Discover how one artist turned his craft into a sustainable freelance career through entrepreneurship and dedication to the digital nomad lifestyle.

Walker Howard produces unique, illustrative design and branding for his company Walking Designs. I came across his Instagram account walkxdesigns, while browsing the many illustration accounts on the platform. Something about his minimal branding design caught my eye, and after seeing the process behind his illustrations on his Instagram stories, I wanted to learn more.

There’s no shortage of the outdoorsy, “Go Explore” sloganism in the world. What struck me as unique in Howard’s work is the hand-skills in his sketches and the seemingly effortless detail mixed with honest reverence of the nature that inspires him. (In turn, his works-in-progress inspired me to order some white gel pens for drawing highlights.) Even more, he’s turned his skills into successful branding for clients.

Howard has carved out a livelihood from freelance design work and travel, so I thought he would have some great advice and information for others seeking to self-sustain through design. I asked him to get deep on freelance, supporting oneself on design and art, and how he came to this vocation.

Insight from the Freelance Designer and Digital Nomad Behind Walking Designs
Insight from the Freelance Designer and Digital Nomad Behind Walking Designs

Aaron White: I found out about you and your Walking Designs site through your Instagram feed. You show a lot of ideas and sketches, which I thought were great on their own. I wanted to find out some more about your background.

Walker Howard: I was born and raised in Bozeman, MT. I have two older sisters and a little brother. My parents were both creative people. We were raised in a homemade cabin (that they traded their van for) outside of town on an amazing piece of property gifted by my mom’s parents at the foothills of the Bridger Mountain range. […]

Family trips both locally and internationally gave me a broader perspective and respect at a young age for diverse landscapes as well as the variety of conditions that people lived in all over the world. We backpacked and car-camped from Montana to the red rocks of Zion. We traveled to Central and South America and lived with host families where we learned spanish and wandered through ancient Mayan, Inca and Aztec civilizations. These trips offered me a new perspective which challenged me to see both the beauty of the world as well as the challenges that so many people endured. Being exposed to these new cultures always kept me curious to explore more.

I was given pens and paper from a young age and picked up drawing at around age three. […] As we took our trips near and far I would follow the lead of my dad who is an artist as well and draw our surrounding areas with pen, brush and stroke.

By kindergarten I knew that I wanted to be an artist. I enjoyed other subjects, but art was where I excelled. By college I had a couple of shelves full of sketchbooks and I thought that I was on my way to becoming a fine artist. I attended Montana State University in my hometown of Bozeman to stay close to the mountains. But in my first year of University I began to shift away from the idea of becoming a fine artist and grew a deeper interest in pursuing this new career option called Graphic Design.

Graphic Design seemed like a profession where I was free to create, but I could also turn a paycheck as opposed to kick starting my career as a fine artist, which had no guarantees that anyone would be interested in my physical prints.

During these college years I began to find my illustration/design style where I would start with creating drawings in the sketchbook and revise and finalize my work on the computer. During my third year in college I studied abroad in Costa Rica where I took Graphic Design classes in Spanish and learned how to surf. […]

Insight from the Freelance Designer and Digital Nomad Behind Walking Designs

AW: Many young design entrepreneurs may think they have to handle everything on their own. That totally-DIY concept seems to be what’s so daunting about going freelance. Some don’t realize they can team up with someone better equipped to handle the spreadsheets, if you will. What are some lessons or thoughts that stand out about your experience with business relationships?

WH: Right out of college I jumped into the side-hustle lifestyle. I was approached by a loose and wild entrepreneur named Vesa. He had the funds, I had the creativity. We started a t-shirt printing business even though we both knew nothing about shirt printing or running a business. Dub V Tees (our company name) started out in a garage. We hustled our first few clients by walking around to local businesses and so began the uphill battle of running your own business.

After five years of blood sweat and hustle, Dub V Tees had grown into a big warehouse and had 1 employee and 1 intern. We were not making money, we were just making enough to pay the bills and cover all the overhead. Things needed to change. Vesa did not like me leaving on surf trips for months on end and I didn’t enjoy spending my free time printing shirts.

Around this time I read a book called The 4 Hour Work Week by Tim Ferriss. The book introduced the idea of working less and being more efficient by working on an 80/20 principle. The idea here is that 80% of your results come from 20% of your efforts.

At this point Vesa and I took a step back and we sold our equipment, split up our clients and that was that. The idea of being on my own as a freelance Graphic Designer was both daunting and thrilling, and I knew I was ready.

