We’re excited to introduce you to the always interesting and insightful Derrick Whitfield Sr.. We hope you’ll enjoy our conversation with Derrick below.

Alright, Derrick thanks for taking the time to share your stories and insights with us today. Alright, so we’d love to hear about how you got your first client or customer. What’s the story?

When I left the Navy in late 2014, I didn’t have a portfolio or a business plan. I just knew I wanted to create. By 2015, I was in design school, learning the craft, but I also knew I had to get my work out into the world. So I started dropping off art prints at skate parks, comic book shops, and clothing stores. Places that felt alive and connected to the culture I cared about. No pitch. Just me leaving pieces of my work and my business card behind, and hoping someone would notice.

For a few months, nothing happened. Then I got an email from The House of Blues. I don’t know if they came across my art drop-offs, but they invited me to be part of their art show. I showed up with everything I had. I didn’t make any sales that night, but a few days later, someone who had seen my work at the show reached out. They weren’t a friend, just someone who connected with what I made.

They asked me to design a logo. It wasn’t a huge job, but it was the first time someone paid me for my creativity. That first dollar meant everything. It was proof that the late nights, the quiet doubts, and the random print drops had led to something real. That moment was the start of my journey as a working designer.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I never really “got into” the design industry. The truth is, I have always worked outside of it. I was never hired as a designer. I did not wait for permission. The first day I walked into college for design, I started my business the same day. That mindset, build while you learn, lead while you grow, has shaped everything I do.

I create logos, apparel design, product packaging, visual identity systems, and commercial illustration for puzzle and watch companies. My clients are often unconventional. I work with small business owners who need professional design that actually works, and I help larger businesses build easy-to-use brand kits that keep everything consistent while still letting teams customize when needed.

What sets me apart is simple: service. I want potential clients and followers to know I am second to none when it comes to customer care. Before I ever designed a logo, I spent nine years in the Navy working in customer service. That experience taught me how to listen, how to respond, and how to deliver under pressure. I bring that same discipline and respect to every project I touch.

I am proud of the work, but I am even prouder of the relationships. My brand is not just about visuals; it is about helping people show up in the world with clarity, confidence, and culture. Whether it is a startup trying to find its voice or a legacy brand looking to evolve, I am here to make sure the design tells the right story.

Can you tell us about a time you’ve had to pivot?

I never saw myself teaching middle school visual art. It wasn’t on my bingo card, and it definitely wasn’t part of my original business plan. But life has a way of rerouting you when you least expect it.

As a full-time creative and business owner, I was immersed in the grind, designing logos, building brands, and working with unconventional clients. I loved the work, but the reality of running a business started to wear me down. Healthcare as a solo entrepreneur is brutal, and the starve-feast cycle of freelance life began to take a toll. I needed stability, but I didn’t want to lose my connection to creativity.

That’s when I pivoted into teaching.

Stepping into a middle school classroom felt like a detour at first. But it turned out to be a masterclass in growth. Teaching art forced me to break down my process, rethink how I communicate ideas, and stay sharp in ways I hadn’t expected. It challenged me to be more intentional, more patient, and more inventive. And it reminded me why I started creating in the first place.

This pivot didn’t just give me a paycheck; it gave me perspective. It expanded my skill set, deepened my understanding of visual storytelling, and connected me to a new generation of artists who are hungry to learn and express themselves.

Sometimes the best moves aren’t the ones you plan. They’re the ones that meet you where you are and push you to become more than you imagined.

How did you build your audience on social media?

Honestly, there’s no secret formula behind how I built my audience on social media. No viral strategy. No perfect posting schedule. I just try to be as authentic as possible, stay consistent, and put out the best design work I can. Some posts resonate, while others don’t. But every piece I share is true to me.

I’ve never chased trends or tried to fit into what the algorithm wants. I post what I believe in—whether it’s a logo I’m proud of, a classroom moment that moved me, or a design that speaks to culture and identity. Over time, that honesty has attracted the right people. Not just followers, but community.

If you’re just starting out, my advice is simple: be real, be consistent, and keep creating. Don’t worry about likes or reach in the beginning. Focus on showing up with work that reflects who you are and what you care about. The audience will come, and more importantly, the right audience will stay.

Contact Info:

• Website: https://www.whitfielddesignsco.com
• Instagram: https://www.instagram.com/whitfielddesigns
• Facebook: https://www.facebook.com/whitfielddesigns
• Linkedin: https://www.linkedin.com/in/derrickwhitfield-sr-b046b01b7/