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GiveWell has spent the last 18 years researching global health and poverty of alleviation, and it directs funding to the highest impact opportunities they've found. Over 150,000 donors have already trusted GiveWell to direct more than $2.5 billion, including some donations from me. Their evidence suggests that these donations will save over 300,000 lives. And thanks to the donors who choose to sponsor their research, GiveWell doesn't take a cut from your tax deductible donation to their recommended funds. If this is your first gift through goodwill, you can have your donation matched up to $100 by the end year or as long as those matching funds last. To claim your match, go to givewell.com and pick podcast and enter the Daily Stoic at checkout. Make sure they know that you heard about GiveWell from the Daily Stoic. To get your donation matched, givewell.org code Daily Stoic to donate or find out more. Welcome to the weekend edition of the Daily Stoic Podcast. On Sundays, we take a deeper dive into these ancient topics with excerpts from the Stoic texts, audiobooks that we like, hear or recommend here at Daily Stoic, and other long form wisdom that you can chew on on this relaxing weekend. We hope this helps shape your understanding of this philosophy and most importantly, that you're able to apply it to your actual life. Thank you for listening. Hey, it's Ryan. Welcome to another weekend episode of the Daily Stoic Podcast. As you know, I love books, I write books, but mostly I love books. And one of the things I have always tried to do is support other authors. Like I started all of this. All of this is Possible traces back to 2008, 2009 when I started the Reading List newsletter, right? I thought, well, I know having a reading list is good, but who's going to want to hear from a person who hasn't done anything? So I started this newsletter where I just recommended books and that started with 40 or 50 people and now it goes out to hundreds of thousands of people all over the world that it's physically manifest in this bookstore. But that was where I learned newsletters. That's where I learned marketing. That's sort of the beginning of it all for me. Nothing makes me happier than when I hear people tell me they heard about a book through me and they liked that book. So one of the things we've been doing the last couple years on these Sunday episodes is like when we have a podcast guest who's really interesting or has a new book, out we go, hey, would you want us to run an excerpt on the podcast? And we've run all sorts of wonderful ones over the years and I'll link to those in today's show notes. But when we had Jay Heinrichs on the podcast, who'd just written this interesting book about persuasion or self persuasion. It's called Aristotle's Guide to Self. How ancient rhetoric, Taylor Swift, and your own soul can help you change your life, I asked if he would be open to us running the chapter that me and the team liked the most. It's a chapter on habits, and he talks about something called Aristotle's Tortoise method. I won't try to summarize it here. It's worth listening to, which is the whole point of these Sundays episode. Just giving you something to chew on, something to think about. And Jay is a fascinating guy. He's the New York Times bestselling author of thank youk for Arguing and he's a persuasion and conflict consultant and a professor at Middlebury College. He has consulted and taught and done strategy for Kaiser Harvard, the European Speechwriters Association, Southwest Airlines and NASA. And in a previous life he oversaw the remake and staff recruiting for more than a dozen magazines. You can grab signed copies of Jay's latest book, Aristotle's Guide to Self Persuasion from the painted porch. He signed him while he was here. You can check out his full episode of the podcast. Thanks to Penguin Random House Audio for granting us permission to run this excerpt. You can grab the audiobook on Audible or wherever you get your audio books and I hope you like this episode. Enjoy deciding what workout to do or how much weight to use. These are all roadblocks ways that we sort of get in our own way. And that's where today's sponsor comes in. Tonal will pick the perfect weight, track your progress, and suggest what to do next based on your muscle readiness. Taking the guesswork out of getting a great workout. Tonal provides the convenience of a full gym and the guidance of a personal trainer anytime at home with one sleep system designed to reduce your mental load. Tonal is the ultimate strength training system system, helping you focus less on workout planning and more on getting great results. 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Chapter 9 habit adjust your routine Aristotle's Tortoise Method the question is asked whether happiness is to be acquired by learning or by habituation or some other sort of training. Aristotle Nicomachean Ethics if you want to know how Aristotle would describe your character, eat dessert. Preferably the kind of chocolate geological event described on the restaurant menu as a sin. If you were trying to maintain a low sugar diet, Aristotle would not judge you by the decadence of the dessert but by the amount of guilt you felt afterward. If you believed you deserved the treat or simply ate it because you wanted to, he would call you self indulgent. If you felt guilty, if you just couldn't help scarfing down that whole gooey mess, then Aristotle would say you were incontinent. Chances are you are not a self indulgent person. If you were, you might be happily binge watching Too Hot to Handle with a side of Oreos instead of listening to this. But most of us are incontinent to some degree. We know the right things to do, but we succumb to the temptations that surround us. The essential problem, Aristotle said, is a disconnection between our ends and our means. Our animal instincts often wander from our goals, away from what he called the ruling part of ourselves. We wish to be fit, healthy, and productive, yet we make choices that fail to reach those ends. We become happy only when we align our wishes with the means to achieve happiness. So, okay, how on earth do we consistently make the right choices? Aristotle's advice? Don't. You need not act like a saint every moment. The trick is to limit the number of choices we must make. This does not mean avoiding decisions. It means sticking to the prudent ones. We're talking about habits. The subject may seem mundane coming from Aristotle, the man who invented logic and tutored Alexander the Great, but habits are more than a means to fitness and productivity. Aristotle