The Lonely Office - podcast cover

The Lonely Office

Glassdoor
Welcome to The Lonely Office: an award winning podcast about making sense of the increasingly blurry line between work and life, brought to you by Glassdoor. We tackle real workplace stories sourced from anonymous firsthand accounts—like the rise of job ghosting, the truth behind unlimited PTO, and dealing with a nightmare boss. We also share insider advice on layoffs, severance negotiations, and wild work stories, from candidates vaping in interviews to employees fired over free speech. The professional world can be chaotic, but 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.

Episodes

Office Parties Gone Wrong (And How to Survive Them)

Office holiday parties walk a delicate line between celebration and career sabotage. When Morgan abandoned her one-drink rule and mixed up the CEO's birthday with the VP's, she learned that some party memories follow you back to your desk on Monday. From inappropriate revelations to ill-timed layoff announcements, we explore the dos and don'ts of navigating the annual workplace ritual. With 12% of employees admitting to romantic encounters and the average attendee consuming 4.1 drinks, are these...

Dec 23, 202425 min

Side Hustles Are Redefining How We Work

In an era where everyone seems to be monetizing their passion, the line between day job and side hustle grows increasingly blurry. When Chelsea's vintage artifact business collided with her corporate role, she learned the hard way that not all companies embrace the hustle economy. From MMA fighters turned TikTok food critics to corporate employees building startups in secret, we explore how to balance your dreams with your day job. Is the remote work revolution making it easier to pursue your pa...

Dec 18, 202424 minSeason 1Ep. 82

Why Great Companies Self-Destruct

How much do failing companies and countries have in common? In this episode of The Lonely Office, we follow Lianna, a young attorney watching her dream of partnership fade away as her firm’s leadership hoards profits and power. Inspired by the Nobel Prize-winning book Why Nations Fail, we explore how the "extractive policies" that doom nations—concentrating wealth and power in the hands of a few—also plague companies. From Blockbuster's $50M Netflix blunder to today's imploding startups, we exam...

Dec 11, 202427 minSeason 1Ep. 81

Can Your Digital Footprints Haunt Your Job Search?

Your past doesn’t always stay in the past—especially online. In this episode of The Lonely Office, we dive into the surprising ways our digital footprints, from Roblox handles to controversial posts, can resurface in professional settings. Are employers justified in scrutinizing these digital traces during interviews, or has the line between personal history and professional qualifications blurred beyond reason? Tune in as we explore stories of online embarrassments haunting job seekers, the eth...

Dec 04, 202425 minSeason 1Ep. 80

My Boss is Delegating Their Entire Job

Remember when delegation meant sharing the workload, not abandoning ship? When Zoe, the intern, found a critical company audit on her desk, with no boss in sight and only "Ask ChatGPT" as guidance, she knew something was wrong. From absentee managers to entry-level employees running entire departments, we explore why modern delegation has gone off the rails. Is your boss actually leading or just delegating their job away? Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.thr...

Nov 27, 202430 minSeason 1Ep. 79

Sorry Boss, I Don't Want That Promotion

Remember when getting a promotion was a good thing? This week, Ellie was offered a better title and salary, she did the unthinkable—she turned it down. And she’s not the only one. 30% of today’s workers quit within a month of promotion. From endless Zoom calls to "forced fun" events, we explore why more professionals are saying "No, thanks!" to moving up. Is the traditional career ladder broken, or are we finally asking for what we're worth? Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbu...

Nov 20, 202422 minSeason 1Ep. 78

Your Coworker is a Secret Influencer. Now What?

This week, we start with the story of a Citigroup analyst, who unexpectedly found himself internet-famous, blending work and social media in ways he hadn’t foreseen. Join us as we dive into the world of low-key influencers—employees hiding behind cubicles by day and thriving online by night. How does this new professional reality affect our workplaces? And what happens when your side hustle becomes the main event? Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net...

Nov 13, 202423 minSeason 1Ep. 77

When Does Adulting Really Start?

We all remember our first adulting moment. For some, it was their first paycheck; for others, it was moving to the big city. For Amani, it was getting kicked off the family phone plan. When does adulthood start? Do you have to stop chasing your dreams to pay the bills? This week, we discussed moving out, paying rent, and everything #Adulting. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc Aaron Calafato Listen to Aaron's...

Nov 06, 202427 minSeason 1Ep. 76

Decoding the Job Market: What Today's Employment Report Really Means (Reaction Pod)

On this episode of The Lonely Office, we dive into the latest economic insights with Glassdoor’s lead economist, Daniel Zhao, as he unpacks the complexities behind two major job market reports—the JOLTS report and the Employment Situation report. With factors like hurricane impacts and the Boeing strike shaping this month's data, we break down what these reports reveal about job openings, hiring rates, and why so many employees feel “stuck” in their roles. Join us for a candid look at the evolvi...

