Episode #465 - Wyly O'Brien (Calamity Jane)
Mighty Blue On The Appalachian Trail: The Ultimate Mid-Life Crisis
Steve Adams
4.8 • 599 Ratings
🗓️ 2 January 2025
⏱️ 65 minutes
🔗️ Recording | iTunes | RSS
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Summary
Wyly O'Brien, or Calamity Jane, is our guest today. Wyly attempted her thru-hike in 2007, researched the trail and her gear to give herself the best chance ot completing the hike, and began with a self-confidence that was ultimately shattered when she quit the trail after more than 1600 miles.

Wyly shares her story of what happened and what she learned along the way.

More than a decade later, Wyly found her journal and decided to write about her "failure," offering tips on what she could have done to imporve her chances. You can check out her new book on Amazon at Done, But Not Thru: Thru-Hiking the Appalachian Trail - A Cautionary Tale

Our new sponsor for the New Year is TSX Challenge, who turn one week into inspiration for a lifetime. And I should know. Chris at TSX told me he could get me to the top of Mt Whitney…and he did! Check out their incredible group hikes at TSX Challenge - Guided Backpacking Trips to Mt. Whitney, Grand Canyon & Beyond, and save 10% at checkout by using the code MIGHTYBLUE.
Our book reading, Happy Hiking, by my friend, Emily Leonard is–of course–written from a woman's POV and a woman's voice. I hope you enjoy listening to my reading of it. If you'd like to buy the book, you can find it on Amazon at Happy Hiking: Falling in love on the Appalachian Trail, or on Emily's website, at Happy Hiking.
I used my hike earlier this year on the South West Coast Path in the UK to help raise money for my absolute favorite charity, Parenting Matters, on whose board I've been privileged to serve for over a decade. You can learn more about the hike and the organization–and donate–by visiting Hike with Steve - Empowering Parents, One Step at a Time | Parenting Matters %. I hope you want to support this critical mission.
Don't forget. Our entire series of videos from our Woods Hole Weekend in 2022 is now FREE and available at my YouTube page at Woods Hole Weekend - Trailer There, you'll find all sorts of tips and tricks that our guests took away from the weekend that helped them with their own hikes this year. Check it out.
I often ask listeners for ideas on who to interview, and I'm sure several of you say, "I could do that. I've got an awesome story to tell." You're the person we need to hear from. If you'd like to be interviewed on the podcast, just register as a guest on the link below, and I'll be in touch. Come on the show!
If you like what we're doing on the Hiking Radio Network, and want to see our shows continue, please consider supporting us with either a one-off or monthly donation. You'll find the donate button on each Hiking Radio Network page at Hiking Radio Network .
If you prefer NOT to use PayPal, you can now support us via check by mailing it to Mighty Blue Publishing, PO Box 6161, Sun City Center, FL 35751. Any support is gratefully received.
Additionally, you can "Zelle" me a donation to steve@hikingradionetwork.com. Or "Venmo" me at @‌Steve-Adams-105. They both work!
If you'd like to take advantage of my book offer (all three of my printed hiking books–with a personal message and signed by me–for $31, including postage to the United States) send a check payable to Mighty Blue Publishing at the address just above.
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Transcript
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| 0:00.0 | You are listening to the Hiking Radio Network, where we talk the walk with shows by hikers |
| 0:05.3 | about hikers for everybody. Mighty Blue on the Appalachian Trail, the ultimate midlife crisis, joins Stephen his guests every week as he staggers from Georgia to Maine. |
| 0:33.6 | Hey guys, happy near you to all and thanks for the many good wishes that have come my way this holiday season from you guys. Much appreciated. Today we're episode number 465 of our podcast, Mighty Blue on the Appalachian Trail of the Ultimate Midlife Crisis. Normally we chat with people who've completed a through hike and who have great stories to share about how they went about getting it done. But today we have something a little different. I've had several emails over the years |
| 0:58.0 | asking me to talk with people who, for whatever reason, after about 1,500 miles, suddenly quit. |
| 1:03.9 | I didn't think I'd get many people who'd fit that description, so I'm afraid I kind of let the |
| 1:07.9 | ball drop on that. Yet recently, Wiley O'Brien or Calamity Jane wrote to me |
| 1:12.2 | wanting to share her story of how and why she did exactly that. She's even written a book, a kind of |
| 1:17.9 | cautionary tale if you will, with ideas on how to avoid ending up in the spot she found herself in |
| 1:22.8 | back in 2007. She learned a lot about herself on the journey and as a reminder, doing 1,600 miles on |
| 1:29.1 | the Appletion Trail is an awesome achievement, so I don't want that to get lost to a conversation. |
| 1:34.2 | Not everyone finishes, yet if we take things away from our hikes, then her life can be enhanced |
| 1:38.2 | by those experiences. Wiley seems to have taken that attitude as well. After Wiley, we'll hear |
| 1:43.9 | the first part of Chapter 20 of Emily Lennon's book, Happy Hiking. |
| 1:47.6 | And this week she starts hitting the rocks of Pennsylvania, meets a huge spider, |
| 1:52.3 | then enjoys an evening of girl time with a bunch of girl scouts. |
| 1:56.1 | A bit of exciting news this week is this. |
| 1:59.3 | I was recently approached by Chris Cosado. You probably remember him |
| 2:02.5 | from previous Mighty Blue podcasts. Well, Chris and his team at TSS Challenge helped me achieve what I'd |
| 2:08.1 | always thought was going to be an elusive goal. I'd never complete. An epic journey that |
| 2:12.9 | culminated in climbing to the top of Mount Whitney. While that trek was just over two years ago, |
| 2:18.3 | I still got very fond memories of that week in the Sierra's |
| 2:21.0 | and of our team, Team 6. |
... |
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