Turning Adversity To Advantage: Ryan Holiday on Why The Obstacle Is The Way

Aug 17, 2015

Ryan Holiday, a bestselling author and philosopher, dives into the transformative power of overcoming adversity. He discusses how stoicism can provide valuable insights in today's fast-paced world. Ryan emphasizes the importance of mastering perception and consciously choosing our responses to life's challenges. He also reflects on the impacts of ego in creativity, advocating for humility to achieve true progress. With his maverick mindset, he argues that personal growth is fueled by a service-oriented approach and authentic connections in our digital age.

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INSIGHT

Stoicism: Practical Philosophy of Life

Stoicism is a practical philosophy focused on how to live well amidst means and adversity.
Key Stoics like Marcus Aurelius and Epictetus addressed universal questions on control, meaning, and virtue.

INSIGHT

Optimism Through Response Control

Stoicism teaches responding positively to what happens is a resilient form of optimism.
It's about mastering perception, choosing your reaction despite uncontrollable events.

ADVICE

Reject Shortcuts, Embrace Hard Work

Avoid seeking shortcuts that promise guaranteed success in creative or uncertain endeavors.
Focus on eliminating distractions to invest fully in meaningful work you enjoy.

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I love talking to smart people. Today's guest is certainly that — and so much more.

Contravening millennial stereotypes, Ryan Holiday is a prolific, rising literary talent. A maverick media strategist. Not to mention a philosopher of sorts — a guy with big ideas often at odds with the status quo.

An autodidact, Ryan dropped out of college at nineteen to apprentice under acclaimed author Robert Greene, author of (among many other great books) The 48 Laws of Power*, later graduating to advise many New York Times bestselling authors like Tim Ferriss and RRP #154 alum Tucker Max, multiplatinum musicians like Linkin Park and startups like Casey Neistat's ( RRP 73 & RRP 144 ) recently launched social media platform Beme.

By the time he was legally allowed to drink (21!) Ryan had already ascended to director of marketing duties at American Apparel, where his iconoclastic campaigns and tactics have been used as case studies by Twitter, YouTube, and Google and written about in places like AdAge, the New York Times, and Fast Company.

Ryan is also the bestselling author of 3 books, including Trust Me I’m Lying* – a highly entertaining and admittedly disturbing first hand look at the machinations behind digital media's dark underbelly — and The Obstacle Is The Way* – a modern and practical reframing of stoicism, the ancient Roman philosophy originated by guys like Marcus Aurelius, Seneca and Epictetus, with a focus on functional applicability of stoic principles for turning modern day obstacles into opportunities and adversity to advantage.

If you think philosophy is purely academic — a useless waste of time reserved for the arrogant intellectual elite — Ryan has a message for you:

think again.

I really love this book. I found it to be eminently practical. An incredibly insightful and utilitarian tool box for navigating crises, strengthening character and maximizing excellence in any situation, irrespective of circumstance.

On RyanHoliday.net and places like Thought Catalog and Observer (where he is editor at large), Ryan writes frequently on a wide variety of business and marketing related subject matters. But it's his fresh and unique take on real life stuff that keeps me coming back.

Enjoy!

Rich