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 particularly chaotic season of life became the reason Crying in Chili's exists.

From growing up with an entrepreneurial dad and working in restaurants and marketing to losing her brother as a teenager, navigating breakups, layoffs, a broken foot, and today's impossible job market, Courtney opens up about the experiences that shaped both her and the podcast.

She also answers a few rapid-fire questions so you can get to know the person behind the microphone—including her favorite Chili's order, her biggest irrational fear, and why Uncrustables absolutely should give her a sponsorship deal.

Whether you're here because you've been laid off, gone through a breakup, started over, or just need someone to split chips and salsa with, this episode is the heart of what Crying in Chili's is all about.

Connect with Courtney:

Instagram: @cryinginchilis

TikTok: @c_hillll

Email: cryinginchilis@gmail.com

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 her life.

Together, they talk about career pivots, corporate burnout, finding work that actually fills your cup, the power of supportive partners, boutique fitness culture, moving to Wilmington, and why sometimes the bravest thing you can do is simply change your mind.

They also debate the merits of Chili's (Kate has... opinions), discuss emotional support grocery stores, relive their emo spin class era, and somehow end up planning the world's most therapeutic day involving spin class, Aldi, Hamilton, and—of course—Chili's.

If you've been wondering whether it's too late to start over, this episode is your reminder that you can always change your mind.

Connect with Kate

• Instagram: @kateclarkcycle
• Recess by Bevan Prince: https://www.recessbybevanprince.com

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 on Pirate Bucks, spring break adventures, questionable decision-making, and the unique chaos of your early twenties. They also talk about where life has taken them since graduation—from fashion merchandising careers and podcasting side quests to CrossFit, dating in your thirties, recovering from setbacks, and learning to trust yourself when life doesn't go according to plan.

Along the way, Caroline shares one piece of advice that's surprisingly stuck with Courtney ever since: approach life with a plum.

If you've ever found yourself missing your college friends, wondering how everyone became a real adult, or trying to navigate an unexpected chapter of life, this episode is for you.

Connect with Caroline:

• Live Laugh Lore Podcast
• Instagram

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, launched a podcast, and somehow still finds time to dream about writing books.

Together, they talk about entrepreneurship, side hustles, social media, following unconventional career paths, and why sometimes the best thing you can do is start before you're ready. They also discuss the power of kindness, the reality of running your own business, crying in yoga classes, and the surprisingly emotional journey of trying to keep bees.

If you've been waiting for a sign to start the thing you've been dreaming about, this might be it.

Connect with Erin:

Website: thepatiofarmer.com

Instagram: @thepatiofarmer

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:

• jaypeine.com
• Open Mind Creative
• Follow Open Mind Creative on Instagram

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 today's chaotic job market to pursuing creative dreams outside of corporate America, Anthony shares how he's balancing freelance work, comedy, and his latest creative project: Buff Jesus—a comedy short film about a conservative priest, a queer graffiti artist, and an unexpectedly effective piece of church marketing.

Along the way, Courtney and Anthony swap interview horror stories, discuss why personality still matters in hiring, debate whether anyone actually enjoys Applebee's, and explore the idea that sometimes rejection isn't a dead end—it's simply redirection toward something better.

Whether you're job hunting, chasing a creative dream, questioning your career path, or just here to find out why Buff Jesus exists, this episode is for you.

In this episode:

• Navigating layoffs and career uncertainty
• The realities of today's job market
• Why rejection isn't always a bad thing
• Recruiter and interview horror stories
• Anthony's original musical
• The story behind Buff Jesus
• Why Chili's will always beat Applebee's

Guest: Anthony Cusumano
Comedian, writer, performer, and creator based in Chicago.

• Follow Anthony on Instagram
• Check out the first scene of Buff Jesus on Youtube!

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 do the damn thing.

Grab your chips and salsa. The emotional debrief is now in session.

Connect with Amanda:

• Instagram
• https://amandaduncan.com/

Through laughter, emotional damage, and a few too many “you genuinely cannot make this up” moments, they talk about the reality of layoffs, the chaos of adulthood, Sabrina Carpenter, friendship, vulnerability, and why sometimes the only thing you can do is laugh before you cry again.

If you’re tired of the polished version of adulthood and craving honest conversations with a side of humor, this episode is for you. Because sometimes rock bottom looks like a single tear falling into your Presidente Margarita.