
Advertise on podcast: Joy of Missing Out (JOMO)
Rating
4.8from
This podcast has
56 episodes
Language
EnglishPublisher
Chloe Shih and Eric WeiExplicit
No
Date created
2024/06/18
Latest episode
2026/10/05
Average duration
74 min.
Release period
9 days
Description
Spent our 20s working for other people and are now living our 30s betting on ourselves. This is the *joy* of missing out. A podcast starring Chloe Shih and Eric Wei. 𝗖𝗵𝗹𝗼𝗲 𝗦𝗵𝗶𝗵 - IG: @chloe.shih tech product manager making educational videos to elevate your career and life! 𝗘𝗿𝗶𝗰 𝗪𝗲𝗶 - IG: @erictway co-founder of Karat Financial, helping creators with finances
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Check latest episodes from Joy of Missing Out (JOMO) podcast
The Human Cost of Convenience | Ex-VP @Yahoo! Srinija Srinivasan
2026/10/05
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 helping build Yahoo! in the early internet
→ what makes the best business partnerships actually work
→ why imagination, creativity, and curiosity matter even more in the age of AI
→ why art is so hard to make money from
→ the human cost of optimizing everything for efficiency
→ why convenience might be the wrong North Star for technology
→ how we can build technology that makes us more human
Submit your Coworker Confessions 👇
https://bit.ly/coworker-confessions
If you like what you hear please follow, rate 5 stars on Spotify and Apple Podcasts ⭐️ and leave a comment! 🫶 It's free~
𝙎𝙊𝘾𝙄𝘼𝙇𝙎
🌸 instagram → https://www.instagram.com/chloe.shih
OD instagram → https://www.instagram.com/officedrama.pod
tiktok → https://www.tiktok.com/@chloeshih
threads → https://www.threads.net/@chloe.shih
linkedin → https://www.linkedin.com/in/chloe-shih/
patreon → https://patreon.com/OfficeDrama
✹ business inquiries: [email protected]
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
30 Years of Career Advice in 1 Hour | Deb Liu (CEO @Ancestry.com, VP of Product @Meta)
2026/09/21
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 a room
→ if work feels misaligned you might just need to be repotted 🪴
→ how to hold high standards as a leader without traumatizing everyone around you
→ when to persist, pivot, or quit (and why quitting is actually the first chapter of her new book)
→ why ambition without joy becomes brittle
this is the episode I have been wanting to make since I started Office Drama. Deb is one of those people who has an answer for every question because she has genuinely lived and reflected on such a variety of experiences in her life. This episode is true hopecore and Deb somehow makes you feel like everything is going to be okay 🥺
➔ Deb's Substack:
https://debliu.substack.com
➔ Deb on LinkedIn:
https://www.linkedin.com/in/deborahliu
➔ Deb on Instagram:
https://www.instagram.com/debliu_
Submit your Coworker Confessions 👇
https://bit.ly/coworker-confessions
if you enjoyed this episode please follow, rate 5 stars ⭐️ and drop a comment — it helps more people find the show and means everything to us 🥹
𝙎𝙊𝘾𝙄𝘼𝙇𝙎
🌸 instagram → https://www.instagram.com/chloe.shih
OD instagram → https://www.instagram.com/officedrama.pod
tiktok → https://www.tiktok.com/@chloeshih
threads → https://www.threads.net/@chloe.shih
linkedin → https://www.linkedin.com/in/chloe-shih/
patreon → https://patreon.com/OfficeDrama
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
The Secret to Being “Likable” at Work | Principal PM @ Microsoft, Ellie Rui
2026/09/07
Thank You to Our Sponsor!
✹ Granola: your AI notepad for meetings → https://granola.ai/officedrama
Ellie 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 years
→ what a great manager actually does for your career
→ what separates junior, senior, and principal PMs
→ whether AI will actually replace PMs
→ why new grads should pick startups over big tech right now
→ and how to be likeable at work!
