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RyanHoliday.net - Meditations on strategy and life
Blog

How To Be Grateful…For Everything (Even the Tough Stuff)

I’m giving a talk in Seattle on 12/3 as part of the Daily Stoic Live tour—grab seats and come see me! I’ll also be in San Diego on February 5 and Phoenix on February 27. More dates will be announced soon—sign up here and we’ll let you know when I’m coming to your area.

Forgiveness is a lovely idea, it’s been said, it’s actually forgiving someone that’s hard. 

Gratitude is another one of those virtues that’s easy to talk about but hard to practice. 

Today is Thanksgiving in America. It’s a day that we’re supposed to center around giving thanks. The usual candidates come to mind: family, health, and the food in front of us. And rightly so. These are the cornerstones of a fortunate life, and they deserve recognition and appreciation.

It’s easy to be grateful for this stuff…because it doesn’t really ask anything of you. Of course you appreciate what is wonderful. 

But what about the things we didn’t ask for?

The obstacles. The frustrations. The wrong turns. The stresses and difficulties. The people that wronged you. The bad days.

Should we be grateful for those too? 

Yes, those especially.

Especially because they are hard to be grateful for.

Marcus Aurelius talks in Meditations about a period of his life where he felt like there was not much to be grateful for. And indeed, it certainly looked like the gods were out to get him. There was the Antonine plague, which would kill literally millions of people during his reign. There were wars, floods, and famines. He would bury several of his children. He was betrayed by his most trusted general in what amounted to an attempted coup. He did not meet with “the good fortune he deserved,” one ancient historian noted, “as his whole reign was a series of troubles.”

It was during all of this that he told himself that it wasn’t all unfortunate that it happened. In fact, he was fortunate that it happened to him and that he’d survived it. Perhaps someone else wouldn’t have known how to do that or what to do with it. Maybe someone else would not have been so lucky in all the senses of the word. 

In another passage, he gets even more explicit (and I think you could argue, nearly superhuman):

“Convince yourself that everything is the gift of the gods, that things are good and always will be.”

Yes, even the pain and the loss and the haters and the problems. 

In the mornings when I sit down to journal, one of the notebooks I try to write in is a gratitude journal. When I first got it, I would fill the pages with the lineup I mentioned above—my family, my health, my career, the people and things and opportunities in my life that mean a lot to me. But after a time, this came to feel sort of pointless and rather repetitive. I was just going through the motions. I wasn’t doing any work. 

What I began to do was try to find ways to express gratitude, not for the things that are easy to be grateful for, but for what is hard. 

I wanted to practice seeing everything as a gift from the gods, as Marcus Aurelius wrote. Because while it’s easy to count my blessings of the good things in life, it’s much more difficult to see the bad things as gifts, too. But with this practice, I’ve learned to see they can be.

After all, don’t we eventually, inevitably come to understand that those heartbreaking or frustrating things that happened helped make us into who we are?

So I write down, in the moment, that:  

I am grateful for that troublesome client—they helped me develop better boundaries. 

I am grateful for that weather delay and that night spent in the airport—not only did I eventually get home safe, thanks to the pilots, but it gave me time to call my wife and have a nice, meandering conversation. I got some writing done. I got a story out of it. 

I am grateful for that rejection email—it forced me to reevaluate and improve my work.

I am grateful for all the bad things people do and have done—it’s a lesson. It’s an opportunity. It gives me, it gives us, the chance to do good (by the way, we’re raising money to donate 3 million meals to hungry families with Daily Stoic. I’d love for you to help!)

I am grateful for that loss—it reminded me of what truly matters in life. I’m grateful for the time I did get with them and losing them make that clear. 

And on and on.

In writing it, I am forcing myself to think it, express it, and after enough times, believe it. 

Epictetus talked about how every situation has two handles. You can decide to grab onto anger or appreciation, fear or fellowship. You can look at the obstacle or get a little closer and see the opportunity. You can pick up the handle of resentment or of gratitude. 

It’s so easy to miss the fact that Marcus Aurelius could not have been Marcus Aurelius without those unending series of troubles. The difficulties that shaped him, refined him, called greatness out of him. It’s also easy to miss, when we focus on all the bad breaks the guy got, all the tragedies he experienced, that on the whole, Marcus was incredibly lucky. After all, this dude was chosen to be emperor. For next to no reason at all, Hadrian selected a young boy and gifted him unlimited power and wealth and fame. Marcus had a wonderful wife, a stepfather he adored, amazing teachers and he discovered Stoicism, which guided him when he most needed it. For everything that went wrong in his life, for everything that was taken from him, the Gods actually gave him an equal number of gifts. That was the handle he constantly reminded himself to grab.

As Cicero pointed out, “You may say that deaf men miss the pleasure of hearing a lyre-player’s songs. Yes, but they also miss the squeaking of a saw being sharpened, the noise a pig makes when its throat is being cut, the roaring thunder of the sea which prevents other people from sleeping.”

