The Key to Building a Creative Career That Actually Lasts with Stewart Cohen
“People want to feel heard. If you don’t create a collaborative space, they won’t come back.”
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How do you build a long, successful creative career when you are the brand?
In this episode, Rain sits down with director and visual storyteller Stewart Cohen to explore the balance between artistry and entrepreneurship. With decades of experience in commercial production, photography, and branded storytelling, Stewart has mastered the dance of creating great work while sustaining strong client relationships—and still making time for passion projects.
They discuss how personal work often leads to professional opportunities, the importance of trust and collaboration, and how to get authentic performances from real people.
Stewart shares how his curiosity drives his creativity, why connection is the true metric for success, and why making stuff just for fun might be the smartest business decision you ever make.
If you're a storyteller trying to make it in a noisy world, this episode is packed with hard-earned wisdom.
In the episode, you will learn to:
Balance creative work and client relationships by focusing on trust, collaboration, and communication.
Use curiosity and personal projects to fuel professional growth and keep your creative spark alive.
Make non-actors feel comfortable on camera by creating a safe, relaxed environment that encourages vulnerability.
Understand how story-first branded content builds stronger emotional engagement than traditional marketing.
Recognize the long game of creative careers and why real relationships outperform short-term wins.
“People want to feel heard. If you don’t create a collaborative space, they won’t come back.”
- Stewart Cohen
If you want to learn the best way to build a video production business over the long term and deepen your connection with clients... this is the episode for you!
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Some of the highlights of the episode:
00:00 - Building a Long-Term Career as a Creative
03:50 - Why Meeting People Is Part of the Work
05:30 - Luck, Momentum, and Putting Yourself Out There
09:24 - Going Deeper with Clients Instead of Wider
11:36 - Using Story in Commercial Work
13:40 - Getting Real Performances from Non-Actors
15:06 - From Still Photography to Film School to Directing
18:22 - What Video Taught Stewart About Telling Stories Faster
20:00 - Trust, Collaboration, and Long-Term Clients
24:57 - Teaching Clients by Leading with Experience
26:49 - When to Start Using Video in Your Business
29:05 - How Brand and Product Work Together
32:11 - Branded Stories That Focus on the Message, Not the Product
34:16 - The First Ever “Just Do It” Ad (and Why It Worked)
36:35 - Storytelling That Hits Without Forcing It
38:31 - The Personal Projects That Led to Commercial Gigs
40:49 - Creating for Curiosity and Adventure
44:35 - Growing with Clients Over Time
46:17 - Exploring Brand and Personal Identity
50:07 - Leaning In to the Next Chapter of Creativity
52:22 - Advice for Aspiring Creatives in the Digital Age
As always, I hope you enjoy the episode!
Rain
Follow Stewart on:
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For more storytelling tips and tricks,
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