Charlie Mackesy - Reclaiming with Monica Lewinsky

Transcript

Monica Lewinsky (0:00)

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Charlie Mackesy (0:20)

I don't think we ever choose to suffer. We don't go bring it on. But in the end, that suffering helps us grow. So, for instance, the boy, as an example, always wants to be brave. And he says, I don't feel very brave. And then the horse says, well, that was a brave thing to say. But the point is. But he. He hits a storm and goes through it and learns just because he has to, how to be courageous and chooses life. He chooses to love. He chooses to hold on.

Monica Lewinsky (0:57)

Guys, thanks for helping me carry my Christmas tree.

Charlie Mackesy (0:59)

Zoe. This thing weighs a ton. Drewski, lift with your legs, man.

Monica Lewinsky (1:02)

Santa.

Charlie Mackesy (1:03)

Santa, did you get my letter? He's talking to you, Bridges. I'm not.

Monica Lewinsky (1:06)

Of course he did. Right, Santa, you know my elf Drew Ski here.

Charlie Mackesy (1:10)

He handles the nice list. And elf, I'm six' three. What everyone wants is iPhone 17 and at T Mobile. You can get it on them. That center stage front camera is amazing for group selfies, right, Mrs. Claus?

Monica Lewinsky (1:21)

I'm Mrs. Claus's much younger sister. And AT T Mobile, there's no trade in needed when you switch. So you you can keep your old.

Charlie Mackesy (1:28)

Phone or give it as a gift.

Monica Lewinsky (1:29)

And the best part, you can make the switch to T Mobile from your phone in just 15 minutes.

Charlie Mackesy (1:33)

Guys, my side of the tree is slipping. The holidays are better. AT T Mobile switch in just 15 minutes and get iPhone 17 on us with no trade in needed. And now T Mobile is available in US cellular stores with 24 monthly bill credits for well qualified customers plus tax and $35 vice connection charge. Credit sentence balance due if you pay off earlier. Cancel financing agreement. 256 gigs, $830 eligible board in a new line.

Monica Lewinsky (1:52)

Summary

Podcast Summary: Reclaiming with Monica Lewinsky

Episode: Charlie Mackesy
Date: December 16, 2025
Host: Monica Lewinsky
Guest: Charlie Mackesy

Episode Overview

In this heartfelt, deeply engaging conversation, Monica Lewinsky sits down with Charlie Mackesy—artist, author of The Boy, the Mole, the Fox and the Horse, and its sequel, Always Remember. They discuss themes of vulnerability, grief, creativity, kindness, and what it means to reclaim agency in our lives. Both Lewinsky and Mackesy draw from their personal journeys to explore the messy, beautiful process of healing and human connection, connecting their own experiences with the transformative power of art, storytelling, and bravery.

Key Discussion Points and Insights

1. Opening & Setting the Tone

Monica and Charlie joke about sleepless nights and quirky travel experiences, bringing a tone of warmth, candor, and self-deprecating humor to the episode.
They reflect on a recent book event, moved by the range of people—children to elders—whose lives have been touched by Charlie’s work.
- “It's pretty amazing to see...I think from 6 to probably 85.” — Monica (05:34)

2. Impact and Reception of Charlie’s Work

Monica highlights the extraordinary success of The Boy, the Mole, the Fox and the Horse, including 242 consecutive weeks on the NYT bestseller list (07:02), and its diverse readers.
Charlie is moved by the stories fans share, especially how his work has found its way into therapy, education, and even pandemic windows.
- “I kind of feel, because I haven't really been here very much, that I don't know that history with them. So I was welling up so much last night…” — Charlie (08:02)

3. Holding Emotional Space for Readers

Both discuss the emotional weight of being a “holder” for others’ stories—especially stories of loss, shame, and survival.
- Monica, referencing her psychology background:
  “So much of what you're doing with your work is healing people and so you're holding space for them...but it is...a lot. Collective energy is a lot.” (09:48)
- Charlie admits he struggles with boundaries:
  “You take it away with me. That can kind of accumulate in you.” (09:30)
They discuss tools to process trauma, like EMDR therapy, with Monica advocating for its accessibility, especially for the care professions and military (13:00–14:43).

4. Vulnerability, Gender, and Courage

Charlie reflects on how his work has resonated especially in traditionally stoic environments (like the military), touching on the importance of normalizing emotional bravery in men.
- “To work your way into gentleness, which is a strength. Work your way into vulnerability, which is brave.” — Charlie (16:14)
Discusses courage as “to dare to tell the truth of who you are with your whole heart.” (17:19)

5. Childhood, Schooling, and Creativity

Charlie shares the pain and survival strategies from his childhood, particularly attending boarding school at age 7 (19:00).
Both lament the Western focus on achievement over character, questioning why kindness and empathy aren’t more valued (21:10).
Charlie credits art for being an emotional sanctuary. He advocates for creative play and breaking out of rigid boundaries—both in coloring and in life (22:32–27:10)
- “The tragedy is not that you stop making good drawings. The tragedy is you've lost a good process.” — Charlie (25:23)
Encourages adults to reclaim childlike creativity for healing.

