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: "Who will you be differently?"

Perfect for anyone questioning their life purpose or seeking deeper meaning beyond external achievements. This episode will challenge everything you think you know about what it means to be truly free.

🎙️ 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 growth, connection, and peace.

– Embrace uncertainty as a starting point

– Develop a curious mindset in life and leadership

– Let go of the pressure to be the expert

– Create space for deeper connection and creativity

🛠️ New Feature: Notes to Nowhere

Struggling to start journaling or writing? Try the new ChatGPT Notes to Nowhere—a simple tool at the end of each blog post to help you move past the blank page.

🔔 Subscribe for weekly reflections on meaning, mindset, and what it means to live well in a noisy world.

📚 Read the full post here: https://www.happyheadingnowhere.com/the-freedom-of-not-knowing/

#Curiosity #BeginnerMind #HappyHeadingNowhere #PersonalGrowth #Leadership #LettingGo #MindsetShift #TheSteveChastain

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, Stoic wisdom, and practical tools for realignment. If you’ve ever felt like you were playing a role instead of living your truth, this one’s for you.

Tune in for five intentional practices to bring your real self—your capital-S Self—into your work, relationships, and daily life.

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 a career change, the end of a relationship, or simply questioning the labels you’ve carried for years, this episode is for you.

Join me as we talk about the power of the rock and the reed, the strength in surrendering, and why—just like in Chris Cornell’s I Am the Highway—you are not just along for the ride. You are the road forward.

Listen in to discover:

✔️ Why identity shifts can feel like loss—but are actually invitations

✔️ How to stop fighting change and start embracing it

✔️ The balance between being grounded and staying flexible

✔️ How to find your true foundation when external identities fade

If this resonates, share your thoughts or story with me. Let’s navigate this journey together.

🎧 Tune in now.

🎙️ 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 about convenience, but commitment

✔️ How to develop friendships that go beyond work or small talk

✔️ Seneca’s wisdom on friendship and why it still applies today

✔️ The three key habits of long-lasting friendships

✔️ Why being okay alone makes you a better friend

💡 Key Takeaway:

The best friendships are built on intentionality, presence, and trust—not just shared history. Want better friends? Be a better friend first.

📌 Chapters:

00:00 – The Truth About Lasting Friendships

01:30 – What Seneca Can Teach Us About Friendship

05:00 – Why Being Alone is a Friendship Superpower

07:00 – How to Be the Friend You Want to Have

10:00 – The Difference Between Real Friends & Fair-Weather Friends

12:30 – Letting the Right People Into Your Life

💬 What’s Your Take?

How do you cultivate deep friendships in your life? Drop a comment below—I’d love to hear your thoughts!

🔔 Subscribe & Join the Journey

Enjoying Happy Heading Nowhere? Hit subscribe for more insights on relationships, personal growth, and building a life that truly matters.

🔥 More Episodes You’ll Love:

➡️ Self-Discovery & The Relationship With Yourself

➡️ Deepening Connections With Your Partner

#Friendship #Stoicism #Seneca #DeepConnections #PersonalGrowth #Podcast #SelfImprovement #HappyHeadingNowhere

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, this guide offers actionable insights to help you on your path. Don’t just exist—thrive by truly knowing who you are.

#SelfAwareness #PersonalGrowth #TransformYourLife #Mindfulness #InnerPeace #SelfDiscovery #LifeCoach #MentalClarity #AuthenticSelf #Empowerment

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 leadership pressures, a manager striving to support your team, or a knowledge worker seeking balance, this episode provides insights to strengthen the most vital relationship you have—your relationship with yourself.

Listen now and start building the foundation for deeper, more meaningful connections.

If you prefer to read this blog, head on over to HappyHeadingNowhere.com. 

Subscribe, like, follow, share it with a friend, and all that other good stuff. 

#Leadership #WorkLifeBalance #SelfAwareness #PersonalGrowth #HappyHeadingNowhere #Relationships #HHNAudioBlog

Uncomplicate Yourself | Happy Heading Nowhere Podcast | Episode 6

00:00 Welcome to the Happy Heading Nowhere Podcast

00:46 Upcoming Series on Relationships

01:30 Deep Dive into the Four Pillars of Renewal

02:31 Preparation: Clearing Life's Noise

03:09 Conservation: Protecting Personal Energy

04:28 Protection: Creating Firm Boundaries

05:39 Adaptation: Flowing with Life's Changes

06:58 The Importance of the Present Moment

09:35 Marcus Aurelius on Simplification and Renewal

11:34 Challenge for Renewal

13:13 Final Thoughts

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 your well-being, and much more. Stay tuned for more on 'overwintering' in upcoming episodes and exciting plans for the new year. Don't forget to share this episode with a friend!

00:00 Welcome to Episode Five!

00:25 Bringing It Indoors: Weather Talk

01:19 Reflecting on Recent Catastrophes

02:32 Overwintering: A New Approach to New Year

03:39 Step One: Preparation

04:14 Step Two: Conservation

04:45 Step Three: Protection

05:31 Identifying What Matters Most

07:23 Setting Boundaries and Self-Care

10:56 Embracing the Power of 'No'

12:02 Wrapping Up and Looking Ahead

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 Overwintering Series blog and details his own plans to unplug and rejuvenate over the holidays, highlighting the need for balance and resistance in pursuing personal passions.

00:00 Welcome to the Happy Heading Nowhere Podcast

00:41 The Yardbird Hat

01:18 Reuniting with the IT Crew

02:32 Embracing Change and Stoicism

03:15 The Overwintering Series

03:35 Clearing Clutter: Physical, Mental, and Emotional

04:56 The Importance of Taking Time for Yourself

07:21 Facing Resistance and Pursuing Your Passion

09:12 Planning for a Holiday Break

10:56 Why Overwintering Matters

12:25 Aligning with Nature and Personal Downtime

13:39 Conclusion and Next Steps