Always Try To Do It The Hard Way

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1:05Welcome 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 here 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.

1:43Hey, it's Ryan. Welcome to a Sunday episode of The Daily Stoic Pod. I'm going to tell you a little story. This is an article I wrote, but I'm going to tell it to you so you don't have to read it. But basically, I was coasting on fumes when this question came in. And because I was tired, I don't think I got the answer exactly right. Now, to be fair, I was 90 or so minutes into being on stage for my talk in Sydney, the ones I've been telling you about. And the guy asked me, as anyone can ask me the question in any of the talks, I do hope to see you in London, Toronto, Vancouver, where else am I going to be?

2:23Rotterdam, Dublin. Anyways, ryanholiday.net. That's not what this is about, but I do hope you come see me as you'll understand a little bit better as I go on. Basically, the guy said something like, if obstacles make us better, should we seek them out or create them for our kids? So I was a smidge pride. I'd just been on stage for quite some time. And I think I said something like, look, life is full of obstacles already. So I'm not sure we need to go around creating new ones. But it's strange that I said this because I was in the middle of doing the exact opposite. And it was Chris Williamson's fault.

3:00I've been on his podcast a bunch of times. He moved to Austin actually from London sometime during the pandemic. So this is the first time we'd ever done it in person. He was telling me back in May, you can listen to that episode, I'll link to it, that he'd just gotten back from his own speaking tour. And I was like, you know, I was curious, I was starting to put my talk together. And I was saying, you know, what kind of presentation did you do? Did you have slides? And I never, like most of the talks I do are like corporate, like I talked to the Naval Academy, I've brought you some of those, or I talked to a hedge fund, or I talk at a corporate offsite, or if it's a conference, it's like put on by a group.

3:36So they're responsible for bringing the people, whereas like for these, you guys are coming. That's why I'm saying, please go to BrianHolliday.net slash tour to buy tickets or else it will be empty. But that's a different kind of audience. It's closer to like a performance or a music show or a comedy show where like they're there to see you. And so I wanted to know how he did it because when you do the corporate stuff, they're like put together a slide deck and the audience isn't familiar with you or your work. So it's a different kind. You can go over the basics in a way that if I just said, here's what stoicism is, you guys would be like, I already know this, right?

4:12So what surprised me is that he said, when he had spoken at some of the same venues, that it was just him and a microphone. And I was like, wow, okay, I've never done something like that. And as helpful as those slides can be, because people can take pictures of them, you can sort of be making a different point that's behind you, they reinforce you. But it also has this extra step, you always know where you are. And you always have something to fall back on. And frankly, you don't have to be as captivating or as funny or as interesting because you've got compelling images behind you. So I was impressed that he did that.

4:47And I don't know, I've just been doing this so long. It's what I got used to. It's what I'm comfortable with. I know the material works. I have it down. I know all the beats. And so when he said he was doing it alone with a mic, I thought, hey, I want to try it that way because it seemed harder and different. General Sherman, the great military strategist and Civil War hero, once wrote in a letter to his friend that he had an old rule never to return by the road he had come. Now, I'm going to do a little digression here because crazy little fact about when I was writing this article. I knew Sherman had that rule or I knew there was a Civil War general that had that rule and I thought it was Grant.

5:26And I was like, I didn't have my, I wasn't at my house when I was writing it. And so, or I wasn't at my office when I was writing it. So I was like, maybe I'll just, I don't want my note cards. How can I Google it? So I pulled up ChatGPT and I said, did, did Grant have a rule about never returning by the road that he came? And ChatGPT goes, yeah, absolutely. And it starts to tell me all about it. And I was like, wait, but are you sure it was Grant or was it Sherman? And then it goes, yeah, yeah, yeah, yeah. It was Sherman. And I go, oh, where did Sherman say it? This is, I'm giving you literally like the back and forth I'm having with ChatGBT.

6:01And it's like chapter 11 in his memoirs. Well, I open up Sherman's memoirs when I get to my office, knowing that I'd marked this exact passage about this rule. And I open chapter 11. Chapter 11 is not about this at all. There's nowhere to be found. So now I'm starting to get really suspicious. I have to go back through all my Sherman books. And I eventually find it in B.H. Liddell Hart's biography of Sherman, which is incredible. We carry it at the bookstore. It's one of my all-time favorite biographers. And it turns out it's not in Sherman's memoirs. It's a line in this letter that he wrote to a friend.

