Is Unlimited PTO a Sham?

From the vault of The Lonely Office is one of our greatest hits—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.

We’ve all worked with great communicators. On the one hand, they razzle and dazzle during presentations, woo the C-suite, rally the troops. On the other, they can overinflate their own achievements, and take credit where no credit was due. This week, inspired by the story of “Maria,” a flaky strategist who’s earned a reputation as a great actress at her company, we discuss the role of communication in the workplace, who it benefits, and how it might just be the key to future jobs in the age of AI.

As the unemployment rate for recent graduates climbs higher than the national average, qualified white-collar workers are turning to unlikely sources for their next job. This week, we discuss a sticky situation involving “Mark,” an Ivy League marketer, and his stint at a Canadian adult entertainment company. What are the moral implications of taking a job in a taboo industry, and how does it impact one’s career? And what exactly is responsible for the dearth of jobs?

Have you ever been ghosted by an interviewer, only to be officially rejected a year later? That’s the story of Karen Young the recruiter. Hers is the inspiration for our episode this week, and in an unprecedented first, she’s also our special guest on the show. We discuss ghosting as an industry-wide plague, how to bring your humanity to these interactions, and the wider cultural phenomena at play. Connect with Karen on Linkedin https://www.linkedin.com/in/kareneyoung/

“Harold” is a disillusioned quiet quitter who finds himself impassioned to act after the House passed a bipartisan bill to ban TikTok. Harold represents some of the younger 175 million Americans fighting to keep the app around, whether as a source of information, entertainment or livelihood. On the other side of the generational divide, there are those who perceive TikTok to be, at best, an app drugging America's youth, and at worst, a means of surveillance for foreign adversaries. Why can't we agree on this ban, what might it mean for our freedom of speech, and what regulatory measures can we put in place to avoid it? That’s our conversation this week.

Film, with all of its cinematic magic, was supposed to be creativity’s last line of defense against artificial intelligence. But when OpenAI’s impressive text-to-video generator Sora is taking meetings with Hollywood’s heads of production, what hope does that leave the rest of us? This week, inspired by the real story of “Lee,” a young film editor who sees his future thwarted by Sora, we discuss the impacts of AGI on creativity. Is it killing creatives’ livelihoods, or democratizing access? And will our sense of passion or purpose survive the AI takeover?

Picture this. You’re the fly on the wall in a layoff call. The employee isn’t getting any of the answers they want. The HR representative isn’t allowed to deviate from their rote, clinical script. It’s all very, very awkward. That’s this week’s topic, inspired by the mortifying tale of “Jenna” the HR newbie, and the viral video from TikToker Brittany Pietsch. In this episode, we chat about what employees deserve in this scenario, how employers can do better, and how this process is fundamentally broken.

Here’s a staggering stat: through 2045, the wealth to be inherited by Generations X-Z is estimated to be 53 trillion dollars, an unprecedented sum in modern times. In this episode we cover the story of “Rich,” a 30 year-old screenwriter who, after receiving a financial windfall left by an uncle, finds himself losing his sense of purpose and creative motivation. Rich’s example and others' have us thinking about this Great Wealth Transfer: Can you inherit financial freedom and still retain your will to work? What happens to passion, persistence, and grit when labor becomes optional?

Unlimited vacation is often lauded as a workplace perk, but who does it actually benefit? On this episode, we reflect on our previous experiences with this “generous” perk, and whether it served us. We also discuss why employers might be incentivized to adopt unlimited PTO policies—and why employees might be getting the short end of the stick.

You just found out that the new, fresh-out-of-college hire at work… makes the same salary you do. What would you do next? That’s the true story from “Lorrie” that inspired this conversation around salary transparency and fair pay. This week, we share some of our own experiences with speaking up (or not) for ourselves, ideas on what companies could do to promote salary transparency, and some tactical recommendations for next steps, if you find yourself in a similar position as Lorrie.