How I failed my first 6 years as a Creative Director

I was given that title — Creative Director — in my 3rd year at a company with 6 employees. For the next 6 years you could meet our entire design team with one handshake. I never had so much as an intern working under my direction.

The reality is that, while my title might have been a bit self-indulgent, my role was pretty typical for a small digital marketing company. There were no significant failures in the quality of work we produced, nor was it an issue of process. My failings had more to do with perspective.

This is me. Don’t be like this.

The assumption that comes with the title of Director is that you will at some point be directing someone. Somehow I missed this and spent the better part of that 6 years hoarding responsibility like Smaug hoarded treasure. The idea was that more responsibilities made me more indispensable — more likely to be rewarded at that yearly review. Instead, I wasted those years ensuring that I would never gain any management experience — choosing to limit myself to junior-level tasks. Our company never grew in that time and those end-of-year rewards never came — and when the company did start growing exponentially, guess who was woefully unprepared to lead real teams and take on management-level responsibilities? This guy.

It makes me sad to think how I (a single employee) stunted my own growth and company growth in that 6 year period without the right perspective. Now take these lessons and don’t be a fake Creative Director like I was:


1. Be a team member and a team leader whenever you can.

Most bosses are willing to give you opportunities to lead if you simply ask. Hire a freelancer for a project and lead that team, get an intern, join design communities for critique and collaboration, and for the sake of all that is good and decent in the world, don’t treat your non-design co-workers as if they don’t have the right to join your process. There’s a reason why one-man bands are usually on the street begging cash. Step one of becoming a Creative Director is to assemble a team to direct — even if it includes the janitor and your mom.

The Bad News Bears. A rag-tag team of misfits worth looking up to.

2. Practice making other people famous.

Of course you want to be famous. You want 30k Twitter followers and a speaking slot at the next big conference, but you’re not gonna get fame by making fame the idol. Step two on your path to Creative Director success is to drop that ego and serve your team. Do everything you can do to get out of the way and let them make something great. Give proper credit for each individual success and own every failure.


3. There is absolutely no room for being a dick.

I’m a dry guy — sarcastic loner type — but I can say confidently, without exception, that being a dick has always been a step backwards in my career. I’m running out of fingers and toes to count the times I’ve upset a co-worker over a comment or joke that either missed the mark or just plain didn’t belong. That crap doesn’t fly. Directors are encouragers and inspirers and if that’s not your personality you need to change your personality.

Thank you, Wil Wheaton. I won’t.

4. Get serious with your boss about where you want to be.

Daggum. I got this one wrong. By the time I sat down with my boss and showed him commitment to my job and career path, I’d already missed several opportunities for growth. On the flip-side, by the time he got serious about showing us aggressive growth goals for the company, I’d almost lost interest in staying. They say communication’s a two-way street. I say cut the crap, tell your boss who you want to be in the company, and ask if he has room for that guy. Don’t waste time waiting for the other guy to read your mind.

Incidentally, my boss is amazing, and the last two years at Waypost have been an incredible time of growth — personally and professionally.


5. Invest in your career (be a Creative Director all the time).

This was a hard one to swallow, but truthfully every investment I’ve ever made in my career — whether time, money, or whatever else — has paid dividends. Anything that’s going to make you better at your job is a good investment — even if the company won’t pay for it. Early on, I took the view that 9–5 was my work time and my paycheck was all mine. That perspective naturally compartmentalizes your identity as a designer and will ultimately discourage you as you reflect on the massive amount of time you’ve sold to the man.

$5 out of your paycheck for colored pencils will be totally worth it when your rag-tag team of misfits starts churning some A1 design.

The work you do is part of who you are, and when you invest in the quality of that work, you’re investing in yourself — regardless of location.


If you’re a relatively new Creative Director like me, I’d love to talk. It shouldn’t be too hard to track me down. Twitter works best. The end.