705: On Becoming: The Art and Craft of Personal Storytelling (Ep 5: The Stains on My Baseball Pants) with Kaila Barber
The College Essay Guy Podcast: A Practical Guide to College Admissions
Release Date: 03/31/2026
The College Essay Guy Podcast: A Practical Guide to College Admissions
Welcome back to the podcast! I'm Tillie Gottlieb, a senior college counselor and content specialist here at CEG. This season, we're sitting down with admission officers to hear their real stories. I spent years on that side of the desk myself, and one thing I want listeners to walk away with is this: these aren't gatekeepers deciding your fate. They're people trying to build a class and a community, often inside a system that feels chaotic from every angle. So over the next few weeks, we're getting to know some of them as people, hearing what actually drives them, and along the way, getting a...
info_outlineThe College Essay Guy Podcast: A Practical Guide to College Admissions
Hi, friends, and welcome back to our series, “On Becoming: The Art and Craft of Personal Storytelling.” I’m Tom Campbell, former Pomona and Holy Cross admissions officer, and one of the CEG podcast co-hosts, alongside my lovely colleagues Tillie and Ethan. In this series, we take a close look at personal essays written by real students, talking about why we love them, what makes them work, and how they came to be. In this episode, we break down an essay that we’re calling The Translator. This student, who worked with one of our amazing essay coaches Lavon Robinson a few years...
info_outlineThe College Essay Guy Podcast: A Practical Guide to College Admissions
Hi friends, and welcome back to the podcast. Today's episode is a special behind-the-scenes look at a live application review I did with Anna, a high school senior I met last year. We recorded this about ten days before her early deadlines, and she was kind enough to let me walk through her entire application in real time: her personal statement, her activities list, and all of her supplemental essays for Yale. Fun fact: Anna emailed me a couple months later to let me know she actually got into Yale (congrats again, Anna!). In this episode, we get into: What it was like for Anna to pivot away...
info_outlineThe College Essay Guy Podcast: A Practical Guide to College Admissions
Hi, friends, and welcome back to our series, “On Becoming: The Art and Craft of Personal Storytelling.” In this series, we take a close look at personal essays written by real students, talking about why we love them, what makes them work, and how they came to be. In this episode, we break down an essay called "The Stomach Whisperer" about a student who used to lie on her grandmother's stomach and wonder if the echoing gurgle I’d just heard was caused by the molasses or by the cinnamon. I'm joined today by Tillie Gottlieb, a former admission officer turned Director of College...
info_outlineThe College Essay Guy Podcast: A Practical Guide to College Admissions
Welcome back to the podcast! Today’s episode is hosted by Tom Campbell, a former admission officer and now a college counselor and content creator here at College Essay Guy. This show often reminds us that beneath the essays, the deadlines, and the color-coded college lists, this whole thing is really about people — and today's guest is exhibit A. Quick disclaimer: this is a feel-good episode. Very “This American Life.” If you've ever needed your faith in public education restored, cancel your other plans. In a content landscape where some of the loudest admissions "experts" run on...
info_outlineThe College Essay Guy Podcast: A Practical Guide to College Admissions
Hi, friends, and welcome back to our series, "On Becoming: The Art and Craft of Personal Storytelling," where we take a close look at personal essays written by real students, talk about why we love them, what makes them work, and how they came to be. In this episode, I'm joined by Amber Patterson, Regional Director of Admission at Texas Christian University. This conversation does two things at once. We read a real student essay closely, line by line, and we get inside an admission reader's head to understand what's actually landing as she reads through it. We get into: What Amber hopes to...
info_outlineThe College Essay Guy Podcast: A Practical Guide to College Admissions
Hi, friends, and welcome back to our series, “On Becoming: The Art and Craft of Personal Storytelling.” where we take a close look at personal essays written by real students, talking about why we love them, what makes them work, and how they came to be. In this episode, I’m joined by Hillary Dickman, Senior Assistant Director of Admission at Colorado College. In past episodes, we've really broken down these essays and gotten into the nooks and crannies of what makes them work. But in this episode, I really wanted to get a sense of how Hillary sees essays from an admission reader's...