→ Find Ellie on LinkedIn: https://www.linkedin.com/in/ellierui/
Submit your Coworker Confessions 👇
https://bit.ly/coworker-confessions
If you like what you hear please follow, rate 5 stars on Spotify and Apple Podcasts ⭐️ and leave a comment! 🫶 It's free~
𝙎𝙊𝘾𝙄𝘼𝙇𝙎🌸
instagram → https://www.instagram.com/chloe.shih/
OD instagram → https://www.instagram.com/officedrama.pod/
tiktok → https://www.tiktok.com/@chloeshih
threads → https://www.threads.net/@chloe.shih
linkedin → https://www.linkedin.com/in/chloe-shih/
patreon → https://patreon.com/OfficeDrama
✹ business inquiries: [email protected]
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
We need to talk about the AI Brand trip situation... ft. Megan Lieu | Office Drama
2026/09/02
Creators got CANCELED for attending an AI brand trip...and we're finally addressing it. 🫣
Today, I have the privilege of hosting Megan Lieu (data science + tech creator) on Office Drama to uncover what really went down on that trip and what it was actually like as a creator "getting canceled".
I've worked professionally in Trust & Safety. I'm passionate about tech ethics, creator industries, and how we all should work together. And I really hope we can actually have constructive conversations on this platform that may push cultural, product, and policy changes for the better.
It's very daunting as a female creator to address a situation like this, so I hope we can show up with empathy, curiosity, and constructive dialogue together. 🫶 Thank you for always making me feel safe to speak up.
In this ep, we talk about:
→ what actually happened on the brand trip
→ the video Megan posted and the moment she realized it was going sideways
→ how the press reaches out when they already know the angle they want
→ why this trip hit a nerve when other AI brand trips didn't
→ why the women creators took the brunt of the backlash
→ how brands and creators should actually give each other feedback
→ where tech creators sit between Silicon Valley's echo chamber and everyone else
→ Find Megan on LinkedIn: https://www.linkedin.com/in/meganlieu
Submit your Coworker Confessions 👇
https://bit.ly/coworker-confessions
If you like what you hear please follow, rate 5 stars on Spotify and Apple Podcasts ⭐️ and leave a comment! 🫶 It's free~
𝙎𝙊𝘾𝙄𝘼𝙇𝙎
🌸 instagram → https://www.instagram.com/chloe.shih
OD instagram → https://www.instagram.com/officedrama.pod
tiktok → https://www.tiktok.com/@chloeshih
threads → https://www.threads.net/@chloe.shih
linkedin → https://www.linkedin.com/in/chloe-shih/
patreon → https://patreon.com/OfficeDrama
✹ business inquiries: [email protected]
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
The Art of Being Tastefully Unhinged | Sr Director of Brand Marketing @Duolingo, Kat Chan
2026/08/24
test
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
My Honest Take on Motherhood vs Career (A Brutal Mid-year Reflection) | Office Drama
2026/08/10
Half of 2026 is officially over... and I've never felt this behind in my career. 😅
In today's episode of Office Drama, I'm doing my mid-year review out loud: what went wrong, what I'm scared of, and the 6 commitments I'm making so December-me doesn't have to go through the same existential disappointment.
Today, we talk about:
→ Why I felt so behind at the half-year mark of 2026
→ The motherhood penalty: how does it impact your career? 👀
→ A mutual creator who lost 10,000 followers overnight after announcing her pregnancy
→ "Would you rather be pregnant or successful?" and why I don't want to choose!
→ My 6 commitments I want us to try for the rest of 2026
Submit your Coworker Confessions 👇
https://bit.ly/coworker-confessions
If you like what you hear please follow, rate 5 stars on Spotify and Apple Podcasts ⭐️ and leave a comment!
