The Lonely Office
Glassdoor
Welcome to The Lonely Office, an award-winning podcast that brings sports-talk energy to real career decisions—fast, funny, brutally practical. It's locker-room candor meets boardroom wisdom, brought to you by Glassdoor. We tackle real workplace stories from anonymous firsthand accounts—job ghosting, the truth behind unlimited PTO, nightmare bosses—and share insider advice on layoffs, severance, negotiations, and career moves. From candidates vaping in interviews to employees fired over free speech, we cover the wild reality of modern jobs. Whether you’re growing your career or simply a jobseeker hunting for an edge, you don’t have to navigate it alone.
TLO is hosted by Matt Sunbulli (serial tech entrepreneur, Founder @ Fishbowl and First Draft AI), Aaron Calafato (Storyteller, Narrative Designer & Content Strategist), and Leah Ova (content creator and advertising executive), with special appearances from industry thought leaders and economists.
TLO is hosted by Matt Sunbulli (serial tech entrepreneur, Founder @ Fishbowl and First Draft AI), Aaron Calafato (Storyteller, Narrative Designer & Content Strategist), and Leah Ova (content creator and advertising executive), with special appearances from industry thought leaders and economists.
Episodes
Mentioned books
Mar 10, 2023 • 29min
When’s a Good Time to Tell the Boss I’m Pregnant?
Pregnancy, disabilities, age—when it comes to sharing sensitive personal information in a professional setting, where do we draw the line? On this episode, we dive into the true story of an HR professional named Diana, a pregnant new hire, and one boss with a big mouth. We’re joined by motherhood content creator Leah Ova to discuss the reasons why expecting women in the workplace may or may not want to disclose their pregnancy during the interview process.
Mar 7, 2023 • 37min
To ChatGPT for Work, or Not to ChatGPT
Is ChatGPT a powerful tool to augment our work, or is it a weapon of capitalism on the verge of taking our jobs? In this episode, we discuss an anonymous story shared by “Megan”, a PR professional whose excellent writing skills are secretly attributed to AI. We’re joined by startup advisor Rusty Rueff this week to debate the merit of AI tools like ChatGPT from all sides—from their innumerable benefits to unintended consequences.
Feb 16, 2023 • 52min
Just Hire Me, or Don’t
A horror story for the remote work era: going through endless rounds of interviews, wondering whether you’ve wasted your time. On this episode, we dive into a real 11-round-interview incident endured by one candidate named “Mike”. We’ll debate the risks and merits of a lengthy interview process, getting caught in the crosshairs of a company’s misaligned objectives, and whether it’s all a sign to get out of the corporate matrix. We’re also joined by special guest Azhar Usman, comedian and writer on the Hulu show, Ramy.
