Ryan Holiday's Expert Method On How To Build Long-Term Success & Overcome Obstacles

Here are the top 10 key takeaways from Ryan Holiday's conversation with Jay Shetty that will transform how you think about success, parenting, and finding meaning in your life.

1. Success should facilitate what lights you up

Ryan Holiday emphasizes that true success should allow you to do more of what brings you joy and fulfillment. He points out that if your achievements don't create space for the activities that only you can do, it's worth questioning what kind of life you're living. Success shouldn't pull you away from your passions but instead create more opportunities to engage with them.

Many people become trapped in a cycle where their professional accomplishments actually prevent them from engaging in the activities that initially brought them meaning. Holiday suggests that we should regularly ask ourselves: "What are the things that light me up?" Success should be measured by how much time and freedom it gives you to pursue these core passions, not just by external markers like wealth or status.

2. Accomplishments alone don't create meaning

Holiday explicitly states that "just piling accomplishments on top of accomplishments is not the way one finds meaning in their life or their existence." This insight came to him after achieving many of his professional goals and realizing they didn't deliver the fulfillment he expected. The emptiness that followed success taught him that meaning comes from something deeper.

When we achieve what we set out to achieve, we often realize it doesn't transform us in the way we anticipated. Holiday describes experiencing this after writing bestsellers and reaching other career milestones. This recognition led him to value relationships, growth experiences, and making a positive impact more than the accumulation of achievements. True meaning comes from connection, contribution, and living according to one's values.

3. Attach goals to what you can control

The Stoics, Holiday explains, advise attaching your goals only to things within your control. When ambitions are tied to external validation like acceptance, sales numbers, or specific income levels, disappointment becomes likely because these outcomes depend on factors beyond our influence. By focusing on aspects you can control, like consistent effort and improvement, satisfaction becomes more accessible.

Holiday recommends tying your motivation to elements that are entirely up to you, such as enjoying the process, developing skills, or growing as a person. He illustrates this with his own writing practice for The Daily Stoic and Daily Dad, explaining how the meditative routine of daily writing has made him a better person regardless of commercial success. This approach allows you to "win" regardless of external outcomes since the primary reward comes from the process itself.

4. The path to success takes longer than expected

Holiday shares Hofstadter's Law, which states that "it always takes longer than you expect, even when you take this law into account." He emphasizes the importance of patience and persistence in building a successful career. Using his own journey as an example, Holiday notes that he wrote online for six years before earning any money from his writing.

The timeline from his first website in 2005 to his first book in 2012, and then five more years until hitting the New York Times bestseller list, illustrates the extended timeframe of meaningful achievement. Holiday cautions against dramatic gestures like quitting a day job too early, arguing that success requires significant runway and methodical building of both skills and audience. He contrasts this reality with the misleading impression created by viral social media successes.

5. Focus on collecting experiences, not achievements

Holiday and Shetty discuss the value of accumulating diverse experiences rather than pursuing specific achievements. They note how seemingly unrelated experiences often connect in unexpected ways later in life. Our varied experiences become material that shapes our work, perspective, and ability to help others.

Holiday quotes his mentor Robert Greene, who said that "one of the great things about being a writer is that it's all material." This mindset transforms even difficult experiences into valuable learning opportunities. Rather than narrowly focusing on achieving specific goals, both suggest embracing a variety of experiences that build a rich foundation of skills, perspectives, and stories that later combine in unique and valuable ways.

6. See obstacles as opportunities for growth

When discussing the philosophy behind "The Obstacle is the Way," Holiday explains that difficulties and setbacks often force growth that wouldn't otherwise occur. He clarifies that this doesn't mean every obstacle magically transforms into success, but rather that challenges shape us in meaningful ways. The growth that comes from persevering through difficulty becomes valuable in itself.

Holiday emphasizes that this perspective isn't about finding superficial silver linings. Instead, it recognizes that the process of facing and overcoming challenges fundamentally shapes who we become. The difficult experiences we endure provide insights, resilience, and wisdom that later inform our work and relationships in ways we couldn't have anticipated. This transforms our relationship with obstacles from pure frustration to seeing them as catalysts for necessary evolution.

7. Being a parent versus having kids

Holiday makes a crucial distinction between simply "having kids" and choosing to be a parent. Having kids, he explains, is merely the biological or legal aspect, while being a parent involves making children a central part of your life and committing to do it well. This distinction highlights the intentionality required for effective parenting.

Many people, according to Holiday, focus intensely on career success while treating parenting as something they hope to get right by winging it. He describes this as a "tragic skewed sense of priorities" given the importance of the parenting role. True parenting requires the same dedication to improvement that people typically apply to their professional lives, with a commitment to making it a central priority rather than an afterthought.

8. Children need to be accepted, not just directed

Holiday emphasizes the importance of accepting children as they are rather than constantly trying to shape them according to parental expectations. He references Marcus Aurelius's wisdom that "things are not asking to be judged by you" and suggests parents would benefit from "having no opinion" more often about their children's interests and choices.

The fewer opinions parents have about their children's natural inclinations, the better their relationship will be. Holiday reflects on how many parent-child conflicts arise from parents trying to enforce arbitrary rules or cultural norms rather than accepting their child's authentic self. He provides practical examples, like accepting a child's interest in video games rather than imposing a negative judgment about the activity. This acceptance creates space for the relationship to flourish.

9. Focus on the moment, not what it might represent

When making parenting decisions, Holiday warns against the danger of extrapolation—seeing a single incident as predictive of a child's entire future. This tendency causes parents to overreact to normal developmental behaviors by viewing them through the lens of catastrophic future outcomes. Instead, he advocates staying present with what's actually happening in the moment.

Holiday provides an example of deciding not to force his anxious son to attend camp, recognizing that one missed day wouldn't determine his child's future resilience. He suggests asking "Does this actually matter?" to distinguish between genuine concerns and exaggerated fears about what a situation might represent. This approach reduces parental anxiety and allows for more responsive, compassionate decision-making based on the child's actual needs rather than projected futures.

10. Reparent yourself to break negative cycles

For those who didn't receive optimal parenting, Holiday suggests the importance of "reparenting" yourself—addressing the unmet needs of your younger self to prevent passing along dysfunctional patterns. If these wounds remain unexplored, they will unconsciously influence your behavior, especially in parenting and other close relationships.

Holiday emphatically states that "there has to be some point where you go, this stops with me," emphasizing our power to interrupt generational patterns. He references Seneca's idea that while we can't choose our parents, we can choose whose children we would like to be. This perspective liberates us from biological determinism and offers the possibility of creating new, healthier patterns. By consciously addressing our own childhood wounds, we become capable of offering others—especially our children—what we ourselves didn't receive.