See, there’s a positive to every negative! 

In the chaos and dysfunction of the world, I try to notice where I have been gifted in the latter category than where I have been deprived in the former. After all, I’m still alive. It could always be worse. And I remain confident in my ability to keep going and to turn this into something good. 

So, as you gather with family and friends this Thanksgiving or Christmas or any other celebration you might partake in, appreciate the obvious gifts—the food, the health, the love in the room. But as the moment fades and life returns to its usual pace, amidst the chaos and dysfunction of the world, challenge yourself to make gratitude a daily practice.

Not just for what is easy and joyful, but for what is hard. For what tested you, stretched you, humbled you. 

Whatever 2025 has been for you—however difficult, however painful—be grateful for it. Give thanks for it. Think about how it shaped you. Think about the good that came of it. Think about how it could have been worse. 

Write this gratitude down. 

Say it out loud. 

Everything is a gift. 

It’s a gift you can give yourself.

***

I’m taking the stage in Seattle, WA at Town Hall Seattle NEXT WEEK on December 3rd!​ I would love to see you there (or at one of the other stops coming up in the new year, which you check out at dailystoiclive.com).

Separately…Over at Daily Stoic, we’re raising money for Feeding America. This has become our annual alternative to the disgusting commercialism of Black Friday and Cyber Monday that now dominates Thanksgiving weekend.

Every year since 2019, instead of pushing sales this time of year, we fundraise to provide meals to families experiencing hunger. We donated the first $30,000 and we’d like your help in getting to our goal of $300,000—which would provide over 3 million meals for families across the country! 

Just head over to dailystoic.com/feeding—every dollar provides 10 meals, even a small donation makes a big difference.

November 27, 2025by Ryan Holiday
Blog

You’re Gonna Need This Now More Than Ever

I’m giving a talk in Seattle on 12/3 as part of the Daily Stoic Live tour—grab seats and come see me! I’ll also be in San Diego on February 5 and Phoenix on February 27. More dates will be announced soon—sign up here and we’ll let you know when I’m coming to your area.

I do all my research on physical notecards.

I only read physical books.

If I have to read a research paper or an article, I print it out and go through it with a pen.

The book I am working on now is currently laid out on an old school cork bulletin board covered in push pins. 

There are many easier and more efficient ways to do all this, I’m sure. But I do it the more difficult and low-tech way on purpose. 

That being said, I am not a luddite and I don’t think there’s anything admirable or impressive about being one. 

There is something fundamentally foolish about instinctively resisting and rejecting new technology—and I refuse to do it. 

I have spent many hours trying to figure out AI tools and large language models, seeing where they can make me better, where they might help me. 

In some cases, they have. On our family trip to Greece this summer, I had dozens of places I wanted to visit, scattered across the country with no obvious order or itinerary to route between them. I fed them all to ChatGPT and asked for the most efficient driving route. In thirty seconds, it produced what would have been extraordinarily difficult for me to figure out on my own and ultimately, allowed us to get everything into the trip that we wanted. 

I’ve spent many joyous mornings (and long car rides) with my kids getting it to render ridiculous pictures or tell us stories. We’ve used it to make mockups of things we want to build and had it explain obscure historical concepts in language appropriate for a child. 

But in other cases, my use of AI has reassured me of the value of the old techniques, like when I tried to confirm and source a quote about Abraham Lincoln that I had written down on one of my notecards. ChatGPT first told me it wasn’t about Lincoln at all, instead it was Tolstoy speaking of Dickens…and then when I pushed back, it then tried to tell me it was from Hay and Nicolay, two of Lincoln’s secretaries. When I asked what page I could find this on then—my copy in hand—it then told me that the quote didn’t actually exist. Only when I went back through, page by page, an eight-hundred-page prizewinning biography was I able to confirm that my handwritten note card had in fact been correct. Tolstoy was not involved at all (although he has a great line about Lincoln), it was a 19th century journalist who had known Lincoln well—and the quote was easily findable in many old newspaper databases and public domain books 

More recently, for a project I’m currently working on, I wanted to know how many U.S Naval Academy graduates died in World War II. To its credit, ChatGPT showed its work. First it told me that 6% of Naval Academy graduates who served in World War II died. Then it added that between 1940 and 1945, approximately 7,500 people graduated from the Naval Academy. And from those two numbers, it concluded—very confidently—that about 450 graduates must have died. 

Of course, that looks like thinking. It looks like real reasoning. And I could see the math was correct. The problem is that these numbers actually had nothing to do with each other. The 6% figure applies to everyone from the Academy who actually served in the war. The 7,500 figure is how many people graduated during the war years. But that wasn’t the question, was it? I happened to know from something I’d read that around 54 Academy classes served in World War II so using the wartime graduation count to calculate wartime deaths makes no sense. The two numbers are totally unrelated. Also, why are we estimating at all? If the 6% figure exists, that means that the total is a known figure (and of course it is, the Veteran’s Affairs have to know this statistic). 

