My So-Called Midlife with Reshma Saujani

Episode Title: Questioning What It All Means with Rasanath Das
Date: August 20, 2025
Host: Reshma Saujani (A)
Guest: Rasanath Das (B)

Episode Overview

In this episode, Reshma Saujani invites her longtime guide and teacher, Rasanath Das—a former investment banker turned monk—for a raw, searching conversation about the restlessness and longing so many feel at midlife, even after achieving everything they’d once hoped for. Together, they probe questions of meaning, ambition, disappointment, spiritual longing, and the courage it takes to go inward when life feels increasingly hollow on the surface. Rasanath offers personal stories and practical guidance for opening the heart, confronting hidden suffering, and beginning a spiritual journey, all through the lens of lived experience and universal wisdom.

Key Discussion Points & Insights

1. The Discomfort and Gift of Midlife

• Transition from Naivete to Awareness

  • Rasanath, at 46, acknowledges the discomfort of midlife, describing it as the end of youthful naivete and the beginning of deep self-examination.
  • Quote: “I know this period is working on me in a way that none of the other periods in my life have worked on me yet... It's uncomfortable because I can no longer avoid. I feel like I see too much to then say, you know what? I'm just not going to see it.” —B, [07:06–10:23]

• Threefold Convergence

  • Dissipation of naivete, appearance of wisdom, and the urge to contemplate come together, making midlife both challenging and exciting.

• The Cycle of Achievement and Emptiness

  • Constant striving loses appeal; what once excited no longer does.
  • Quote: “The shiny objects that I've chased, the shine has worn out for two reasons. One is there is a certain degree of saturation... And then, what did I experience after I got it? It was very heightened for a few days, and then it sort of tapered off and onto the next thing.” —B, [10:25–11:42]

2. Living with an Open Heart

• What Does It Mean?

  • The heart is the seat of value, worth, and real experience—far deeper than intellectual achievement.
  • Emotional openness isn’t just being tearful; it’s about courage, vulnerability, compassion, and empathic presence.
  • Quote: “Living with an open heart means I actually live with the qualities of the heart. I can experience them myself, and others can experience those when they interact with me.” —B, [13:32–16:25]

• Reshma’s Journey

  • She shares how, after working with Rasanath, she went from never crying to weeping readily, realizing it signaled a more open, receptive heart.

3. Compassion, Necessary Suffering, and the Courage to Inquire

• Starting with Your Own Suffering

  • Rasanath urges examining the impact we have on others, not just our own suffering.
  • Quote: “Father Richard Rohr talks about two kinds of suffering. He talks about necessary suffering [and] unnecessary suffering. When we run away from our necessary suffering, we inevitably create unnecessary suffering for us and for everybody around us.” —B, [22:57–24:24]

• Identifying Underlying Suffering

  • Trauma can be dramatic (childhood events) or subtle (shame from not making the top 500 at college).
  • Attachments often underlie our pain—success or validation as proxies for love or self-worth.

• The Inner Critic & Egoic Identities

  • Distinguishing genuine purpose from attachment to ego, validation, or image.
  • “Am I truly in service of that [cause], or do I want the world to see me in a particular light?” —B, [28:57]

4. The Power of Themes and Fears in Shaping Our Lives

• Recurring Emotional Themes

  • Reshma candidly discusses how “rejection” has been a persistent narrative, shaping everything from school to professional life.
  • These themes show up for everyone—other examples include fear of failure or moral superiority.
  • Quote: “When I'm so afraid of [rejection], my fictitious self importance increases because I'm trying so hard to solve that problem…” —B, [32:53–33:19]

• Radical Honesty and Inquiry

  • True transformation demands asking hard questions about our suffering, insecurities, and the origin of our pain (“return to the scene of the crime”).
  • Rasanath’s own Achilles heel was shame; he traced formative moments year by year to recognize how they shaped his ambitions and self-worth.

5. Regret, Envy, and Liberation in Midlife

• Tracing Regrets to Their Roots

  • Our lives are often directed by attempts to heal old wounds (“trying to heal a feeling that we had”).
  • The yearning for a mirror—to find people who truly see us for who we are underneath.

