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Jay Shetty PodcastJay 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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At a glance

WHAT IT’S REALLY ABOUT

Choose process over praise: parenting, patience, and meaningful long-term work

  1. Ryan Holiday and Jay Shetty distinguish between merely having children and consciously choosing to be a parent, emphasizing that parenting should be treated as a central practice rather than something people “wing.”
  2. They discuss setting goals based on what’s controllable—process, effort, and craft—so success doesn’t become dependent on external outcomes like recognition, sales, or status.
  3. Ryan Holiday argues that sustainable fulfillment comes from loving the daily work itself, and he describes how meaningful projects can matter more than the most commercially successful ones.
  4. They describe long-term success as a slow “flywheel” built through years of repetition and patience, warning against expecting instant algorithmic breakthroughs or quitting too early.
  5. Much of the conversation focuses on parenting mindsets—raising readers by matching books to a child’s interests, avoiding comparison traps, staying present in moments without catastrophic extrapolation, and choosing relationship-preserving responses over control.

IDEAS WORTH REMEMBERING

5 ideas

“Having kids” isn’t the same as deciding to “be a parent.”

He contrasts the biological/legal fact of having children with the deliberate choice to make parenting a central, skill-built priority, arguing many people "wing it" compared to how seriously they pursue careers.

If you’re not ready to be changed by parenting, you’re not ready for it.

He says parenting should transform you emotionally and practically, and that resistance to that transformation harms both parent and child; he adds he only understood this fully once he became a parent.

Attach goals to what’s in your control, not external validation.

He argues goals should be rooted in what you control—your effort, craft, and consistency—rather than outcomes like sales, status, or invitations, because those can be derailed by circumstances.

Intrinsic motivation makes the work sustainable; outcomes become “extra.”

He emphasizes loving the “day-to-dayness” of the craft (writing, playing, training) so that success is a bonus rather than the source of meaning, and he uses his own “worst-selling” but most meaningful book as an example of growth-driven work.

Long-term success is built with reps and runway, not a single bold leap.

He pushes back on dramatic “quit and bet it all” narratives, describing years of unpaid, repetitive practice and “flywheel” momentum that requires patience before it spins fast.

WORDS WORTH SAVING

5 quotes

Just piling accomplishments on top of accomplishments is not the way one finds meaning in their life or their existence.

— Ryan Holiday

Success should facilitate you being able to do as much of those things as you want to do.

— Ryan Holiday

You need way more reps than you think that you do.

— Ryan Holiday

The goal of every conversation as a parent is to get to have the next conversation.

— Ryan Holiday

If you didn't get it, you're never gonna get it.

— Ryan Holiday

Read the available transcript
Being a parent vs having kidsStoic goal-setting and controlIntrinsic motivation and loving the craftPatience, runway, and the “flywheel”Obstacles as growth and “material”Raising readers and meeting kids where they areComparison traps, dad guilt, and saying no

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SPEAKERS

  • Ryan Holiday

    guest

    Author and Stoicism writer best known for The Obstacle Is the Way and for running The Daily Stoic.

  • Jay Shetty

    host

    Podcast host and author; former monk and ex-Accenture consultant known for On Purpose with Jay Shetty.

High quality AI-generated summary created from speaker-labeled transcript.

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