Ryan Holiday

Be more philosophical

January 5

If you want to make a positive difference in the world—or simply maintain your sanity—you need to step back. You need to learn how to be more philosophical—which means being more discerning about what you let into your mind and learning how to see the big picture, calmly and with perspective.

~ Ryan Holiday, from This Habit Is Making You Miserable

Just in case you had a negative reaction to the word philosophical: I distinctly recall when I thought “being philosophical” meant telling others how to do things, or at least pontificating about how I do things better. I distinctly recall learning that the word comes from “the love of truth”—and how that struck me deeply. I distinctly recall that the more I learned about philosophy in general, the more I wanted to learn about my philosophy—first discovering that I didn’t have a definitely chosen one, and then beginning to choose.

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Excellence

November 26

What I understand today is that when the Stoics said that there was an opportunity in every obstacle, what they meant was the opportunity to practice virtue. To be a good person despite the bad things that have happened. To do good in the world despite the bad that has befallen you. They were speaking of the idea of arete. Excellence—in all forms.

~ Ryan Holiday

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Life skills

July 12

It struck me that this has become a kind of dividing line between success and failure within my team. Those who haven’t worked out haven’t been able to start the clock or return the ball very quickly. It’s not just my team—it’s a source of frustration that fills the letters and dispatches of just about every great general, admiral, and leader throughout history.

~ Ryan Holiday from, You Can’t Succeed In Life Without This Skill

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I’ve never had the nothingness problem. I’ve always been a starter (and an over-achiever, and an over-thinker.) For me the challenge is always to find ways to create change, without destroying myself and health in the process. Set goals, yes. But also leave no-goals-today space. Have aspirations, yes. But don’t assess my self-worth based on my distance from those aspirations.

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Start the clock

June 16

I sometimes talk about “moving forward” as a default mindset I have. For example, all other things being equal, go to the airport and wait in the terminal, not a home. But in the end, it all boils down to my having deeply apprehended the lesson that the first 90% of everything is vastly easier than the second 90%. So I generally tend to do-now, rather than wait.

It struck me that this has become a kind of dividing line between success and failure within my team. Those who haven’t worked out haven’t been able to start the clock or return the ball very quickly. It’s not just my team—it’s a source of frustration that fills the letters and dispatches of just about every great general, admiral, and leader throughout history.

~ Ryan Holiday from, https://ryanholiday.net/you-cant-succeed-in-life-without-this-skill/

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Unfortunately, in my case, do-now can become a millstone upon which one can be ground to oblivion.

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Discipline

June 2

I’ve recently started reading a book about the importance of having exactly one thing upon which to focus. As with priority, becoming priorities, focusing on exactly one thing soon becomes two, and then three. Suddenly, it’s 23 things. And since the first 90% of any thing is vastly easier than the second 90%, in short order I’m busy, overwhelmed, sprinting in multiple directions. As the Russians say: Chase two rabbits and you’ll catch neither.

Do you want to be the artist who loses their joy for the process, who has strip-mined their soul in such a way that there is nothing left to draw upon? Burn out or fade away—that was the question in Kurt Cobain’s suicide note. How is that even a dilemma?

~ Ryan Holiday from, https://ryanholiday.net/the-indiscipline-of-overwork/

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To answer Holiday’s first question I say emphatically, no! Thus I’m currently well into clearing the decks of multiple focuses. I’m imagining endings for things, major pivots and minor adjustments. There’s a great quote from Epictetus about how any idiot can steer the ship when the wind, sea and weather are good, but in challenging times all it takes is but an instant of distraction to lose the whole ship.

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Just say no

April 21

I like to think that there’s nothing new on my blog. (That’s not a typo.) Rather, this is all just me working with the garage door up. I enjoyed this article from Holiday and it’s wonderful advice, which I need to hear much much more often.

Say no. Own it. Be polite when you can, but own it.

Don’t say maybe. Don’t give a bunch of reasons (which invite an argument). Don’t push it until later.

Say NO.

~ Ryan Holiday from, This is Your Reminder to Say ‘NO’

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My intention here with 7 for Sunday is to give you interesting things to ponder. Sometimes I worry that I might be making your life worse by enticing you with even more rabbit holes than you’d otherwise stumble upon. This item is a sort of penance then, as I hope you have built up your nope-muscle sufficiently to get through 6 more items today.

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Listening

February 23

I’ve now done a lot of recorded conversations for podcasts. I’ve spent a lot of money, and I’ve spent a vast amount of time. I’ve had every imaginable problem. I’ve been stressed out. I’ve literally worked myself to exhaustion and illness.

The line from Zeno was that we were given two ears and one mouth for a reason. That reason? To listen more than we talk.

To learn from people who can teach us. To find something that makes us better.

~ Ryan Holiday from, 27 Things I’ve Learned From 150 Million Podcast Downloads

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The rewards I’ve gotten—the things I’ve learned and the people I’ve met and the experiences I’ve had—have been worth every penny and every moment and every hardship.

The opportunity to speak with hundreds of people (most of whom I’d never have crossed paths with, let alone had a good conversation with) is priceless.

