The Future of Logo Design, AI & Building a Creative Career | CJ Cawley @HowardPinsky
The Future of Logo Design, AI & Building a Creative Career | CJ Cawley  @HowardPinsky
Uploaded July 2026 | Updated September 2026, 3 weeks ago
Brand designer CJ Cawley joins me to chat about his journey from a difficult childhood and homelessness to building a successful branding studio, why telling your story matters more than ever, and how mental health has shaped both his life and creative career.

We also tackle one of the biggest conversations happening in design today: AI.

Is AI replacing designers? Or is it simply raising the bar for creativity?

00:00 Intro
00:38 Who is CJ Cawley?
03:57 Mental health & finding purpose
16:28 Discovering creativity through skate culture
21:27 Why modern branding feels too safe
27:46 AI vs human creativity
39:19 Illustrator, Photoshop & design tools
49:07 Community Q&A
49:07 Avoiding imposter syndrome
51:18 Should designers redesign famous logos?
55:18 Getting clients through social media
58:27 Approaching companies with bad branding
1:00:38 Quitting a full-time job
1:06:13 Handling difficult client feedback
1:08:40 Building an audience from scratch
1:12:16 Agency life vs freelancing
1:17:02 Where to find CJ
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The Future of Logo Design, AI & Building a Creative Career | CJ Cawley

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