I set up my own business in 2015 called Walking Designs, which is the same company I own today, where I was able to outsource all of my t-shirt printing. This meant I no longer had to sit on inventory that wasn’t being sold, and instead I would only sell t-shirts with designs that had already been ordered.

Working for yourself is tough because there are so many roles to fill. You have to promote, you have to represent the face of the company, and of course you have to create all the content. You also have to email, invoice and do all the nitty gritty, non-glamorous work in between.

To be a successful freelancer you have to self-motivate and be okay with putting countless hours into projects that may not always pay well, or at all! But all this hard work leads to what I believe is the most rewarding benefit of all. Ultimate freedom.

Insight from the Freelance Designer and Digital Nomad Behind Walking Designs

AW: Was there a turning point when you discovered you wanted to be self-employed, or did you always know?

WH: I think that deep down I always knew that I wanted to be a freelancer. The idea that you could work from anywhere in the world always seemed right up my alley, so I never applied to work for anyone (even though some professional work could have been helpful starting out).

For years out of college I had a healthy mix of freelance graphic work and seasonal paychecks. During the summer I was a raft guide, and during the winter I was a lift operator at the ski resorts. These were great jobs and kept me outside and doing the things I love.

Every year for two months in the spring and three months in the fall I would go on surf/travel adventures. In 2016 I stepped away from seasonal work and started fully depending on the income I was making from my company Walking Designs, and it has been amazing.

The work hours are inconsistent and much more than a normal 9-5 work week, but the tradeoff is amazing. I have fully embraced the digital nomad lifestyle. I revamped my Instagram during the Instagram boom in late 2016 and the feedback as well as the amount of work and exposure from that platform has felt pretty surreal.

To be a freelancer, you have to be determined to work hard and do your best to not compare yourself to your competition, especially when platforms like Instagram make it so accessible to view other people’s work. There is an endless amount of talent out there, which is really inspiring to see.

AW: Do you have any particular viewpoints on design, branding, the outdoors, working abroad, etc. that you’d like to share?

WH: Life is short and goes fast. Every day I wake up grateful that I get to do what I genuinely love the most in life. I appreciate the technology that enables me to do this, I appreciate the planet, and I try to get outside everyday and connect with nature whether it be in the surf, the forest, or the mountains. […]

My career is a mix of play, work, creating for fun, learning how to improve and hustle. Some weeks the work flows in the door. Some weeks there is no work and as a freelancer that is the way it goes. I find that these moments can be an effective time to reflect on what’s working in the business and what isn’t and taking advantage of this time to teach myself new things (youtube is my go-to) for improving on how to get more work and be more professional.

There is ALWAYS something new to learn.

Insight from the Freelance Designer and Digital Nomad Behind Walking Designs

Walker’s Tips from the Freelance Road

  • Be efficient with your money: I cook healthy food at home, I avoid the bar scene, I only buy thing that are quality and necessary, not just because it’s on sale. For the most part I have lived and traveled to countries that are cheaper than the USA or have a good exchange rate.
  • Simplify your life: Get rid of stuff (donate) that you never use. I find that having a neat physical space to work in helps with a clear, productive mind and makes more room for the stuff that really matters.
  • Get outside and take deep breaths: Connecting with nature is good for the soul and helps with productivity and creativity. Also deep breaths oxygenate the brain!
  • Look away from your screens: This is a critical reminder for most people these days. Even though my work is entirely reliant on my phone/computer screen I make sure that my day always starts with getting outside, and moving my body before diving into emails and design. Also, real human connection is more and more rare these days. Make sure to lift your head up away from your screen and look around and actually talk and listen to people and their stories. These are the relationships that really matter in life.
  • Learn the credit card game: If you’re from the USA, you have an opportunity to stack up points for free travel. Do you research and go see the world!
  • See new places, break up your routine: It’s good to change it up, it will spark new creativity and open the doors for new opportunities.
  • Drink water: Get a reusable water bottle (consider the planet) and drink from it all the time for health.
  • Create daily: Whether it’s for a client, or just for fun. You’re alive, create!
  • Keep an open mind and look for the best in people: Everyone has stuff going on in life. Even if you don’t say hello, offer a smile.
  • Be you and follow your passion: It will take you on an amazing journey.
  • Appreciate Everything.
Insight from the Freelance Designer and Digital Nomad Behind Walking Designs

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