info_outlineThe College Essay Guy Podcast: A Practical Guide to College Admissions
Hi, friends, and welcome back to our series, “On Becoming: The Art and Craft of Personal Storytelling.” In this series, we take a close look at personal essays written by real students, talking about why we love them, what makes them work, and how they came to be. In this episode, we break down an essay that is one of my new favorites. It’s conceptually rich because even though it’s on molding clay, it could be considered any of these montage types: I love/I know, Essence Objects, Skills/Superpower, Identity, Home, or Uncommon extracurricular activity. That’s not a goal I’m...
info_outlineThe College Essay Guy Podcast: A Practical Guide to College Admissions
Hi, friends, and welcome back to our series, “On Becoming: The Art and Craft of Personal Storytelling.” In this series, we take a close look at personal essays written by real students, talking about why we love them, what makes them work, and how they came to be. In this episode, we share an essay that begins: “Robes are the textile version of comfort food; they’re my chicken noodle soup.” And it is indeed about the different robes the student wears and how each one reveals a different aspect of who the author is. I'm joined today by Andrew Callery, a college counselor...
info_outlineThe College Essay Guy Podcast: A Practical Guide to College Admissions
Hey friends, and welcome back to the College Essay Guy podcast. Today’s episode is a special follow-up with Alisha, who you might remember from our series last season where we walked through her personal statement process step-by-step. Now that she has officially received her results, Alisha is back to share the final chapter of her journey and reflect on the experience of reaching the finish line. In this session, Alisha and I explore: The emotional ups and downs of receiving college acceptances and rejections Alisha’s advice for students currently navigating the application process What...
info_outlineShow Notes:
Hi, friends, and welcome back to our series, On Becoming: The Art and Craft of Personal Storytelling. In this series, we take a close look at personal essays written by real students, talking about why we love them, what makes them work, and how they came to be.
In this episode, we break down an essay on… wait for it… baseball. Wait, what? But Ethan, I thought writing about a common topic was a fast track to blending in. And yes—in many cases, it can be. But this essay offers a great example of how a familiar topic can become something more layered, specific, and personal.
To dig into how that happens, I’m joined by Kaila Barber: essay coach at CEG, Associate Director of 1-on-1 Coaching, and professional track star. Together, we explore how to stand out with a common topic, how to weave in challenge without letting it take over the story, and one specific technique for crafting a strong, memorable ending. If you’re the kind of person who enjoys seeing how things get made, whether it’s a great meal, a film scene, or a piece of writing, I have a feeling you’ll enjoy this one.
Kaila Barber has been helping students prepare for college in various capacities since 2018. After graduating from the University of Notre Dame with a master’s degree in Global Health, a bachelor’s degree in PreProfessional Science, and a minor in Education, Schooling, and Society, Kaila decided to serve her local school district as an educational assistant. For two years, she worked closely with students who had learning differences, tailoring lesson plans and materials to better suit the needs of her students. Kaila enjoys walking side-by-side with students, guiding them through their memories and insights, while they discover new ways to make meaning from their lives that can be highlighted in creative and compelling essays.
We hope you enjoy.
Play-by-Play:
- 2:07 – Who is the student behind the essay, and what made his approach to a sports topic stand out?
- 4:44 – Kaila reads the essay we’re calling, “The Stains on My Baseball Pants”
- 8:40 – What stands out about the essay’s use of showing vs. telling?
- 10:27 – How did the essay evolve from a baseball topic into a montage centered on stains?
- 12:56 – How does the essay incorporate themes of identity and belonging without making them the central focus?
- 15:38 – How were the different “stains” chosen to represent key parts of the student’s story?
- 19:52 – What does the kimbap stain reveal about family, culture, and leadership?
- 22:00 – What does the dirt stain reveal about growth, belonging, and identity?
- 26:57 – What new role or identity is revealed through the eye black blotch paragraph?
- 31:51 – What does the “parents’ pilot” metaphor reveal about the student’s role in his family?
- 36:20 – How does the ending bring the theme of “stains” back while highlighting community and belonging?
- 40:15 – What does Kaila hope students take away from the essay writing process?
- 41:31 – Closing thoughts
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