Nov 01, 202418 min

Blue-Collar Job Envy: Myth vs. Reality

As the sparkling promise of a college education turned into the shadow of crushing student debt, many are signing up to be mechanics, technicians, and electricians—and desk workers are yearning to make the switch. Are the tides finally turning on the trades? Or is it a case of romanticizing the other, and wanting what you can’t have? This week, we talk the pros and cons of blue collar jobs, living to work vs. working to live, and the quest for meaning within it all. Hosts: Matt Sunbulli https://...

Oct 30, 202432 minSeason 1Ep. 75

How to Negotiate Like a Pro Athlete

In the sports world, contracts go far beyond the numbers. From deferred payments to ‘love of the game’ clauses, there’s a lot we can learn from athletes like Shohei Ohtani and Michael Jordan. Can you negotiate like the pros? And how much leverage do you really have? We’ve got answers, advice, and tips to help you get paid. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc Aaron Calafato Listen to Aaron's 7 Minute Stories Le...

Oct 23, 202428 minSeason 1Ep. 74

Startup Gamble: What are Your Odds?

In this episode of The Lonely Office, we dive into the world of startups and the hard truths behind venture capital. Peter Walker, Head of Insights at Carta, joins us to break down the numbers, offering key advice on when to take that leap into entrepreneurship—or when to hold back. Special Guest: Pete Walker Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc Aaron Calafato Listen to Aaron's 7 Minute Stories

Oct 18, 202420 min

Beat the Algorithm to Get a Job?

In the age of algorithms, getting noticed by employers can feel like trying to go viral. When did applying for jobs morph into a social media contest? Sometimes, the best way to outsmart the system is to circumvent it altogether. In this episode, we share stories and research on some age-old tactics that can help land you a job. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc Aaron Calafato Listen to Aaron's 7 Minute Stor...

Oct 16, 202434 minSeason 1Ep. 73

Job Hunters Are Draining 401ks to Stay Afloat

401ks were meant to be our generation’s retirement plan, but now they’re becoming many workers’ only means of survival. With Social Security drying up and a chaotic job market, our financial future hangs in the balance. Are we really spending too much money on coffee? Or are we innocent victims of a broken system? Today, we’re talking retirement, 401ks, and all about the moolah. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraf...

Oct 09, 202428 minSeason 1Ep. 72

Is Amazon's Return to Office a Layoff in Disguise?

Amazon’s company-wide return-to-office mandate sent shockwaves through the tech world. And 72% of employees said they were ‘reconsidering their future’ with the company. Is Amazon’s decision a mass layoff in disguise? Will more companies follow suit? Stanford economist Nick Bloom joins us to find the truth behind the headlines. Special Guest: Nick Bloom Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc Aaron Calafato Subscr...

Oct 02, 202429 minSeason 1Ep. 71

"Open to Work" Badge on LinkedIn (Reaction Pod)

In this episode of The Lonely Office, we bring chief correspondent Aki Ito on to discuss the heated debate over LinkedIn's "open to work" banner. The "Open to Work" badge makes some job seekers feel embarrassed. But can it actually land you a job? Special Guest: Aki Ito, Chief Correspondent at Business Insider https://www.linkedin.com/in/itoaki Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc Aaron Calafato https://www.7mi...

Sep 27, 202419 min

Evolution of Resumes in the Age of Algorithms

Nowadays, resumes must beat applicant tracking systems and "wow" hiring managers. From TikTok handles to colorful redesigns to mindfulness sections, Gen Z is trying everything to get a return phone call. What are resumes even good for anymore? And should you tailor yours to the machines or humans? We chat with comedian Azhar Usman about the new generation of resume builders. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc...

Sep 25, 202429 minSeason 1Ep. 71

Job Market Reality Check & Decoding Job Report Numbers

In this episode of The Lonely Office, we dive into the disconnect between economic data and the job seeker’s reality, exploring why many still feel gaslit despite reports of a "booming economy." Joined by economist Guy Berger, we break down the real challenges of the job market, highlighting the frustration of job seekers navigating slow hiring and overstated job openings in today’s labor landscape. Special Guest: Dr. Guy Berger, Director of Economic Research @ Burning Glass Institute https://ww...

Sep 23, 202424 min

Is Amazon Forcing Return to Office for Everyone? (Reaction Pod)

With more CEOs going on record about their return to office mandates, it has us wondering: was the golden promise of working from home too good to be true? On this episode, we discuss the hidden market players who want you back in office and how companies like JM Smuckers are rolling out their hybrid work policy. (Re-air) Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc Aaron Calafato https://www.7minutestoriespod.com/ htt...

