Why Success Doesn't Feel Like Success | Simon Alexander Ong

What happens when you finally achieve the life you've been working towards... and something still feels missing?Build the career. Reach the goals. Tick every box.And still find yourself wondering why success doesn't feel the way you thought it would.How does that happen? And how do you know whether you're building a life that's truly yours — or simply becoming successful at someoneelse's definition of success?Simon Alexander Ong is the bestselling author of Energize, an award-winning coach, and an internationally sought-after keynote speaker whose work on energy, leadership, and purpose has built a global following.This isn't a conversation about becoming more productive. It's about asking whether the version of success you've been chasing is actually your own.Together, we explore what happens after success — when everything looks right on paper, but something doesn't quite feel right inside. We talk about the difference between achievement and fulfillment, the stories we inherit about what success should look like, and the quieter questions that often emerge only after we've reached the goals we once believedwould make us happy.We also get into a story involving Richard Branson that Simon rarely tells — and a strange decision-making exercise he still uses before making hard choices, involving a room that doesn't exist and six people, some living, some dead.🎙️ In this episode:Why success doesn't always feel the way we expect it toThe subtle difference between achievement and fulfillmentHow to tell whether you're pursuing your own ambitions — or someone else'sWhy two people can work equally hard and experience work completely differentlyThe four dimensions of energy that shape how we live and leadThe role courage plays in changing the direction of your lifeA simple exercise Simon returns to whenever he's facing one of life's biggest decisions⏱️ Chapters:00:00 Trailer01:15 From Investment Banking to Finding Purpose03:20 "On Paper, I Had It All"06:00 The Signs You're Living the Wrong Life10:00 The Four Types of Burnout15:45 Why Purpose Gives You Energy20:14 Create an Environment That Makes Success Inevitable28:30 Journaling & Closing the Loop33:50 The Loneliness of Reinventing Yourself36:20 The Imaginary Room with Six Mentors38:02 Stop Saying "Should"42:45 The Wormhole Effect43:35 Richard Branson, a Paper Airplane & Courage46:15 Ambition Without Losing Your Peace53:00 Is Hustle Culture Doing More Harm Than Good?58:00 Recharge Yourself Like Your Devices1:01:15 Plan Tomorrow the Night Before1:04:40 Can You Have Energy Without Purpose? 1:08:40 Where to Follow Simon 🔗 Follow Simon's work:Website: https://www.simonalexanderong.com/Instagram: @simonalexanderongLinkedIn: https://www.linkedin.com/in/simonalexanderong/Simon’s best-selling book Energize: https://www.penguin.co.uk/books/321571/energize-by-ong-simon-alexander/9780241502761 📺 Watch more episodes:Catch The Upswing is a podcast for people building meaningful things in a rapidly changing world. Honest conversations with leaders, founders, investors, and changemakers about what itactually takes to keep going, lead well, and stay hopeful about the future.New episodes every week. Subscribe so you don't miss one.🔗 Follow & connect:YouTube: https://www.youtube.com/@CatchTheUpswingInstagram: https://instagram.com/CatchTheUpswingTikTok: https://tiktok.com/@catchtheupswing