Totally Booked with Zibby

Guest: Matt Eicheldinger, Author of Holes in My Underwear: Over 100 Poems That Will Knock Your Socks Off

Date: October 15, 2025
Host: Zibby Owens

Episode Overview

In this episode, Zibby Owens hosts Matt Eicheldinger, acclaimed author, educator, and storyteller whose latest book Holes in My Underwear brings together over 100 uproarious and heartfelt poems for kids. The conversation delves into Matt's remarkable journey from sixth-grade language arts teacher to New York Times bestselling author, the power of storytelling in education, his viral presence on social media, and the deeply personal experiences that anchor his writing. The episode is filled with poignant anecdotes from Matt's classroom days, live readings from Sticky Notes, candid insights about teaching and writing, and a preview of what's next in his literary career.

Key Discussion Points & Insights

Matt’s Path: From Teacher to Author

[04:40–09:22]

• Teaching Origins: Matt taught sixth-grade language arts beginning in 2009.
  • Discovered his “thing” in teaching by sharing embarrassing childhood stories with students to engage and motivate them.
  • “I started telling students embarrassing stories from my childhood as a way to, like, incentivize them…” (A, 04:59)
• First Book Roots: Began documenting memories at age 21, compiled them (“Ten Broken Toes”) printed on the school copier, and used it for students who were reluctant readers.
• Long Road to Publication: Spent 15 years learning the publishing world and facing rejection before self-publishing during the pandemic.
  • “There was no one to mentor me. I was just throwing things to the wall to see what stuck.” (A, 06:32)
• Social Media Breakthrough: Growing an online audience by sharing mini-stories from classroom experiences.
  • Led to more book deals—work, like “Sticky Notes” and poetry, grew organically out of his practical teaching needs.
  • Emphasizes authenticity: "I'm not trying to copy anybody else. It's just things that I've done because I needed to." (A, 08:47)

The Reality of Sudden Success

[09:22–10:53]

• Became an “instant” New York Times bestseller, but still approaches each opportunity with “hustle” and humility.
• Discusses financial risk and uncertainty in leaving teaching; regards current career as potentially fleeting but deeply special.
  • “A lot of how I work now is out of fear because I feel like this is just going to go away as quickly as it came…” (A, 10:19)
  • “Treating it as if it’s a moment in time makes it special.” (A, 10:42)

The Power of Connection & Story

[10:53–13:51]

• Matt’s approach centers on seeing and listening to kids for who they are.

  • “I have 15 years of so many individuals...I see their faces, I hear their voices…” (A, 11:27)

• Zibby reads aloud favorite stories from “Sticky Notes”:

  • "Brownies" [11:53–12:53]: A student brings Matt a “brownie mountain” on an especially rough day.
    • Key takeaway: Small acts of kindness can turn someone’s day around.
      • “Maybe they just need to be given a genuine dose of kindness to bring them back. Or, you know, a tray full of brownies couldn’t hurt either.” (Excerpt read by B, 12:47)

• Matt’s creative process: Jotting down quick memories, expanding on reflections in adulthood to reveal deeper meaning.

  • “As an adult, when you sit and think about that for a long time, you start to see all these little things in there about humanity, and you’re like, oh, that’s what that moment was.” (A, 13:13)

Understated Teaching Moments: Impact and Memory

[13:53–15:11]

• Second reading: "Silence and Stars"—Taking city students to an overnight camp in Minnesota, where student Joyce discovers the power of silence under the night sky.
  • “I didn’t know what silence was until today,” she says. (Excerpt read by B, 14:40)
  • Matt reflects on the teacher’s unique position as “holder of stories,” often only able to sense—not see—the long-term impact on students.
    • “Those are the things that help you leave work feeling lighter than you came in, which can be very hard in teaching.” (A, 15:06)

Navigating Burnout & Pressure in Teaching

[20:26–23:14]

• Realities of teaching: Societal pressures, policy changes, personal sacrifices, and the acute challenges of supporting students beyond academics.
  • Example: Needing to call child protective services for a student while managing his own family responsibilities.
  • “There’s society, right? …But there’s also the stories from kids and the things that you hear from their life that they’re dealing with.” (A, 20:34)
• Strategies for resilience:
  • Starting class with “circle time” to build classroom community—a safe space outside the curriculum.
  • “That for me was a way to like rejuvenate why I do what I do.” (A, 22:30)

Advice for Parents of Tweens and New Teachers

[23:25–24:34, 26:58–28:54]

• Tweens are “trying on hats,” figuring out identities; adults should show them possibilities rather than prescribe identities.

