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Crying in Chili's

Crying in Chili's

Kindness Is a Career Strategy

Crying in Chili's · Jun 12, 2026 · 50:39

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After layoffs, rejection emails, and sending resumes into the void, sometimes the most valuable thing you have isn't your resume—it's your reputation.

This week, Courtney sits down with former coworker and creative leader Jay Peine to talk about navigating today's job market, building confidence during uncertain seasons, and launching something new when the traditional path isn't working.

Together, they discuss the realities of job hunting in an AI-driven world, the importance of networking, and why genuine relationships still open more doors than any algorithm ever will. Jay shares the story behind launching Open Mind Creative, while Courtney reflects on career pivots, personal branding, and what it means to bet on yourself when the future feels uncertain.

They also somehow end up talking about shark teeth, Amelia Island, remote work cats, and main-character energy in airport terminals.

If you've ever felt stuck, discouraged, or unsure of what's next, this episode is a reminder that kindness isn't just a personality trait—it's a career strategy.

Connect with Jay Peine:

Episodes: Crying in Chili's

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