Good Life Project: “Feeling Like You’ve Fallen Behind in Your Own Life? This’ll Help.”

Host: Jonathan Fields
Release Date: September 11, 2025

Episode Overview

In this special solo episode, Jonathan Fields curates and performs a spoken-word roundup of his most popular, thought-provoking essays from his “Awake at the Wheel” newsletter. Through deeply personal storytelling and reflection, Jonathan explores the feelings of falling behind in life, the meaning of purpose and presence, how we connect (and disconnect) with others, and his recent insights gained from a month in Japan. Each essay invites listeners to reconsider what it genuinely means to “live a good life,” moving beyond conventional measures of success toward true connection, meaning, and self-compassion.

Key Essays & Themes

1. Letter From Love: On Feeling Left Behind

[08:25 – 16:30]

• Origin: Written at the request of author Elizabeth Gilbert for her “Letter from Love” community, this essay is Jonathan’s introspective answer to feeling he’s “fallen behind” in life.
• Main Reflection: Jonathan challenges the standard of comparison—asking behind “what, exactly?”—and traces the origins of these measuring sticks to overblown teenage dreams and societal expectations.
• Powerful realizations:
  • The real milestones of life are often not wealth or status, but relationships, presence, health, and love.
  • Self-compassion is essential:

    “You are and have always been exactly where you need to be. Here, now, seen, held, capable, well and loved.” – Jonathan ([14:15])

  • The cure: presence—let go of “what could have been” for “what is.”
• Tone: Vulnerable, reassuring, and warmly direct.

2. The Creative Boomerang: Art, Serendipity, and Impact

[16:31 – 23:55]

• Story: A chance encounter with an Oakland street artist reveals a surprising connection: the artist’s life pivot was inspired by Jonathan’s own book, “Career Renegade.”
• Key Insight:
  • Creative acts—our “work”—can ripple back and impact us in unpredictable, life-affirming ways, long after we’ve sent them into the world.
  • On artistic validation:

    “Makers gotta make... And then every once in a while, if you’re lucky and stay in it long enough, the universe gives you a sign, the dent. Your work boomerangs back to you, letting you know—keep going. This matters. You matter.” – Jonathan ([23:45])

• Takeaway: The value of creating isn’t just intrinsic—it can unexpectedly inspire, empower, and connect others, often without the creator’s knowledge.

3. Less Show, More Soul

[23:56 – 32:30]

• Scene: Jonathan recounts leading a large yoga class during a teacher training retreat, only for the lead instructor to whisper:

  “Less show, more soul.” ([27:18])

• Self-Reflection:
  • He admits “show” (performance, bravado) became his “Soul’s shield” to hide his imperfection and vulnerability.
  • Over time, he noticed this showmanship pattern—hiding behind personas—leads to superficial connections:

    “All that hiding, living behind a shield, though, takes its toll. You find yourself surrounded not by friends, lovers, and community, but by an audience. And you learn...an audience stays as long as you perform; a friend or love stays as long as you unfold…” ([30:16])

• Lifelong Task: Unlearning the habit, allowing more authenticity and less self-protection.

4. The Compound Interest on Being There

[32:31 – 44:55]

• Examines Two Views on “Success”:
  1. Financial Compounding: The classic advice—work relentlessly and invest early to build wealth, planning to enjoy life later. Jonathan warns of its hidden tolls:
     • Most people don’t end up as secure as they’d hoped.
     • This path often compounds “stress and complexity, worsening health, deepening loneliness…” ([36:40])
  2. Relational Compounding (“Version Two: Compounding Presence”):
     • Suggests focusing, instead, on the “compound interest” of relationships, love, and being present—especially during the moments when it matters most.

     “What is the compound interest on being emotionally present and deeply engaged...?” ([39:48])

• Research-backed Claim: Deep human connection surpasses wealth in predicting a meaningful, regret-free life.

5. Are You Pushing People Away Without Realizing It? (Conversational Dynamics)

[44:56 – 54:35]

• Dynamic: The reflex to “one-up” or share our own stories immediately after someone shares theirs can unintentionally sabotage connection.
• Practical Framework: “Prompt, Ask, Ask, Ask, Share.”
  • Prompt: Invite the other to share.
  • Ask: Show curiosity—“Tell me more,” “And then what happened?”, “How did that make you feel?”
  • Share: Only after asking and allowing, share your own story as complement, not competition.
• Quote:

  “It's about laying a foundation, creating a conversational dynamic where each person has the chance to feel seen and heard and elevated by the way the experience unfolds…” ([53:20])

• Result: Richer, more reciprocal, and connected conversations.