• Spiritual Work as the Path to Freedom

  • Real liberation comes not from surface achievement, but from spiritual inquiry—asking “Who am I?” and seeking loving mirrors (people who see your true self).
  • Quote: “To discover your true self is not a cheap thing.” —B, [40:56]

6. The Spiritual Journey: Starting Points and Practice

• Beginning a Spiritual Practice

  • Start with cultural familiarity if it helps (e.g., learning from the Bhagavad Gita), but it’s not necessary; the key is to find a living teacher, not just a text or institution.
  • Meditation classes or individual mentorship can be as powerful as formal religions.

• Universal Wisdom Beyond Institutions

  • Genuine teaching comes from those who embody their wisdom, not just preach from authority.

7. Reframing Midlife: The Big Show, Humility, and the Second Half of Life

• Midlife as the True Adventure

  • Drawing from Richard Rohr’s Falling Upward, Rasanath highlights that the first half of life is building the “container”; the second half is for deeper meaning.
  • Midlife isn’t about continuing or expanding old scripts—it’s the invitation to radical risk-taking and humility.
  • Quote: “Midlife is a place that is cultivating, that is actually creating humility for us…” —B, [48:15–49:05]

• The Role of Crisis and Boredom

  • “The crisis doesn’t have to appear in the form of an external thing... To me, emptiness is the most cutting of tragic things in life.” —B, [49:37–51:10]
  • Boredom and emptiness are themselves subtle crises that can spur growth if deeply attended.

• Becoming a Seeker

  • The true beginning is humility—accepting not knowing, asking the questions you can’t answer, and inviting the quiet discomfort that brings transformation.

Practical Guidance & Takeaways

Five Next Steps to Begin the Inner Journey ([53:04])

1. Start Small:

   • Even five minutes of meditation or a quiet walk can begin the process.
   • “The most powerful practice is the one you actually do.”

2. Ask Better Questions:

   • Replace “What’s wrong with me?” with “What is this moment teaching me?”

3. Read to Move the Heart:

   • Try Falling Upward (Richard Rohr), the Bhagavad Gita, the Tao Te Ching, Psalms, or Rumi.

4. Find a Teacher:

   • Seek out someone who lives what they teach, whether formally or informally.

5. Create Space:

   • Give yourself quiet time—disconnection and margin are required for spiritual growth.

Closing Wisdom

• “Remember, you got to go in to go up.” —A, [53:50]
• Write down the questions you don’t have answers to; acknowledging your confusion or longing is the start of real humility and spiritual growth.

Notable Quotes & Memorable Moments

• “The heart is the seat of human experience... When the heart is blocked, when it's closed... even after accomplishing so many things, we can still continue to feel empty.” —B, [13:32–14:50]

• “Midlife is a time where the convergence of the disappearance of naivete, the appearance of experience, and an internal structure to grapple with both—those three things coming together is what makes it likable and transformative.” —B, [09:30–10:23]

• “Living with an open heart doesn't mean I walk around crying all the time. Living with an open heart means I actually live with the qualities of the heart.” —B, [15:30–16:25]

• “When we run away from our necessary suffering, we inevitably create unnecessary suffering for us and for everybody around us.” —B, [23:00–24:00]

• “Am I truly a servant of the cause or do I want the world to see me in a particular light?” —B, [28:57]

• “To discover your true self is not a cheap thing.” —B, [41:54]

Timestamps for Key Segments

• [06:59] Entering midlife: Discomfort and transformation
• [13:32] Opening the heart: Beyond touchy-feely to true courage and compassion
• [22:57] Necessary vs. unnecessary suffering; beginning with our own pain
• [28:57] Attachment, ambition, and ego
• [32:53] Emotional themes: Rejection, fear, and the root of our stories
• [39:09] Regret, liberation, and seeking the right mirrors
• [43:58] Beginning your spiritual practice
• [46:26] Midlife as the “big show”: Reframing risk and humility
• [51:47] Practical advice: Start by writing the questions you can’t answer
• [53:04] Five steps to begin the inward journey

For Listeners New to the Episode

This conversation is for anyone feeling unmoored or dissatisfied in midlife, even while technically “having it all.” Reshma and Rasanath illuminate how midlife’s discomfort, if paid attention to, can unlock depth, meaning, and spiritual awakening. The journey is less about changing externals and more about turning inward, inquiring honestly, and finding new mirrors and new questions. If you’re ready to go in, this episode is your gentle, wise invitation.