Striver's Compass

Derek Pilling
  • 5.0 (2)
  • CAREERS
  • UPDATED DAILY

Striver’s Compass explores the intersection of achievement, meaning, and human flourishing. Hosted by Derek Pilling — investor, operator, and executive coach — the series helps high-achievers “strive wisely” — blending timeless philosophy with modern science. Each episode offers practical tools and reflections on how to pursue excellence without sacrificing well-being, and how to align ambition with values across work, family, community, and self. Because striving isn’t the problem — losing sight of what we’re striving for is. Striver’s Compass helps you recalibrate toward goals worthy of you.

Episodes

  1. 10/30/2025

    Designed to Strive

    In Episode #2 of Striver’s Compass, I explore the evolutionary, physiological, and psychological roots of human striving through both scientific and philosophical lenses. From the dopamine-driven reward circuits that make pursuit itself feel good, to our ancient instincts for status and belonging, to the Stoic idea of areté — excellence as the fullest expression of our potential — we’ll uncover why striving isn’t a flaw to fix, but a force to understand, embrace, and direct. Because when we learn to work with our striving nature — and channel it with intention toward getting better every day — striving becomes less about proving our worth and more about living in alignment with our design.

    13 min

  2. 10/07/2025

    Introducing Striver's Compass

    In the first episode of Striver’s Compass, we explore why so many high-achievers find success yet still feel unfulfilled — and how shifting from extrinsic to meaningful, values-aligned goals can change everything. Drawing from Viktor Frankl, Stoic philosophy, and modern psychology, Derek Pilling shares how to harmonize your striving nature with a deeper sense of meaning — so achievement becomes a source of flourishing, not fatigue. Watch full episodes on YouTube: https://youtu.be/o41A1mxGGRM

    9 min
  • 2 Episodes

Ratings & Reviews

5
out of 5
2 Ratings

About

Striver’s Compass explores the intersection of achievement, meaning, and human flourishing. Hosted by Derek Pilling — investor, operator, and executive coach — the series helps high-achievers “strive wisely” — blending timeless philosophy with modern science. Each episode offers practical tools and reflections on how to pursue excellence without sacrificing well-being, and how to align ambition with values across work, family, community, and self. Because striving isn’t the problem — losing sight of what we’re striving for is. Striver’s Compass helps you recalibrate toward goals worthy of you.

Information

  • Creator
    Derek Pilling
  • Years Active
    2K
  • Episodes
    2
  • Rating
    Clean
  • Copyright
    © Derek Pilling
  • Show Website
    Striver's Compass