Dates for the Live Deep Dive Sessions are as follows:

• Sept 30th from 12-1pm CST
• Oct 5th from 2-3pm CST
• Oct 21st from 12-1pm CST
• Oct 28th from 12-1pm CST
• Nov 18th from 12-1pm CST

Can’t attend a Deep Dive session? Don’t worry!

Each live Deep Dive session will be recorded and posted within the course so that you can access it when you’re able to! If you want to ask a question but can’t attend, you can post your questions to the discussion board. That way, if you can’t make the Deep Dive, you’ll still have a chance to have your question answered by Ryan.

Ryan Holiday – The Daily Stoic Leadership Challenge: Ancient Wisdom for Modern Leaders

In a world that demands constant decision-making, unwavering clarity, and moral courage, leadership is no longer about charisma—it’s about character.

The Daily Stoic Leadership Challenge, created by bestselling author and modern Stoicism advocate Ryan Holiday, is a powerful 21-day experience designed to help leaders, aspiring or established, cultivate enduring wisdom from the Stoic tradition. Drawing on the time-tested principles of Marcus Aurelius, Epictetus, and Seneca, this course offers a compelling blend of philosophical insight and actionable daily practice.

It’s not leadership theory—it’s leadership forged in fire. Grounded in discipline, resilience, and virtue, The Daily Stoic Leadership Challenge invites you to lead not louder, but deeper.

What This Leadership Journey Offers

Each day, you’ll be challenged—not with vague reflection, but with focused actions and timeless lessons that sharpen your sense of responsibility, integrity, and clarity under pressure.

Inside the Challenge, You Will Explore:

The Stoic Foundations of Leadership
Internalize the Stoic virtues—wisdom, courage, temperance, and justice—as the bedrock of sustainable influence and ethical decision-making.

Stillness as a Strategic Tool
Discover how inner quiet strengthens outer command. Learn to remain grounded amidst noise, conflict, or chaos.

Discipline in Action
Move beyond motivation. Use deliberate habits and self-restraint to lead with consistency, not just charisma.

Moral Clarity & Decision-Making
Approach leadership dilemmas with timeless principles rather than temporary emotion or external pressure.

Ego Management & Legacy Thinking
Shift from short-term gain to long-term vision. Detach from vanity metrics and refocus on impact, contribution, and service.

Daily Prompts, Tasks & Meditations
This is an experience, not just a course. Each lesson comes with a real-world challenge to embody the teaching and refine your leadership through action.

By the end of 21 days, you won’t just understand what it means to lead well—you’ll have practiced it, lived it, and felt it.

Who This Is For

• Founders, executives, and team leads seeking more clarity, purpose, and restraint in their roles

• Creatives and entrepreneurs facing uncertainty and decision fatigue

• Coaches and professionals who want to model character-driven influence

• Anyone drawn to timeless principles for navigating modern complexity

• Students of philosophy or Stoicism ready to translate theory into real-world discipline

If your goal is not just to lead—but to lead with wisdom, this challenge will reshape how you think, choose, and show up in the world.

About Ryan Holiday

Ryan Holiday is a bestselling author, strategist, and one of the most influential voices in the modern Stoic movement. His books—including The Obstacle Is the Way and The Daily Stoic—have sold millions of copies and reshaped how leaders, athletes, and creatives approach success and adversity. With this challenge, Ryan distills decades of historical insight into a focused, practical journey toward stronger, saner leadership.

Why This Program Stands Out

• Based on ancient principles, adapted for real-world leadership

• Experiential and reflective—you don’t just learn Stoicism, you live it

• Daily micro-practices that create lasting transformation

• Equips you to lead under pressure, not just in ideal conditions

• Taught by one of today’s leading public intellectuals and writers on wisdom and virtue

Lead Yourself First—Then Others Will Follow

The Daily Stoic Leadership Challenge isn’t about becoming someone else. It’s about shedding the noise, silencing ego, and stepping into the kind of leader the world needs now—grounded, clear, resilient, and humble.