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

I was always an artist, and growing up, that was where my focus was taking me. I struggled with academics in school, but excelled at art and music. It wasn’t until going back to a high school equivalency program that I realized I was actually VERY good at academics like math and science, but failed miserably to adapt to the public school system as a teenager.

Once I had my equivalency diploma, I studied film making and animation for two years, another two years of fine art and finally two years of design and illustration. It was really during those last two years that I decided the creative industry rather than film was the best fit for my temperament and skills. It’s funny to look back now and recall my love of physics, but inability to make that work in high school.

Maybe I would have become a scientist if things had pitched a little differently – it’s still a passion that I only entertain by way of watching online lectures and demonstrations by theoretical physicists and the like. Regardless, I’ve been a pretty successful creative pro and semi-pro musician, so it all worked out.

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

I got started as a teenager (just before my final two years of studies) doing commissioned art and design, although I wasn’t very experienced at either at the time. During the summer break from design studies I worked in a print shop doing light Mac work – the Mac was a new thing back then – and some basic print shop labour like cutting, finishing, etc.

When I completed my studies, the first long-term job was for a telecom company in their internal design department. I did that for two years, then tried freelancing for another two years. My first real industry job was as a studio artist for an ad agency. I landed that by joining a freelance placement agency and being hired full-time by the ad agency and it all went forward from there.

The biggest obstacle I faced in those early years was trying to break away from being a studio artist to becoming an Art Director. It was hard back then to transition from what was considered technical work into creative (or concept) work. That took several years of waiting and willingness to keep working and contributing, all while pitching myself as a potential creative asset.

I was placed in an ad agency through another freelance resource service and after doing studio work for a week or two, there was an opportunity to take on a creative project. It was due the next morning from scratch – it was 5:30pm. I decided to do it, no matter how much effort it would take. I was there until midnight and delivered the work the next morning. A week later, I was a full time Art Director working on beer campaigns.

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

For me, clients have come almost exclusively from referrals. Now that I’ve been in the industry for a little over thirty years, I have a pretty solid reputation, and clients are happy to take me along when they change gigs and refer me to colleagues.

I’ve been self employed now for about five years running, and to be fair, my years in the agencies is really where I built the credibility and portfolio to get new clients and gigs now.

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

I generally keep clients, just by being valuable to them. I take their business problems seriously and try to help them solve those problems. If no one knew me and I had to start from scratch, that’s the foundation from which I’d be pitching new business. What I’ve learned over the years from some of the best account people around, is that building business is all about the relationships you create.

The same is true for large brands – they build a relationship with consumers. The process is different but the idea is the same. My clients know that when they call me, they’ll be treated the same way each time. I follow the same process, and they know what to expect from me. I’m not cheap and I don’t play the price game. However, with all the clients that matter, I’ve never lost a gig by being more expensive than someone else – at least not with regular clients. They keep coming back because I deliver on my promises and communicate clearly. In other words, it’s a relationship they get value from.

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

Late payments are a pretty regular part of business. I’ve never taken the “hard ass” approach and sent any clients a letter from a lawyer. That’s just not my personal style. Generally, payments are on time, but when they’re not, I start with an email to the appropriate people including the invoice and a note saying something like, “Checking in on this invoice that’s overdue – let me know when it’ll be sorted or if there’s anything further you need from me.” That often gets things rolling – most times it’s just an oversight.

However, in the rare situations when it becomes more than just late and there’s an obvious problem, I’ll escalate an email or call to the head/president/owner to say “What’s up?” If for some reason it’s all gone sour, I just walk away and cut my losses. It’s important to point out that I’m not advising that as “a good way to handle invoices” or as an opinion on them – it’s just the way I handle things now.

I’m also clear with clients that if trust is breached, I won’t hand over any more work or take any new projects. I give everyone the benefit of the doubt, but I don’t “chase ambulances” as it were. So far, our clients have been solid with only a few exceptions here or there.

6. What does your typical work day look like?

A typical day for me is two hours of design work in the mornings for the clients that retain us for daily website updates and such. After that, I update the job list and send out estimates and invoices as needed.

Otherwise, I work on projects that are in the queue. When there’s downtime, I make a list of YouTube videos to create or premium courses I want to create. So, my average day is about 50% admin, and 50% design. Around all that, I make some time for music practice and playing when I can.

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

The most important thing, I think, anyone can do is self-evaluation. Take some time to think about what you’re doing and if it makes you happy or not. If it doesn’t make you happy, then does it serve an important purpose (like pay the rent)? If so, that’s a good thing. However, that also means you have to make time for something else that DOES make you happy, and then do it.

I personally took a huge risk when I left the agency world to build Booster Rocket Media. After some bad investment decisions and a couple past marriages in my wake, I was in no condition to cut a steady paycheck, but I wasn’t happy. I went out on my own so that I’d have time for music and things that give me joy. I was really fortunate to have great relationships and was able to build up a business base to support me and some partners.

For someone reading this, it might be the exact opposite – maybe getting a steady gig is the best way to find some joy in the work they do. All that is just to say – take a look in the mirror now and again and just make sure the person looking back at you is someone you’re proud to be. I didn’t want to “sell sugar to fat children” anymore, so I stopped. If you have similar demons keeping you from being happy… time to purge them.


You can connect with Shawn Barry on YouTube and Twitter.

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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