  • “Let your kids try on all these hats. They’re just trying to figure out who they are.” (A, 24:19)

• Advice for aspiring teachers:

  • Joy and connection with kids is real.
  • It takes time and experience to grow your unique teaching style—allow yourself that space.
    • “You need to give yourself time, a lot of time, to recognize what kind of teacher you are. And that takes years.” (A, 27:45)

• Power of Presence:

  • On the importance of “holding space”—simply being there rather than always fixing.
    • “I use the phrase the power of the pause where you just don’t do anything.” (A, 24:57)

Hard Truths: Poverty and Hidden Needs

[25:34–26:54]

• Classroom anecdotes reveal unseen struggles, such as a student asking to take home leftover pizza for her food-insecure family.
  • “Now I know this family doesn’t have food. So now it’s on me to do something for this kid.” (A, 26:12)
• Teaching goes far beyond delivering lessons; it’s about recognizing and supporting children as whole human beings.

Current Projects and What’s Next

[29:02–32:53]

• Matt Sprouts series: Third book just released—reflects his early teaching efforts to engage reluctant readers.
• Holes in My Underwear: Poetry collection born from a need for fresh material in the classroom—features 15 years’ worth of child-tested poems, illustrated and humorous.
  • “This is 15 years of highly vetted poetry that I was able to push out.” (A, 29:56)
• Upcoming:
  • Young adult trilogy: When the Rain Came (first book releasing in March).
  • Marvin Baby Blob series for younger readers (Simon & Schuster) based on doodles with his own child.
  • “I think I’m just going to keep writing in the same genre… I really think I’m a middle grade writer, which is hard because that’s a tough category to sell right now. But I think that’s my journey.” (A, 32:35)
• Mindful about pursuing projects aligned with his values and his family’s legacy.

Notable Quotes & Memorable Moments

• On Author Success:
  • “I still treat this like I’m hustling an independent book every day, like getting on this podcast. This is a huge opportunity for me.” (A, 09:54)
• On Joy in Teaching:
  • “Kids give you energy. And I’m missing that right now, like, I miss the moments with kids sitting alone in my basement.” (A, 27:35)
• On Lasting Impact:
  • “Teachers are the holders of stories... to be able to recognize how that might resonate years down the line for a kid or even for yourself is really hard.” (A, 15:13)
• On Being Present:
  • “The power of the pause where you just don’t do anything... Sometimes, if you just allow yourself to slow down, other people rise to the occasion.” (A, 24:57)
• On Middle Schoolers:
  • “They’re trying on so many different hats… As kids try on all their hats, they’re just looking for validation.” (A, 23:38)

Timestamps for Important Segments

• Matt’s Teaching & Writing Origin Story: 04:40–09:22
• Overnight Success & Its Reality: 09:22–10:53
• Live Reading: "Brownies": 11:46–12:53
• Live Reading: "Silence and Stars": 13:58–15:11
• The Hard Parts of Teaching & Burnout: 20:26–23:14
• Advice to Parents of Tweens: 23:25–24:34
• On “Holding Space” for Kids: 24:57–25:34
• Invisible Struggles (Pizza Anecdote): 25:34–26:54
• Advice for Aspiring/New Teachers: 26:58–28:54
• Current & Upcoming Projects: 29:02–32:53

Tone & Atmosphere

Genuine, warm, and conversational, the episode weaves humor with vulnerability. Matt is honest about the everyday joys and heartaches of teaching, the unpredictable business of writing, and his sense of purpose in connecting with both readers and students. Zibby’s admiration and gentle curiosity highlight the depth and humanity of Matt’s work.

Final Thoughts

Matt Eicheldinger’s journey exemplifies persistence, heart, and creativity born of necessity. Whether through poetry about underwear, touching anecdotes, or advice for budding educators and parents, his work radiates humor and compassion. Listeners are left feeling inspired by Matt’s resilience, reminded of the overlooked heroics of teachers, and eager to check out his new books—especially Holes in My Underwear.