We caught up with the brilliant and insightful Kelsey Askew a few weeks ago and have shared our conversation below.

Kelsey, thanks for joining us, excited to have you contributing your stories and insights. It’s always helpful to hear about times when someone’s had to take a risk – how did they think through the decision, why did they take the risk, and what ended up happening. We’d love to hear about a risk you’ve taken.

Leaving my corporate job at Nike to pursue freelance work was the biggest and most soul-led risk I have ever taken. I had worked hard to land a creative position at a globally recognized brand, and from the outside, it looked like I had made it. But inside, I felt a creative restlessness that I could not ignore. I have always made art from the heart, from painting dog portraits as a teen to building a design career through grit, curiosity, and deep care for the people I work with. Sitting in a corporate office, I began to realize I was craving more than creative freedom. I wanted a deeper connection to my work and how it impacted the world.

At the time, I had no backup plan. I was now sitting on savings, and I did not have a strategy other than trusting myself. I just knew that if I did not take the leap then, I would regret it for the rest of my life. So I gave notice, left the comfort and stability of a full-time job, and stepped into the unknown.

The early years were scrappy. I said yes to every opportunity, trusted my instincts, and prioritized building real relationships with my clients, from grassroots startups to larger companies. What started as a survival move eventually turned into something expansive. I was not just freelancing, I was creating my own lane. Over the past seven years, that risk has evolved into a full-time design studio, a Benefit Company that gives back to Earthjustice with every project, and community programs like art clubs that bring people together through creativity.

That leap taught me that risk is not about being fearless. It is about choosing alignment over comfort. I chose to believe in my vision when nothing was guaranteed, and as a result, I have built a life and business that reflect who I truly am.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m a multidisciplinary artist and designer with 13 years of experience in graphic design and over 20 years in fine art. I got into design as a practical decision. It felt like a way to make a stable living while using my natural ability to draw and create. I started with portraits and illustration commissions, then formally studied design at the Art Institute of Seattle. I took a break from school to work in customer service, then returned to Portland Community College with a clearer sense of purpose.

My work today spans a wide range of industries. I provide graphic design, illustration, brand development, and environmental design for clients across:

Health & Wellness
Thrive, Sierk Orthodontics, Gasow Wellness

Apparel
Nike, VF Corporation, Noorfit

Food & Beverage
Sip of Life Teas, Hedonisme, Prime Cuts

Cannabis
The Re-Up

Accessories
Amalia

Home & Garden
L’or de Seraphine Candles

Music
Beast Parade

Environmental Design
Murals, Bijou floral installations, Timbers and Thorns wall mural, large format floral prints

Personal Service
Tattoo design

At the core of all of this, my favorite part is creating something out of nothing. Whether I am illustrating from a concept, combining strange or thoughtful ideas into one image, or building a brand identity from the ground up, I love the challenge of turning energy into something visual. I thrive on the in-between space where inspiration meets intuition.

What I am most proud of is that I am fully aligned with every creative project I take on. That alignment is everything. It is what allows the work to feel intuitive, collaborative, and emotionally resonant. I am here to support bold, creative people and brands in telling their stories. I want my art and design to feel like an offering. Something that moves people emotionally, helps them feel seen, or gives shape to a vision they could not quite express until now.

Whether it is branding, murals, illustrations, or tattoos, I hope people experience my work as something rooted in clarity, honesty, and emotional connection.

Let’s talk about resilience next – do you have a story you can share with us?

The biggest lesson I have learned over the past seven years is how important it is to stay centered in your own vision, no matter what comes your way. This field is filled with beautiful opportunities, but it also comes with challenges that can wear you down if you are not prepared. I have experienced scams, false promises, people who drain your energy, and projects that looked exciting at first but turned out to be completely misaligned. The truth is, not everyone in this industry has a clear vision or respect for creative work.

For a while, I took things personally. I overgave. I said yes when I should have said no. But every experience like that became a teacher. I learned to listen more deeply to my instincts, to protect my time and energy, and to only collaborate with people and brands that feel grounded and honest. Resilience for me has meant continuing to show up for my work even after setbacks. It has meant learning to pause when something feels off, to not force anything, and to never let other people’s chaos throw me off course.

Perseverance is everything. If you want to last in this industry, you have to build a strong sense of self, keep your boundaries clean, and know why you are doing what you do. I have learned how to stay connected to that deeper why. That is what keeps me going.

Specific story:
One of the most defining experiences in my freelance journey came from working with a client who, at first, seemed like a dream. I was brought in to help build what appeared to be a bold, exciting vision. The project was creatively rich, and I poured myself into it. Over time, that relationship grew and I stepped into an Art Director role, adding new skills to my belt and taking on more responsibility.

But as the years went on, cracks began to show. There was no clear structure, no long-term plan, and no real vision behind the work. The leader of the project relied heavily on freelancers to build everything, but when things didn’t come together, the blame was placed on us. Payments were consistently delayed, communication became chaotic, and the lack of leadership became painfully clear.

It felt like the ultimate betrayal, to give so much creative energy and care to a project that had no solid foundation. This stretched out over three years. It was a painful, personal, and professional lesson in boundaries, trust, and the importance of alignment.

I am still deeply grateful for the experience, because it taught me what to look out for and how to protect my creative energy. Resilience, to me, means being able to walk away from what no longer serves you and continue on your path with more clarity, strength, and self-respect. That chapter helped me become the artist and business owner I am today.

For you, what’s the most rewarding aspect of being a creative?

Being an artist for a living makes me feel the most alive.

Contact Info:

• Website: https://askewcollective.com
• Instagram: https://www.instagram.com/kelsey.askew/
• Linkedin: https://www.linkedin.com/in/kelsey-askew-307072a8/

Image Credits
Image Credit: Kelsey Askew