Ryan Holiday – Daily Stoic – Slay Your Stress: A Daily Stoic 20 Day Challenge (2022)

Inspired by these last few difficult years, we’ve assembled the best Stoic wisdom into an actionable course—Slay Your Stress: A Daily Stoic Challenge. So far it’s been an incredible success—we heard from more people after its debut in 2020 than almost anything we’ve produced. Well, with the current state of the world we decided there wasn’t a better time to enhance this course and bring it back.

The new 20-day challenge, which includes 6 new days, is designed to equip you with the strategies and mindsets needed to reclaim your life from the negative effects of stress and anxiety.

How much more enjoyable would your days be without the constant dread of stress looming over you? How much more productive would you be without spending hours per day indulging in imagined troubles? How much better would your relationships be?

Stoics have been trying to domesticate feelings of anxiety and stress for two millennia. They didn’t always win, but they managed to make progress, the same kind of progress you want to make. We’ve designed this course to help you reclaim your life from stress and anxiety. In this 20-day challenge, we will lay out the most actionable ways to manage those counterproductive emotions, backed by thousands of years of research and practice.

You’ll learn to:

• Seize what is in your control and ignore the rest.
• Make your to-do list more manageable
• Stop sweating the small stuff
• Get out of your own head
• Gain perspective by zooming out
• Wash off the mud of life

And much, much more…

Additionally, there will be 3 recorded Q&A sessions with Ryan Holiday, the bestselling author whose books about Stoic philosophy have sold more than 5 million copies in over 30 languages. Along with his writing, Ryan owns a small-town bookstore he opened during the pandemic, travels around the globe to teach people and organizations how to apply Stoicism to their actual lives, and has two young sons. Like the ancient Stoics whose teachings and lived experiences we will be drawing from, Ryan has a lot of experience using Stoicism to domesticate feelings of anxiety and stress.

How many hours per day do you lose to stress and anxiety? That’s what the Stoics wanted to ask. Now multiply that by 365. Now multiply that by the rest of your life. Imagine what you could do with those hours, those weeks and months, those years.

Don’t you think it’s time you did something about this?

Ryan Holiday – Slay Your Stress: A Daily Stoic 20-Day Challenge (2022)

A Practical Stoic Reset for the Modern Mind

In a world overflowing with noise, urgency, and endless digital tension, the ability to remain calm is not just rare—it’s revolutionary.

Slay Your Stress, created by bestselling author Ryan Holiday and the team behind The Daily Stoic, is a 20-day guided challenge designed to help you confront stress with clarity, resilience, and ancient wisdom. This isn’t about suppressing what you feel—it’s about learning to respond differently, with inner steadiness and perspective grounded in Stoic principles.

Through daily insights, actionable prompts, and timeless quotes, you’ll learn how to stop reacting—and start reclaiming peace from within.

What You’ll Experience Over 20 Days

This challenge isn’t another crash course in positivity or empty affirmations. It’s a structured, day-by-day journey that weaves together philosophy, reflection, and self-mastery—crafted to help you navigate modern stressors through a timeless lens.

Inside the Program:

Stoic Fundamentals for Everyday Calm
Gain tools to dismantle anxiety, overthinking, and emotional spirals using the wisdom of Seneca, Epictetus, and Marcus Aurelius—without needing to be a philosopher.

Daily Video Guidance from Ryan Holiday
Receive short, powerful lessons delivered by Ryan himself—each one designed to inspire thought and anchor your mindset through daily life chaos.

Journaling and Self-Inquiry Prompts
Engage in purposeful reflection that sharpens focus and allows you to observe without judgment, rather than spiral in overwhelm.

Simple, Tactical Practices
Implement small yet transformative Stoic habits—like voluntary discomfort, value-based prioritization, and strategic silence.

Progressive Layering
Each day builds on the last, creating a mental architecture of calm that becomes stronger and more accessible as you move forward.

This is philosophy in motion—not abstract theory, but grounded practice.

Who This Challenge Is For

• Professionals dealing with burnout, pressure, or decision fatigue

• Individuals seeking clarity and control in emotionally reactive environments

• People new to Stoicism looking for a structured, daily approach

• Longtime followers of The Daily Stoic seeking practical implementation

• Anyone who wants to respond, not react—and reclaim command of their inner state

Whether you’re drowning in to-do lists or fighting emotional reactivity, this challenge offers a way out—and a way through.

About Ryan Holiday

Ryan Holiday is one of the most influential voices in the modern Stoic movement. With bestselling titles like The Obstacle Is the Way and Stillness Is the Key, he brings ancient philosophy into the center of contemporary life. Ryan’s clarity, honesty, and ability to translate timeless ideas into daily habits have guided millions to think better, feel lighter, and live more intentionally.

Why Slay Your Stress Works

• Action-based Stoicism tailored for 21st-century chaos

• Daily doses of perspective, delivered in Ryan’s grounded voice

• Combines timeless insight with concrete strategy

• No fluff—just clarity, courage, and calm

• Designed for real life, not theoretical ideals

Calm Is a Skill—This Challenge Will Help You Build It

Slay Your Stress is not about being unaffected. It’s about becoming unshaken.