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Small but mighty

February 9, 2024

There’re countless decisions one makes and simply put, the smallest decisions are just as important as the biggest ones. Few are biggest. Innumerable are the smallest. Plus, there’s huge variation in the amount of time I have to consider—or to over-think as the case may be—each choice. Some say choose sooner; Some say delay choosing. Even when we choose to not decide, that’s still a choice.

Every event has two handles, Epictetus said: “one by which it can be carried, and one by which it can’t. If your brother does you wrong, don’t grab it by his wronging, because this is the handle incapable of lifting it. Instead, use the other—that he is your brother, that you were raised together, and then you will have hold of the handle that carries.” Another way to say that is that there are multiple ways to look at every situation, multiple ways to determine how you’re going to react. Some of them are sturdy and some of them are not. Some are kind and resilient, some are not. Which will you choose? Which handle will you grab?

~ Ryan Holiday from, These 14 Small Mindset Shifts Will Change Your Life

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There are a handful of small but mighty ideas that have the ability to often get me off the floor, or out of bed, when all seems pointless. This particular one works quite often. Pick that article apart. Keep what you find useful. Discard the rest.

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Downstream

December 29, 2023

Here’s a hack for improving your life: When you have a significant decision, ask yourself which of these options would Future You most appreciate? For example, “Should I watch this Sci-fi series, or write?” Future Me gets the rewards from good decisions, (the result of small sessions of writing.)

All success is a lagging indicator…all the good stuff (and bad stuff) is downstream from choices made long before.

~ Ryan Holiday from, 36 Lessons on the Way to 36 Years Old

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I was tempted to write my own 52 Lessons On the Way to 52 Years Old, but decided that would not be a gift to my 3-hours later, still only part-way done, self.

The challenge for me, is that the significant decisions go past unnoticed. It doesn’t even occur to me that my automatic urge to begin the next thing that I can imagine as being useful, is actually a choice. If I was able to reign that in, then perhaps I’d do only 11 things, and then relax with that Sci-fi. It doesn’t occur to me in the moments of the day, that better balance would be the choice that’s the real gift to my future self.

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I appreciate your time and attention

December 3, 2023

There are countless instances where I’m reminded that “tomorrow” is not a given. I pay attention to those, and do my best to do it now. To say— Thank you. I appreciate you. I appreciate what you did there. I appreciate you’re taking the time to… You get the gist.

For me, I’ve tried to take from this experience a relatively simple lesson: I tell people how I feel about them when I have the chance.

~ Ryan Holiday, from This Is Why You Can’t Wait Until Later

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Memento mori.

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This right here is just fine

November 13, 2023

There are only two things which seem to work for me: Plain old discipline, and regular, high-intensity exercise. Make a plan. Work the plan. Follow through. I don’t have to finish it all. (That used to be a huge problem too.) Each day, make a plan. And yes, some days the plan is, “today there’s no plan just follow your nose.” Where the mental freedom to believe that’s a good plan is banked during the days with a more plan-looking plan. The exercise acts as a baseline reset.

The result? An inevitable sense of disappointment. A sense that other people are doing better than us. We feel guilt. We feel pressure. We think “Oh, if only I had more money, or a better job, or lived in France where the child care benefits were different, if I had more custody, then things would be good…”

~ Ryan Holiday from, https://ryanholiday.net/all-time-is-quality-time/

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Slowly, daily, my false sense of urgency ratchets up. It’s not healthy, but going out and doing something high intensity resets my personal brand of insanity. Every time I’m in the worst of moods, all I have to do is head out and just start running like I hate myself. (This is rare, but frequent enough that it’s useful to have a strategy ready.) I can go just a couple minutes running like I stole something, and then my crazy-brain starts bargaining… okay, uh, if we can just slow down a bit, I promise to stop acting crazy. I’m pretty sure that’s not the best way to deal with things, but it’s definitely a coping strategy that works well. And the side effects are awesome.

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Ancients’ philosophy

September 1, 2023

Clear communication is a sign of understanding. Understanding the idea to be communicated is necessary, but not sufficient, for clear communication. I think in language (I point this out because I wonder if some people don’t think in language) and that leads me to word-smithing. I’m often searching for just the right word or phrase, and then delighted with myself if I find it. Having such labels for larger ideas is a check-point for myself, internally, that I actually have understanding.

Gregory Hays, one of Marcus Aurelius’s best translators, writes in his introduction to Meditations, “If he had to be identified with a particular school, [Stoicism] is surely the one he would have chosen. Yet I suspect that if asked what it was that he studied, his answer would not have been ‘Stoicism’ but simply ‘philosophy.’”

He then notes that in the ancient world, “philosophy” was not perceived the way it is today. It played a much different role. “It was not merely a subject to write or argue about,” Hays writes, “but one that was expected to provide a ‘design for living’—a set of rules to live one’s life by.”

~ Ryan Holiday from, https://ryanholiday.net/19-rules-for-a-better-life-from-marcus-aurelius/

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Just because I have a label for something—Stoicism in this case—doesn’t mean I label myself as that. The obvious reason is that my label has a lot of other context attached (in my mind) and chances are little to none that any of that context is present for another person. Labels are useful as shorthand, but only if we have the shared understanding.

