Alright – so today we’ve got the honor of introducing you to Kelsey Reifler. We think you’ll enjoy our conversation, we’ve shared it below.
Alright, Kelsey thanks for taking the time to share your stories and insights with us today. To kick things off, we’d love to hear about things you or your brand do that diverge from the industry standard.
I’ve been in the design world for over 12 years, wearing different hats from designer to art director and now creative/design director. I’ve hopped between jobs and industries, from publishing to branded content to advertising to branding shops, where I have had the opportunity to learn from some amazing people and work with household brands. However, (almost) every place I worked I consistently observed the disconnect in communication between clients and creatives.
In my experience, often creatives find themselves not interacting directly with clients or only doing so during the initial pitch. The creative team often relies on secondhand feedback through account managers and client reps, and it’s a loop that can eat up countless hours with revisions and leaves both parties frustrated. It is a big problem. Design is nuanced, and client feedback like “make the headline bigger” can signify broader issues with hierarchy, not just increasing type size.
Needless to say, I made the leap to freelance and started my own business because I wanted the freedom to connect directly with clients, and to really have that relationship and dialogue with them through every step of the process. There’s something incredibly rewarding about speaking with a company’s founder and truly understanding their mission and overall vision. I enjoy partnering with clients and working with them as just that; a partner. Together we can bring their vision to life, and that is what drives me in my work.

Kelsey, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
Sure! Hi, I’m Kelsey, a creative director and designer based in Brooklyn. With a history of working in advertising, editorial design, and branding, I recently shifted from agency work to freelancing. My true passion lies in collaborating with small businesses and founders. There’s something incredibly fulfilling about directly engaging with clients, understanding their vision, and bringing it to life through collaboration. Creating tangible expressions that reflect their unique vision and values is not just a job for me—it’s a labor of love and the greatest accomplishment.
When I am not designing, I love hosting and bringing people together. I’m a major foodie and exploring new neighborhood bars and restaurants is one of my favorite things to do. I live with my fiancée Staten and our french bulldog, Bogey. Together we hope to one day design and open a boutique hotel.

What else should we know about how you took your side hustle and scaled it up into what it is today?
My side hustle evolved into my full-time career and business during my time working in ad agencies. I was feeling increasingly frustrated with the lack of clear communication between client and agency, so I began freelancing for startups and small companies on the side. My agency hours were pretty nuts so the bulk of my freelance was done either late night or on weekends.
The turning point for me wasn’t an “aha” moment but rather a slow burn. It’s scary to leave full-time work and take a chance on yourself. While working on smaller-scale projects with smaller brands on the side, I felt my impact was much greater. I realized I was more excited about my freelance projects than my advertising work, so I decided to stop living a dual creative life and fully commit to my side-hustle.

What’s worked well for you in terms of a source for new clients?
I’ve been freelancing for 8 months now, which is a relatively short time in the grand scheme of my career. Most of my clients have come through word-of-mouth referrals, although I understand that this may not always be the case. I’m actively creating a network of fellow freelancers to whom I can refer clients when their needs exceed my expertise or availability. I also hope that they will do the same for me when the opportunity arises.

Contact Info:
- Website: www.kelseyreifler.com
- Linkedin: https://www.linkedin.com/in/kreifler/

