How 7 Influential Designers Overcame Creative Challenges


Working in the creative field comes with an abundance of unique challenges—collaborating with finicky clients, competing for business in an oversaturated market, and perfecting an ever-changing craft.

Luckily, we’ve rounded up seven influential designers to ask them one inspiring question:

“How have you overcome your greatest design challenges?” Here’s what they had to say.

Pelun Chen – VP Design, Dollar Shave Club


“I try to look at every new design challenge as the greatest, because each one is different: with its own factors, audience and surrounding context. Whether designing a product, a brand, a team, a presentation or even the words of this sentence—they’re all important and deserve equally considered thought behind its creation.

That’s what’s pretty cool about design: It’s not a medium—its a way of thinking, and a process. You can apply the approach to almost anything and come out with a sweet, tailor-made, solution. Of course you’d like to leverage and build on past experiences to guide decisions—but ultimately each situation is kind of unique. You can’t really cut and paste.”

Dina Rodriguez – Hand Lettering Artist, Letter Shoppe


“When I first started hand lettering, I had a really hard time coming up with unique compositions and interesting type styles. Since I was new to this trade, I was just taking stabs in the dark along with mashing up references and inspiration I had found online. I wasn’t taking the time to actually practice my craft the right way, but instead was taking short cuts to finish projects that were sub-par at best.

It wasn’t until I had learned the right way to practice hand lettering — where you learn each type style letter by letter, so you can build a type library in your head—that I started to create more interesting pieces. The trick here is to start with the classics like serif and san-serif to fully understand what makes each character tick.

My big takeaway here is that you have to take the time to learn things the smart way to improve your skills enough in order to make a profit from them. But if you try to take the easy way out, you’ll actually just hurt yourself in the long run while watching your competitors surpass your skill set.”

David Airey – Graphic Designer, Author of Logo Design Love


“One of my greatest design challenges has been staying in business as a self-employed graphic designer for more than ten years. I’ve accomplished this by keeping my website regularly updated—it makes it much easier for clients to find me. Most of my new business comes through organic searches, so I’ve been publishing blog posts for almost as long as I’ve been self-employed.

From this, I’ve learned not to take anything for granted. There’s so much design talent around the world and I know my clients could easily choose someone else for the job. It’s up to me to set realistic expectations, then surpass them.“

Ian Paget – Graphic Designer, Logo Geek


“At the agency I work for, I’d design a solution that I had confidence in, and an account manager would present the work. I would then be given specific feedback about design changes I needed to implement. This resulted in designs being ‘ruined’, both from a visual perspective as well as performance. It was frustrating for everyone involved. To solve this, I introduced a training session with each new account manager that explained a more constructive way to present a design.

As part of this session, I present a stapler in two ways. First I simply ask, “I’ve designed this for you. What do you think?” They often pick up the stapler looking for problems, and start suggesting their own ideas on how to make it better.

In comparison, I would talk through the features in relation to the brief. For example, I would explain that it’s easy to hold in one hand, that it’s effortless to staple 20 sheets of paper, that it’s easy to reload with new staples, and so on. I then ask, “Do you agree that this meets the goals we agreed upon?”

In this situation, I could easily have continued to design work to a poor standard and blame the client, but instead I took responsibility and did my bit to improve the process. It saved considerable time (and money), improved the product, and made everyone happy.”

Brent Galloway – Graphic Designer, Blogger at Your Freelance Career


“One of my greatest design challenges has been finding my artistic voice and being noticed in this noisy market. I had to take things to the next level to make a sustainable living from my design work, so I took a step back, evaluated my strengths, and really considered what it was I loved to do most. Out of all the dabbling in design I’ve done over the years, it was logos and t-shirts that I enjoyed spending my time on most. It was a daunting decision to make, but I took the leap and focused my career around that direction and stuck with it.

By focusing the work I do, I’ve began to develop my own personal style, which in turn garnered more attention from clients. Even though I still feel like I’m barely scratching the surface to finding my voice and art style, I’m definitely headed in the right direction. That’s growth, and I’m loving every step of the way in my journey freelancing.”

Jacob Cass – Graphic Designer, JUST Creative


“Challenges come in all shapes and sizes, both from small and large clients. The key to solving these issues is understanding the actual problem, and that comes by listening to your client and working with them to come to a solution. One example of this was when I was collaborating with Jerry Seinfeld on the branding for his web series, Comedians In Cars Getting Coffee.

I was working on the logo for the show, and we explored hundreds of different options: logomarks, logotypes, and everything in between. Some were quite clever, however in the end, they were just too much. Instead, we drew a custom drawn “sketchy” typeface. This allowed us to emphasize different words within the logo, which was useful for the horizontal and vertical formats of the logo, while looking relaxed and approachable—perfect for the series. We then used this established style for the rest of the brand’s collateral: website, posters, and advertising.

What I learned from this branding process is that the most creative work is not always the best and that when done correctly, type becomes image. That’s gold Jerry! Gold!”

Nicole Whittle – Creative Director, Marley Coffee


“For emerging brands, such as Marley Coffee, the design challenge is to stay nimble to evolving brand touchpoints, employ dynamic marketing strategies, and grow global partnerships. We overcome this by balancing critical thinking in the design process, and embracing flexibility and simplicity in the creative.

Personally, I’ve learned to adapt a collaborative approach within multidisciplinary teams and use research-led insights when needed. I’ve found that this leads to a richer design execution.”

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