Interview with Ryan Holiday

Jay Shetty's recent conversation with best-selling author and modern Stoic philosopher Ryan Holiday offered a profound exploration into the subtle art of living well, challenging conventional notions of success, happiness, and discipline. Far from a simple self-help chat, this interview delved deep into ancient wisdom, providing a practical roadmap for navigating life's inherent complexities without succumbing to perpetual misery.

The Subtle Traps of Pleasure and Ambition

The conversation kicked off by dissecting humanity's innate tendency towards pleasure-seeking and how often we push good things too far. Ryan Holiday, drawing from Epicurean philosophy, illustrated this with a simple truth: "drinking is great, but if you have a hangover the next day was it actually so great?" This highlights how immediate gratification often blinds us to long-term consequences, turning potential pleasure into pain. Our minds, he explained, are remarkably good at playing tricks on us, especially in the moment: "your mind is very good at tricking you just as your mind often tells you like stop you're too tired... your mind also tells you you need this thing you won't regret it it's amazing."

This self-deception extends deeply into ambition, where many, particularly ambitious individuals, tell themselves a dangerous lie: "I will be happy when I accomplish X." This conditional happiness, be it a New York Times bestseller status or a gold medal, becomes a false pretense under which we operate, never allowing us to be truly present or content. Jay Shetty added to this, noting that "a part of us that always believes that we are the exception," thinking we're smarter, wiser, and immune to the pitfalls that ensnare others—a classic manifestation of ego.

Key Insights:

• Immediate pleasure can lead to long-term regret if not balanced with wisdom and self-control.
• The mind is a master deceiver, often placing "blinders" on us that obscure future consequences.
• Conditional happiness tied to external achievements (e.g., career milestones, financial goals) is a common, yet ultimately false, premise.

Key Practices:

• Step back and ask: "What am I going to think about this after I get it?"
• Engage in meditative practices, philosophy, or journaling to "argue with yourself" about the stories you tell yourself.

Redefining Discipline: Beyond Pushing Harder

Jay and Ryan then pivoted to a crucial redefinition of discipline, moving beyond the common perception of constantly pushing oneself to do more. While conventional discipline often involves getting off the couch or resisting unhealthy urges, Ryan introduced a higher level: "discipline about discipline." This involves curbing the very impulse to always do more, especially for those who have already tasted the rewards of relentless effort. He likened it to athletes who overtrain, emphasizing that sustainability, rest, relaxation, and recovery are equally vital. "People think discipline is the I always push myself to do better do more discipline can also be curbing that very impulse," Ryan explained.

Jay Shetty offered a compelling personal example: after years of working "18-hour days" to "break through that first level," he made the conscious, disciplined choice to reclaim his evenings, stopping work at 6 p.m. This wasn't laziness; it was a strategic move that led to increased focus and productivity, allowing for better recuperation. As Ryan clarified, "at the end of the day self-discipline is the ability to have an emotion an instant a feeling to do a thing and then to catch yourself and go is that actually the right thing to do yes or no," drawing on the Stoic concept of "assent"—the choice to agree to a feeling or not.

Key Changes:

• Shift from "always push yourself to do better, do more" to strategically curbing that impulse.
• Prioritize sustainability, rest, and recovery as integral parts of discipline.
• Consciously decide when to stop working, even when the urge to continue is strong.

Key Learnings:

• True self-discipline is the ability to step back, evaluate an impulse, and choose the right course of action, even if it feels counterintuitive.
• The Stoic idea of "assent" empowers us to choose our response to internal feelings and external circumstances.

The Untamed Wilderness of Personal Discipline

The conversation deepened as Jay Shetty brought up the challenging concept of "dad guilt," highlighting how easily professional ambition can overshadow personal responsibilities. Ryan resonated, acknowledging the insidious way we rationalize by saying, "I'm doing this for my family," while often doing it for ourselves. He powerfully stated that "love is spelled T-I-M-E," urging a stark audit of how we allocate our most precious resource. Every "yes" to a professional opportunity, he reminded, is a "no" to something or someone else – often a child or partner.