Sep 20, 202427 min

68% of Vacations Are Fake: PTO Is Broken

Workers are taking less and less PTO, yet working more and more when they do. This week, Malcolm’s ‘staycation’ turns into an anxiety-filled week of self-reflection that leads to him reconsidering his career. Why aren’t we using our full PTO allowance? Are we at fault, or is it the company? And is our mental health deteriorating as a result? Comedian Chanel Ali joins us to talk about vacation. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https:...

Sep 18, 202431 minSeason 1Ep. 62

Job Hacks & What Happened to the Career Fair?

Could it be that choosing degrees in the humanities is actually a smart, tactical move for the future? As tech job markets tighten, we explore how skills rooted in creativity and human insight are becoming more valuable—and share key strategies for standing out in this evolving landscape. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc Aaron Calafato https://www.7minutestoriespod.com/ https://www.aaroncalafato.com/

Sep 16, 202416 min

Is the Job Hopping Party Over?

Job hopping can be great for your wallet, but is it detrimental to your career? This week, Ferris’ job hopping led to pay bumps and new positions until layoffs stopped him in his tracks. Is it the key to making more money? Or does job loyalty pay off in the long run? Comedian Azhar Usman joins us to talk about the new social contract between workers and companies. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc Aaron Cala...

Sep 11, 202430 minSeason 1Ep. 61

Is Your Boss Watching You?

In this reaction pod of TLO, we dive back into the controversial world of workplace surveillance with special guest Cody Rogers, Chief Product Officer at Hubstaff. Are these tools about transparency and efficiency, or are they enabling a culture of micromanagement? Join us as we explore the fine line between monitoring and trust. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc Aaron Calafato https://www.7minutestoriespod....

Sep 09, 202418 min

Job Search Woes: Tapping into 401(k)s

On today's TLO Reaction Pod, Matt & Aaron dive into the stark realities of job hunting in an unpredictable economy—where even the most prepared knowledge workers might be forced to dip into their 401(k)s just to stay afloat. With layoffs climbing and job openings dwindling, the remote worker could be facing the same fate as the Rust Belt worker of the past. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc Aaron Calafat...

Sep 06, 20247 min

Stop the Job Search & Start a Company

Starting your own business is something many dream about, but few actually do. This week, ‘Emma’ is torn between taking a job promotion or pursuing her passion. Is there ever a right time to make the leap? Do you really have to say ‘goodbye’ to your social life? We take you through the hard truths of forming that first LLC. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc Aaron Calafato https://www.7minutestoriespod.com/ h...

Sep 04, 202434 minSeason 1Ep. 60

Fake Jobs Reaction & Are Job Seekers Being Gaslit?

The latest government job report issued a massive revision on the number of jobs that were actually in the market, throwing a wrench into the narrative of the "booming market" earlier this year.. We break down how these inflated job numbers, especially in the professional services sector— tech, finance, consulting—misled workers and painted a false picture of opportunity. Joining us this week is Bob Coursey, an employment lawyer, who sheds light on the rise of fake job postings and what it could...

Aug 30, 202413 min

Remote Jobs Most at Risk for AI Takeover

AI is eating our skills and taking away our remote jobs. From the operating room to the cubicle, it appears that our trusty sidekicks may be planning a takeover. How is this different from the software revolution? And which jobs are most at risk? Matt Beane, author of The Skill Code, joins us this week to take on the machines. Special Guest: Matt Beane Learn more about Matt's book: The Skill Code: How to Save Human Ability in an Age of Intelligent Machines https://www.mattbeane.com/ https://www....

Aug 28, 202429 minSeason 1Ep. 59

Choose One: Your Job or Kids?

Career or kids? That’s the question facing many young adults like Kennedy who are in the middle of job transitions. Can you be a great parent and have a successful career? And what's behind the rise of 'childless cat owners'? We get real with comedian and parent Azhar Usman. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc Aaron Calafato https://www.7minutestoriespod.com/ https://www.aaroncalafato.com/ Leah Ova https://www...

Aug 21, 202435 minSeason 1Ep. 58

Fake Job Posts Are Everywhere

Unfortunately for job seekers, fake job posts have flooded career sites. This week, a fake job post aimed at replacing ‘Serenity’ led her to work double and hire her little sister. Why do companies do it? And how do you spot one? Corporate recruiter Karen Young joins us to dish the truth on fake job posts. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc Aaron Calafato https://www.7minutestoriespod.com/ https://www.aaronca...

Aug 14, 202438 minSeason 1Ep. 57

Is Your Job Spying on You?

The shift to remote work has led companies to invest in surveillance software in attempt to increase worker productivity. Is it a breach of privacy? Why do companies resort to it? And should you buy a mouse jiggler from TikTok? This week, we cover it all with comedian Chanel Ali. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc Aaron Calafato https://www.7minutestoriespod.com/ https://www.aaroncalafato.com/ Leah Ova https:...

Aug 07, 202435 minSeason 1Ep. 56
For the best experience, listen in Metacast app for iOS or Android
Open in Metacast