1. When did you realize you wanted to be a designer?

I got my first design job in 1997. Growing up I wanted to be an artist, I drew all the time and painted but as time went on I realized that fine artists didn’t always get paid very much and that I would need a backup plan.

Design was the closest thing that I could find creatively and it started from there. Around 2009 the scale sort of tipped and my love of design surpassed my love of art. My career has really shifted quite a bit since then. Right now I would say I want to be a designer around 91%. I leave some hope for Artist and Astronaut in that order.

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

My first job out of high school was as a colorist doing children’s books for Disney. I dropped out of college and began coloring comic books for DC Comics full time as well. That early opportunity was hard for me to understand or appreciate at that time.

I lived in the middle of a snow covered corn field in Central Illinois all of my life and I just needed to move away, even if it meant giving up such an awesome job. I came to the south where I have made my home. I love the south. Oh, and Disney hasn’t called me since. Oh well.

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

It changes as time and technology change. So be versatile, but networking is huge for local work and regional work and Instagram is great for reaching everyone else. I get a lot of work through Instagram. I see all those as types of word of mouth. It takes time and consistency.

I find when you do good work for a client and are fun to work with, especially a bar or restaurant, they tend to brag on you to their friends and that leads to more work almost immediately.

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

I am real with them from the beginning. No surprises. I have a background in publication design so I never miss deadlines and I roll with the punches pretty well. The majority of people that I am lucky enough to work with enjoy working with me and I enjoy working with them. Having fun on both sides is a big part of it.

I think if you start treating clients like they are your next payday they will treat you the same way and find a cheaper designer to work with. Sometimes they don’t need to work with me forever, if that’s the case, I find them someone who can help them out long term. Usually one of my buddies. They appreciate that.

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

I find the more business you take care of on the front end, the less confusion there will be throughout the process. I send an agreement in writing before I start any work and spell out all the details very clearly. I always do three equal payments. Beginning, middle and end. Timeline is usually the deal breaker for me. Never money.

If I am already booked up and can’t devote the time your project deserves, I will tell you before I ever take a dime. They appreciate that honestly, some of them even wait until I can do the job. I send out these agreements knowing that it might not work for them and that is just how it goes. You can actually win them all if you don’t mind losing a few here and there.

6. What does your typical work day look like?

My work day is almost always the same, I get up at 5:30am, play racquetball and run. That’s where I do a lot of thinking. By 8:30 I am looking at my list and creating something. Afternoons I am following up with clients, having meetings, etc. I go home at 5:30. What is really unique is my work week. I work 25 hours a week for an art and music festival called Westobou.

I spend the rest of my time split between my own office and an analog print studio that I share with a couple of my friends. I have 3 desks that I go to at different times during the week, I crank out a ton of work that I am really happy with and I manage to do it all before dinner. I rarely have any late nights anymore unless its a really unique situation. I go to bed at 10 and repeat.

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

In the past year I have started to firmly believe that whatever you put out there is what you will get back. The world will reflect you immediately. That goes for your work, your attitude and your personal life. If you are doing cool logos, you will get more cool logo work. If you are a jerk, you will meet a lot of other jerks. It goes on and on. It sounds sort of corny to say that, but it really is true. If you don’t believe me, think about the last new car you got. Didn’t you see them everywhere right after you got one?

So if you spend your time making family reunion shirts (which was my next job after Disney) and putting it out there, you will get more of that work. So, go home after work, design a nike shirt and put it out there instead. Then another and another. Nike will most likely not call you, but the next under armor might. Or a cool gym owner. In the meantime, learn all the skills that you can and figure out who you are as a designer so when that dream client does call (Run the Jewels), you are ready to do you. Then go to bed at 10 and repeat.

Also, don’t forget the reason why you started doing this in the first place. None of us got a job so we could work forever, we got a job so we could save up for a skateboard or a car. We didn’t buy those things so we could get to work faster either, we bought them so we could go hang out and have fun with our friends. If you haven’t done that in a while, it might be time to go outside.


You can see more of Jason’s work on Instagram

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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