6:34So the point is, ChatGPT can be amazing for a lot of things. Actually, a lot of the slides that I do have in my talks, I'll use ChatGPT to put together to illustrate scenes that we only have descriptions of, but no pictures of. Anyways, it's just a reminder to me that you actually have to do the work and you can't trust, just like people used to trust Wikipedia when it first came out or Cyclopedia Britannica. You got to know your shit and you can't just trust the newest, easiest thing. It would have been embarrassing. I would have been having this section in the article and the episode totally wrong.

7:06So anyways, that's a digression. But what I took that quote to mean is that Sherman didn't like to retrace his steps. He wanted to blaze new trails, and he was always picking the more difficult journey over the easy and the familiar. And this is a great rule for life. Actually, in meditations, Marcus Rios writes about holding the reins in his non-dominant hand, both as an exercise to practice and as a metaphor for going towards the more difficult thing. He wanted to get good at doing things with both hands, both ways, developing the ability to thrive in any and all situations. Because naturally, we're more confident where we're dominant.

7:42But the problem is you become progressively weaker in the hands or the areas you neglect through this favoring, however pronounced it is. And I just felt like I'd gotten comfortable with one way of speaking. And so why not change it up? Well, I guess one reason is you don't want to fail in front of 2000 people. That would have been mortifying, especially in a foreign country. I've traveled all this way. But that reason, it struck me, that was what would be motivating about it. The danger, the difficulty of it would be invigorating and challenging. And as Robert Greene talks about, sort of when you're on a death ground strategy and you can't fail, you work hard to ensure that you don't.

8:22Epictetus said that when a challenge is in front of you, you want to think of yourself as an athlete getting paired with a tough competitor or a sparring partner. You want to be Olympic class? He says it's going to take some sweat to accomplish. And so doing the talks in Sydney and Melbourne took a lot more preparation. much more so than if I'd done it the way I normally do. I would have just showed up, reviewed my slides the night before, and then just done the thing. And I would have known it would have done pretty good, but I also knew, would have known there'd be a ceiling on it and I wouldn't have delivered or brought my best to it.

8:56So I had to settle some nerves, but I don't know, to me, like these are features, not bugs of picking the harder path. And the point is, if it's easy, you're not growing. Not that everything that's hard is good, of course, but almost everything good and worth it is hard. Think about the things that you're good at. There was a time when you weren't good at them, right? There was a time when they were hard, but you chose to work at it despite that initial difficulty. Even though it was frustrating, even though you had to fight the urge to quit, you saw a glimpse of goodness, you clawed out a bit of progress.

9:27You felt a glimmer of confidence and you chose to keep it, to keep pushing. And you grew from the fight against that resistance. Even more, you found something on the other side of it all, a you that you realized you didn't quite entirely know before and possibly never met. You learned something valuable about yourself that you're capable of more than you know. And this is why the Stoics urge us to fight our tendency towards complacency and stasis. We have to keep pushing and adapting and shaking things up. We have to seek out challenges because would we know anything about ourselves if we never did?

10:03And I don't mean that in just in the big ways. It's also in the small ways because every day you stand at little crossroads, decisions about how to do things and what things to do. Should you walk 15 minutes to your meeting or take an Uber? Should you pick up the phone or have that difficult conversation or leave it to an email? Can you choose to do kick turns in the pool instead of just push off? Can you choose to pick up a journal instead of your phone first thing in the morning? And as you weigh these competing options, try to lean towards the hard one.

10:41Thanks to Toyota Trucks for sponsoring this episode. When I bought my ranch in 2015 out here in Basko County, I drove my car about halfway down the dirt road that we live on, thought this isn't going to work, stopped, parked it, walked the rest of the way home, borrowed my wife's car, drove into Austin and bought a truck. What I bought was a Toyota Tacoma. And this truck wasn't just transportation getting me to and from my house. It unlocked a whole different style of living for us, not just on the ranch, but in our little Texas towns. There were places I could go now that I couldn't go before, especially out here in the piney forests, through the fields, and on the unpaved roads like the one that I lived in.

11:26We got to go deep into the hill country's wild beauty. We've driven all the way out to East Texas. We've driven across the country. And by we, I mean not just my wife, but both my kids who I drove home from the hospital in that truck. Toyota trucks are built for those who understand that the best adventures happen when you're willing to veer off course. Because you never know when you'll end up on a Toyota adventure detour. And of course, this is stoicism too, because every detour, every obstacle is an opportunity. But it's helpful if you can handle the difficulty inherent in that. If you've got the resilience and the right companion to make it wherever the road takes you.

12:06Discover your uncharted territory. Learn more at toyota.com slash trucks slash adventure dash detours.