Ryan emphasized that our true values aren't what we say but what our calendar and bank statements show: "if someone looked at your account you say you put your family first... but then if I looked at your calendar what would it show? ... what would the receipts show? Do you actually value them? Do you put them first?" He cited Marcus Aurelius, who noted how we might be "a better wrestler but not a better forgiver," excelling professionally with clear, quantifiable goals, yet "winging it" in our personal lives. The humility required for personal growth, where we often confront a lack of control compared to our professional domains, is precisely why it's so challenging and yet so vital.

Key Learnings:

• Our true values are reflected in how we spend our time and money, not just in our words.
• Saying "yes" to one thing inherently means saying "no" to another; conscious choice is paramount.
• Personal discipline, especially in family life, demands a different kind of effort and humility than professional pursuits.
• Optimizing professional life doesn't automatically improve personal life, but the reverse is often true.

Building the "Muscle" of Inner Fortitude

Jay highlighted a crucial modern dilemma: being stuck in the "feeling generation," where we chase feelings (like happiness) without understanding the underlying thoughts and actions required. Ryan clarified that "almost all the things you want in life are accidental byproducts of habits processes systems routines." Happiness, as Viktor Frankl noted, "can't be pursued; it must ensue." It's a result of getting the fundamental habits right. For Ryan himself, his prolific writing career isn't from focusing on publishing, but from the daily discipline of writing.

He counterbalances this sedentary intellectual work with daily "hard" physical practices—running, swimming, biking, even cold plunges. For him, the value of a cold plunge isn't just health benefits, but cultivating the "muscle" of forcing himself to do something unpleasant. As he put it, "the muscle for me is is the cranking of the knob of the looking at the coal punch at my house and going it is going to be unpleasant to get in there but I I have the ability to force myself to do that that's the muscle that you want to cultivate." This principle extends to inner stillness, which Jay mentioned as the hardest discipline for "Yes Theory" co-founder Ammar Kandil: sitting with thoughts for just 15 minutes. Pascal's observation from centuries ago still rings true: "All of Humanity's problems stem from her inability to sit quietly in a room alone."

Key Practices:

• Focus on building consistent habits, processes, and routines, understanding that desired outcomes are often their byproducts.
• Cultivate physical disciplines to build mental resilience and the ability to push through discomfort.
• Consciously seek and practice "uncomfortable" personal disciplines, such as sitting in stillness, to strengthen inner fortitude.
• Remember that "the way you do it is by just starting it."

Obstacles as the Path: Redefining Practice

The interview concluded with a powerful reflection on how we approach difficulties. Instead of trying to "destroy a habit that we hate," Ryan proposed a gentler, more effective approach, like "snakes shed their skin"—a natural, organic process of slithering out of the old. Jay's personal experience with hernia surgery, which forced him into unprecedented slowness and mindfulness, became a testament to this. Ryan connected this to the core of Stoicism: "we don't control what happens; we control how we respond to what happens." Our "superpower," he asserted, is our "ability to respond to that to find good in it to be made better for it." He shared the poignant Zen master's dying words, bleeding and frail, yet observing: "This too is practice."

This mindset transforms every unwelcome event—a personal injury, a global pandemic, a career setback—into a profound learning opportunity. He referenced Phil Jackson, who, forced to coach from a chair after back surgery, learned new ways of communicating and leading, ultimately improving. This echoes Marcus Aurelius's timeless wisdom, "the impediment to action advances action. What stands in the way becomes the way," mirroring the Zen expression, "the obstacle is the path."

Key Learnings:

• Rather than fighting unwanted habits, focus on cultivating new ones that naturally allow the old ones to be "shed."
• Life's greatest challenges are often disguised opportunities for growth, teaching us resilience and adaptation.
• Our response to uncontrollable events is our ultimate "superpower."
• Adopting a mindset that "this too is practice" allows us to find meaning and growth even in the most difficult circumstances.

"The impediment to action advances action. What stands in the way becomes the way. The Zen expression is the obstacle is the path." - Ryan Holiday