In any case, my actual solution was much more low tech. I just found a plaque that listed all the names. 

The point is: If I hadn’t already read deeply in these areas—had I not known roughly what I was looking for—I would have been fooled. I might have written that Tolstoy called Dickens the only real giant of history. If I didn’t have my own brain, I might have been persuaded by what seemed like a math equation but was in fact, nonsense. 

This is what people miss about AI. There’s a lot of talk about why we should be worried about AI making us or certain things obsolete. It’s going to make the humanities obsolete. It’s going to make books, artists, knowledge workers, and expertise itself obsolete. 

But the opposite is true! To use these tools well—to not be used by them—you need exactly the things we’re told are becoming obsolete. A broad liberal arts education. Domain expertise. Critical thinking. A feel for what humans actually sound like. The ability to spot when something seems off. 

Just the other day—while this article was in progress, actually—I got an email from someone pitching me some book for The Daily Stoic podcast? The email address was legitimate. The pitch itself was somewhat compelling. But it was riddled with those AI flourishes that no human I know would ever use. An overuse of words like “crucial,” “unlock,” and “harness.” Phrases like “a tapestry of” and “in today’s fast-paced world.” And those green checkmark emojis.

I’ve used AI enough to know that ChatGPT or Gemini wrote this pitch…which meant I could promptly delete it.

We’re entering a world of AI slop. Not just on social media. It’s not just content creators who are sadly outsourcing their writing and ideating and scripting and pitching to these tools. It’s everywhere. Emails from coworkers. Press releases from corporations. Journalists, marketers, politicians, thought leaders—everywhere you look, people are quietly passing off AI’s “writing” and “thinking” as their own. 

So the essential skill of our time isn’t prompt engineering or coding—it’s having a finely tuned bullshit detector. It’s knowing enough about how humans actually think and write to spot bullshit. It’s having read widely enough to recognize when an answer is hollow, even when it’s dressed up in confident prose. It’s understanding your domain well enough to know what questions to ask and, more importantly, which answers to reject.

We need to know how AI works and what kind of answers it spits out so you don’t get manipulated by people who do. 

We need to have read enough Tolstoy to know when a Tolstoy quote doesn’t sound like Tolstoy. 

We need to know enough history to catch when two figures or events are being linked that never overlapped. 

We need to understand basic statistics well enough to spot when two unrelated numbers are being jammed together just to give you an answer. 

This is the kind of work we have to be willing to do…that we have to choose to do. In the new book, Wisdom Takes Work, I quote Seneca, “No man was ever wise by chance.” We must get it ourselves. We cannot delegate it to someone or something else. There is no technology that can do it for you. There is no app. There is no prompt, no shortcut or summary or step-by-step formula. There is no LLM that can spit it out in thirty seconds.

A little while back, I asked Robert Greene what ​he thought about AI. “I think back to when I was 19-years-old and in college,” Robert said. In a class learning to read and translate classical Greek texts, “They gave us a passage of Thucydides, the hardest writer of all to read in ancient Greek. I had this one paragraph I must have spent ten hours trying to translate…That had an incredible impact on me. It developed character, patience, and discipline that helps me even to this day. What if I had ChatGPT, and I put the passage in there, and it gave me the translation right away? The whole thinking process would have been annihilated right there.”

This is why I do all my research on physical notecards. It is not fast, easy, or efficient. And that is the point. Writing things down by hand forces me to engage and struggle with the material for an extended period of time. It forces me to take my time. To go over things again and again. To be immersed. To be focused, patient, and disciplined. To come to understand things deeply. 

The irony of AI, this cutting-edge technology, is that it makes the oldest skills more valuable than ever. Reading. Thinking. Knowing things. Having taste. Understanding context. Detecting lies or nonsense.

The machines are getting better at sounding smart. 

Which means we need to get better at actually becoming smart.

We need the judgment to separate signal from noise.

We need the discernment to know something seems a little off.

We need the curiosity to not be satisfied with first answers. 

We need patience and discipline.

We need wisdom.

Now more than ever.

 

November 19, 2025by Ryan Holiday
Blog

The Simplest Way To Feel Better In Terrible Times

I’m giving a talk in Seattle on 12/3 as part of the Daily Stoic Live tour—grab seats and come see me! I’ll also be in San Diego on February 5 and Phoenix on February 27. More dates will be announced soon—sign up here and we’ll let you know when I’m coming to your area.

It’s easy to feel disoriented and disillusioned right now.

There’s so much happening in the world, and so much of it feels terrible. There is dysfunction. There is conflict. There is outright lawlessness. There is corruption. There is cruelty.

