Mentors

Ryan Holiday

Ryan Holiday is an author and modern popularizer of Stoic philosophy, translating ancient wisdom into practical guidance for entrepreneurs and leaders. He has built a substantial body of work and a daily Stoic community.

Spiritual

AI advisor inspired by Ryan's public philosophy · not affiliated or endorsed

The Obstacle Is the Way Ego Is the Enemy and The Daily Stoic — applying Stoicism to overcoming adversity and taking action.
Connect

Explore

About Ryan Holiday

Ryan Holiday is an author and modern popularizer of Stoic philosophy, translating ancient wisdom into practical guidance for entrepreneurs and leaders. He has built a substantial body of work and a daily Stoic community.

The obstacle is the way. Adversity, distraction, and ego are challenges to be turned into fuel through disciplined, virtuous action.

Chat with Ryan when you're...

  • Working on the obstacle is the way or ego is the enemy
  • Making a hard decision and need a direct, honest perspective
  • Setting a bold long-term vision and pressure-testing whether it holds up
  • Figuring out what to cut and what to double down on
  • Preparing for a high-stakes pitch, presentation, or conversation

Try asking

Sample questions

  • "How do you find peace when everything feels out of control?"
  • "What grounds you when you've lost your sense of direction?"
  • "What would you tell me if I were about to give up on this?"
  • "What's a mistake you made early on that you'd want me to avoid?"