“The one thing I wish I’d known…”

Wanting to get the best insights from some of the best SA freelancers, I put this one out to my community of freelance colleagues, asking: ‘What’s the one thing you wish you’d known when starting out as a freelancer?’

Mine was: I wish I’d known that freelancing is as much about being a good business manager as being a good writer/editor. (Although, knowing me back then, this would probably have put me off.)

I got some fantastic responses…


You will never, ever, close your laptop without worrying about missing an ‘important’ mail. – @kerryhaggard

I wish I’d known that, while working from home has its perks, it can be very lonely. I now schedule regular meetings and interviews outside of my home office, and make dates with people in the same boat so that we can have “water cooler” catch-ups and brainstorming sessions. I’ve really learnt the value of office chatter. – Tamara Oberholster

Having more holidays/time to yourself is a total myth 🙂 – @joduxbury


I wish I’d known not to feel shy about asking for a good, sustainable rate, and charging for time (like meetings). – @kerryhaggard

I wish I’d known that it’s never worth it to work for a less-than-fair rate. They’ll never up your rate, they’ll ask for additions and rewrites as if they’re paying top dollar, and they’ll still quibble when it comes to invoicing. It didn’t take me too long to learn that it’s only worth working for the clients who were willing to pay me what I was worth gladly and on time. – Georgi Guedes

I wish I’d known that it’s okay to say No. – @cathjenkin


I wish I’d known to ask for signed contracts up front. – @anjavanstaden

Freelancing is a business. It should be treated as such. Too many freelancers do not take the mental leap from being a journalist/editor on a salary to owning a business that provides content. – Ed Richardson

It doesn’t take long to realise that some companies require you to jump through all sorts of hoops to get paid. Always ask about the invoicing requirements and submit your invoices early so that you don’t miss their payment cycle deadline while you’re making all the changes and finding the documents that they require. – Georgi Guedes

I wish I’d known cash-flow would be the hardest thing to manage. – Fiona Zerbst


I wish somebody had told me to ask sources at the end of an interview about other potential story ideas. Expert sources are often ahead of the curve and can tell you about trends that haven’t been reported elsewhere, and ‘real people’ know about stories that you’ll otherwise never have access to. – Rebecca Weber

Quite early on in the freelancing game, someone told me that you have to work out your annual earnings across 10 months, not 12. This makes perfect sense because you don’t earn at all in December and hardly in January. So for the rest of the year, you should be putting money away for those quiet months. – Georgi Guedes


I wish I’d known that it’s okay to feel some level of self-doubt (especially at first) and that we all do, at some point. – @cathjenkin

I wish I’d known that there’s a difference between what you imagine your work is going to be, and what the market needs. It’s one thing to pitch yourself as a specialist at X, but after a while you find a niche where your skills are relevant and in demand and that’s what ends up being your biggest earner. So it’s best not to be a slave to what your vision of yourself is/was. – Hagen Engler

And finally, covering almost all bases:

I wish I’d known…

  • That one should get large jobs signed and sealed in a contract;
  • That some clients will rip you off if given the opportunity;
  • That you won’t fail as a freelancer by not constantly being on your phone and answering your emails;
  • That in fact having your email on your phone (and being on call 36 hours a day) prevents you from switching off and relaxing, and may result in burn-out;
  • That burn-outs suck ass, and are way more serious than being a bit tired and over-stretched;
  • That you need a lawyer;
  • That you need an accountant; and
  • To say no once in a while. – Miriam Mannak

What do you think? Is this an exhaustive list? Did we leave something out?

* A version of this article originally appeared on Tiffany’s May 2014 Stable Door column on Freelance Central.