Reclaiming with Monica Lewinsky

Episode: "A Year of Reclaiming"

Date: January 27, 2026
Host: Monica Lewinsky (Wondery)

Episode Overview

This milestone episode celebrates a year of "Reclaiming" with Monica Lewinsky by weaving together answers from all 48 guests to her signature closing question:
"What is something you're working on reclaiming right now?"

Throughout, listeners hear personal reflections from a wide array of voices—famous figures, experts, creatives, and everyday people—illustrating just how broad, messy, and meaningful reclaiming can be. The show explores themes of identity, agency, joy, trauma, time, and the everyday process of finding one's way back to oneself.

Key Discussion Points & Insights

The Elasticity of Reclaiming

• Monica introduces the episode, emphasizing that reclaiming is an ongoing, deeply personal journey, not a destination. Guests interpret reclaiming in vastly different ways—from relationships to creativity, autonomy to humor, health to time.

Reclaiming Creativity & Passions

Savannah Guthrie

• (03:02): Shares her desire to reclaim singing and songwriting, an old passion lost to career and motherhood:

  “Having kind of the courage to pick up my guitar and try to figure it out and sing a little bit is something I'd very much like to reclaim.”
  (Savannah Guthrie, 03:20)

Miley Cyrus

• (06:35): Frames her album as her “last lap around the sun in this particular way,” describing the reclaiming of her relationship to music as an act of letting go and allowing her creativity to become someone else’s joy.

Mark Duplass

• (54:20): Talks about mourning the loss of a once central identity as a musician, while gently seeking ways to reconnect without being consumed or defined by it.

  “I have a journey to reconcile that person, and I don't know what it's going to be.”
  (Mark Duplass, 55:30)

Autonomy, Agency, and Inner Compass

Malala Yousafzai

• (04:40): Describes the challenge—and necessity—of reclaiming one’s own agency amidst external expectations and noise:

  “I want to reclaim more of my own autonomy and agency... ensure that I am listening to myself and being true to myself.”
  (Malala, 04:50)

Charlie Mackesy

• (1:07:28): Shares that, after years of feeling “like a leaf being blown around,” he’s learning to create boundaries and make choices that fill him up rather than drain him.

Reclaiming Self-Worth, Joy, and Presence

Gabrielle Union

• (12:10): Describes wanting to reclaim confidence to do mundane things (like driving her child alone), illustrating how trauma and anxiety may shrink one’s world.

Sarah Paulson

• (35:05): Wants to reclaim the sense that “where I am and what I'm doing is absolutely fine and enough,” striving for presence and acceptance over constant self-improvement.

Olivia Munn

• (29:50): After a cancer diagnosis, she reframes parenthood struggles:

  “Whenever I feel tired or I'm like, oh, he made this mess... I think about being 80... I would say, make the mess. I don't care. I will not remember the mess when I'm 80.”
  (Olivia Munn, 31:00)

Adam Scott

• (28:05): Hopes to reclaim the part of himself ridden with parental guilt after sending his son to college.

Margaret Cho

• (1:13:30): Seeks to reclaim wonder and childlike innocence, “not jaded... not cynical.”

Navigating Career, Identity, and Transitions

Ronan Farrow

• (09:02): Shares the transformative power of “not running from” one’s difficult family history, using pain as a source of strength.

John Oliver

• (16:35): Jokingly suggests the British reclaim India, but then thoughtfully discusses the inoculation against humiliation that stand-up comedy provided him:

  “Once you've bombed 100 times on stage you'll be fine because there is nothing an audience can take from you after that.”
  (John Oliver, 17:30)

Tony Hawk

• (57:40): Speaks on literally reclaiming his legacy by remastering his legendary video game series—highlighting the intertwining of personal and professional reclamation.

JoJo

• (1:23:45): Recounts reclaiming her “voice” from a legal/industry perspective—owning her masters, her music, her narrative.

Reclaiming Time, Health, and Balance

Brooke Shields

• (1:01:55): Wants to reclaim peace of mind and the buoyancy she lost after years of seriousness, loss, and frustration with fame.

Nicole Byer

• (1:03:42): States she's “working on reclaiming [her] health” in the context of diabetes and other health challenges—emphasizing that it's not about weight or appearance.

