Ep 556: Why Achieving Everything Still Leaves You Wanting More

Sep 16, 2025

This discussion dives into the powerful truth that true fulfillment comes from within—not from external achievements. Real-life stories from surfers and billion-dollar founders illustrate how chasing societal milestones can leave us feeling empty. The podcast encourages self-reflection and meditation, emphasizing that happiness is often found in unexpected places. It also tackles the complexities of parenting, suggesting that true joy and connection are rooted in self-sufficiency rather than unmet expectations. A compelling reminder to seek inner peace!

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INSIGHT

Fulfillment Is Not External

External achievements rarely produce lasting inner fulfillment despite cultural promises.
Advaita Vedanta summarizes this as: 'It's not out there.'

ANECDOTE

John John Florence: Nothing Changes

Surfer John John Florence said winning his second world title felt like 'nothing changes.'
His reaction illustrates how major achievements often fail to deliver lasting transformation.

ANECDOTE

Justin Kan’s Post-Sale Depression

Justin Kan described feeling unable to get out of bed for days months after selling Twitch for a billion dollars.
His experience shows how monetary success can still leave people depressed and unfulfilled.

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In today’s episode of The Daily Vedantic, we reflect on one of the most powerful and deceptively simple truths in Advaita Vedanta: It’s not out there. Together, we explore the illusion that external achievements—career success, relationships, having children, or financial milestones—can give us the lasting fulfillment we seek. Drawing from real-life stories of world champions like John John Florence, billion-dollar founders like Justin Kan, and timeless Vedantic teachings, we examine how this pursuit often leaves us feeling empty. As we engage with the perennial practices of Shravana (listening), Manana (reflection), and Nidhidhyasana (meditation), we’re reminded that true peace, joy, and wholeness are already within us. This is a call to stop chasing the mirage and start living from the inside out.

The Daily Vedantic is a daily podcast and YouTube channel dedicated to the timeless wisdom of the Upanishads (https://thedailyvedantic.com/). Dating back to over 5,000 years ago, the source of nearly all Eastern Philosophy, and loved by Western giants from Emerson to Thoreau to Carl Jung and Alan Watts, studied daily by Joseph Campbell to Aldous Huxley to Arthur Schopenhauer and countless others, The Daily Vedantic aims to make this ancient philosophy as modern and accessible as it is simple, practical — and profound.

James Beshara ( https://www.twitter.com/jamesbeshara ) is a renowned startup founder of multiple companies, a prolific startup investor in 200+ others including some of the biggest startup names on the planet, a husband and father of three little girls, and philosophy student and teacher in Los Angeles.

James also co-hosts Yoga For Your Intellect (https://www.YFYI.co), a biweekly long-form conversational podcast with his teacher Joseph Emmett ( https://www.instagram.com/yogaforyourintellect )

James is a student of Swami Parthasarathy, the acclaimed author of Vedanta Treatise (Vedanta Treatise – The Eternities) and teacher at Vedanta Academy in Malavli, India. As James says often, when you’re ready for the real thing, Swami’s daily lectures are where the true wisdom and systematic discovery of the world’s oldest continually studied philosophy resides: https://www.vedantaworld.org