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Deep Dive with Ali Abdaal

You’re Not Lazy: How To Make Discipline Easy - Ryan Holiday

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Ryan HolidayguestAli Abdaalhost

Dec 21, 20232h 7mWatch on YouTube

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CHAPTERS

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Chapter summaries

Cold Open and Writing a First Book: Structure and Planning
After a short cold open and a plug for Ali's book, Ryan and Ali revisit the advice Ryan gave three years earlier on starting a book. They discuss knowing your destination, why proposals and forcing functions help, and how plans differ from planning.
- •Ryan says people often don't know where they're heading when they start a book
- •Ali says his final book barely resembled his proposal beyond the word productivity
- •Ryan cites Eisenhower: plans are worthless but planning is everything
- •Ryan thinks most self-published books fail because there's no deadline or approval forcing function
Deadlines, Self-Imposed Constraints, and Flexible Routines
Ryan explains that success removes external constraints, so you have to impose your own, and describes pushing his book a year. He describes moving from rigid routines to flexible practices, with an example of his morning that day.
- •Ryan pushed a book a year and questions whether that was laziness or balance
- •Ali filled his empty pandemic calendar with lessons for structure
- •Ryan cites the final law of the 48 Laws of Power, assume formlessness
- •He now keeps consistent practices (early rising, walking, hard exercise, writing first) rather than a fixed routine
How Kids Change Work and the Value of an Empty Calendar
Ali asks how having children changed Ryan's relationship with work. Ryan describes kids as ballast rather than baggage, and the discussion moves to Ali's burnout and his wish for an empty calendar.
- •Ryan says kids blow up your routine but tether you to reality
- •Lin-Manuel Miranda's story of having to go home after Hamilton shows how a child can protect you from stratospheric success
- •Ali feels burnt out from book promo and wants an empty calendar
- •Ryan says you want a calendar empty of what you don't want to do
Stoicism, Analytics, and What You Can Control
Ryan notices Ali doesn't track his view counts, and Ali explains how stoicism and the dichotomy of control shape his relationship with analytics. They cover audience capture, outsourcing titles and thumbnails, and how success can be as distracting as failure.
- •Ali avoids analytics because views are partly outside his control
- •He fell into audience capture by putting productive in every video title
- •Ryan says once something is published it's out of your hands
- •Ryan warns that basking in success costs a day of productivity
Focus on the Process: Chop Wood, Carry Water
They use the zen proverb chop wood, carry water to focus on process over outcome. Ryan explains how book contracts kept him on the next project regardless of how the last one did, and compares it to comedians and weekly video makers.
- •Before and after enlightenment, you chop wood and carry water
- •Ryan had sold the sequel before The Obstacle Is the Way took off
- •He locked in a four-book series so he wasn't renegotiating his rate
- •Staying in a rhythm of making the next thing insulates you from others' opinions
Trusting the Process and Embracing Bad First Drafts
Ryan argues that it is hard to trust a process you haven't been through, using false fall and roller coaster analogies. Ali and Ryan discuss crappy first drafts, editing, and how mastery means conserving energy.
- •You can only trust a process once you've gone through it
- •Ali no longer minds a crappy first draft after seeing editing transform his book
- •Ryan cites Hemingway that the first draft of everything is shit
- •Mastery brings conservation of energy and less wasted material
Why Obsessing Over Productivity Is Procrastination
Ryan asks why people are obsessed with productivity tools. They agree that tool-hunting and optimizing something you aren't doing is procrastination, and that big-picture questions matter more than gear, though tools can sometimes help build a habit.
- •Ryan says amateurs obsess over tools; tools aren't in his top ten contributors
- •Ali researches running shoes and sauna protocols while barely exercising
- •Ali's tools video outperformed the one with the real substance
- •Ryan says constantly switching systems is the amateur quality; pick one and stick with it
Pick a Few Things and Do the Thing
Using Ali's magician analogy and stories about conferences and a costly mastermind, they argue for repeating a few things rather than chasing novelty. Ryan quotes Seneca on fools always getting ready to start, and says the writing routine is his one constant.
- •Professional magicians perform the same tricks to 100 audiences
- •Ryan: when you beat the casino, leave
- •Seneca: all fools are always getting ready to start
- •Ali keeps experimenting with ways to make videos, while Ryan's writing routine stays essentially unchanged
Does Hard Work Have to Feel Good? Higher Self vs Lower Self
Ali asks Ryan how much he enjoys writing, and Ryan says he enjoys showing up and finishing. Ali explains feel-good productivity through play and choice. Ryan adds that important things are hard and that talent carries obligation, and describes the tension between higher and lower self.
- •Painters like painting; writers like having written
- •Ali's thesis: it needn't feel good, but it's more energizing when it does
- •Lowering the stakes made book writing more enjoyable for Ali
- •Ali's have to becomes get to reframe from his hospital shift
- •Ryan frames the question as higher self versus lower self and asks whether rest is recovery or avoidance
