Courtney Hill

Crying in Chili's

Business EN ↓ 9 episodes

Welcome to Crying in Chili’s — the podcast for anyone currently experiencing a character-building season against their will. Hosted by Courtney Hill, this show dives into career chaos, layoffs, relationship drama, life pivots, bad decisions, quarter-life crises, and all the messy in-between moments that somehow become funny later. Equal parts vulnerable, witty, and unhinged in the most relatable way, Crying in Chili’s feels like debriefing life with your smartest and funniest friends over chips, salsa, and a Presidente Margarita. Expect honest conversations, plot twists, guest interviews, emot...

Author

Courtney Hill

Category

Business

Podcast website

riverside.com

Latest episode

Jul 10, 2026

Where to listen?

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Episodes

Episode 9: Unfuckwithable: Turning Pain Into Purpose 10.07.2026

Episode 9: Unfuckwithable: Turning Pain Into Purpose What happens when life forces you to stop, rebuild from the ground up, and figure out who you are on the other side? This week, Courtney sits down with her former coworker and friend Sarah Weygandt for an honest, funny, and deeply vulnerable conversation about layoffs, burnout, addiction, recovery, mental health, and the power of turning pain in...

Episode 8: The Story Behind Crying in Chili's 03.07.2026

Episode 8: The Story Behind Crying in Chili's This week, you're getting something a little different. When a last-minute guest cancellation left an unexpected opening in the schedule, Courtney decided it was finally time to answer one of the questions she gets asked the most: Why is the podcast called Crying in Chili's? In this solo episode, she shares the real story behind the name and how one pa...

Episode 7: You Can Always Change Your Mind 26.06.2026

Episode 7: You Can Always Change Your Mind This week, Courtney sits down with spin instructor, fitness coach, and "curator of experiences", Kate Clark. Kate shares the unexpected story of walking away from law school to pursue a career in fitness, why choosing purpose over prestige turned out to be the best decision she ever made, and how building genuine community has shaped both her career and h...

Episode 6: Approach Life With A Plum 24.06.2026

Episode 6: Approach Life With A Plum Bonus episode alert! We've been recording so many great conversations lately that I couldn't wait until next week to share this one. This week, Courtney is joined by longtime friend Caroline Pearson for a conversation that feels a lot like catching up with your college gal pal over margaritas. The two look back on their East Carolina University days, surviving...

Episode 5: The Bees Left Me 19.06.2026

Episode 5: The Bees Left Me This week, Courtney sits down with longtime family friend and entrepreneur Erin Hostetler, founder of The Patio Farmer. Unlike many recent Crying in Chili's guests, Erin never took the corporate route. Instead, she built a business helping people grow their own food, spent time farming in Iceland and Pennsylvania, managed an urban farm, taught gardening classes, launche...

Episode 4: Kindness Is a Career Strategy 12.06.2026

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...

Episode 3: Rejection, Redirection & Buff Jesus 05.06.2026

Episode 3: Rejection, Redirection & Buff Jesus What do layoffs, comedy, job searching, and a ripped version of Jesus have in common? This week on Crying in Chili's , Courtney sits down with comedian, writer, and former coworker Anthony Cusumano to talk about rejection, redirection, and what happens when life forces you to rethink the path you thought you were on. From navigating layoffs and to...

Episode 2: Do The Damn Thing 29.05.2026

Episode 2: Do The Damn Thing Courtney is joined by former coworker and creative powerhouse Amanda Duncan for a conversation about layoffs, burnout, freelancing, music, and figuring out who you are when your job title disappears. From corporate chaos to creative dreams, they discuss perfectionism, trusting your instincts, crying in public, and why sometimes the best plan is to stop waiting and just...

Episode 1: Q2 Chaos 22.05.2026

Most of us are just trying to survive the chaos — whether it’s a breakup, a layoff, or a broken foot — and somehow laugh through the mess. In the very first episode of Crying in Chili’s , Courtney and her forever bestie Vickie unpack the absolute rollercoaster that has been Courtney’s Q2 of 2026: losing her job, breaking her foot, moving apartments, spiraling over health insurance, and questioning...

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