1. When did you realise you wanted to be a designer/creative?

High school. I have always been a creative type, and I grew up drawing all the time, but it wasn’t until I got into the indie music scene that I discovered poster design and considered it as a career.

2. How did you get started and what was the biggest hurdle you overcame?

I graduated from the University of Huddersfield in the UK in 2008 and started doing freelance illustration gigs and part time Graphic Design. The biggest hurdle for me remains the same: ADHD. This is a condition that is misunderstood, misused and made into a joke in society, and yet those who deal with it have real significant struggles. It’s also in many ways a super power.

ADHD really lends well to creative thinking, but it also makes it nearly impossible to be an outstanding employee in a traditional sense. So for me starting out, I did really well with freelance jobs, but struggled with my part time employment. Getting through to full time freelance was a major challenge, and it took several years, but once I broke through things have been much better!

3. What’s been your most successful way of getting clients?

The most straightforward way of saying it is content marketing. Instead creating ads or promo that steals people time and attention to then take their money, I’ve always tried to create remarkable value that people were willing to trade for their attention and then sometimes eventually their money.

Basically I’ve always had public facing personal projects that often didn’t bring financial reward to me, but gave away real value, whether that be entertainment or informational.

When you make something that has real value and give it away for free, people tell other people and eventually it turns into work.

4. How do you get clients to stay with you and use you for more work?

I think of it in the way that Seth Godin calls being a “linchpin”. The most successful client collaborations come from jobs that no one else could do. For instance, I have a client called Cushion. It’s an app for budgeting time and money for freelancers.

They pay me to create a podcast called “Ask A Freelancer” and to illustrate the podcast art on a reoccurring basis. This relationship works because there are nearly no other illustrators with this exact skill set (podcasting + editorial illustration). The linchpin isn’t the boss but they are indispensable. Create interesting mashups of your unique skills, become best in the world at a very tiny thing! Then they have to return to you, you’re the only choice!

5. Do you ever have issues with clients paying late? How do you manage that?

Hmm. I know this is a really common problem, but for the most part I work with people who are used to paying for illustration on a regular basis and have good systems in place to make this happen systematically.

I think this is more of an issue when you’re working with folks who don’t regularly contract designers. For instance, a logo design for a restaurant may be the only time this client will pay a designer ever, and therefore there are many obstacles for them to get you paid.

6. What does your typical work day look like?

I get up between 4-7am. I finish any deadline work that needs to be done. I help the kids get to school. I come home and do anything else that has to be finished that day, and then I try to spend time with my family. Pretty simple.

I work from home and home life balance is really weird. If anything, I could use to work less! I’m kind of naturally obsessed with making stuff, so productivity isn’t really an issue. Switching off is much tougher for me.

7. Any piece of advice/wisdom that you’d like to give the readers at This Design Life?

See your creative career as the ultimate creative act. There are no labels or slots that can perfectly old your creative mold because you’ve never existed. When you realize you have the ability to carve out your own existence, it’s like Neo seeing the matrix as code for the first time. It’s transcendent. You can hodge-podge-mashup whatever system of money making you need to in order for YOU to thrive.


You can connect more with Andy here. Or check out his new book, Creative Pep Talk.

Chris Green

Chris Green at This Design Life
Chris Green is a designer and marketer. He runs an agency called Calloway Green and is also the founder of This Design Life.

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