believed that choicelessness is a crucial key to happiness. This might sound positively un American. After all, we enjoy the most self indulgent culture on the planet, where the snack food aisle might as well have been guaranteed somewhere in the country constitution. But you also know that making choices, especially those that fall on the continuum from good for you to avoid the doctor is stressful. To be happy, Aristotle implied, we need to put much of our life on autopilot. This principle made him the first great evangelist of daily habits. I've come across other habit evangelists over the years, but one particularly stands out in my memory. Back when I was young and single, I visited a dentist's office that employed an attractive young hygienist. Halfway through scraping my tartar, she nudged my arm with her hip. Know what I like to do with my dates? I shook my head. I flossed them. She nodded toward the little sink and I spat into it. You floss them? I do. I floss them. If they don't let me, there's no second date, huh? In my dating life, I had met some interesting women but had not yet experienced one with a flossing jones. She resumed cleaning my teeth. You can tell a lot about a person by their gums, she continued. What kind of lives they lead. People lie, but their gums don't. She reached over for the dental floss and broke off a section, lovingly wrapping it around her long fingers. Your gums, she said, squinting into my mouth, aren't bad at all. I bet you don't even bleed. Were we flirting? Did she consider this appointment a sort of dental Advanced Placement, allowing us to skip the relationship's flossing stage? I'll never know. She gave me her number, but I didn't call it. Still, you might say that her gum centric test of a date's virtue counted as Aristotelian. My decent gums revealed a soul capable of at least one steady habit. It so happened that I had been flossing for so many years that it seemed a necessary bedtime ritual. This, in both Aristotle's and the hygienist's terms, was a sign of virtue.
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Unexciting upside of being regular. Humans are already a habitual species. Only cats seem more regular than we are. Unlike cats, we are also extraordinarily adaptable. We can get used to almost anything. What seems ghastly at first eventually becomes natural, even de rigueur. If you had somehow never heard of flossing and someone introduced you to the idea of taking a string and painstakingly forcing it into every tiny gap between your teeth, the chore would seem arduous and a little disgusting. But do it every evening, year after year, and it becomes robotic, even necessary to your identity, a perfect alignment between your daily self and your gum preserving soul. Admittedly, this adaptability can turn life bland when you travel to a new city. Try this ride public transportation to the suburbs and back, just to see what it might feel like for a resident. Some commutes the Seattle ferry to Bainbridge island, with its spectacular view of Mount Rainier, or the Metro north railroad line that follows the beautiful Connecticut coast to New York City seem like miniature cruises. Yet the notable thing about being a guest commuter in these places is how little people pay attention to the ride. This is understandable. Most of the passengers have gotten used to it. But it still seems amazing when you ride the Yellow Line Metro over the Potomac river in Washington, D.C. and see no one look up from their smartphone to gaze at the spectacular views of the monuments. The regular commute takes something special and turns it into the everyday. Our daily meals can take on this same aspect of commuting Give a donut to a 2 year old and you'll see pure passion. Stop by a Dunkin for a Boston cream every morning, on the other hand, and it offers little more indulgent pleasure than a good floss. But adaptability has its upside. Yes, it might extract color from our lives, but it also holds the secret to turning bad habits into good ones. Replace the donut with a protein bar for the first time and it feels like a letdown. You really don't need that early in the morning. But continue for a month to swap protein for cream filling. And never mind what it does to your body. The bar seems just as naturally boring as the doughnut once did. Keep it up for a year and the thought of an early morning donut might seem unnatural, even stomach turning. The hard part is to get to that quotidian stage. Aristotle considered the act of sacrificing instant pleasure for a long term goal to be a form of courage. But do this with your good habits and that courage becomes a kind of super habit all its own. People who are into CrossFit, the competitive workout system, have a Embrace the suck, welcome the pain that leads to gain, and it becomes a habitual part of your identity. Reaching that point, though, requires courage all its own. Aristotle distinguished between the courage to embrace the suck and the habit of avoiding temptations. Resisting passing pleasures is its own virtue. He called it temperance. The temperate person avoids seconds and skips dessert. She drives a sensible car and never goes outside without sunscreen. She does not embrace the suck so much as avoid life's harmful allurements. The courageous person seeks ways to replace bad habits with good ones. The temperate person never acquires bad habits in the first place. At our best, we tend to embody a mix of the two. But temperance and courage make sense only if steady habits and suck embracing lead to happiness. Michael Pollan, author of the Omnivore's Dilemma and a champion of temperate nutrition, once made the mistake of appearing on the NPR show Wait, wait, Don't Tell me. The comedian Paula Poundstone offered a contrarian view of nutrition. One of the things that has made my life worth living is ring dings, she told him. Pollen conceded that an occasional ring ding wouldn't kill her. The ultra processed pastries counted as special occasion foods, he said. What the hell's the matter with you? Poundstone retorted, I said it's what makes my life worth living. You may know a lot about food, but you don't know the first thing about living, buddy. Aristotle might accuse Poundstone of being self indulgent. But if Ring Dings really are her soul's delight, who are we to tell her to switch to fiber? Poundstone is no fool. She undoubtedly knows what Ring Dings do to her gut biota, but she embraces that suck in her pursuit of the meaningful life, which clearly includes snack cakes. Okay, maybe she's just rationalizing the fact that she gives in to temptation and but you could also say the woman shows courage.
