The Daily Stoic Leadership Challenge: Ancient Wisdom For Modern Leaders


The Daily Stoic Leadership Challenge: Ancient Wisdom For Modern Leaders

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“For I believe a good king is from the outset and by necessity a philosopher, and the philosopher is from the outset a kingly person.” — Musonius Rufus,

What are the traits of good leaders? Who should you model for leadership? How can I be a better leader - of my family, company, team, audience, group of friends, or myself?

We created this course, Ancient Wisdom for the Modern Leader: A Daily Stoic Guide To Leadership, to answer all those questions and more. 

For thousands of years, the Stoics have not only been leaders, but the resource other leaders have turned to for advice and guidance:

  • George Washington quoted Cato to spur and deter his troops. 
  • John Adams declared that “all the ages of the world have not produced a greater statesman and philosopher united in the same character” as Cicero. 
  • Admiral James Stockdale knew Epictetus’ works by heart and recited lines regularly. General James Mattis didn’t enter a battlefield without Marcus Aurelius’ Meditations

What is the cost of not living up to your potential as a leader? Maybe it’s a missed promotion at work, an unnecessary argument at home, a lack of respect from peers. No matter what your situation, it’s always possible to become a better leader. To make situations and people better. 

And the best way to learn leadership is to “go straight to the seat of intelligence” as Marcus Aurelius put it. 

That’s what we did in this course. We designed this 9-week course to mirror the kind of education that produced historically great leaders like Marcus Aurelius. Specifically, we built it around one of the key lessons from Marcus’s own development: the idea that leadership is less a position and more a process. 

Indeed, Marcus worked at it day after day, as you would do when perfecting a skill or getting in shape. You don’t work at it for eight hours a few times a month or go to a week-long intensive retreat every year. No, you work at it diligently and consistently, a little bit each day.

Each week you will learn around a new theme:

  • Week 1: Becoming a Life-Long Student of Leadership
  • Week 2: Mastering Your Emotions
  • Week 3: Dealing With People
  • Week 4: Preparing For and Getting Through Adversity
  • Week 5: Decision Making
  • Week 6: Problem Solving
  • Week 7: Culture
  • Week 8: Leadership Philosophy
  • Week 9: Leadership Challenges

Participants will receive:

  • Private Community Platform —gain access to our latest addition to The Daily Stoic, our very own community platform. Here you'll be able to access the course, fill out journal entries, add to discussion boards, and connect with your fellow students of stoicism. 
  • 9 weeks of custom emails—written by bestselling author Ryan Holiday (63 total emails, over 30,000 words of exclusive content). You will receive an email every day!
  • 5 BRAND NEW Leadership Deep Dives—we've added five new Deep Dive panelists to the course. These Deep Dives are exclusive video sessions with Ryan Holiday and a prominent leader. You'll get the opportunity to sit in on each private Zoom call and listen to Ryan and our leaders discuss the themes of the week!
  • Q&A Sessions—each Deep Dive will be followed by a Q&A with Ryan Holiday to answer your questions and reflect on what you've learned so far in the course. 
  • Course Calendar—a 9-week printable calendar filled with custom illustrations and graphics to help track progress


  • 8 Recorded Leadership Deep Dives—gain access to recorded video sessions with Ryan Holiday and our former prominent leaders from our previous launch of The Leadership Course. These leaders include: RC Buford, Robert Greene, Annie Duke, and more!
  • 4 Recorded Q&A’s—2 hours of recorded video sessions with Ryan Holiday. These session were entirely dedicated to questions from the original course participants.

Each day you will receive an email that helps you take the right steps along that week’s path. Not only have we assembled the best Stoic wisdom on what it takes to become a great leader, we’ve also assembled some of today’s great leaders to be for you what Antoninus was for Marcus. 

AND throughout these 9 weeks, there will be FIVE new video session where Ryan Holiday will be joined by one of our surprise prominent leaders as his guest for a one-on-one conversation about topics relevant to the week’s theme, after which Ryan will take questions from course participants. You can view the recorded conversations from:

  • Mayor G.T. Bynum - A dedicated mayor known for his leadership, focusing on economic development and community engagement.
  • Ryan Hawk - An author, advisor, and host to what Forbes describes as “the most dynamic leadership podcast out there”.
  • LTC Joe Byerly - An awarded military leader, author, and founder known for his insightful perspective on military leadership and professional development.
  • Dorie Clark - A keynote speaker and Wall Street Journal bestselling author that consults Google, Microsoft, the World Bank, and others on personal branding, professional reinvention, and leadership.
  • Mayor Rusty Bailey - A former mayor whose experience at West Point and as an Army Officer guided his solution-focused approach to leading others and impacting his community.

    BONUS CONTENT includes recorded Deep Dive sessions from these prominent leaders:

    • Randall Stutman - Founder of the Admired Leadership Institute
    • Dr. Lisa Barrett - Among the top 1% of the most-cited scientists in the world
    • Robert Greene - Bestselling author and sought-after consultant and strategist
    • Jeni Britton Bauer - Founder and chief creative officer of Jeni’s Splendid Ice Creams
    • Annie Duke - Professional poker player turned bestselling author
    • Shaka Smart - Head men's basketball coach at Marquette University
    • RC Buford - CEO of Spurs Sports & Entertainment
    • Major General Dan Caine - Director of Special Programs and the Department of Defense Special Access Program Central Office (DoD SAPCO), the Pentagon

    Ancient Wisdom for the Modern Leader is a masterclass in leadership with the cadence and rigor of a bootcamp. This is the recorded version of the September 2023 Leadership Challenger. Engage with your fellow students of stoicism through our brand new community platform! Sign up today!