𝙎𝙊𝘾𝙄𝘼𝙇𝙎 🌸
instagram → https://www.instagram.com/chloe.shih/
OD instagram → https://www.instagram.com/officedrama.pod/
tiktok → https://www.tiktok.com/@chloeshih
threads → https://www.threads.net/@chloe.shih
linkedin → https://www.linkedin.com/in/chloe-shih/
patreon → https://patreon.com/OfficeDrama
✹ business inquiries:
[email protected]
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
You Should Quit Being a Creator | @Tafokints NASA, Esports, Content, Tech
2026/07/27
Thank You to Our Sponsors!
✹ Storyblocks: unlimited stock footage, music, and SFX for creators → https://storyblocks.com/officedrama
We've heard time and time again about the burnt out tech employee who quits a stable job to chase the dream. This time we're exploring the reverse!
Daniel "Tafo" Lee has lived more careers than I can count on two hands. JPL engineer, coach to Melee god Mang0, Yahoo Esports show host, CLG General Manager, the internet's Tetris teacher, Web3 economist, Andreessen Horowitz, and now, at 37, starting over in big tech. He's no stranger to the creator economy and his honest take on who should actually pursue it might save you five years of your life.
In this ep, we talk about:
→ how he coached a Melee god while working full time at NASA JPL
→ the ultimatum from his wife that finally made him quit and move to Esports
→ why 90% of streamers won't make it, and why minimum wage might be the better option
→ betting on yourself at 37: relearning how to code from scratch in the AI era
→ and how becoming a dad made him reevaluate the value of his time
This episode is for anyone who's ever been told to follow their passion and quietly wondered if that advice is a trap. Tafo is proof that the real flex isn't dying on one hill but maybe knowing when to walk away towards the next one.
→ Find Tafo:
https://www.instagram.com/tafokints
https://www.linkedin.com/in/daniellee912
https://x.com/tafokints
Submit your Coworker Confessions 👇
https://bit.ly/coworker-confessions
If you like what you hear please follow, rate 5 stars on Spotify and Apple Podcasts ⭐️ and leave a comment! 🫶 It's free~
𝙎𝙊𝘾𝙄𝘼𝙇𝙎 🌸
instagram → https://www.instagram.com/chloe.shih/
OD instagram → https://www.instagram.com/officedrama.pod/
tiktok → https://www.tiktok.com/@chloeshih
threads → https://www.threads.net/@chloe.shih
linkedin → https://www.linkedin.com/in/chloe-shih/
patreon → https://patreon.com/OfficeDrama
✹ business inquiries:
[email protected]
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
We Went on MasterChef and Lost Our Minds | @igumdrop @AngelsKimi @AriaSaki | Office Drama EP8
2026/07/20
Nobody tells you that when you get cast on MasterChef, you get to choose three people to fly out as your friends and family. Jaime ( @igumdrop ) chose Aria ( @AriaSaki ) , Kimi ( @AngelsKimi ) and I, and we spent a week on set with NO phones, 7AM call times, and a front-row seat to watching her cook on the biggest stage of her life.
In this ep, we talk about:
→ why Jaime almost went alone
→ the mandolin accident that didn't make it to air
→ what Gordon Ramsay is ACTUALLY like
→ the moment Aria destroyed a MasterChef contestant
→ what traditional TV gets right that creators don't
→ why chasing perfection as a creator isn't sustainable
→ the narratives that get rewritten about women in gaming and streaming
→ Find Jaime:
https://www.youtube.com/@igumdrop
https://www.twitch.tv/igumdrop
https://www.instagram.com/igumdrop/
https://www.tiktok.com/@igumdrop
→ Find Aria:
https://www.youtube.com/@AriaSaki
https://www.twitch.tv/ariasaki
https://www.instagram.com/ariasaki/
https://www.tiktok.com/@ariasaki
→ Find Kimi:
https://www.youtube.com/@AngelsASMR
https://www.youtube.com/@AngelsKimi
https://www.twitch.tv/angelskimi/
https://www.instagram.com/angelskimi/
https://www.instagram.com/gentleflamestudio/
https://www.tiktok.com/@angelskimii
A huge thank you to the MasterChef production team for letting us share these stories!
