Why I quit my job as a Creative Director. The importance of being creatively happy.

So why did I quit a job that I spent 8 years working towards. I think the best way to sum it up is an excerpt from Steve Jobs commencement speech for Stanford. It was this speech that I had listened to over and over again that I'd realised that I needed a change. If you are unfamiliar with it you can view it below. First off I've been extremely fortunate to have worked for some great agencies alongside amazing co-workers with whom I have called my friends and family. And this couldn't be truer for the last agency I worked at where I spent 5 years from Mid-weight, to Art Director to Creative Director.

If today were the last day of my life, would I want to do what I am about to do today? And whenever the answer has been ‘No’ for too many days in a row, I know I need to change something.


It was a great time and we did some great work for some great clients. From Nintendo to Australian national banks to government bodies and ecommerce sites that were generating millions a year. However as I began to move up the ladder my time would be divided up to more meetings and management. Which I really enjoyed to begin with, because I love taking on challenges and learning new things. And this experience was definitely invaluable as I learnt how to deal with large scale pitches, dealing with marketing executives and justifiying the work that my design team and I had done. I also enjoyed mentoring designers and nurturing talent. But within the final months and moving closer to my 5 year tenure I did some deep soul searching and reflection. I realised I just wasn't creatively happy anymore. The work was becoming too routine and I was doing more large scale projects that involved extensive usability testing, risk mitigation and limitations with legacy systems. A necessary demon for sure but not exactly things that got me excited to get up in the morning. In the early days we were like a startup, when we'd win large scale accounts it was exciting. Continually we'd push the boundaries of what was possible and the potential of our work. But after 5 years and scaling we just weren't that company anymore.

We had won awards for the work we were doing but I had never bothered to keep an active online presence. It was around this time that I started posting my work online on sites like Dribbble for fun and for some laughs. Surprisingly after building a small Dribbble following I was getting job offers and work from top agencies from London, New York and around the world. Agencies and companies that I had looked up to and admired. To date here are some great agencies and companies that have reached out Huge, UENO, Envoy, Rally Interactive, Airbnb and Shopify. As well as large scale ad agencies. I did not expect this at all, I was truly humbled. All this wouldn't have happened if I hadn't put myself out there. I was one of those designers who didn't like marketing myself or my work, it always felt iffy to me. But I've completely changed my tune if you are a designer please post and share your work with others! Great things will become of it I promise.

At that point I thought about the Steve Jobs quote deeply. Most days I would wake up and be excited to go to work, but slowly the mundaness of work was chipping away at me and I was no longer excited. Everything was easy, comfortable, I had great friends and I was making great money so what was wrong? In the end the work has always been the most important thing to me. Creatively I wasn't growing anymore. If I had continued on my body of work wouldn't have been reflective of the type of work I wanted to be doing. I was engaged with more thinking, meetings and less 'creating' per se. So I bit the bullet and handed in my resignation. It was a tough decision, it was like leaving something dear to you behind. A favourite sweater that just didn't fit you anymore, an old toy that you had once loved but had grown out of. And in this case a group of wonderful friends that you'd grown with over the last five years.

The original plan was to move to New York after my wedding and in the mean time I would freelance for a while. But like my career so far blind luck has lead me to unexpected places. After leaving I had time to have a think and decide what I wanted to do. So I created some side projects such as the Influencers project. Which has since received great reception and has brough me many job leads, not bad for a spur of the moment passion project. Also I'd save just enough “fuck you money” to last me a few months.

Fuck you money(noun) - essentially money you have saved so you can feed yourself and your family and not have to take dead end jobs from clients who just send alarm bells into your retina and skull. Giving you the upper hand to say fuck you and pass on these horrible jobs. This is essential freelance 101. Jokes aside though just politely decline these jobs no need to be a dick!

Unbelievably though my freelancing took off, and not only that but I was lucky enough to choose the work that I wanted to do and for some truly lovely clients. One thing is after 8 years of 9-6pm I realised that I just wasn't that productive. A lot of the time I could've completed tasks in a third of the time, if it wasn't for the extensive meetings and just trying to clock up enough hours.

It felt like unnecessarily we were all just trying to hit that magic 40 hour week and it was a very outdated and rigid structure built from some old world thinking.


So after 1 year in the great unknown I'm still alive! Whilst it was a hard decision to leave my job as a Creative Director it was on of the best decisions I've ever made. I now work half as much as when I worked for an agency and amazingly have managed to earn more. I'm now efficient as ever. So I have more time to read, spend time with my family and friends, my dog butters and go play tennis. If this story resonates with you even remotely I urge you to 'not settle' save some 'fuck you money' and make the big move. I plan to write a road map about some of my experiences freelancing and the things that I've learnt so do reach out and I will try to help you any way I can. After doing freelance fulltime I don't think I could move back to an agency environment again but never say never I guess. I want to stretch my entrepreneurial spirit for a bit, which is why I built this blog. Try my hand at creating a passive income stream all while hopefully creating valuable content for my readers. Most importantly though today I am back to being a hands on designer and am truly loving it.