Career Cafe: Is The Career Ladder Worth It? (+ Pizza Night)

What do seven internships, leading 600+ people and a successful corporate career have in common? 🤔 These are things we walked away from. Gen Z is questioning the ladder before they've even started climbing. Millennials are halfway up and wondering if the view is worth it. And some of us have already stepped off entirely. Join us for an honest cross-generational conversation about ambition, burnout, and what success looks like when you stop copying someone else's answer. Over pizza! Your speakers: Huiyan (@itsmehuiyan) spent 15 years climbing the corporate ladder - 4 promotions in her first 5 years, regional marketing head, led hundreds of people, the whole thing. Then she left. Today she coaches middle managers who are starting to ask the same questions she did: how much of this is actually mine, and how much of it was just autopilot? As founder of Career Big Sis & Co., she helps ambitious professionals lead without burning out in the process. Chelsea (@OffbeatSingaporean) works as an account manager in fintech and runs Offbeat Singaporean, an Instagram page for Singaporeans questioning the default life script they've been following. She stacked seven internships, felt the pressure to find a good job, and then solo-travelled her way into a completely different idea of what a good life actually looks like. Now she uses her platform to help others build life on their own terms. Jing Ying is a fractional CMO with 15+ years across B2B tech, fintech, and purpose-driven organisations. As founder of LUMOS Marketing Co., she helps founders and lean teams build marketing clarity and systems to grow. She partners with teams across strategy and execution: auditing, GTM, brand and positioning, content, and coaching.