Why Millennials Can’t Stop Overthinking Their Careers | Co-Founder @ Runbook (Ex-Discord PM), Chris Ramesh

Thank You to Our Sponsors! ✹ Granola: your AI notepad for meetings → https://granola.ai/officedrama ✹ Uncommon Goods: unique gifts for everyone on your list → https://uncommongoods.com/officedrama How do you go from a soul-crushing finance career to actually liking your job... and somehow stay optimistic through all of it? Chris Ramesh has had one of the most aggressively prestige-maxed career paths ever 😭 He started at Blackstone, moved into private equity, worked at Social Capital, became my PM coworker at Discord, and is now building his own AI startup. Somehow, through all of that, he is also one of the happiest people I know. In this ep, we talk about: → what working at Blackstone and private equity was actually like → the career lesson he had to unlearn after leaving finance → why perfectionism can actually slow you down → how to actually "find your passion" → why Chris left his job to become a founder → how to actually deal with procrastination → the importance of optimism → the downside of living too much in your future self → what it’s like starting an AI company in 2026 → why Chris thinks passion can develop through curiosity + persistence → and yes... the story of Chris trying to kiss his coworker 😭 Coworker Confessions: https://bit.ly/coworker-confessions Follow Office Drama / Chloe: Instagram: https://www.instagram.com/chloe.shih Office Drama 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] #officedrama #officedramapodcast See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.