Happy Heading Nowhere

Happy Heading Nowhere

Where deep thinking meets life’s detours. It’s all about rolling with the punches, embracing the chaos, and finding meaning—even when you have no idea where you’re headed.

Episodes

July 3, 2025 5 mins

What does true freedom look like? After walking away from corporate life at 61, Steve discovered that real freedom isn't about doing whatever you want—it's about choosing who you become.

In this July 4th episode, discover why freedom through restraint is more powerful than freedom through impulse, and learn the one question that changes everything: "W...

Listen
Watch
Mark as Played

🎙️ Not Knowing Can Set You Free | Beginner’s Mind & the Power of Curiosity

In this episode of Happy Heading Nowhere – The Podcast, Steve Chastain explores the unexpected freedom that comes from not having all the answers. Through a personal story of loss and a deep dive into the concept of “beginner’s mind,” this 7-minute reflection offers insight into how curiosity—not certainty—can open doors to g...

Listen
Watch
Mark as Played
March 28, 2025 10 mins

In this 10th episode and the final part of our four-part Identity series, we explore what it really means to live authentically. This episode is a reflection on the quiet, internal shift that happens when your values and your actions no longer align—and how to start reclaiming that alignment.

Steve walks through the tension between external approval and inner truth, drawing from personal journal entries,...

Listen
Watch
Mark as Played
March 19, 2025 11 mins

What happens when the identity you’ve built no longer fits? In this episode, I share my personal story of transformation—how stepping away from a belief system I once built my life around forced me to redefine who I really am.

We explore the unsettling but necessary process of letting go, why identity feels so tied to stability, and how embracing uncertainty can lead to real growth. Whether you’re facing...

Listen
Watch
Mark as Played
February 25, 2025 13 mins

🎙️ In this episode of the Happy Heading Nowhere podcast, we’re talking about friendship—the kind that actually lasts. Drawing wisdom from Stoic philosopher Seneca, I break down what it means to build deep, meaningful friendships, why true friends are rare, and how to be the kind of friend you want to have.

 

🔹 What You’ll Learn in This Episode:

✔️ Why real friendships aren’t...

Listen
Watch
Mark as Played
February 14, 2025 17 mins

Let's go on a transforming journey of self-discovery and personal growth. In this video, Steve dives into the essence of self-awareness and its profound impact on every facet of your life. Learn practical strategies to enhance your understanding of yourself, leading to improved relationships, career success, and overall well-being. Whether you’re seeking to break free from external influences or aiming to align with your true self,...

Listen
Watch
Mark as Played

Your relationship with yourself sets the foundation for every other connection in your life. In this first episode of our four-part February series, Relationships That Define You, we explore the importance of self-awareness, self-trust, and personal growth.

How do you shape your inner dialogue? What impact does your mindset have on your well-being and success? Whether you’re an executive navigating leade...

Listen
Watch
Mark as Played
February 4, 2025 13 mins

Uncomplicate Yourself | Happy Heading Nowhere Podcast | Episode 6 Welcome to the sixth episode of the Happy Heading Nowhere Podcast! Steve delves into the conclusion of the Overwintering series, focusing on the four pillars of renewal: preparation, conservation, protection, and adaptation. Discover how to embrace renewal from a place of authenticity, not just resolution. Plus, hear the news about upcoming series on HHN, includi...

Listen
Watch
Mark as Played
January 17, 2025 14 mins

Welcome to the fifth episode of the Happy Heading Nowhere podcast! In this episode, Steve continues exploring the concept of 'overwintering,' a method to prepare yourself for growth and renewal. We'll discuss three critical steps: Preparation, Conservation, and Protection. Learn how to clear distractions, build sustainable habits, and safeguard what matters most to you. Join us as we share insights on setting boundaries, bolstering...

Listen
Watch
Mark as Played
December 23, 2024 14 mins

In this episode, Steve shares insights from his backyard, discusses the significance of taking time for overwintering, and recounts his recent experiences with the Liberated Brands / Volcom crew's Christmas gathering. He revisits the concept of impermanence in stoicism, underlines the importance of decluttering physically, mentally, and emotionally, and emphasizes self-care during the busy end-of-year season. He also introduces the...

Listen
Watch
Mark as Played
December 13, 2024 14 mins

Welcome to Episode 3 of the Happy Heading Nowhere podcast!

Join us for a cozy fireside chat on the back porch as we reflect on Thanksgiving, our Vegas trip, and the onset of the holiday season. We'll dive deep into handling uncertain times, focusing on core values, and maintaining perspective. Learn about the 'Overwintering' series and how to use this period for personal growth and renewal. Plus, hear some inspiring quotes from Ma...

Listen
Watch
Mark as Played
November 26, 2024 22 mins

In this episode, Steve discusses the importance of being authentic and true to oneself. Steve also announces the formation of his new venture, EUDA Collective, aimed at promoting work-life balance and meaningful work. He touches upon themes like imposter syndrome, encouraging listeners to embrace their roles and be grateful. Steve wraps up by discussing his plans for Thanksgiving, emphasizing the importance of gratitude and spendin...

Listen
Watch
Mark as Played

Welcome to the inaugural episode of the Happy Heading Nowhere Podcast!

Join Steve as he introduces the podcast's philosophy of finding contentment and direction amid life's unpredictability. From expressing gratitude to discussing the importance of perspective and personal growth, Steve sets a compassionate and insightful tone for the series.

Tune in for deep conversations, wisdom from Stoic philosophy, and practical guidance on ha...

Listen
Watch
Mark as Played

Popular Podcasts

    If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

    Dateline NBC

    Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

    Betrayal Weekly

    Betrayal Weekly is back for a new season. Every Thursday, Betrayal Weekly shares first-hand accounts of broken trust, shocking deceptions, and the trail of destruction they leave behind. Hosted by Andrea Gunning, this weekly ongoing series digs into real-life stories of betrayal and the aftermath. From stories of double lives to dark discoveries, these are cautionary tales and accounts of resilience against all odds. From the producers of the critically acclaimed Betrayal series, Betrayal Weekly drops new episodes every Thursday. If you would like to share your story, you can reach out to the Betrayal Team by emailing them at betrayalpod@gmail.com and follow us on Instagram at @betrayalpod and @glasspodcasts. Please join our Substack for additional exclusive content, curated book recommendations, and community discussions. Sign up FREE by clicking this link Beyond Betrayal Substack. Join our community dedicated to truth, resilience, and healing. Your voice matters! Be a part of our Betrayal journey on Substack.

    The Joe Rogan Experience

    The official podcast of comedian Joe Rogan.

    NFL Daily with Gregg Rosenthal

    Gregg Rosenthal and a rotating crew of elite NFL Media co-hosts, including Patrick Claybon, Colleen Wolfe, Steve Wyche, Nick Shook and Jourdan Rodrigue of The Athletic get you caught up daily on all the NFL news and analysis you need to be smarter and funnier than your friends.

Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2026 iHeartMedia, Inc.

  • Help
  • Privacy Policy
  • Terms of Use
  • AdChoicesAd Choices