#MasterChef #MasterChefGlobalGauntlet @MasterChefonFOX @FOXTV @FoodClubFOX
Submit your Coworker Confessions 👇
https://bit.ly/coworker-confessions
If you like what you hear please follow, rate 5 stars on Spotify and Apple Podcasts ⭐️ and leave a comment! 🫶 It's free~
𝙎𝙊𝘾𝙄𝘼𝙇𝙎
🌸 instagram → https://www.instagram.com/chloe.shih/
OD instagram → https://www.instagram.com/officedrama.pod/
tiktok → https://www.tiktok.com/@chloeshih
threads → https://www.threads.net/@chloe.shih
linkedin → https://www.linkedin.com/in/chloe-shih/
patreon → https://patreon.com/OfficeDrama
✹ business inquiries: [email protected]
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
The Truth About My MasterChef Debut | Jaime @iGumdrop (Home Chef, Streamer, 2M+ Creator)
2026/07/13
Over the past decade, Jaime (@iGumdrop) has built a 2M+ following, founded her own successful clothing brand, dropped out of college to pursue streaming, and now she's on the cast of Season 16 of MasterChef!
In this week's episode of Office Drama, we get into the version of the story you don't see on TV.
In this ep, we talk about:
→ why she almost said no to MasterChef
→ what it's like to be on the cast of MasterChef
→ the insane reality TV background check nobody warns you about
→ what Gordon Ramsay is ACTUALLY like in person
→ the roti canai controversy
→ the truth about agents, managers, and the people you work with as a creator
→ why "the interview never matters" and what she actually hires on
→ how she skipped the 5-year plan and went straight to a deathbed plan
This episode is for anyone who's ever been underestimated, boxed into one version of themselves, or scared to take the leap because they might look like a fool. Jaime is one of the most earnest, chaotic, hilarious people I know, and watching her bet on herself, publicly, after ten years of quietly putting in the work is exactly the kind of story I started this show to tell.
→ Find Jaime:
https://www.youtube.com/@igumdrop
https://www.twitch.tv/igumdrop
https://www.instagram.com/igumdrop/
https://www.tiktok.com/@igumdrop
A huge thank you to the MasterChef production team for letting us share these stories!
#MasterChef #MasterChefGlobalGauntlet
@MasterChefonFOX @FOXTV @FoodClubFOX
Submit your Coworker Confessions 👇
https://bit.ly/coworker-confessions
Thank You to Our Sponsors!
✹ Storyblocks: unlimited stock footage, music, and SFX for creators → storyblocks.com/officedrama
✹ Quince: luxury-quality essentials without the markup → quince.com/officedrama
If you like what you hear please follow, rate 5 stars on Spotify and Apple Podcasts ⭐️ and leave a comment! 🫶 It's free~
𝙎𝙊𝘾𝙄𝘼𝙇𝙎 🌸
instagram → https://www.instagram.com/chloe.shih/
OD instagram → https://www.instagram.com/officedrama.pod/
tiktok → https://www.tiktok.com/@chloeshih
threads → https://www.threads.net/@chloe.shih
linkedin → https://www.linkedin.com/in/chloe-shih/
patreon → https://patreon.com/OfficeDrama
✹ business inquiries:
[email protected]
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
The Life Lesson That Cost Her $1M | jasminericegirl, Head of Creators @Suno
2026/07/06
Rosie Nguyen is the Head of Creators at Suno, the world's leading AI music company. Before that she co-founded Fanhouse, joined Cantina, and went viral more times than I can count. She's bright, passionate, and comes into this episode with so many wild stories and experiences.
In this ep, we talk about:
→ growing up on food stamps and supporting immigrant parents
→ getting demoted at her own company, then watching it get sold behind her back
→ the phone call that saved her life
→ going viral again and again and the attention that brings online
→ why her current era makes her prouder than raising $20 million ever did
This one is for anyone who's ever been underestimated, flattened into one dimension, or had to rebuild from zero. Rosie is one of the most earnest and hilarious people I know, and this convo originally went almost THREE hours.
