of some good thermal underwear, you learn a lot.

1. You have time.

You’ll find time you never had before. I’ve learned to develop new hobbies (like publishing Medium articles) which help stave off any worries about lack of productivity. I suppose I already had hobbies but drinking claret and smoking a pipe was expensive. And can stain your teeth.

2. Your website doesn’t matter but don’t screw it up.

You need a website. So it looks like you actually do what you say you do. And it gives you something to show your mum. Just because no one reads it, you still have to make sure everything’s spelled correctly. You’re a copywriter, so don’t let some guy in Bangalore write it. And don’t fob off the design on a failed chalk artist moonlighting on Fiverr.

3. Grow a beard.

Until now I’ve risked going without a beard. It’s dangerous work. Navigating the agency halls, twenty-somethings in designer toques and starter-beards exchange surreptitious glances as I go by. And more than once I’ve had to dodge the odd CFO intent on ousting any creative who didn’t look productive. Facial hair seems to be a sign of creativity. Creatives all seem to sport some. Even some of the women.

4. Use Starbucks’ WiFi.

Second only to giving agency staff access to their Instagram accounts, the agency’s WiFi network is designed to humiliate newbies. There are usually two. If they give you the staff network, no one knows the password because they’ve forgotten. And if it’s the guest network, IT will have changed it last week. If you’re lucky enough to track down the password, it’ll be scrawled on the back of a crumpled post-it note. Your next few hours will be spent fecklessly typing in Øs where Os should be until, by lengthy process of elimination, you can get on and verify that the links in the brief don’t work.

5. Know where the Gents is.

The first day freelancing at a new place will give you all the angst of a first day at work and none of the dental benefits. An experienced freelance friend suggested I try to break the ice by being confident, outgoing and affable. Given my success, I’d recommend sitting quietly in a corner and trying not to break anything.

6. Wear pants.

Working from home, pants are optional. Truth is, I find there’s something freeing taking a conference call in my dressing gown. But if you go in to the agency, they seem to frown on these liberties.

7. Your lap isn’t just for entertaining strippers.

I can work on my Macbook anywhere. Perched at the little Bob Cratchit desk between the agency photocopier and the boxes of office Christmas decorations. Going home on an overcrowded subway with more bodies pressed together than a Vatican summer camp. On the way to a client presentation in an Uber with a driver who has no depth perception and a perpetually whistling nose nugget. It doesn’t matter. If you can type, you can work.

8. Invoicing doesn’t mean getting paid.

At first, charging for my services seemed grand. Joyously, I created and sent my first invoice. Soon it gets boring. After that it gets tedious. Then you realize it’s wrong and it has to be re-sent. Then you wait. Invariably no payment arrives. So you send another invoice. Then you wait some more. Usually, you have to do the process again. A few more times. And while you wait, you contemplate how nice it would be not to charge anything at all, just to avoid the horrors of invoicing.

9. Work. When you get it.

When you’re working at an agency you’re there to solve problems, not create them. Whatever nugatory bother threatens to distract you from turning in your best effort, put it behind you. Your mother was arrested for gross indecency at the Legion. Your kid needs a crotch transplant. Whatever. Focus on the task at hand. You want to be invited back.

10. Embrace insanity.

Within the first few weeks of working from home, I was talking to myself. Almost three years later, I shout at passing squirrels, collaborate with invisible friends and look forward with eager anticipation to interruptions from passing Jehovah’s Witnesses. I spend hours in my own head. Which can make me feel like I’m going mad. But out here madness makes you a better writer.

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James Dunlop
Social Club

Toronto-based, national and international award-winning freelance copywriter. Trying to blend into society.