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
Jul 7, 2023 • 25min
Should I Work for an “Evil” Corporation?
From the excesses of Wallstreet companies in the 90s to Tech companies pillaging our privacy for gold in the 2000s, how have workers’ considerations of evil companies evolved with the rise of frameworks like ESG? This, talk about digital gold miners in World of Warcraft, and more all on this episode of Lonely Office.
Jun 13, 2023 • 40min
You’ve Been Laid Off. Now What?
It’s happened. You’ve been laid off. What do you do next? Do you jump on LinkedIn with a heartfelt post? Do you go live on TikTok? Inspired by the true story of “Maggie” - we talk about how to set yourself up for success before and after a potential layoff—from warming your professional network to re-evaluating your options.
May 30, 2023 • 45min
How to Get Fired and Negotiate Severance
Whether you’re a frequent job hopper or company loyalist, you’ll likely be affected by layoffs at some point in your working life. “Dylan’s” IRL layoff story got us thinking: are you ready for what happens next? On this episode, joined by corporate content creator Leah Ova, we’re talking about how to prepare for layoffs—what you should keep in mind, what you should enquire about, and what data to have in hand.
May 17, 2023 • 43min
Can Career Coaches Really Help Your Career?
There are an estimated 70,000 professional career coaches worldwide. But are they the answer that lost professionals are looking for? On this episode, we discuss the real story of “Jamie”, whose expensive career coach falls short of expectations. We’re joined by special guest Cindy Gallop (advertising consultant, founder of MakeLoveNotPorn, and yes, career coach) to debate the approaches career coaches take today—and whether the profession provides as much value as it touts.
May 5, 2023 • 41min
Get Back to the Office, or You’re Fired
Whether you see it as a privilege or a right, companies are changing their tune when it comes to remote work—like popular advertising agency TBWA, whose policies inspired today’s story. Should employees be going back in, or should they be walking out? On this episode, joined by corporate content creator Leah Ova, we chat about the benefits and impacts of returning to office, and what the alternatives can be.
Apr 27, 2023 • 29min
How Much of Your Self Do You Bring to Work?
Just be yourself, they say. But not that self. In a culture that preaches authenticity one day and cancels you the next, how do you know how much of your personality and selfhood to reveal in a professional setting? Inspired by the true story of “Bill”, who struggles to socialize at work, we talk about the risks and rewards of bringing your full self to work—and whether the whole concept is a carryover from a bygone era.
Apr 13, 2023 • 37min
Your Next Coworker Might Be ChatGPT
With artificial intelligence becoming more intelligent by the hour, who will lose their jobs first? Where will they go? And is this a case for universal basic income? On this episode, joined by comedian and writer Azhar Usman, we follow the rapid rise of AI to its professional, social, and ethical conclusions.
Apr 4, 2023 • 46min
Boomers Vs. Millennials in the Workplace
Are the younger generations really coddled and entitled, or is this just a classic case of “OK Boomer”? When it comes to workplace attitudes, there’s a clear generational divide, especially in the case of “Allie” and “Randy” (protecting their anonymity!) who inspired today’s story. In this episode, we’re joined by beloved guest Leah Ova to unpack these stereotypes—and how remote work might be making everything worse.
Mar 22, 2023 • 38min
Is Unlimited PTO a Scam?
Unlimited vacation is often lauded as a workplace perk, but who does it actually benefit? On this episode, we’re joined by marketer and content creator Leah Ova to discuss why employers might be incentivized to adopt unlimited PTO policies—and why employees might be getting the short end of the stick.
Mar 15, 2023 • 27min
How Much Should I Care about My Job?
After working overtime, “Mo” expected a nice work perk, but received branded snacks instead. Their anonymously-shared story prompted us to ask the question(s): What should be the reward of a job well done? A sense of purpose? A round of applause? A box of pretzels? This week, we’re joined by comedian Azhar Usman and content creator Leah Ova to debate the full spectrum of how we might feel about our work—from meaningful to meaningless.