→ Find Rosie on LinkedIn: https://www.linkedin.com/in/jasminericegirl/
Submit your Coworker Confessions 👇
https://bit.ly/coworker-confessions
If you like what you hear please follow, rate 5 stars on Spotify and Apple Podcasts ⭐️ and leave a comment! 🫶 It's free~
𝙎𝙊𝘾𝙄𝘼𝙇𝙎 🌸
instagram → https://www.instagram.com/chloe.shih/
OD instagram → https://www.instagram.com/officedrama.pod/
tiktok → https://www.tiktok.com/@chloeshih
threads → https://www.threads.net/@chloe.shih
linkedin → https://www.linkedin.com/in/chloe-shih/
patreon → https://patreon.com/OfficeDrama
✹ business inquiries:
[email protected]
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
I Quit My Dream Job to Start Over at 32...| @Elevenlabs Head of Partner Marketing, Sophia Noel
2026/06/29
Sophia is one of my best friends, the officiant of my wedding, and one of the most cracked marketers I know. She's led campaigns at Airbnb, Databricks, and ElevenLabs. She won Best Dance Film at the LA Film Awards. She's also going through her biggest plot twist yet: leaving tech to pursue her art. Full time. For good. 🙂↕️
In this episode, we talk about:
→ why AI will never replace storytelling, taste, and human connection
→ her honest take on the job market, what 20-somethings are getting wrong, and what a great interview actually looks like
→ how she faced being belittled in by an interim CMO who said they need someone "more senior" when she led the campaign all along
This one is for anyone who has done everything right and still felt like they were playing it too safe. Sophia is the most elegant proof I know that the pivot you're scared of might be the one you were always supposed to make.
→ Find Sophia: https://www.instagram.com/sophianoel_
Submit your Coworker Confessions 👇
https://bit.ly/coworker-confessions
If you like what you hear please follow, rate 5 stars on Spotify and Apple Podcasts ⭐️ and leave a comment! 🫶 It's free~
𝙎𝙊𝘾𝙄𝘼𝙇𝙎 🌸
instagram → https://www.instagram.com/chloe.shih/
OD instagram → https://www.instagram.com/officedrama.pod/
tiktok → https://www.tiktok.com/@chloeshih
threads → https://www.threads.net/@chloe.shih
linkedin → https://www.linkedin.com/in/chloe-shih/
patreon → https://patreon.com/OfficeDrama
✹ business inquiries: [email protected]
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
I got laid off 2 years ago...Let's talk MONEY. 💸
2026/06/22
It's been ~2 years since I've been laid off from my dream job at @Discord, and the most COMMON question you've asked me is: "Have you matched or beaten your tech salary after becoming a creator?"
I never liked this question because it's sincerely not apples to apples. I also dislike it when creators say "I made my corporate salary in 1 brand deal!!" Because there are SO many nuances, caveats, tradeoffs, and financial implications when choosing between both paths. But I finally break that down in today's episode of Office Drama.
Today, we get UNFILTERED and talk about:
→ How I overcame feeling like a failure after getting laid off
→ How I felt comparing myself to friends in tech/corporate
→ Whether my creator salary matched or beat my tech salary 👀
→ How pregnancy and family planning impacts everything
→ How I actually figured out how to pivot my career (with my Life PRD)
I really don't think these conversations can fit into a 1 min short form video or a 10 min YouTube video, so I hope you enjoy this real, brutally honest breakdown of what it was like going from tech to content to media.
