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 to answer all of 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.

What this course includes:

  • Private Community Platform —gain access to our latest edition 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: Randall Stutman, Dr. Lisa Barrett, Robert Greene, Jeni Britton Bauer, Annie Duke, Shaka Smart, R.C. Buford, and Major General Dan Caine!
  • 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 guide you with each week's theme. 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.

Throughout these 9 weeks, there will be FIVE DEEP DIVE video session where Ryan Holiday will be joined by one of our surprise prominent leaders as his guest for a one-on-one conversation over topics relevant to the week’s theme, after which Ryan, will take questions from course participants.

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.

**Deep Dive Sessions dates are subject to changes

An author, advisor, and host to what Forbes describes as “the most dynamic leadership podcast out there”.

  • A dedicated mayor known for his leadership, focusing on economic development and community engagement.
  • A awarded military leader, author, and founder known for his insightful perspective on military leadership and professional development.
  • 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.
  • 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.

The Leadership Challenge

One-time payment of $179

  • Daily emails over the next 9 weeks
  • Sit in on 5 Deep Dive sessions with Ryan Holiday and our surprise guests followed by a Q&A at the end
  • Access to our previously recorded Deep Dives with guests that include Annie Duke, RC Buford, and Robert Greene.
  • Access to 2-hours worth of previously recorded Q&A sessions with Ryan Holiday
  • Connect on our new community platform with fellow Stoic students throughout the challenge

Daily Stoic Life

First year for $249

  • Get The Leadership Challenge for FREE
  • All Daily Stoic courses & challenges are included
  • A members-only gift set including a DSL-exclusive medallion and a bound collection of our Stoic wisdom
  • Access to exclusive content on the DSL private hub hosted on our brand new community platform
  • Limited edition hardcover book: The Daily Stoic Meditations

Remember, this course starts September 25th, 2023. Enroll now so you don't miss out!

If you have any questions about The Leadership Course or Daily Stoic Life, please don't hesisate to reach out to courses@dailystoic.com. We are a small team and will answer emails in the order that we receive them. Please allow 1-3 business days for a response.