Freelancing Creative Director Failure

My career has never been the norm, not by any standards. I did not get a matric, I dropped out of college, I was self-educated in design, computers, development etc and instead of joining an agency, I started freelancing from day one. But eventually I joined an agency and was quickly hired as a Creative Director and did a descent job of leading the digital charge within the Ad industry. But it was never smooth sailing and I have had to resort to freelancing again, with very little success. Now if I had the answers, I would at least have a fighting chance of understanding why after 10 years of successfully freelancing, I was suddenly unable to. So I have a whole lot of assumptions as to why, freelancing as a Creative Director is doomed to fail.

Before I start explaining, I want to apologies for the mixed use of CD and Creative Director, I simply felt it made sense to use one or the other as I typed it. It’s how I roll … deal with it.


Any good freelancer will tell you that one of the must have things you need to go it alone, is a pretty strong network. Well I have been a CD is some of the most respected agencies in the country, if not the world. I have successfully worked on many campaigns for multiple brands and formed relationships not only with my colleagues, but the clients too. I don;t mind saying I contacted everyone I felt comfortable enough to reach out to, but with very few people able to offer much more than encouragement. Which leads me to wonder, why that is.


My first thought is that people may think I’m an asshole, it’s possible, but I can’t control what people think of me and I try not let that get me down, besides that would make a lot of people pretty two-faced, cause I generally feel pretty liked. So my next thought has to be that people assume I am too expensive. Truth is, I probably am too expensive. While I would not dare charge the rates an agency does, I do believe given my experience, I am worth a descent wage. Even if I wanted to work for less, I’d also have to be responsible and charge the type of money, I am used to earning, or what am I doing this for. I can;t exactly be a homeless CD, it just doesn’t work like that. Any CD would understand what I’m saying, firstly we don’t earn as much money as people think, we gave up getting rich a long time ago when we chose creativity as the main focus of our career, by joining the creative leadership team at an agency. It was a very conscious decision. The hope being that maybe one day we might be promoted into a higher earning position, get profit share or some day get our name on the door. The industry is pretty good at coming up with reasons not to give you the annual 5 – 8% increase agency folk might get, there is no pay for overtime and a world cup period where festive bonus cheques comes once in a lifetime, at least it did for me. But still, I believe I charge a fair rate, so much so that the number I had in my head is actually less than I earned, before I joined an agency.


You’re the big cheese, you direct creative, so your skills are probably a little rusty. Now I’ll explain this in detail next, but to be clear, you cannot freelance as a creative director, you are a creative director freelancing in digital. So it means you have to do the work, the teams you used to manage did. You have to design, develop, art direct, write and so on. And truth be told, there’s a lot of CD’s I know who were never very good at doing any of those things before taking on the CD role, they were good at brown-nosing the man who hired them over Friday drinks. But that’s not me, as I said, I successfully freelanced for a decade prior to becoming a CD, and given that I was self-taught, I made it a habit to constantly keep learning, so despite being a CD by day, I used to study at night. I admit my confidence in this area, was not as high as I would like, but that’s only due to the high standards I aspire to for myself. I was always a believer, that I need to know as much as anyone I manage, so I can make informed decisions. I am also quite a geek, and wanted to stay up to date and engage with colleagues in my industry who were doing big things, away from managing talent within agencies.


The creative part of what I do, combined with the skills I have, means I’m pretty much covered. It’s the director part that I debate, even if it’s only with myself. Good CD’s lead by doing, they have the respect of their teams cause they lead from the front, but another important thing is relationships of mutual respect. If you think it’s easy to walk into an agency and actually freelance as a CD, let me tell you, it’s tough work. Creatives in agencies have mis-guided egos, so trust me, being told to lead a team is challenging. A CD is supposed to direct creatives, and depending on the agency, be responsible for not just the teams, but the direction creativity goes within the agency, but if you’re only a temporary resource, it’s not likely you will factor into the operational or drive the vision. It has been my experience that other than being a contractor, you are rarely ever asked the CD at an agency. Often I have been asked to help with campaigns etc, but I tend to fill the role of an art director or designer. Positions on a freelance level that are not a whole lot of fun for someone who has been leading creative teams for the better part of 7 years.


Freelancing is supposed to be about working for yourself, choosing when, how and what you work on. Waking up late, going to bed later. Sure there’s a bunch of challenges associated with that, but for a long time I did it, producing some amazing work, that spans a client base and a network across the globe. But then things were simpler, I had no education, so I earned enough money to pay the few bills I had, but it provided me the opportunity to free up my time to learn more, usually by playing. However now, as I furiously head towards my 40’s and I’m responsible for more than just myself, but now a 6-year-old kid and some poor financial decisions, I can no longer earn what I need to be a freelancer, yet alone a freelance Creative Director. I don’t know that I have explored this in it’s entirety, so perhaps there will be a follow up post and it might only be a play on words or my own understanding of responsibility, but you might be an art director, a designer or even a contracting creative director, but you will never be a freelancing Creative Director, it simply makes no sense and you are setting yourself up to fail.