Trail Map is a podcast about people charting bold, unconventional paths through life. Hosted by Matt Gregory and Patrick Dyer Wolf, each episode features a conversation with someone who’s forging their own way — from musicians and athletes to entrepreneurs, scientists, and chefs. Together, we explore the decisions, detours, and defining moments that shape meaningful work and personal growth. Inspiring, unpolished, and full of surprises, Trail Map is a guide for anyone navigating their own unmarked trail.
Peter Smith – Writing Other People's Books, the Freedom of Anonymity, and Why Story Beats Style
Peter Smith is the writer you've never heard of behind books you've probably read. He grew up in Milton, Massachusetts, the son of two Milton Academy teachers, sold his first novel at 25, and spent almost ten years at Oprah's magazine writing headlines and channeling her voice. That led to a career collaborating on about fifteen books with CEOs, performers and athletes, none of whom he'll name. We get into why he keeps his clients to himself, how he ends up "becoming" the people he writes for, and the difference between intimacy and privacy on the page. Peter talks about how many bestsellers have a writer like him behind them, why great storytelling beats beautiful writing, and why AI prose reads like "a Marriott lobby in Atlanta." We also cover shrinking attention spans, why most people can't write a warm email, and his unvarnished take on Boston versus New York.
Show notes:
Brookline Booksmith: https://brooklinebooksmith.com/ (https://brooklinebooksmith.com/)
A Confederacy of Dunces, John Kennedy Toole: https://brooklinebooksmith.com/book/9780802130204 (https://brooklinebooksmith.com/book/9780802130204)
Breathing Under Water, Richard Rohr: https://brooklinebooksmith.com/book/9798217423668 (https://brooklinebooksmith.com/book/9798217423668)
Jeff Tweedy's book: https://brooklinebooksmith.com/search?q=jeff%20tweedy (https://brooklinebooksmith.com/search?q=jeff%20tweedy)
Stephen King, Pet Sematary, The Institute and On Writing: https://brooklinebooksmith.com/book/9781668075760 (https://brooklinebooksmith.com/book/9781668075760) https://brooklinebooksmith.com/book/9781982110581 (https://brooklinebooksmith.com/book/9781982110581) https://brooklinebooksmith.com/book/9781982159375 (https://brooklinebooksmith.com/book/9781982159375)
The Atlantic piece on a "post-literate" era: https://www.theatlantic.com/magazine/2026/08/reading-crisis-postliterate-age/687618/ (https://www.theatlantic.com/magazine/2026/08/reading-crisis-postliterate-age/687618/)
David Foster Wallace, "This Is Water": https://brooklinebooksmith.com/book/9780316068222 (https://brooklinebooksmith.com/book/9780316068222)
William Styron, "Darkness Visible": https://brooklinebooksmith.com/book/9780679736394 (https://brooklinebooksmith.com/book/9780679736394)
Oliver Burkeman, Meditations for Mortals: https://brooklinebooksmith.com/book/9781250397676 (https://brooklinebooksmith.com/book/9781250397676)
What We Can Know, Ian McEwan: https://brooklinebooksmith.com/book/9798217007943 (https://brooklinebooksmith.com/book/9798217007943)
Richard Holmes, Dr. Johnson and Mr. Savage: https://brooklinebooksmith.com/book/9780007204557 (https://brooklinebooksmith.com/book/9780007204557)
1 Sept 2026
Lynn Vidler – From Ballet to Provost, Leadership Without Toxicity, and Knowing When to Step Aside
Lynn Vidler was the Provost at the University of Colorado Colorado Springs — the university's chief academic officer. But their first career was as a professional ballet dancer with the California Ballet Company in San Diego, where they'd been training since age four. Lynn left it, went 3,000 miles across the country to NYU, and built an academic career in 17th century Spanish drama that eventually took them to West Point for 12 years, then South Dakota, then Colorado.
In this conversation, Lynn walks us through a path that keeps bending toward curiosity. We get into what they learned about leader development at West Point after 9/11 — that you can get results through a positive, authentic approach or a toxic one, and that whichever you choose scales up into the next generation. Lynn talks about coming out publicly as transgender and non-binary at almost 50, and what it's like to suddenly feel the systems that govern how people are treated. And they share what's next: a decision to resign and leave the country, and what leadership looks like when you no longer hold the title.
Show notes:
Lynn Vidler's leadership & performance coaching business: https://bloomingbranchgroup.com/ (https://bloomingbranchgroup.com/)
Brown University ACT leadership coaching program: https://www.actleader.com/ (https://www.actleader.com/)
International Coaching Federation: https://coachingfederation.org (https://coachingfederation.org)
University of Colorado Colorado Springs: https://www.uccs.edu (https://www.uccs.edu)
4 Aug 2026
Jon Sciambi – Play as a Philosophy, Calling Cubs Baseball, and the ALS Fight He Can't Walk Away From
Jon "Boog" Sciambi has been the television voice of the Chicago Cubs since 2021, calling games from the same booth where Harry Caray once sat. He grew up on Roosevelt Island in New York City, played baseball at Regis High School, and found his way to broadcasting after getting cut from the team at Boston College — by walking straight into the campus radio station on day one.
In this episode, Jon (who happens to be Pat's first cousin) talks about play as a professional philosophy — and how channeling a six-year-old's mindset has shaped 30 years in the booth. We get into what it means to call a game for the journey, not just the highlights; how Jon is protecting his love of the craft by being more selective as his career matures; and the story of Project Main Street, the ALS foundation he started after his childhood friend Tim Sheehy was diagnosed in 2005. Jon also tells the story behind the greatest text he's ever received — sent from a Seattle number he almost didn't pick up.
Show notes:
Project Main Street (End ALS): https://projectmainst.org/ (https://projectmainst.org/)
End ALS shirts: Obvious Shirts and Ivy Shop: https://obviousshirts.com/products/end-als (https://obviousshirts.com/products/end-als)
John Cleese on Play: https://www.youtube.com/watch?v=r1-3zTMCu4k (https://www.youtube.com/watch?v=r1-3zTMCu4k)
Jon's MLB The Show episode on Pablo Torre's show: https://www.youtube.com/watch?v=adoX3IC336o (https://www.youtube.com/watch?v=adoX3IC336o)
#TrailMapPodcast #Baseball #ChicagoCubs #SportsBroadcasting #ALS #EndALS #ProjectMainStreet #Podcast #CareerPath #LouGehrigDay #Broadcasting #Storytelling
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
5.0 / 5
5 ratings
Spotify
4.9 / 5
8 ratings
Podcast Authority Score: 13 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
13
Social presence
0
YouTube
0
Engagement
32
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