p.s. please excuse the lighting changes in this one! 🫶
My Vision Board + Template 👇https://www.figma.com/community/file/1462690089129320366/2025-vision-board-by-chloe-shih-chloe-shih
Submit your Coworker Confessions 👇https://bit.ly/coworker-confessions
If you like what you hear please follow, rate 5 stars on Spotify and Apple Podcasts ⭐️ and leave a comment! 🫶 It's free~
Special shoutout to Drama Llama Emily Huang for supporting Office Drama on Patreon! 🦙
𝙎𝙊𝘾𝙄𝘼𝙇𝙎 🌸
instagram → https://www.instagram.com/chloe.shih/
OD instagram → https://www.instagram.com/officedrama.pod/
tiktok → https://www.tiktok.com/@chloeshih
threads → https://www.threads.net/@chloe.shih
linkedin → https://www.linkedin.com/in/chloe-shih/
patreon → https://patreon.com/OfficeDrama
✹ business inquiries:[email protected]
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
I Quit My Dream Job to Take an "Adult Gap Year" ft. Julia Fei (Sr. Data Scientist at Notion)
2026/06/15
I've seen a pattern of senior ICs deciding to quit to bet on themselves, but we rarely get to see what it took to get there.
Julia Fei, Sr. Data Scientist at Notion (and my dear creator friend), just made her decision to leave her dream job to pursue something she's always been curious about. But it was a calculated, deliberate decision that she spent years preparing for.
In this week's episode of Office Drama, we reveal the inner drama of Julia's thought process and the conversations she's had navigating the transition.
In this ep, we talk about:
→ why Julia quit Notion when she genuinely loved her team, her manager, and her job
→ how to know if you're actually growing or just getting comfortable
→ why "stability" is a scam
→ the double life of being a creator in tech
→ how to build a financial runway for the leap before you're ready to take it
→ and how to know when it's finally time to take a risk on yourself
This episode is for anyone who has done everything right and still felt like they were playing it too safe. Julia is one of the most calculated, self-aware people I know and watching her finally bet on herself after years of preparation is exactly the kind of story I started this show to tell.
→ Find Julia:
https://www.linkedin.com/in/juliafei/
https://www.youtube.com/@juliafei
https://www.instagram.com/julia.fei/
https://www.tiktok.com/@julia.fei
Submit your Coworker Confessions 👇
https://bit.ly/coworker-confessions
If you like what you hear please follow, rate 5 stars on Spotify and Apple Podcasts ⭐️ and leave a comment! 🫶 It's free~
Special shoutout to Drama Llama Emily Huang for supporting Office Drama on Patreon!
🦙𝙎𝙊𝘾𝙄𝘼𝙇𝙎 🌸
instagram → https://www.instagram.com/chloe.shih/
OD instagram → https://www.instagram.com/officedrama.pod/
tiktok → https://www.tiktok.com/@chloeshih
threads → https://www.threads.net/@chloe.shih
linkedin → https://www.linkedin.com/in/chloe-shih/
patreon→ https://patreon.com/OfficeDrama?utm_medium=unknown&utm_source=join_link&utm_campaign=creatorshare_fan&utm_content=copyLink
✹ business inquiries:[email protected]
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
The “Anti-Hustle High Achiever” Mindset | Product Design Manager @Discord, Tobi Bisiriyu
2026/06/08
My old Discord work bestie just got promoted *twice* in one year and I needed to know how he did it without losing himself in the process. Tobi Bisiriyu is a Product Design Manager at Discord and he's one of those rare people who is genuinely great at his job, actually likes it, and still makes work the least interesting thing about him. He cosplays, he goes to anime conventions, he walks one hour every day without exception, and he has a philosophy about life that I think more people in tech need to hear.
In this ep, we talk about:
→ Why looking competent is actually what's holding junior designers back
→ the "contract you write for yourself" and how to know if you're breaching it
→ why middle management is actually a "death" trap
→ say yes to the scary thing...before you talk yourself out of it.
→ being greedy "with integrity" and why it's good to want it all
→ and why getting a four in life matters more than getting one at work
This episode is for anyone who is good at their job but wonders if there's a version of success that doesn't require you to give everything else up. Tobi is one of the most intentional people I've ever worked with and somehow he got even more thoughtful since we last worked together.
