Why Are You Surprised? | What Little Wins Can You Find

“In June of 2001, Paul Wolfowitz, then U. S. Deputy Secretary of Defense, addressed the cadets at West Point. While the speech he gave was not itself a historical moment, one remark in it would go down in history. Because it was one of those quotes that history would, in retrospect, make particularly poignant, if not outright ironic.”Ryan explains why you should never be caught unprepared, and reads this week’s meditation from The Daily Stoic Journal, on today’s Daily Stoic Podcast. Sign up for the Daily Stoic email: http://DailyStoic.com/signupFollow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:04Ryan Holiday?

  Welcome to the Daily Stoic Podcast. Each day, we bring you a meditation inspired by the ancient Stoics, illustrated with stories from history, current events, and literature to help you be better at what you do. And at the beginning of the week, we try to do a deeper dive, setting a kind of Stoic intention for the week, something to meditate on, something to think on, something to leave you with, to journal about, whatever it is you happen to be doing. So let's get into it.

• 0:33Ryan Holiday?

  Why are you surprised? In June 2001, Paul Wolfowitz, then the US Deputy Secretary of Defense, addressed the cadets at West Point. While the speech he gave was not itself a historical moment, one remark in it would go down in history because it was one of those quotes that history would, in retrospect, make particularly poignant, if not outright ironic. "Surprise happens so often," Wolfowitz said, "that it's surprising we're still surprised by it." "It was time," he said, "for leaders and soldiers and citizens alike to replace a poverty of expectations within anticipation of the unfamiliar and the unlikely." Just three months later,

• 1:15Ryan Holiday?

  Wolfowitz and most, if not all, of the US government would be stunned when jihadists crashed two planes into the World Trade Center and one into the Pentagon. Wolfowitz himself would come to call the events of 9/11 "a wake-up call" and thus illustrate a timeless piece of Stoic wisdom that saying and knowing are not the same thing, that it's incredibly easy, tempting even, to pay lip service to an idea without being fully able to integrate it into your life and your profession. Remember when Seneca said "the only unforgivable excuse is, 'I did not think it would happen.'" We can nod our head at that. We can acknowledge how right he is, but it matters very little if you do not also, as Epictetus said, embody that philosophy.

• 2:01Ryan Holiday?

  Look at where we are right now. Plenty of people warned about the risk of pandemics. Plenty of smart people noted that a decade-long bull market could not last. Plenty of people spelled out the worst-case scenarios that accompany cronyism, egotistical leaders, and political polarization. Michael Lewis wrote an entire book titled "The Fifth Risk", about what happens when governmental bureaucracies are allowed to operate understaffed, without clear priorities or accountability. Seneca asked you to do a premeditatio melorum. Maybe you even carry a coin reminding you of that in your pocket. And yet, here we are, surprised, unprepared, disappointed.

• 2:43Ryan Holiday?

  We knew, but we didn't know. We talked about it, but we didn't live it. So that's on us, that it never happened again.

• 2:53Ryan Holiday?

  What little wins can you find? Zeno, the Phoenician merchant who founded the Stoic school on the painted porch, the Sto apo kilae of the agora after a shipwreck, said that happiness was a matter of small steps. While the Stoics believed in the perfectibility of human beings, they knew that so much stood in the way of realizing that potential. So they would be skeptical of the so-called epic wins and quantum leaps that our culture obsesses over today. Instead, they would urge you to focus on your daily duties, on making incremental progress. Spend your time this week thinking about small wins. What little gains can be had from this improvement or that one? A decision here, or a decision there?

• 3:34Ryan Holiday?

  Be satisfied with each small step. Keep moving, and don't give up. This is from this week's entry in the Daily Stoic Journal. "366 days of writing and reflection on the art of living", from yours truly. You can find this anywhere books are sold. And of course, we also have signed books in the Daily Stoic store. But we have a quote from Marcus, a quote from Epictetus, and a quote from Zeno today. "Do what your nature demands", Marcus Aurelius says in Meditations 9:29. "Get right to it if it's in your power. Don't look around to see if people will know about it. Don't await the perfection of Plato's Republic, but be satisfied with even the smallest step forward and regard the outcome itself as a small thing." Then Epictetus says, "We don't abandon our pursuits

• 4:19Ryan Holiday?

  because we despair of ever perfecting them." That's Discourses 1.2. Well-being is realized by small steps, Zeno says, according to Diogenes Laertes, but it is no small thing. I was actually just thinking about this this morning. I'm in the middle of writing the book that I'm working on now. And there's a great writing rule, you know, just a couple crappy pages a day. Just put in the time, put in the work. That'll get you to a manuscript, like a draft one. Then you can edit draft one, but you can't edit what doesn't exist. So people, as Epictetus says, who despair of progress because it's not perfection, they never get there.

• 5:03Ryan Holiday?

  But the person who shows up and does work every day gets there. So I was actually writing this in the, in my journal today. I was saying, okay, just show up, put your ass in the chair, do a little work. And as I was writing this in the journal, I was thinking like, put your ass in the chair, be at the desk. And then this story popped in my head because I've been trying to write this chapter about like keeping your workstation clean. That'll be in like two books from now. But the point is, as I was thinking about this, I remembered this little thing that I'd read about Robert Moses in Robert Caro's book, The Power Broker. And I wrote down on my note card and, and I, I just, boom, the chapter just unlocked itself. So my point is, I wasn't even, I wasn't even, my point is, I was thinking about the

• 5:48Ryan Holiday?

  process when the process got to work and solved a problem that I was having trouble solving. I got to my desk, I got to sit down, I pulled the power broker off the shelf, started going through my folded pages and there on about page 280, something was it, the exact story that I needed. In about an hour, I busted out the first draft of this chapter and that was all I have to do for the day. That was all I have to do for today's contribution to the book. Now, a lot of days like this add up. As, as George Washington was fond of saying, many mickles make a muckle. You show up enough days, you do this enough times, gets you to phase one, then you improve, then you go on to phase two, phase three, and finally you get your completed product.

• 6:33Ryan Holiday?

  So today, it's not about sort of big, huge wins. Like this was a minor, minor win. This is maybe three paragraphs of a book that's going to be 60 plus thousand words. It's going to have to go through lots of rounds of editing that won't come out until 2020. Three, probably. And who knows, maybe it'll even get cut from the book. But the point is, I followed the process. I showed up. I did the work. I didn't wait around. I put my ass where I wanted my heart to be, to quote Steven Pressfield. And I made the smallest step forward, as Marcus said. I'm not going to get too high about this. I'm not going to get too excited. I'm going to, as Marcus says, regard it as a small thing.

• 7:16Ryan Holiday?

  But I'm also confident enough, experienced enough, to know that these small things add up. And that's what I'm excited about. And I know that I just have to do this enough times for long enough that I'll eventually get to the other side of where I need to go. And that is true for your problems, for your projects, wherever you are, whatever you're doing. Show up, put your ass in the chair, do the work, let the process guide you to the eventual inevitable accomplishment.

• 7:43Ryan Holiday?

  This idea of premeditatio malorum, a premeditation, of evils, as Seneca called it, I think is one of the most powerful reminders in Stoic philosophy. That's why we make the premeditatio medallion, the challenge coin in the Daily Stoic store. Check that out at store.dailystoic.com. On the front, it's got a picture of a shipwreck, which Seneca sort of prepared himself to experience. He said, "All the lot, all the terms of the human lot should be before our eyes, meaning we should be ready, our eyes should be open. We should not let things catch us by surprise. We should manage our expectations, as Wolfowitz said, and we should not be surprised by history." So check that out, store.dailystoic.com, premeditatio malorum.