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Date: November 9, 2025
Guest Excerpt: Jay Heinrichs (from his book Aristotle’s Guide to Self-Persuasion)
Host: Ryan Holiday
On this weekend episode of The Daily Stoic, Ryan Holiday explores the surprising, nuanced approach Aristotle took to the formation of habits as a key to lasting happiness and self-mastery. Drawing from Jay Heinrichs’ new book, Aristotle's Guide to Self-Persuasion: How Ancient Rhetoric, Taylor Swift, and Your Own Soul Can Help You Change Your Life, the episode presents a chapter focusing on “Aristotle’s Tortoise Method”—a philosophy for habit creation that emphasizes limiting daily decision fatigue and steering life toward meaningful automaticity.
Character Defined by Habits, Not Willpower
Aristotle would not judge you for indulging in a decadent dessert; rather, he’s more interested in whether you feel guilt or contentment afterward. This illustrates his distinction between self-indulgence and incontinence:
Ends vs. Means
The “essential problem,” as Heinrichs puts it, is a disconnection between what we desire and the actions we actually take. Aristotle argues our instincts often derail us from our goals unless we deliberately form habits that align with our higher intentions.
Happiness Through Alignment
True happiness, in Aristotle’s view, is achieved when one’s wishes (ends) harmonize with one’s habits and routines (means).
“Our animal instincts often wander from our goals, away from what he called the ruling part of ourselves.” – Jay Heinrichs (07:58)
“This does not mean avoiding decisions. It means sticking to the prudent ones. We’re talking about habits.” – Jay Heinrichs (09:42)
Habits as a Key to Happiness
Aristotle elevated the formation of habits from mundane routine to one of the primary tools for living a contented, virtuous life.
Modern Cultural Contrast
Heinrichs humorously points out that this flies in the face of American culture, where endless choice and self-indulgence are glorified.
“People lie, but their gums don’t.” – Dental Hygienist, quoted by Jay Heinrichs (11:14)
Adaptability is Both a Blessing and a Curse
Humans (and cats!) are creatures of habit, often acclimating so thoroughly that even the spectacular becomes routine and unremarkable—like commuters ignoring stunning cityscape views.
From Passion to Routine
Heinrichs draws on the example of a child’s ecstatic first donut versus the blandness of a daily Dunkin’ run—habits strip novelty but are also the engine for healthier rituals if harnessed well.
“Adaptability...holds the secret to turning bad habits into good ones.” – Jay Heinrichs (13:37)
‘Embracing the Suck’ vs. Temperance
Aristotle distinguishes between two virtues:
Super Habits
With enough repetition, virtuous habits cease to feel like hardship and become “super habits,” simply part of one’s identity.
Modern Examples
Competitive athletes (like those in CrossFit) are cited as embracing struggle, while others (like the ever-prepared sunscreen wearer) exemplify steady temperance.
“One of the things that has made my life worth living is ring dings.” – Paula Poundstone, cited by Jay Heinrichs (16:25)
On Instinct & Reason:
“Our animal instincts often wander from our goals, away from what he called the ruling part of ourselves.” – Jay Heinrichs (07:58)
On Habits as Freedom:
“Aristotle believed that choicelessness is a crucial key to happiness.” – Jay Heinrichs (09:17)
On Regularity:
“Only cats seem more regular than we are. Unlike cats, we are also extraordinarily adaptable.” – Jay Heinrichs (12:09)
On the Mundanity (and Power) of Habits:
“But do it every evening, year after year, and it becomes robotic, even necessary to your identity…” – Jay Heinrichs (12:53)
On Virtue in Modern Life:
“People lie, but their gums don’t.” – Dental Hygienist, quoted by Jay Heinrichs (11:14)
On Indulgence vs. Living:
“You may know a lot about food, but you don’t know the first thing about living, buddy.” – Paula Poundstone (16:31)
Aristotle’s “surprising habit hack” is the idea that happiness and virtue do not require constant, draining effort—instead, they are best achieved by consciously constructing routines that minimize daily choices and temptations. By allowing healthy behaviors to become automatic, we create space for true happiness and freedom, aligning our everyday actions with our innermost goals.
Jay Heinrichs’ witty storytelling and accessible analogies render Aristotle’s ancient wisdom immediately applicable to modern life, demonstrating that habits—trivial as they may seem—form the very foundation of character and contentment.