12:17Don't be the person that Seneca talks about. The one who skates through life without being tested and challenged. and challenge who deprives themselves of opportunities to grow and improve. Jump into the colder water. Have the tough conversation. Use the weaker part of your game. Take ownership where you can. Choose the more difficult options. Seek out the challenge. Lean into it. Iron sharpens iron. After all, resistance builds muscle. Sparring partners make us Olympic class. You'll be better for it, not only for the improvement that comes from the challenge itself, but for the willpower you are developing by choosing that option on purpose.

12:55So to revise my response to the question I was asked in Sydney, life is full of obstacles, yes, but if you want to be more adept at overcoming them, you should always try to do it the hard way. You should find obstacles to challenge yourself against. And it wasn't until I was offstage coming down after the rush of trying something new in front of that many people that I could really fully understand that. And now that I'm going into these talks in November, I'm thinking about it again. How do I not just do the same thing, but how do I do a new thing? How do I make it different and special in each one of the cities so that instead of doing the same thing five times, I'll do it five different ways and get better each way.

13:35And so I hope to see you there. By the way, you can grab those tickets at ryanholiday.net. But a couple of other things came up. So I wrote this article for my blog and I heard from a couple of people, someone said, you know, you still didn't answer the question, right? Which is what about kids? Should you seek out and create challenges for your kids? I would still say no, sort of. I mean, look, there's this idea, Lucker at Emurgo struggle, and they emerge that kids thrive on challenges. But I don't try to like force my kids into challenges, but I try to challenge them. So my kids and I were at Deep Eddie today, and my son was swimming around.

14:09And I said, hey, do you think you could swim from here to there? So I didn't say you have to do it. I don't wake up and try to make his life harder, but I try to get him excited to lean into the challenging way. When we're on walks, I say, hey, do we want to go this way or that way, that way? And I try to get them excited about doing the challenge. So I don't necessarily force them to do it, but I do try to inculcate this habit. First off, I try to model it. And second, I try to show them the rewards that come from doing it. And then the second thing, a lot of very nice people who were at Sydney and Melbourne shot me a note after they heard this piece or read this piece.

14:43And they said that they were surprised that I'd never done that talk before, which was very lovely to hear. And that's the result of the practice that went into it. We stayed at two Airbnbs there in Australia and I took the upper floors and I would just practice it every day. I would start building up the first several minutes of it. Chris actually told me that he rented out a theater in Austin, like a black box comedy theater, and he practiced with audiences. I didn't have the bandwidth or the interest in doing that, but I would practice. I built up the first several minutes and then I did it in chunks.

15:17And then I would sort of randomly throw myself in different parts of the talk just to see if I could do it this way, see if I could do it that way. And then I didn't want to do it so many times that I got tired and boring, but I eventually got all the pieces together. And I actually made a joke in the Sydney talk. I'll let you listen to it. And in fact, the reason I was here when I sent in the main strip for the obstacles away is I was giving one of my first ever public talks, which I'm sure was horrible for everyone involved. I noticed particularly that for my wife who had to listen to me go over it, over it, and over and over again on that walk from Mon-Eyed to Monty.

15:56and in fact to get her to come on this trip and bring it in, I have to promise that I will not subject her to one single version of it. So I screw up tonight into a fall. I didn't get a cracker. So I didn't subject my wife to it. This was all practice I was doing on my own, but it was awesome. There's things I want to do differently and better. It didn't go off flawlessly. It never does. But that is part of the challenge, too, is getting comfortable not hitting your standards necessarily. and being at work in progress and then wanting to go back and change and challenge yourself and grow. So that was really exciting.

16:32That was awesome. And like I said, I'll be in Toronto, Vancouver, London, Dublin, Rotterdam, all in November. You can grab dates and tickets at ryanholiday.net slash tour. And if you ever listen to our Thursday episodes where I answer questions, a lot of those come from stuff like this. So if you want to hear yourself on the podcast or if you've got a question you're dying to ask me, you can come and think the VIP thing beforehand end is like a private Q &A session. So there'll be that. And then there's the audience Q &A at the end. And I just look forward to meeting and talking with all of you.

17:01It was just an overwhelming, amazing experience there in Sydney. Not just because I challenged myself and I grew from it, but because it was just genuinely fun and cool and sort of a bucket list thing. And I'm looking forward to doing that again. I will see you all very soon. Happy Sunday.

17:22thanks so much for listening if you could rate this podcast and leave a review on itunes that would mean so much to us and would really help the show we appreciate it and i'll see you next episode

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