→ Find Tobi on LinkedIn: https://www.linkedin.com/in/tobibisiriyu
Submit your Coworker Confessions 👇
https://bit.ly/coworker-confessions
If you like what you hear please follow, rate 5 stars on Spotify and Apple Podcasts ⭐️ and leave a comment! 🫶 It's free~
𝙎𝙊𝘾𝙄𝘼𝙇𝙎 🌸
instagram → https://www.instagram.com/chloe.shih/
OD instagram → https://www.instagram.com/officedrama.pod/
tiktok → https://www.tiktok.com/@chloeshih
threads → https://www.threads.net/@chloe.shih
linkedin → https://www.linkedin.com/in/chloe-shih/
patreon → https://patreon.com/OfficeDrama
✹ business inquiries: [email protected]
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
I Asked My Manager Why I Got Laid Off... | Principal Product Manager @Roblox, Derek Yang
2026/06/01
It's been about 2 years and 3 mo since I was infamously laid off from my dream product manager job at Discord. And today, I finally sit with my old manager to talk about life after layoffs.
Derek Yang is now a Principal Product Manager at Roblox, and before that he was at YouTube, Twitch, Yik Yak, Facebook, and Discord where he was also my last ever corporate manager.
In this ep, we talk about:
→ What it actually means to "make it" in tech (spoiler: he still doesn't think he has)
→ the performance review that humbled him and forever changed
→ how he approaches his career
→ why working hard is not enough and what actually gets you recognized
→ what he gave up becoming a new dad
→ and why sustainability is his whole era right now
This episode is for anyone who has ever put their whole heart into their work and still felt like it wasn't enough. Derek is one of the most thoughtful people I know and I learned something new about him even after years of friendship.
→ Find Derek on LinkedIn:
https://www.linkedin.com/in/dereklyang
Submit your Coworker Confessions 👇
https://bit.ly/coworker-confessions
If you like what you hear please follow, rate 5 stars ⭐️ and leave a comment! 🫶
business inquiries: [email protected]
𝙎𝙊𝘾𝙄𝘼𝙇𝙎 🌸
instagram → https://www.instagram.com/chloe.shih/
tiktok → https://www.tiktok.com/@chloeshih
threads → https://www.threads.net/@chloe.shih
linkedin → https://www.linkedin.com/in/chloe-shih/
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Podcast reviews
Read Joy of Missing Out (JOMO) podcast reviews
aditi!! 2026/06/22
best podcast ever
I’m an avid podcast listener across genres, and although Chloe’s content is tech-oriented (not what I’m interested in) I listen because she’s the best...
sda2208 2024/10/22
I really like this podcast
I enjoy hearing Chloe and Eric’s dynamic. In S2 I will love to see something similar as “not stupid questions podcast” that the producer at the end of...
bertoliu2019 2024/10/18
Love this pod
Really enjoy the topics and the personalities of the speakers. Please listen!
Rando Calabrian 2024/08/07
I love these two!
As someone who has never been particularly good at the corporate or creator game, I am amazed at how these two have excelled at both while being so ge...
chaposuxxx 2024/08/05
zzz
ever wonder what 2 vapid dummies who think sending emails and gossiping about coworkers is a hard job think about? well listen and find out!
Cld_fire 2024/08/03
Love JOMO
I'm 23 and work in tech, and while I'm not AA I've also been on a non-traditional career path where I've found myself struggling at times to find my w...
TLS91 2024/08/01
🤔
I support y’all, as a fellow AA and as someone who also decided to choose a path, away from corporate, their 30’s.Unfortunately, the first few episode...
mar308 2024/08/01
I could not love them more!
If someone had told me Chloe Shih (someone I’ve been following for years) would have a podcast with someone else, I would’ve been against it. I never ...
12 feet under 2024/07/31
Figuring out 20s/30s
Interesting take on middle life with a slice of mid life concerns (career/family/context creation) sprinkled in. Nice to have on the background while ...
eekprice 2024/07/25
Relatable
Corporate girly here. Chloe is my personality doppelgänger, which gives me such hope for my future success. 🥹🥹🤞🤞
Thanks both of you for sharing. ...
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