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January 2, 2025 65 mins

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 

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 , 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 .css-j9qmi7{display:-webkit-box;display:-webkit-flex;display:-ms-flexbox;display:flex;-webkit-flex-direction:row;-ms-flex-direction:row;flex-direction:row;font-weight:700;margin-bottom:1rem;margin-top:2.8rem;width:100%;-webkit-box-pack:start;-ms-flex-pack:start;-webkit-justify-content:start;justify-content:start;padding-left:5rem;}@media only screen and (max-width: 599px){.css-j9qmi7{padding-left:0;-webkit-box-pack:center;-ms-flex-pack:center;-webkit-justify-content:center;justify-content:center;}}.css-j9qmi7 svg{fill:#27292D;}.css-j9qmi7 .eagfbvw0{-webkit-align-items:center;-webkit-box-align:center;-ms-flex-align:center;align-items:center;color:#27292D;}


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