What Motivates Ryan to Write: Meaningful Work and Lasting Good
Ali cites Bertrand Russell and asks why Ryan keeps writing. Ryan says he writes books he finds interesting and that make him better, compares writing to running and flow, and quotes Musonius Rufus on the effort passing but the good enduring.
- •Russell: the first sign of an impending nervous collapse is believing your work is terribly important
- •Ryan expects Justice to be the worst-selling in the virtue series but writes it anyway
- •He seeks self-sufficient standards of success
- •Musonius Rufus: shame from pleasure endures, good from hard effort endures
Fatherhood, Ambition, and Learning by Writing Daily Dad
Ali asks how to balance career and being present for kids. Ryan says working for them is often selfish, then explains why he started Daily Dad, the page-a-day format, and the lessons he's learned about presence, patience, unconditional support and repair.
- •Ryan says claiming you work hard for your kids often cloaks selfishness in selflessness
- •Success is your kids wanting to be with you when you're an adult
- •Writing Daily Stoic made him better, so he did the same with parenting
- •Key parenting lessons: presence, patience, unconditional support, repair over perfection
- •Seneca: we learn as we teach
Relationship Advice and Staying in Shape
Ryan shares that the secret to a long relationship is not to break up, and that parenting also lets you re-parent yourself. He then explains his fitness practice of daily cardio, why it matters, and how he lifts weights occasionally.
- •Ryan has been with his wife for 17 years and says the secret is to not break up
- •Dating apps make it easy to leave rather than endure the sacrifice relationships need
- •Having kids lets you re-parent your inner child
- •He does run, swim or bike daily as practice in keeping his word and for flow
Running Your Own Race: Comparison, Ego, and Expectations
Prompted by Ali's recall of Ryan's real estate comment, Ryan discusses Seneca's euthymia and not comparing yourself to others. He tells the story of James Clear's book outselling all his, and says to be honest about the choices you made and not expect figs in winter.
- •Seneca's euthymia: tranquility is knowing your path and not being distracted by others
- •Jealousy ignores what it's actually like to be the other person
- •Ryan is at peace with Atomic Habits outselling his books
- •Choosing an obscure subject like ancient philosophy means a lower ceiling
- •Don't expect figs in winter
The Second Marathon: Publishing and Marketing a Book
Ali asks for advice ahead of his book launch. Ryan says finishing a book is only the first of two marathons, and recounts how The Obstacle Is the Way missed bestseller lists for years yet sold close to a million copies by lasting.
- •Writing the book is the first marathon; marketing and selling it is the second
- •Don't expect the world to owe your book success
- •Make something without an expiration date and be patient
- •The Obstacle Is the Way hit a bestseller list only in 2019 after nearly a million copies
- •Weekly sales matter less over time and new readers keep discovering it
Saying the Same Ideas and Staying Fresh
Ali relays a listener comment that Ryan says the same things on every podcast. They discuss how most people are encountering ideas for the first time, how creators overestimate their audience's attention, and how repeated ideas stay fresh because life and experience change.
- •Most people consume your content for the first time
- •Creators suffer a little main character energy
- •Ryan can only answer the questions he's asked
- •The Greek idea that we don't step in the same river twice keeps the Daily Stoic fresh
Passive Income and the Freedom of Extra Income Streams
Ryan asks why people are so interested in passive income and whether it exists. Ali describes its appeal, and both discuss how extra income streams create freedom, including a note on how health insurance in the US discourages risk-taking.
- •Ali's mind was blown by the idea of earning while you sleep
- •Ryan is skeptical of the idea that eventually you won't have to do anything
- •Ryan treats other income streams as a trust fund that let him choose creative decisions
- •Ali sees passive income as a Trojan horse for learning to create and capture value
Taking Risks: Asymmetric Upside and Fear Setting
They discuss why quitting a job or school feels irreversible when it isn't, using Ryan's college dropout story and Tim Ferriss's fear setting. They talk about the asymmetry of risk, Jeff Bezos's swing analogy, and how seeing role models makes goals seem attainable.
- •Ryan's college leave was a pause, not a permanent decision
- •Fear setting shows the worst case is rarely as bad or as hard to recover from
- •Ali cites Bezos on entrepreneurship's infinite upside
- •Surrounding yourself intellectually with people who have done it demystifies it
New Year Productivity Advice and Stoic Lessons
Ryan asks what Ali would tell someone who wants to be more productive next year. Ali gives a three-step approach, names overthinking as the habit to drop, and cites the dichotomy of control, while Ryan offers Marcus Aurelius's question: is this essential? The episode closes with thanks and a reflection on the book existing.
- •Ali's three steps: figure out where you want to go, convert goals into weekly actions, put them in the calendar
- •The Odyssey Plan helps with divergent thinking about goals
- •Ali says procrastination is mainly an emotional problem and overthinking holds people back
- •Ali cites the dichotomy of control and control over the process
- •Ryan: eliminate the inessential and do the essential better

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