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Ryan Holiday, author and owner of The Painted Porch bookstore, explores how to overcome reading slumps through strategic book selection. He shares his three go-to approaches: something really short, daily page-by-page reads, or books so compelling they 'rip your face off.'
The episode begins with Stoic philosophy as medicine for the soul, referencing Meditations by Marcus Aurelius and the healing power of philosophical study. Holiday then transitions to practical book recommendations across three categories: daily devotionals, single-sitting reads, and gripping true stories.
Drawing from 20 years of reading experience and bookstore curation, Holiday presents only books that have changed lives - his own, his wife's, or customers' - focusing on works that make readers wonder 'where has this been?' The recommendations span from Calendar of Wisdom by Tolstoy to contemporary works like The Tiger by John Vaillant.
Daily Devotionals That Transform Reading Habits
Calendar of Wisdom by Tolstoy represents the classic daily devotional genre, featuring quotes from Stoics, Chinese wisdom, the Bible, and Transcendentalists - 'This book was actually banned shortly after it came out by Soviet Russia and it was only rediscovered in the late 80s'
The Daily Laws by Robert Greene emerged from Holiday's suggestion for a 'greatest hits album' approach, combining daily Meditations on power, seduction, mastery, strategy, and human nature
The Daily Drucker by Peter Drucker inspired Holiday's own The Daily Stoic, which approaches its 10-year anniversary and offers one page of Stoic philosophy daily
The Daily Dad provides parenting Meditations that run to 80 entries before restarting, designed as daily guidance for fathers
Single-Sitting Books That Pack Maximum Impact
The War of Art by Steven Pressfield should be read 'again and again and again' - Holiday reads it before starting any creative project
Gift from the Sea by Anne Morrow Lindbergh offers beach vacation reflections on 'modernity, quietness, stillness, writing on youth, age, love, and marriage, peace, solitude, and contentment'
Courage Under Fire by James Stockdale spans just 21 pages, documenting 'a man testing the doctrines of Epictetus in the Hanoi Hilton as a prisoner of war in Vietnam'
Small Things Like These by Claire Keegan runs 114 pages but delivers an ending that 'is gonna fuck you up, but it's very good'
Letter to His Father by Franz Kafka presents a 120-page outpouring to his 'overbearing, imperious, judgmental father' that serves as both parenting guide and resource for those with difficult parents
Creative Inspiration Through Austin Kleon's Trilogy
Steal Like an Artist, Show Your Work, and Keep Going by Austin Kleon form a creativity trilogy with 'lovely little drawings and doodles' for those wanting to 'be more creative, more inspired, do better work, build an audience'
Levels of the Game by John McPhee delivers 150 pages about the Arthur Ashe vs Clark Graebner tennis match - 'one of the greatest sports books ever written' combining 'exquisite piece of sports writing and character study and psychology'
True Stories That Defy Belief
Night of the Grizzlies documents the first grizzly attacks in Glacier National Park history in 1967 - 'When you read about the lead up to it happening, you realize it was inevitable. Like they would have shows where they would feed the bears trash'
The Tiger by John Vaillant stands as 'the best animal versus man's narrative nonfiction book' - 'I just can't tell you how good this story is. And if you haven't read it, I don't know what you're doing with your life'
Marriage at Sea parallels Moby Dick and In the Heart of the Sea, following a couple whose boat is sunk by a whale halfway from London to New Zealand, forcing survival in an inflatable raft while examining their strained marriage
The Stranger in the Woods and The Art Thief by Michael Finkel present two incredible true stories: a man who disappeared into Maine woods for 27 years and an art thief who stole 'literally billions of dollars worth of art from tiny museums all across Europe'
Historical Figures and Literary Legacies
The Black Count reveals the story of 'a Black general in Napoleon's army, who also just happened to be the father of Alexander Dumas' - author of The Three Musketeers and The Count of Monte Cristo
The River of Doubt chronicles Theodore Roosevelt's post-presidency South American expedition 'where he almost dies' and notably 'took a copy of Epictetus with him'
On Tyranny by Timothy Snyder offers 126 pages of political analysis - 'If people could just read these pages, we would be in better shape'
From The Daily Stoic. Get a note like this from every new episode.