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Episode 60 - Why success won’t make you happy & what actually will
Are you hustling for money, titles, or prestige—yet secretly scared you’ll feel nothing when you finally “make it”? In Episode 60 of The Struggle we pull back the curtain on the darker side of ambition and reveal the missing ingredient that turns achievement into genuine purpose.
🎧 What You’ll Learn in This Episode:
🔍 Why striving for success can secretly make you miserable
🧠 How the arrival fallacy tricks high-achievers into depression
💸 Why money, fame, and status don’t fix internal struggles
🚴♂️ What the hedonic treadmill is — and how to step off it
📚 Insights from Tim Ferriss, Oliver Burkeman, and Alan Watts
🌞 How Chris Williamson’s “Huberman Effect” reveals a modern trap
🥾 Why hiking (and other atelic activities) may be the key to meaning
🎯 How to balance ambition with fun and fulfillment
🎵 Why life isn’t a journey… it’s a song to be danced to
👍 If this episode helps you, subscribe and follow wherever you’re listening so you never miss an episode and share it with another high-achiever who needs a reality check.
📩 Sponsor
Sign up for The Struggle Newsletter here - https://gregorthomson.com
📺 Watch The Struggle
YouTube - https://youtube.com/@GregorSThomson?si=wTfFwPVYKhJxKAsD
📱 Get In Touch
Instagram - https://www.instagram.com/gregorsthomson/
Tiktok -https://www.tiktok.com/@gregor.s.thomson?_t=8ioMNLUnA25&_r=1
Email - [email protected]
🎵 Music
Conal Mooney - https://www.instagram.com/conalmooneyaudio?igsh=dGxqdThlNnNoNzh6
Reference List & Credits
Burkeman, O. Four Thousand Weeks: Time Management for Mortals (2021) – concept of atelic vs. telic activities; hiking quote (ch. 13).
Ferriss, T. The Tim Ferriss Show, Ep. 716 “The Dark Side of Achievement” (2025) – commentary on striving and depression.
Ben-Shahar, T. – Coined the “Arrival Fallacy”; discussed in his course Positive Psychology (Harvard, 2006).
Diener, E., et al. (1999). Subjective Well-Being: Three Decades of Progress. Psychological Bulletin. – foundational research on the Hedonic Treadmill.
Williamson, C. Modern Wisdom Podcast, Ep. 693 “The Huberman Effect” (2024).
Watts, A. (1966). The Book: On the Taboo Against Knowing Who You Are – “Life is music, not a journey” analogy.
ChatGPT (OpenAI o3, 2025) – Assisted with SEO title generation, description drafting, and structural editing for clarity and engagement.
#SelfDevelopment #Ambition #SuccessMindset #MentalHealth #OliverBurkeman
View all episodes
By Gregor S ThomsonAre you hustling for money, titles, or prestige—yet secretly scared you’ll feel nothing when you finally “make it”? In Episode 60 of The Struggle we pull back the curtain on the darker side of ambition and reveal the missing ingredient that turns achievement into genuine purpose.
🎧 What You’ll Learn in This Episode:
🔍 Why striving for success can secretly make you miserable
🧠 How the arrival fallacy tricks high-achievers into depression
💸 Why money, fame, and status don’t fix internal struggles
🚴♂️ What the hedonic treadmill is — and how to step off it
📚 Insights from Tim Ferriss, Oliver Burkeman, and Alan Watts
🌞 How Chris Williamson’s “Huberman Effect” reveals a modern trap
🥾 Why hiking (and other atelic activities) may be the key to meaning
🎯 How to balance ambition with fun and fulfillment
🎵 Why life isn’t a journey… it’s a song to be danced to
👍 If this episode helps you, subscribe and follow wherever you’re listening so you never miss an episode and share it with another high-achiever who needs a reality check.
📩 Sponsor
Sign up for The Struggle Newsletter here - https://gregorthomson.com
📺 Watch The Struggle
YouTube - https://youtube.com/@GregorSThomson?si=wTfFwPVYKhJxKAsD
📱 Get In Touch
Instagram - https://www.instagram.com/gregorsthomson/
Tiktok -https://www.tiktok.com/@gregor.s.thomson?_t=8ioMNLUnA25&_r=1
Email - [email protected]
🎵 Music
Conal Mooney - https://www.instagram.com/conalmooneyaudio?igsh=dGxqdThlNnNoNzh6
Reference List & Credits
Burkeman, O. Four Thousand Weeks: Time Management for Mortals (2021) – concept of atelic vs. telic activities; hiking quote (ch. 13).
Ferriss, T. The Tim Ferriss Show, Ep. 716 “The Dark Side of Achievement” (2025) – commentary on striving and depression.
Ben-Shahar, T. – Coined the “Arrival Fallacy”; discussed in his course Positive Psychology (Harvard, 2006).
Diener, E., et al. (1999). Subjective Well-Being: Three Decades of Progress. Psychological Bulletin. – foundational research on the Hedonic Treadmill.
Williamson, C. Modern Wisdom Podcast, Ep. 693 “The Huberman Effect” (2024).
Watts, A. (1966). The Book: On the Taboo Against Knowing Who You Are – “Life is music, not a journey” analogy.
ChatGPT (OpenAI o3, 2025) – Assisted with SEO title generation, description drafting, and structural editing for clarity and engagement.
#SelfDevelopment #Ambition #SuccessMindset #MentalHealth #OliverBurkeman