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Jay Shetty Podcast

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

Discover the hard-won secrets to building lasting success and conquering life's obstacles. Ryan Holiday, bestselling author and founder of The Daily Stoic, strips away the myths of achievement to reveal what you TRULY need to do to succeed.

Ryan HolidayguestJay Shettyhost

Sep 16, 20241h 21mWatch on YouTube

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CHAPTERS

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Chapter summaries

Meaningful success: make time for what only you can do
Ryan Holiday opens by challenging the idea that stacking accomplishments equals meaning. He argues that success should create space for the work and activities that genuinely light you up, otherwise the “success” is hollow.
- •Success should enable more time for the things that energize you
- •Meaning isn’t found by piling achievement on top of achievement
- •If you don’t have time for the unique work only you can do, something is off
- •A turning point idea is deciding “this stops with me” rather than endlessly chasing more
Choosing to be a parent vs. merely having kids
Jay Shetty shares how career changes reshaped his and his wife’s expectations about timing and readiness for children. Ryan distinguishes between the biological/legal act of having kids and the deliberate commitment to being a parent.
- •Jay frames the question as readiness for the life change of parenting, not just timing
- •Ryan argues many people “have kids” without making parenting a central commitment
- •He critiques ‘winging it’ in parenting compared with intentionality in careers
- •Jay links the idea to a verse about taking responsibility for enlightening a child
Parenthood should change you: openness, readiness, and emotional shift
Ryan says the key prerequisite is being ready for parenting to change you. He reflects that he only learned this through experience and that earlier career achievements helped him see that external wins don’t provide lasting meaning.
- •Parenting should change you emotionally and spiritually, not just practically
- •Resisting change harms both parent and child, Ryan says
- •Ryan describes achievement letdowns: hitting goals doesn’t ‘fix’ what you thought it would
- •He emphasizes disconnecting self-worth from external markers of success
Setting goals you control: intrinsic practice over external outcomes
Ryan explains a Stoic approach: attach goals to what’s within your control rather than to status, money, or public approval. Jay shares how he oriented goals around growth, service, and community rather than fame or scale.
- •Ryan: tie ambition to controllables—practice, craft, effort—rather than outcomes
- •He critiques arbitrary “one-up” goals based on other people’s numbers
- •Jay: choose goals based on the growth required, not the trophy
- •Jay shares a story about performing for community rather than chasing accolades
Love the craft: pride in the work even when it’s not the biggest hit
Ryan uses his book "Conspiracy" as an example of work he’s most proud of despite it being his worst-selling. He argues that if you love the day-to-day craft, then success becomes a bonus rather than the reason you do it.
- •Ryan describes being most proud of his most challenging, growth-producing project
- •He stresses enjoying the “playing” part of the work—process details, not just wins
- •External results can be derailed by uncontrollable events, so process has to satisfy
- •Ryan notes his evolution from caring mostly about performance to mostly about the work
Stuck in a job you hate: start small, build runway, and don’t romanticize quitting
Jay describes finding ways to align his corporate job with his interests by creating “idea days.” Ryan rejects the notion that you must blow up your life to pursue a dream, emphasizing small starts, audience feedback, and long timelines.
- •Jay shares how he made corporate life tolerable by building curiosity-focused projects
- •Ryan says you can build alongside a job and use leverage if you’re good at your role
- •He warns against quitting before you’ve shipped small work and learned from feedback
- •Ryan describes years of publishing online before earning money and the need for runway
Patience and the flywheel: why timing matters and “later” can be better
Ryan and Jay discuss how long success often takes and how early breakthroughs can be misleading. Ryan argues you often aren’t ready when you think you are, and that backloaded success can be healthier if it arrives after skill and capacity are built.
- •Ryan introduces the flywheel idea: slow turns before momentum builds
- •He reflects on media opportunities arriving over a decade later than expected
- •Ryan argues getting big opportunities too early can leave you unprepared to deliver
- •He emphasizes discipline and patience, including in readiness for parenting
Accumulating experiences: everything becomes material for your best future work