But there’s a really simple way to feel better. 

I don’t mean turning off the news—though you should definitely do that, as we’ve talked about. I don’t mean taking care of yourself—though that matters too and you should. Go for a run. Meditate. Eat better. Go to therapy. This is all great.

I’m talking about something simpler. Something that works immediately. Something that every wisdom tradition has taught but we keep forgetting:

Do something nice for someone else.

It may seem like a small thing. In fact, it’s everything.

There’s an old story about a boy who comes upon a beach covered in starfish—hundreds, thousands of them washed up on the shore. It’s an appalling, tragic sight. On the verge of tears, he begins throwing them back into the sea, one by one.

“It doesn’t matter,” an adult tells him. “You’ll never even make a dent in this.”

“It matters to this starfish,” the boy says, as he rescues another one.

He’s right. To the person you’re helping, to the person whose burden you are lessening, there is nothing “small” about it. When the Talmud says that he who saves one person saves the world, maybe that’s partly what they meant—you certainly save that person’s whole world.

We get this backwards so often. Despite the expression “all politics is local,” we tend to think big picture before we think little picture. We obsess over grand gestures, complete solutions, systemic change. Meanwhile, there’s suffering right in front of us. A neighbor who needs help. A food bank down the street. A person we could make smile today.

Marcus Aurelius in Meditations talks about a period of his life where he felt like good fortune had abandoned him. And indeed, it certainly looked like it had. There was the Antonine plague, which would kill literally millions of people during his reign. There were wars, floods, and famines. He would bury several of his children. He was betrayed by his most trusted general in what amounted to an attempted coup. He did not meet with “the good fortune he deserved,” one ancient historian noted, “as his whole reign was a series of troubles.”

But instead of throwing himself a pity party, instead of despairing, he rewrote his definition of “good fortune.” It was not getting everything you wanted, he said. No, “true good fortune is what you make for yourself. Good fortune: good character, good intentions, and good actions.

About five years ago, increasingly disgusted by the commercialism of Thanksgiving and Christmas—at least here in the US—I was thinking about just not participating. I hated that every year businesses were expected to offer bigger and bigger sales for Black Friday and Cyber Monday. I hated the clips on the news about people fighting over a deal on a flat screen television. But I decided instead of just writing about it, I would try to do something about it with my own small business. 

So on Black Friday and Cyber Monday, we ran a fundraiser for Feeding America, a nonprofit that works to provide meals to families experiencing hunger, instead. I put in the first $10,000 and we raised another $100,000. The next year we did it again and every year since. Cumulatively, we’ve raised something like $1M or 10,000,000 meals for people in need. 

Did that save the world? Of course not, but it definitely made someone’s world a little better. And you know what else? It made me and my world better too. 

That’s what generosity does, by the way. Yes, it helps the person who receives it but it also changes you into the kind of person who does stuff like that. 

Yes, this world is filled with overwhelming, intractable problems. We face massive “collective action problems,” as the economists call them. Systems that seem too broken to fix. Suffering too vast to address.

And yet.

And yet it falls to each of us to do what we can, where we can, with what we have.

Seneca reminds us that every person we meet is an opportunity for kindness. The elderly neighbor sitting alone on their front porch. The parent in the airport trying to wrangle their toddlers and carry-ons through security. The coworker who seems to be overwhelmed. How are you doing? Do you need anything? Can I help you with that? These opportunities are everywhere, every day. The question is whether we see them. Whether we take them.

Of course, you don’t need to donate to a fundraiser to make a difference. Money isn’t the only currency of generosity. You can give your time. Your energy. Your attention. Your patience. Your kindness.

You can go on hoping or holding your breath until you’re blue in the face, Marcus Aurelius writes in Marcus Aurelius. People are going to keep doing what they do. If you want to feel good, if you want to see good…you’re going to have to do it. 

I’ve been disappointed and appalled at the idea of SNAP benefits being used as political leverage (to almost complete indifference) here in the U.S the last month. So after seeing our local food bank post about the overwhelming demand they were facing, my wife and I walked over and covered a big hole in the budget. In anticipation of everyone moving the announcements of their Black Friday sales up, we thought, hey, let’s move up our food drive too. 

So that’s what we’re doing!

We donated the first $30,000 and I’d love your help in getting to our goal of $300,000—which would provide over 3 million meals for families across the country! (Just head over to dailystoic.com/feeding—every dollar provides 10 meals, even a small donation makes a big difference.) 

The point is: It’s on us.

We don’t control what’s happening globally, but we do control how we act locally. We control who we are. We control what we do. 

If you want to feel better, do better. Do more. 

Give. 

Give enough that it hurts…and see how great you feel. 

Do something nice for someone else.

It makes life better for them.

And I promise—it will make you feel better too.

November 12, 2025by Ryan Holiday
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