I believe we should pay more attention to our childhood dreams.
For instance, I wanted to be a Chinese restaurant owner and a video game designer when I grew up, and as it turns out — I still love video games and Chinese food.
Well, when I was tracing drawings of Dragonball Z characters on printer paper, Kyle Barrett was listening to his dad’s CD collection, studying liner notes and letterforms, and drafting logos at age four. Years later it should be no surprise that Kyle was the first designer ever hired at Whiteboard and he became a longtime creative partner to Ryan O’neill of Sleeping At Last, a prolific songwriter and one of Kyle’s favorite musicians.
Kyle is the son of a draftsman and a freelance copywriter, he’s a drummer, a designer, and an entrepreneur and all his life he’s bucked the pressure to specialize in one thing or fit into neat categories and that has made all the difference.
If you've ever the felt pressure to "pick just one thing", then this conversation’s for you.
Episode Overview
Designer, drummer, and creative entrepreneur Kyle Barrett shares his unconventional journey from Whiteboard's first employee to building a successful freelance practice specializing in music industry design. This conversation explores the reality of multi-creative careers, the challenges of freelance creative work, and building sustainable practice that honors your full creative identity rather than forcing specialization.
Key Takeaways
Creative careers rarely follow linear paths: Kyle's journey from childhood fascination with CD typography to pharmaceutical consideration to design specialization demonstrates the non-linear nature of authentic creative development
Early creative obsessions often signal future professional direction: His childhood hours spent studying album liner notes directly connected to his eventual specialization in music industry design
Community and mentorship accelerate creative career development: From Jonathan Cattrell's introduction to Whiteboard founders to AJ Cheek's first album project, relationships opened doors that solo effort couldn't
Specialization can coexist with creative diversity: Kyle developed deep expertise in music industry design while maintaining his identity as a drummer and exploring other creative outlets
The freelance landscape requires constant adaptation: Success means navigating business cycles, client relationships, and industry changes while maintaining creative quality and personal sustainability
Physical practices support creative work: Regular exercise and movement are essential for maintaining creative flow and mental clarity during long design sessions
Timestamps
00:00 - Meet Kyle Barrett
07:29 - Early creative influences and childhood design fascination
15:37 - Realizing creative work could be a career
20:35 - Balancing multiple creative identities (design + music)
26:15 - Transition from Whiteboard to freelance practice
32:07 - Following creative interests vs. pressure to generalize
34:10 - Building music industry specialization
39:47 - Landing the Sleeping At Last collaboration
44:18 - The ups and downs of freelance creative practice
49:20 - Portfolio career approach and changing creative landscape
54:42 - Advice for multi-creative professionals
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