6. Navigating Grief and Loss

Discussion turns to personal loss—Charlie's mother, friends, and his beloved dog Barney (45:41–50:05).
- “Grief is grief, and we’re not very good, I think, at navigating or even recognizing it.” — Charlie (46:03)
- They reflect on the unique chasms created by each loss, including loss of imagined futures (50:30–50:43).
Charlie talks about how these losses shaped his new book, Always Remember (48:34).

7. On the Purpose of Storms and Suffering

They discuss the metaphor of the storm—both as a character in Charlie’s new book and through a Haruki Murakami quote about emergence and change (41:32–44:17).
- Charlie’s take:
  “I don’t think storms have purpose...But in the end, that suffering helps us grow.” (42:17, 42:26)
Storms as something that happen, not with intention, but from which active choices can lead to growth and empathy.

8. The Power of Agency and Reclaiming One’s Narrative

Both Monica and Charlie emphasize reclaiming agency, making choices that fill rather than drain, and recognizing where power has been unconsciously given away (66:02–69:39).
- “Getting some agency back to really value my own choices...Working out what is a drain and what is a tap.” — Charlie (66:02)
- Charlie’s therapist’s wisdom:
  “At what point was it, do you think, that you chose to give them power?...Can I suggest to you that you choose to take it back?” (68:11–68:56)

9. Behind the Animated Film: Stories of Instinct and Casting

Charlie shares the serendipitous, heartfelt story of casting for the Oscar-winning animated film and the instinctual, transformative performance of voice actor Jude Hollander (56:14–61:43).
- “I said, ‘What do you feel like, we’re trying to make this little film and I don’t know how you feel about being a horse.’ [Gabriel Byrne:] ‘Charlie, I am the horse.’” (58:26)
- Importance of leaving room for creative intuition, as Jude’s line reading revealed a new nuance:
  “He wasn’t comparing or putting himself above the other horses. The emphasis on love, not a comparison.” — Charlie (61:43)

10. Reminders of Worth and the Role of Friendship

Both reflect on how affirmations from loved ones anchor identity, especially in times of public shaming or adversity (62:53–64:55).
- “I love when people remind you who you are and your value and your worth, because it can go. It can just go through your feet.” — Charlie (63:26)
- Monica recalls her family’s mantras of love during her time of global scrutiny.

11. Final Reflections: Reclaiming, Self-Gentleness, and Change

Monica asks Charlie what he is currently reclaiming (65:41–69:39).
- Charlie:
  “Getting some agency back to really value my own choices...There will always be things that empty you...but to remember that you must make choices that are also good for you, that fill you, that give you back.” (66:02)
Emphasis on self-kindness and letting self-love spill over to others (70:01).

Notable Quotes & Memorable Moments

On Bravery and Vulnerability:
“Courage is to dare to tell the truth of who you are with your whole heart.” — Charlie Mackesy (17:19)
On Collective Grief and Care:
“Empathy and kindness is such a crucial part of being human. But as you say, it’s also very important to learn how to...not carry other people’s [pain].” — Charlie Mackesy (11:16)
On Permission to Be Kind:
“Do you realize that your book gave them permission to be kind? That it was...talking about how they felt was brave.” — Neighbor, as told by Charlie (54:35)
On Processing Grief:
“You have to be kind to allow it and let it move through you and come out of you...like a glacier that tears you from within and moves and it can take a long time.” — Charlie Mackesy (46:03)
On Self-Agency:
“At what point do you think that you chose to give them power?... Can I suggest to you that you choose to take it back?” — Charlie’s therapist (68:29–68:56)
On Creative Process:
“The tragedy is not that you stop making good drawings. The tragedy is you’ve lost a good process. So it’s not about how it finishes, it’s how it feels when you make it...” — Charlie Mackesy (25:23)

Timestamps for Key Segments

Impact and Reader Stories: 07:02–08:21
Emotional Labor of Holding Stories: 09:17–11:16
Therapy & Processing Trauma: 13:00–14:43
Courage, Vulnerability, and Gender: 16:14–18:11
Art as Sanctuary, Coloring Outside the Lines: 22:32–27:10
Grief, Loss, and Healing: 45:41–50:05
Storms and Suffering: 41:32–44:17
Reclaiming Agency: 66:02–69:39
The Animated Film: Casting and Intuition: 56:14–61:59
Reminders of Worth and Identity: 62:53–64:55
Closing Reflections: 65:41–70:19

Takeaways

This episode offers a rare, genuine glimpse into two people who have each navigated the weight of public scrutiny and personal loss, and who now offer others tools for healing, agency, and reclaiming the lost or hidden parts of themselves. With stories, vulnerability, and wisdom, Monica Lewinsky and Charlie Mackesy remind listeners that gentleness, bravery, and creativity are not just traits for childhood, but for all of us, always.

Listener Reflection:
If you ever lost your creative spark, felt consumed by collective emotional heaviness, or wondered how to carry your own “storms,” this conversation offers not just solace but practical encouragement:

Try coloring outside the lines, reclaiming your choices, and being as gentle with yourself as you are with others.