Give Yourself Permission to be Weird with Jason Jacobson | April 28, 2025
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In this episode of Monday Meeting, host Lee Smalt welcomes creative director Jason Jacobson to discuss the art of pitching unconventional ideas and finding the courage to present concepts that push boundaries.
This episode includes:
- Jason's 20-year journey from copywriter to creative director, and how his experience with improv comedy has shaped his approach to pitching creative concepts
- The value of the "chicken wing construct" - presenting ideas in escalating levels of boldness to gradually build client comfort with more adventurous concepts
- Why presenting multiple ideas is essential, with Jason noting "2/3 of my ideas are going to be cut, and that's okay" - creating resilience against rejection
- Insights on psychology in pitching, including using premium options to make middle-tier options more appealing to clients
- The power of creating interactive experiences that invite audience participation, like installations that turn passive viewers into active participants
- Thought-provoking examples of successful bizarre pitches, including a concept featuring a pet camel that resonated surprisingly well with a technical college audience
- The reminder that "no one remembers controversy after two years" - encouragement to take creative risks in a world of short attention spans
Next week kicks off the new theme of "Identity" with Kendall Hotchkiss hosting a discussion on how identity relates to illustration and branding in motion design.
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