Life is short. There are ends—things I have done which others can observe. There are the means I’ve chosen to those ends. And then there’s justification. I don’t have the time (nor the inclination) to explain everything—and frankly no one wants to hear that much from me (or from anyone.) I just find it interesting when I discover something I do (or say or think) for which I’ve not really thought through the labels… thought through the justification.

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Who we are

May 1, 2023

The Stoics believed that, in the end, it’s not about what we do, it’s about who we are when we do it. They believed that anything you do well is noble, no matter how humble or impressive, as long as it’s the right thing. That greatness is up to you—it’s what you bring to everything you do.

~ Ryan Holiday from, Discipline is Destiny: 25 Habits That Will Guarantee You Success

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Depending on where you are on your own journey, this could be the greatest 25-item list you’ve ever seen, or it could be 24 items of hogwash. How great is that? For me, it’s the one about being kind to oneself which I need most to let sink in farther. Every absolute rule, every simple guideline, and every pithy virtue becomes problematic when taken to the extreme. It’s almost as if *gasp* life is complicated, and I’m a complex person.

I feel like I’m living in the negative. My life isn’t a passing timeline of “this is nice” punctuated with some stuff that qualifies as work, chores, and maintency-things. Instead, I feel like any time I’m in a span of “this is nice”, I’m on borrowed time. It’s is always “this is nice, but…” followed by something I feel I should be doing just as soon as I’m done loafing. It’s as if my personal demon is relaxing, just out of sight at the bar as I loaf here on the veranda, but still dutifully keeping track of exactly how long I’ve been loafing. I continuously feel like things will go better for me (in the way mobsters would say that) if I choose to stop loafing rather than waiting to see how long I can get away with it. That’s not healthy and thus my awareness of the need for self-kindness.

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Shoes on your feet

April 19, 2023

A degree on your wall means you’re educated as much as shoes on your feet mean you’re walking. It’s a start, but hardly sufficient. […] Just as you can walk plenty well without shoes, you don’t need to step into a classroom to understand the basic, fundamental reality of nature and of our proper role in it. Begin with awareness and reflection. Not just once, but every single second of every single day.

~ Ryan Holiday

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Bitter or better?

March 31, 2023

The Stoics would agree that the world can be ugly and awful and disappointing. They would just remind us that what we control is what we do about this. We control what difference we try to make. We control whether it makes us bitter or makes us better—whether we complain or just get to work.

~ Ryan Holiday from, Why I Pick up Trash at the Beach

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My grasp is failing. My ability to keep track of this, and make a plan for organizing that, is waning. Each year I more quickly become frustrated at unforeseen twists and foreseen complexities. Believing I’m successfully juggling just two things, I’m surprised to discover one has already hit the floor. I’ve moved beyond having a to-do list long enough that many items are below the fold; the regularity of adding items near the top means the items below the fold will never get done. Instead, I have multiple systems piled up in sedimentary fashion. Entire segments of my life, which I thought were integral to my identity, have fallen below the fold.

And every day my life gets better. I wish I’d learned the lesson sooner.

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Take some time to reflect

December 26, 2022

On your deathbed, you would do anything, pay anything for one more ordinary evening. For one more car ride to school with your children. For one more juicy peach. For one more hour on a park bench. Yet here you are, experiencing any number of those things, and rushing through it. Or brushing it off. Or complaining about it because it’s hot or there is traffic or because of some alert that just popped up on your phone. Or planning some special thing in the future as if that’s what will make you happy. You can’t add more at the end of your life…but you can not waste what’s in front of you right now.

~ Ryan Holiday from, 35 Lessons on the Way to 35 Years Old

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This blog started initially as a place for me to post a eulogy, and then it grew to serve many more purposes. It’s now solidly a way for me to reflect, and to work with the garage door up. Discovery, reflection, and efficacy are pretty frickin’ important to me and keeping up with the ‘ol bloggin’ forces me to keep up with daily discovery and reflection. I’ve a bunch of other processes beyond this blog.

It’s a rare post where I both have a point and state it explicitly: Whether you go off to Holiday’s article and follow that thread, follow my links in this email or this post, or my series teaching daily reflection matters not. It only matters that you take time to reflect.

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I have a problem

November 13, 2022

If you find yourself wanting to speed up the reading process on a particular book, you may want to ask yourself, “Is this book any good?”

~ Ryan Holiday from, https://ryanholiday.net/13-reading-strategies/

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Long-time readers will be well aware of my self-diagnosed problem with books. I’ve spent a lot of time reading about reading about books, but this list by Holiday made me think about a few things in a new light. Yes, of course; It’s a post by Holiday so it’s going to have some ancient Stoic philosophers in it. Schopenhauer had a sublime lament about time for reading. Holiday’s strategies won’t help you there. There’ll preserve some of your reading time for, well, more reading. But I still think the hardest part about reading is making it a priority. (Recall: “I don’t have time to…” is bullshit.)

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