703: On Becoming: The Art and Craft of Personal Storytelling (Ep 3: The Pilgrim and The CEO) with Jane Longley

Welcome back to the College Essay Guy podcast and our series On Becoming: The Art and Craft of Personal Storytelling. I’m one of your cohosts, Tom Campbell, former Pomona and Holy Cross admissions officer, turned essay coach and college counselor.

In this series, we look at real personal statements from real students: what choices were made, what was revised, and why it works.

For this episode, we sit down with Jane Longley, one of our amazing essay coaches here at CEG, to unpack an essay that one of her student wrote titled “The Pilgrim and The CEO.” It tells the story of two challenging yet rewarding experiences central to one student’s identity and growth: hiking the Camino and starting her own skincare line. They seem like wildly different journeys in that bite-sized, one sentence description, but as you’ll see from the essay, they’re anything but disparate. This essay, which seamlessly tells two stories in tandem, is a masterclass on balance. Which is really what college essays are all about. On one side, they should genuinely reflect the student — their voice, their lived experiences, the moments that have shaped how they see the world. On the other, they need to do some real work: helping an admissions reader understand the student’s character, values, and potential, and making it easier to advocate for them in committee.

We’ll walk through key excerpts, unpack the strategic decisions behind them, and share practical insights for counselors, teachers, and anyone guiding students through the writing process.

Jane Longley has been an essay coach for eight years. She graduated from Oxford University with a degree in Modern Languages and spent ten years teaching in the UK before moving to Nicaragua, where she has lived for more than two decades. Along the way, Jane trained in Person-centred Therapeutic Counselling and Boarding Education — experiences that inform how she works with students today. As an essay coach, she focuses on helping students clarify their ideas, identify meaningful through-lines in their experiences, and find language that feels precise and authentic. And we, for one, are so glad she’s come to share her expertise and her calming British accent with you all. 

We hope you enjoy the episode.

 

Play-by-Play:

• 2:18 – What is Jane’s background in essay coaching? 
• 4:54 – Jane shares context for the essay and what it was like working with the student who wrote it
• 8:47 – In what ways can brainstorming exercises uncover unexpected topic ideas?
• 9:49 – How does the values exercise serve as the foundation for an essay?
• 15:06 – What other brainstorming tools helped shape the student’s direction?
• 18:05 – How did the student’s early topic ideas transform into a final product? 
• 21:42 – What influenced the essay’s final structure? 
• 29:40 – Jane reads the essay, “The Pilgrim and The CEO”
• 34:16 – Tom shares his initial thoughts on the essay 
• 35:46 – Jane shares how the author developed the two narratives in the introduction  
• 39:07 – How did the student decide what essential context about the Camino needed to stay?
• 41:39 – How did authenticity shape the student’s decision to include moments of unpreparedness?
• 44:34 – How did the student identify the specific, vivid details that brought each journey to life?
• 51:53 – How did collaboration become a central theme across both journeys?
• 55:20 – How did the student’s honest reaction at the end of the Camino strengthen the essay?
• 59:30 – How does the tone shift from collaboration to appreciation in the final paragraphs?
• 1:00:53 – How can students revisit the same experience across essays without repeating themselves?
• 1:03:52 – Closing thoughts 

 

Resources:

• "The Pilgrim and the CEO" Essay
• The Values Exercise
• The Roles and Identities Exercise
• The 21 Details Exercise
• The Essence Objects Exercise 
• College Essay Guy’s Personal Statement Resources
• College Essay Guy’s College Application Hub