Becoming a freelance copywriter

If you’re an advertising copywriter who has decided that it’s time to leave the agency life behind and start freelancing, may I say to you, “excellent choice.” Sure, it’s a big decision, and there will be pros and cons to sort through. But if you wanted affirmation that it’s a viable career move, here it is.

You need three basic things to get started.

1. Talent. You have to be good at what you do, and you have to be honest with yourself about it. If you work at an agency, your clients don’t get to choose their creative team – they’re stuck with you! In the freelance world, if your clients don’t like your work, they’ll stop calling you.

2. Experience. Sorry about this one. You’re probably going to have to slug it out at an agency for a while before you hit the eject button. Build up a portfolio, try to get a broad range of category experience too. Every new client is a bit like a new employer, and you’ll have to look good on paper (see also basic thing #3).

3. A professional network. Personal references are the best way to get solid, rewarding gigs. There are more ways than ever to find jobs if clients aren’t coming to you of their own volition, including sites like JobBliss and of course freelance agencies if you prefer that model. But have a look through your LinkedIn connections (LinkedIn is a necessary evil, I’m afraid) and see how many agencies you have friends at.

To help you with your list of pros and cons, I’ve listed a few off the top of my head. They’re thought-starters based on my own personal experience, can be mitigated in most cases, and may not apply to you or anyone you’ve ever met. If you want to augment or take issue with them, please avail yourself of the comment section.


Job security. This sounds like a joke but it really is true. I’ve seen people dedicate themselves utterly to their agency clients for years only to have the business disappear because of some decision made on a golf course in another country by two guys they’d never met. As a freelancer, you’ll be your own boss, and there may be some anxiety that goes along with that, but you’ll never be at the mercy of a new chief executive brought in from another city who decides to “shake things up a bit.”

Your own stuff. You make the purchasing decisions, so you get the computer and software you decide you need (assuming you can afford it). You’ll never have to put up with some patronizing gatekeeper in IT giving you a hard time about your request for a new mini DV adaptor.* You’ll have your own kitchen, with coffee that you selected and then ground yourself, just now. You’ll have your own bathroom, for god’s sake.

The quiet. Can you hear it? Shhhhhh.

No daily commute. You may end up on full-time contracts, but you will also have the option of working exclusively from your own home office. For me, that’s an hour of my life I get back every business day compared to my last full-time gig, and traffic certainly hasn’t gotten better since then. No more getting stuck on packed streetcars that short-turn in the middle of a blizzard.

Better client relationships. You’ll work with people who have chosen to work with you. When it comes to job satisfaction, this is a big deal. We’ve all been in presentations with clients who couldn’t wait for the flakey agency types to wrap up the dog and pony show and stop wasting everyone’s time. People will call you up because they want your help, and you will help them, and everyone will be happy when it’s done – friends, in many cases.

Flexible schedule. Get a haircut. Do some shopping. Work on the weekend if you feel like it, or in the evening if there’s nothing good on Netflix. Your time is your own to manage. I personally have a hard time getting anything meaningful done on my own time when I’m working office hours. I recently asked a friend who works a full-time, 9-to-5 job, “When do you actually accomplish stuff?” She replied, “I don’t.”

Also: About 95% fewer meetings, working in sweatpants/sweatshirts/t-shirts, fewer dry cleaning bills, sleeping in till 8:55 and still getting to work on time.


Solitude. I’m fine with it but many people aren’t. If you’re an extrovert who has to be around people every minute of the day, this may not be the gig for you. You can choose to team up with a creative partner, or opt for in-house contracts. In the long term, you’re on your own. But then again, aren’t we all?

Financial stability, absence of. In the investment world they call this risk tolerance. Are you going to get squirrelly if this month’s billing is half of last month’s? It’s something you might have to get used to. You’ll need an emergency fund to start (which you should have anyway) and a facility for budgeting. This doesn’t mean you’re going to be perennially cash-poor, but you can’t necessarily determine how much you have to spend simply by what’s in your bank account.

Less conceptual work. This will depend on your clients to a large degree, but I think the only time an agency creative director would give juicy conceptual briefs to a freelancer would be if the entire department has up and quit on him/her, or if he/she is trying to get them to quit. If you live for awards and accolades you might still get those opportunities now and then, but they won’t be what you make your living off of as a freelancer.

Benefits, absence of. This is an obvious one, depending on your own health and your family’s needs. Ideally, you should have a spouse with a benefit plan you can get in on, but I realize that’s a bit of a cheat. If you don’t, it may be time to shop for some insurance.

Accounting. Taxes, expenses, estimates, billing, and the dreaded chasing down of delinquent accounts. There are some great cloud-based services to help you out with this kind of stuff, but it all becomes your responsibility. If you live in Canada, be prepared for the abject horror of knowing exactly how much the government charges you for making a living.** You’ll want an accountant and probably a lawyer.

Vacations, absence of. It’s tough to schedule time off or take a sick day without actually being in a hospital. Put this beside “flexible schedule” from the Pros column. Are you going to set an auto-responder for your home email address? Didn’t think so. I suffered through a conference call once while a kidney stone was rolling around in my giblets. It was difficult to concentrate.***

Also: That time you became allergic to the air in your house, seeing your old work friends hitting your favourite hamburger joint for lunch on Instagram, being mauled to ribbons by hungry cats.

Coming soon: Workstation essentials and productivity tips for the freelance copywriter, Macintosh edition.

*IT people were actually pretty amazing at the last place I worked – almost unfailingly helpful and friendly. But there was that help desk operator who gave me a hard time about a video adaptor for no imaginable reason.

**I’m not trying to start a political debate here. I’m actually a bit of a lefty bike-riding pinko commie, and my approval level of the social policies my taxes pay for is pretty high. But you get a cheque, and your heart goes pit-a-pat, and then you slice a huge chunk of it off and put it into your tax account to send off to Revenue Canada. You feel it every time. It’s like sticker shock in reverse. Yes you can recoup some of it, and incorporation is an option.

***In retrospect, if I had begged off that one my clients would likely have understood. When the call started I was still trying to convince myself it was just indigestion.