John Chu

• (1:22:12): Struggles with finding a healthy balance between passionately pursuing his craft and being present for his children.

Dr. Mary Claire Haver

• (1:27:02): Describes striving for continued independence as she ages so her daughters do not have to care for her—reclaiming agency over her aging process.

Grief, Healing, and Reclaiming Community

Beanie Feldstein

• (50:23): Speaks movingly about “reclaiming how our society sees grief,” emphasizing the power of community to mitigate loneliness in loss.

Tarana Burke

• (1:17:42): Summarizes the ongoing, multifaceted work:

  "There’s a different part of me that I have to decide every day, my whole self... I have to fill in those gaps all the time, and it’s okay as long as I get up and I keep going."
  (Tarana Burke, 1:18:00)

Humor and Self-Compassion

Amanda Knox

• (1:10:34): Describes developing a “dark sense of humor” after prison as a crucial release valve, illustrating how reclaiming humor can coexist with trauma and public scrutiny.

Sarah Silverman (as referenced by John Oliver)

• (18:30): Reclaimed “bravado” and resilience from public humiliation as a child and comedian.

Notable Quotes & Memorable Moments

• On Joy:

  “My biggest responsibility needs to be my happiness.”
  (Sarah Silverman, paraphrased by Monica, 19:35)

• On Self-Acceptance:

  “Radical self love and acceptance for this one body that God gave me... What you think about my body has nothing to do with what my body and me are about.”
  (Anne Lamott, 1:23:00)

• On Freedom:

  “I am reclaiming freedom in every way—not just my voice, but anything and everything that takes me away from myself.”
  (Ke$ha, 1:37:45)

• Monica’s Closing Thought:
  Throughout, Monica Lewinsky refreshes the theme: reclaiming is continuous, personal, and requires humor, patience, and compassion. She encourages listeners to apply the question to their own lives—to notice what it would mean for them to reclaim something lost or longed for.

Thematic Timestamps (Approximate)

• 00:05 – Introduction to the theme of reclaiming; Monica's rationale for repeating the question
• 03:00–07:30 – Guests on creative and personal passions (Savannah Guthrie, Miley Cyrus)
• 09:00–11:00 – Family history and embracing pain (Ronan Farrow)
• 16:30–19:30 – Humor, dignity, and public failure (John Oliver)
• 28:00–33:00 – Parenthood, guilt, and presence (Adam Scott, Olivia Munn)
• 50:20–58:00 – Music, creativity, and authentic self (Mark Duplass, Tony Hawk)
• 1:01:50–1:07:45 – Peace of mind, time, health (Brooke Shields, Nicole Byer, Charlie Mackesy)
• 1:10:30–1:14:00 – Humor as survival (Amanda Knox, Margaret Cho)
• 1:17:40–1:19:50 – Daily self-reclamation and nuanced balance (Tarana Burke)
• 1:23:00–1:31:30 – Self-acceptance and radical self-love (Anne Lamott, Jamie Kern Lima, Dr. Mary Claire Haver)
• 1:37:30 – Freedom, safety, and the importance of supportive spaces (Ke$ha, Monica Lewinsky)

Summary of "Reclaimings" Shared

A non-exhaustive list of what guests are working on reclaiming:

• Creative passions and lost hobbies
• Agency, autonomy, and their “inner compass”
• The ability to be present and find daily joy
• Confidence, peace of mind, self-worth
• Humor, wonder, and a sense of play
• Balance between ambition and relationships
• Health, time, and personal space
• Self-definition and identity
• Acceptance, love for one's body
• Their physical or metaphorical “voice”
• Freedom from trauma, expectations, and societal stifling
• Community and joy amidst grief or adversity

Tone & Style

The conversations remain candid, often vulnerable and humorous. Monica and her guests balance gravity with laughter, reinforcing that reclaiming is both difficult and hopeful, individual and communal.

Conclusion

This episode of "Reclaiming" tenderly compiles a year's worth of voices into a multifaceted meditation on what it means to reclaim pieces of ourselves. It serves as an invitations for listeners to ask:
What are YOU working on reclaiming right now?