Don't Make a "Vision Board". Make THIS Instead in 2026.

More from Office Drama

1. 

   E33 · 30 Mar 2026 · 55 min

   The Subtle Art of Creating Your Own Luck

   today is all about how to manufacture luck in your career and why it's less about chance and more about the moves you make *before* the moment arrives. we get into the five key ingredients to luck, the behaviors that kill it, and how to stay motivated when you're doing everything right and nothing seems to be working yet. if you feel like things aren't always going your way... this one's for you. love, chloe & eric 💌 See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

2. 

   E32 · 23 Mar 2026 · 1 hr 17 min

   Dating When You're "Too Successful" ft. Kristin Chen (Ex-CPO, Director of Product)

   today is all about dating when you're a successful, ambitious woman... and why it's so much harder than it should be.kristin has some of the most insane dating lore we've ever heard. we're talking breakup contracts, rough conversations around net worth, a hawaii date that turned into a job interview, and so much more. it gets crazy. if you're someone who's ambitious and has ever wondered why the green flags always seem to fade... this one's for you. love, chloe & eric 💌 See Privacy Policy at https://art19.com/privacy and California Privacy Notice at…

3. 

   E31 · 16 Mar 2026 · 1 hr 11 min

   The Great Millennial Career Crisis is Here. Here's What To Do.

   today is all about the "millennial career crisis" — what it is, why so many of us are in it, and what we're actually supposed to do about it.we talked about the "dream" we were sold growing up, the moment you realize the corporate ladder might not be going anywhere good, and how to start building something that actually fits your life instead.if you've ever sat at your desk thinking "wait… is this just it?" — this one's for you.– chloe & eric 💌 See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

4. 

   E29 · 2 Mar 2026 · 1 hr 13 min

   How Happiness Changes at 30: Comparing With Friends, Career Plot Twists, Dating Again...

   this is our first real reflection of the current state of our 30s: friendship, comparison, dating, career.today, we talk about: • Why friendships feel deeper (and harder earned) in your 30s• The weird tension between success and comparison• Being ready to date again + reminiscing on old flames 🔥• Getting invited into “big rooms”… and still questioning everything• Our answers to the question: "are we actually happier now in our 30s?" love,chlo & eric See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

5. 

   E28 · 23 Feb 2026 · 58 min

   The Dark Side of "Making It": Why Success Doesn't Let You Rest

   today, we unpack the dark side of ambition - what happens when you tie your self-worth to success, why reaching milestones doesn't always bring relief, and our complicated feelings about burnout when we've technically "made it". If you've ever thought "when I get there, I'll finally be happy," this one's for you. this was a moment when I learned about the term "toxic gratitude" where you feel you're not allowed to complain and you should be grateful for the job or position you have. we just quietly suppress our struggles and then we implode by binging manhwa 😳- chlo & eric See Privacy…

6. 

   E27 · 16 Feb 2026 · 1 hr 14 min

   The Modern Career Crisis: Having 1 Job Is No Longer Enough

   today is all about unpacking modern career life, side hustles, personal branding, burnout, and why we’re all so tired.is building a personal brand even a real thing? are side hustles empowering - or dystopian - and should you focus more on building something or marketing yourself~we get real about the cost of the grind and how to romanticize your own life despite all the struggle- hope you enjoy this honest conversation about career chaos 🤍 See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

7. 

   E16 · 8 Oct 2026 · 1 hr 19 minNew

   The Hottest Product Manager in Tech Right Now 🔥 OpenAI’s Holly Li Talks About Dots | Office Drama

   How do you go from a self-described “nobody PM” to becoming one of the most talked-about product managers in Silicon Valley?Holly Li’s career is kind of insane. She started at Google, bought a one-way ticket to San Francisco and convinced the team at Adept to create a PM role for her, became the founding PM of Figma Make, and is now building at OpenAI, where she famously launched Dots at OpenAI’s Dev Day.In this ep, we talk about:→ how Holly became one of the hottest PMs in tech→ how she landed PM roles in AI→ how she became the founding PM of Figma Make just weeks after joining→ what the…

8. 

   E15 · 5 Oct 2026 · 1 hr 32 min

   The Human Cost of Convenience | Ex-VP @Yahoo! Srinija Srinivasan

   We’ve spent decades making everything faster, easier, and more convenient, but what if we optimized away some of the things that actually make us human?Srinija Srinivasan is basically a founding mother of the internet. She was employee #5 at Yahoo, spent 15 years there as Editor-in-Chief and VP, helped shape how the early internet was organized, chaired the board of SFJAZZ, served on Stanford’s Board of Trustees, and later co-founded Loove, bringing technology and the arts together. And now, she’s building an entirely new kind of college.In this ep, we talk about:→ what it was really like…

9. 

   E14 · 21 Sep 2026 · 1 hr 14 min

   30 Years of Career Advice in 1 Hour | Deb Liu (CEO @Ancestry.com, VP of Product @Meta)

   okay I need you to understand that this episode genuinely changed me 🥹✨Deb Liu is one of the most decorated women in tech. She spent 12 years at Facebook where she founded Facebook Marketplace, rose to VP, and then became CEO of Ancestry.com. She has 4 million+ views on her Substack, she's a board member of Poshmark and Intuit. She is simply built different!In this episode we get into:→ how Facebook Marketplace launched and immediately got a New York Times headline about drugs, guns, and baby hedgehogs 💀→ the invisible rules of power and influence that nobody tells you before you walk into…

10. 

    E13 · 7 Sep 2026 · 1 hr 9 min

    The Secret to Being “Likable” at Work | Principal PM @ Microsoft, Ellie Rui

    Thank You to Our Sponsor!✹ Granola: your AI notepad for meetings → https://granola.ai/officedramaEllie Rui got promoted every single year of her career. Six years at Microsoft, from new grad PM to Principal, and now she's a beloved senior PM at Netflix. Her answer for how is simpler than you’d think: hard work doesn't paint the full picture. We get into what actually drives fast career growth, how one great manager changed the trajectory of her entire career, and how the PM landscape is changing faster than ever.In this ep, we talk about:→ how she got promoted every single year for six…

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