Ryan Holiday is wise beyond his years and a talented writer and media strategist. His books wrestle with two main topics: Stoicism and media. We have just done a complete, and very stoic, deep dive on his stoic work for the Moonshots Podcast(part 1, part 2, part 3, part 4). I highly recommend his books, but given they span various substantial topics, I recommend reading Ryan Holiday books in this order.

The best place to start with Ryan Holiday

A challenging starting point for the stoic works of Ryan Holiday is Ego is the Enemy: The Fight to Master, Our Greatest Opponent. This book is a well-needed smack in the face. The truth is that the world does not revolve around us. An inflated sense of self-importance holds us back from being the best version of ourselves.

I found this to be the perfect book to wipe the slate clean and embark on new practices to improve myself. After confronting us with some hard truths about our ego, Holiday shares classic philosophy in modern and related advice. Here is a selection of a few essential practices for defeating our egos from the Holiday’s book

1. Be a curious and humble student.

2. Be a team player

3. Trust and respect others.

In this world of social media, virtue signaling, and fakeness, I found this quote from Holiday to hit the spot.

“When we remove ego, we’re left with what is real. What replaces ego is humility, yes—but rock-hard humility and confidence. Whereas the ego is artificial, this type of confidence can hold weight. Ego is stolen. Confidence is earned. The ego is self-anointed, its swagger is artifice. One is girding yourself, the other gaslighting. It’s the difference between potent and poisonous.”
― Ryan Holiday, Ego Is the Enemy

Here are two classic Moonshots reviews of the book that captures the spirit of the book.

"This is a book I want every athlete, aspiring leader, entrepreneur, thinker, and doer to read. Ryan Holiday is one of the most promising young writers of his generation."
— George Raveling, Hall of Fame Basketball coach, Nike’s Director of International Basketball

"Removing the ego is a daily struggle, but it feels a little easier after reading this."
— Martellus Bennett, NFL Tight End, Super Bowl Champion

The next part of our Ryan Holiday adventure

Now that we embrace a learner’s mindset, a prevalent Moonshot mindset, we are ready to face challenges. That’s why I next recommend reading The Obstacle is the Way: The Ancient Art of Turning Adversity to Advantage.

This book resonated with me so much. I loved the stories of hardship that Holiday shares in the book. From the Ancients to President John F Kennedy - they were all instructive lessons.

We often give up when we face adversity or when things just don’t go our way. But it is those who persevere succeed. So I found these ideas about mindset and perception from the book to be just what I need to remember when things a going sideways; 

1. Problems are opportunities

2. Embrace discomfort, it leads to growth.

3. Focus on what we control

“It’s how we see and understand what occurs around us—and what we decide those events will mean. Our perceptions can be a source of strength or of great weakness. If we are emotional, subjective, and short-sighted, we only add to our troubles. To prevent becoming overwhelmed by the world around us, we must, as the ancients practiced, learn how to limit our passions and their control over our lives.

It takes skill and discipline to bat away the pests of bad perceptions, to separate reliable signals from deceptive ones, to filter out prejudice, expectation, and fear. But it’s worth it, for what’s left is truth. While others are excited or afraid, we will remain calm and imperturbable. We will see things simply and straightforwardly, as they truly are—neither good nor bad. This will be an incredible advantage for us in the fight against obstacles.”
— Ryan Holiday, The Obstacle is the Way: The Ancient Art of Turning Adversity to Advantage

Roger Dooley said it best in his Forbes article, when reviewing the bool.

“A short, inspiring book packed with stories describing how famous leaders and entrepreneurs achieved success by pragmatic action in the face of overwhelming odds.”
— Roger Dooley, Forbes

The Third step is stillness. 

It might be tempting to read Stillness is the Key: An Ancient Strategy for Modern Life first. It’s a celebration of reflection, mindfulness and, not surprisingly, stillness. 

However, I found to be instructional when I was facing a challenge at work. I was 100% consumed by a large workload amid the COVID chaos. This book gave me the tools to calm my mind in a sea of turbulence. 

Finding control and being focussed are two subjects that we study a great deal at Moonshots. This book brings these two practices front and centre, and there’s plenty of pragmatic advice for readers who are looking to be more in control and peaceful in their lives. The mindsets that resonated with me were;

1. Slow down in times of trouble.

2. Use a journal to reflect.

3. Transform routines into rituals.

4. Stop regretting yesterday.

5. Stop worrying about tomorrow.

6. Be in the here and now.

There were two epic quotes from the book that really made me chuckle.

“All of humanity’s problems,” Blaise Pascal said in 1654, “stem from man’s inability to sit quietly in a room alone.”
― Ryan Holiday, Stillness is the Key

“Martin Luther King Jr. observed that there was a violent civil war raging within each and every person—between our good and bad impulses, between our ambitions and our principles, between what we can be and how hard it is to actually get there.”
― Ryan Holiday, Stillness is the Key

The everlastING practice with Ryan Holiday.

I would read this Ryan Holiday book last: The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living.

Daily Stoic is the book by Ryan Holiday that you’ll open every single day. It’s a page-a-day format makes a tool, a weapon even, for the struggle to be the best version of ourselves.

The book is structure around the days and months of the calendar. It guides there reader through key Moonshot mindsets such as perception, action, and will.

Here are some themes and goodies from the Daily Stoic that I thoroughly enjoy;

1. Focus on what we can change and what we can’t.

2. Make all decisions with poise and purpose.

3. Accept fate and what nature has in store for us.

As a final embrace of all things stoic, here’s a great review quote about the Daily Stoic book. 

'A generous gift of guidance on modern living culled from a canon of wisdom hatched long ago.' 
― Maria Popova, editor of Brain Pickings.