The Obstacle Is the Way

Reviewed by Diario de un Inversor · UpdatedJune 13, 2026

Our review

Ryan Holiday published «The Obstacle Is the Way» in 2014, before his Stoic trilogy became a publishing phenomenon. The book draws on an idea from Marcus Aurelius: impediments to action become, with the right perspective, the very path forward. Holiday structures the argument around three Stoic disciplines — perception, action, and will — and illustrates them with historical cases ranging from Rockefeller to Amelia Earhart, including presidents and generals. For the investor, the most useful framework is that of perception: Holiday argues that the difference between those who capitalise on a crisis and those who suffer it is, to a large extent, the ability to see the obstacle as information rather than catastrophe. The book's weakness is shared with the entire trilogy: historical cases are selected to confirm the thesis, not to test it. The Stoicism Holiday presents is also a Stoicism optimised for modern Western success, considerably softened compared to its classical sources. Even so, as a cognitive reframing tool, the book offers real value.

Key takeaways

• Perceiving an obstacle as a threat or as an opportunity is, to a large extent, a choice that can be trained.
• Disciplined action in the face of adversity — persistent but flexible in methods — is the Stoic response to failure.
• Will, the third Stoic discipline, is the ability to accept what cannot be changed without that destroying the determination to act on what can.
• Investors who remain calm during market corrections and act from analysis rather than fear have historically performed better over the long term.

Fact

The book was published in 2014 and was adopted by several NFL teams as required reading for their players and coaches, which contributed to its wide dissemination.