Ryan suggests that daily effort may be preparation for an unseen future moment where ‘the man and the moment meet.’ Jay adds that collecting experiences, skills, and relationships often only makes sense in hindsight.
- •Ryan imagines his work as preparation for an idea or moment he can’t yet foresee
- •He references the value of reps and readiness when opportunity arrives
- •Jay describes how different life phases combined into his current career
- •Ryan shares a mentor’s view that for a writer, everything that happens is material
Planting trees for the future: measuring life by what you give and build
The conversation turns to long-term contribution and legacy—benefiting people you’ll never meet. Ryan asks what you are planting and giving away, suggesting that service to the future is a meaningful way to evaluate a life.
- •Jay describes work done for significance beyond one’s lifetime
- •Ryan reflects on benefiting from past investments others made for the future
- •He asks what difference you’re making and what you’re contributing forward
- •They discuss how works can be rediscovered and valued later
Raise a reader: meet kids where they are and make reading personally relevant
Jay asks about a chapter titled “Raise a Reader” and shares how nonfiction and biographies sparked his love of reading. Ryan argues that elitism about “real literature” blocks people from becoming readers, and that parents should match books to a child’s interests.
- •Jay shares that biographies and autobiographies turned him into a reader
- •Ryan critiques snootiness about what counts as reading or literature
- •He describes reading Minecraft-related books with his son to build the habit
- •Ryan argues interest and context improve comprehension and motivation
Read to solve real problems: humility, curiosity, and learning from others’ mistakes
Jay explains he recommends books based on what someone is struggling with. Ryan emphasizes that nearly every human problem has been explored before and that refusing to learn from existing knowledge is inefficient and sometimes irresponsible.
- •Jay frames reading as problem-solving: start with what you’re struggling with
- •Ryan says most problems aren’t new; people have written about them for ages
- •He emphasizes humility: learning requires admitting you don’t already know
- •Ryan describes modeling curiosity with kids by looking things up together
Parenting tension: protect vs. prepare—and prioritizing the relationship
Ryan explains the challenge of sparing kids from suffering while not making them fragile. He shares a guiding idea: the goal of each parent conversation is to earn the next one, keeping doors open so kids come to you when it matters.
- •Ryan: aim for a life that’s “good but not easy” for kids
- •He warns against “snowplow parenting” that removes all obstacles
- •Ryan shares his own experience of needing parental support after a risky choice
- •He emphasizes keeping communication open as the foundation of future trust
Unconditional support and fewer opinions: letting kids be who they are
Jay reflects on his parents’ steady presence even when they didn’t fully approve of his choices. Ryan argues conditional support harms kids, and suggests a practical starting point: have fewer opinions about who your child should be.
- •Jay contrasts rooting vs. neutral non-blocking support from parents
- •Ryan warns about chasing parental approval and the risks of living for recognition
- •He cites the value of “having no opinion” as a way to support children
- •Ryan argues many parent-child conflicts are about enforcing norms over relationship
Re-parenting yourself and stopping cycles: choosing a different path for your kids
Ryan says that if you didn’t get what you needed from your parents, you may never get it—and continuing to chase it can distort adult life. He describes “re-parenting” the inner child, and shares a story about deciding not to force his anxious child to attend camp.
- •Ryan argues chasing missing parental validation can become a lifelong trap
- •He describes re-parenting: giving your younger self what was missing, now
- •Ryan shares the camp drop-off moment as a conscious choice to break old patterns
- •He reframes discipline decisions by asking what’s truly at stake in the moment
Comparison, dad guilt, and fear: trade-offs, saying no, and managing your temper
Ryan discusses how parenting invites comparison from the start and can create unnecessary anxiety. He addresses dad guilt, arguing that time and presence matter deeply, and closes by describing temper management, stepping back, and apologizing when you lose control.
- •Ryan critiques the comparison game (percentiles, milestones) and tuning out noise
- •He reframes dad guilt as a sign of caring, but not necessarily helpful by itself
- •Ryan emphasizes trade-offs: your calendar reveals priorities, and “no” protects family time
- •He names temper as a key fear, and describes stepping away, owning mistakes, and apologizing

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