On the eve of turning thirty, Jedidiah Jenkins quit his dream job and embarked on a 16-month bike trip from Oregon to Patagonia. This memoir chronicles his adventure, the people and places he encountered, and his internal journey grappling with what it means to be an adult, his struggle to reconcile his sexual identity with his conservative Christian upbringing, and his belief in travel as a way to 'wake us up' to life back home. The book is an honest reflection on adventure, identity, and living a life without regret.
This book gathers the best of Cheryl Strayed's 'Dear Sugar' advice columns, initially published on The Rumpus. Strayed, writing under the pseudonym Sugar, provides deeply personal and frank responses to queries on various subjects such as professional jealousy, relationship issues, and coping with loss. The book is rich with humor, insight, and compassion, making it a balm for the challenges of life. It includes never-before-published columns and a new introduction by Steve Almond. Strayed's advice is grounded in her own personal experiences, offering a unique blend of memoir and advice that resonates deeply with readers[1][4][5].
In 'Eat, Pray, Love', Elizabeth Gilbert chronicles her journey as she leaves behind her outwardly successful but inwardly unfulfilling life in the United States. The book is divided into three parts, each set in a different country: Italy, where she seeks pleasure and indulges in the local culture; India, where she delves into spiritual practices and meditation; and Bali, Indonesia, where she aims to find a balance between worldly enjoyment and divine transcendence. The memoir is a personal and introspective account of Gilbert's struggles, growth, and self-discovery during her travels.
In this ambitious one-volume history, Jill Lepore examines the origins and rise of the United States, focusing on the core ideas of political equality, natural rights, and the sovereignty of the people. The book spans over five centuries, from 1492 to the present, and delves into various themes such as the legacy of slavery, the persistence of inequality, and the impact of technological change. Lepore's narrative is characterized by its elegant prose and comprehensive coverage of American politics, law, journalism, and technology, highlighting both well-known and lesser-known figures in American history[2][5][3].
Today we get esoteric on the things that matter most—ego, family, friendship, love, work, death, and the soul. The value of living an examined life. And how sharing our uniqueness gives glimpse into the universal.
Returning for his third appearance on the podcast, our cipher for said exploration is one of my very favorite humans—a former social entrepreneur, human rights activist, and lawyer turned world adventurer, magazine publisher & mystic memoirist.
Meet Jedidiah Jenkins.
Several years ago, I stumbled across Jedidiah’s Instagram feed. His photos are always great, but it was his prose that altered my state. Enamored by his unique lens on the human condition, he quickly become my favorite follow.
Determined to learn more, I invited Jedidiah on the show (RRP #186), wherein he shared insights gleaned from an epic sixteen-month, 10,000-mile bike journey pedaling from Oregon to Patagonia. This conversation remains one of my favorites to date.
I then made him promise to return (RRP #395) upon completion of his first book, To Shake The Sleeping Self. A coming-of-age memoir set against the technicolor backdrop of his bicycle adventure, the book went on to become a New York Times bestseller, crowning Jedidiah as a new and compelling literary voice.
An exquisite storyteller with an elegant gift for exploring the interior landscape, Jedidiah has continued to mature as a writer. His latest New York Times bestselling flex, Like Streams To The Ocean, is a touching and immersive deconstruction of the things that make us who we are and the decisions that shape our one and only life.
His best work to date, it’s a masterclass on leveraging the specifics of one’s experience as a vehicle to better connect with the universal the resides within us all.
So here we are again. Me wanting to know more.
This conversation isn’t about any one thing. It’s kind of about everything.
We discuss the writing process. How to find a voice. And what it means to be an observer of both nature and people.
We talk Enneagrams, the commodification of ‘authenticity’, and how to cultivate focus in a distracted world.
It’s also about identity. Belonging. Finding meaning in work. And what it means to live a creative life.
It’s about the empathy required to find common ground with people of divergent world views. And why cultivating community is critical.
But more than anything, this is a meditation on who we are. Why we’re here. And the struggle to glean truth from the intangible.
FULL BLOG & SHOW NOTES: bit.ly/richroll582
YouTube: bit.ly/jedidiahjenkins582
As brilliant in conversation as he is on the page, I relish our conversations. And this one does not disappoint.
Let your love affair with Jedidiah begin!
Peace + Plants,
Rich
The Rich Roll Podcast 