6. Ikigai: Not What You Think (Lessons from Japan)

[56:55 – 65:50]

• Personal Story: Recounts slow, deliberate travel along Japan’s Nakasendo Trail, contrasts it with frenetic Tokyo, and reflects on the deeper meaning of “ikigai” (reason for being).
• Critical Evaluation: Jonathan unpacks Western misappropriations of ikigai as a career or monetization framework (the iconic four-circle Venn diagram), calling it “reductionist” and “just plain wrong.”

  “Your reason for being doesn’t have to earn your living… Nor must you be masterful at it… The very fact of your existence endows you with value, with worth.” ([64:45])

• Essence: True ikigai is found in what brings meaning, big or small, paid or unpaid, public or private.

7. How Different Cultures Feel (Or Not): Final Reflections from Japan

[65:51 – 70:28]

• Setting: Final night in a legendary, intimate jazz club in Tokyo.
• Cultural Contrast: While Jonathan and family are visibly moved by the music, the Japanese audience sits still and seemingly unmoved.
• Reflection: Wonders about cultural norms around self-expression, emotional containment vs. release, and the hidden costs of propriety versus exuberance.
  • Parallels this with his own life:

    “How often have I held back out of a fabricated self of self-consciousness and mandated propriety, unwittingly annihilating the possibility of genuine elevation and connection?” ([68:35])

• Insight: A call to examine what holds us back—individually and culturally—from fully feeling, expressing, and participating in the “magic” moments of life.

Notable & Memorable Quotes

• On letting go of “shoulds”:

  “The dream of the life you’ve fallen behind on was measured by things you didn’t yet know barely mattered, and devoid of things that matter beyond measure.” – Jonathan ([13:30])

• On creative work and impact:

  “You never know how the work you create will land… But you really never know. You keep doing it, largely because it’s the thing you can’t not do… And then, every once in a while, if you’re lucky… the universe gives you the sign, the dent…” ([22:35])

• On performing vs. revealing:

  “Show had become Soul’s shield. So much bravado, posturing, all to distract from the simple fact I had no idea who I was or what I was doing.” ([28:08])

• On relational wealth:

  “Is there really any greater wealth in life than knowing there are people who see you, know you, love you, and have genuinely got you? And you’ve got them?” ([42:44])

• On the cost of immediate self-sharing:

  “You think it’s a bonding moment — and maybe done right, it is. But equally, if not more often… it transforms it from bonding moment to feeling disconnected at best, and diminished at worst.” ([47:38])

• On ikigai’s true meaning:

  “Plenty of people do things they don’t love… And yet it can also serve as a powerful source of meaning and purpose… Your reason for being doesn’t have to earn your living or even a single dime…” ([62:11] and [64:45])

• On the courage to express and participate fully:

  “How often do I afford myself the freedom to not just be affected, but to fully embody the transference, to let it show, to offer myself to the collective in a way that lets more of the real me out and helps to co-create more of that collective magic…” ([69:20])

Segment Timestamps

| Essay/Segment | Approx. Start | Approx. End | |---------------------------------------------|---------------|---------------| | Letter From Love | 08:25 | 16:30 | | The Creative Boomerang | 16:31 | 23:55 | | Less Show, More Soul | 23:56 | 32:30 | | Compound Interest on Being There | 32:31 | 44:55 | | Are You Pushing People Away? | 44:56 | 54:35 | | Ikigai: Not What You Think | 56:55 | 65:50 | | How Different Cultures Feel (Final Tokyo) | 65:51 | 70:28 |

Episode Highlights & Takeaways

• Self-compassion in the face of feeling “behind” in life is liberating and transformative.
• Creative impact is unpredictable; sharing your work can inspire and connect in ways beyond your knowledge.
• Authenticity trumps performance—real belonging comes from showing up as your whole self, not a persona.
• Relationships and presence are the most valuable “compound interest” in life, potentially above wealth or status.
• Truly good conversations are built on curiosity, listening, and making others feel seen before taking the metaphorical mic.
• Purpose (ikigai) isn’t defined by productivity, monetary value, or mastery. It can be simple, plural, and personal.
• Cultural norms shape how we express emotion and participate in life’s magic; it’s worth questioning what is lost or gained in these expressions or their absence.

Closing Note

Jonathan encourages listeners (and himself) to cultivate gentleness, openness, and a willingness to more fully inhabit their lives—alone and with others. “Live with more soul, less show; more presence, less pretense.”

To explore these essays further or join the discussion, visit the 'Awake at the Wheel' newsletter (linked in show notes).