What's on Your Bookshelf?

116-The Obstacle Is The Way: Part 2, Episode 2; Practice, Persistence, and Iterate

• Denise Russo and Sam Powell • Season 2 • Episode 116

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We explore the concept of persistence from Ryan Holiday's "The Obstacle is the Way" and discover how persisting through challenges is the key to effective action in life and leadership.

• The best way out of any challenge is always through, not around
• Persistence and pertinacity are key assets demonstrated by historical leaders like General Grant
• Uphill goals require uphill habits and relentless determination
• Having a clear "why" statement fuels persistence when motivation naturally wanes
• Iteration allows us to learn from failures and adjust our approach without losing momentum
• Creating space between our identity and our failures prevents emotional paralysis
• Viewing obstacles as feedback provides precise instructions for improvement

If you're getting value from this podcast, we'd love to hear from you and please share these episodes with others who might benefit. The book is "The Obstacle is the Way" by Ryan Holiday.


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Speaker 2:

Welcome to what's on your Bookshelf, a life and leadership podcast where we live out loud the pages of the books that are on our shelves with your host, denise Russo, and Sam Powell.

Speaker 1:

Hi everyone, welcome back to another episode of what's on your Bookshelf. This is our life and leadership podcast, where we're living out loud the pages of the books that are on our bookshelves. The book that's off the shelf right now is called the Obstacle is the Way by Ryan Holiday. My name is Denise Russo, I'm here with my co-host, sam Powell, and we are today going to be walking through a pathway of practicing persistence.

Speaker 2:

Sam, it's good to be here with you, good to be here we are still in our section on action of this book. So this is part two of the book, which is action, because we got our head right with perception and now we are getting our body right with action. I don't know we're getting in the game, it's essentially what we're doing, but I hearted, I highlighted and hearted the quote at the beginning of this chapter which is from Robert Frost, and it says he says the best way out is always through. And I agree to that. Or insofar as I can see no way out but through, and all I could think about and I think I that. Or in so far as I can see no way out but through, and all I could think about and I think I said this in an episode on something at some point. It just reminded me of that.

Speaker 2:

I'm going on a bear hunt song, you know, like a little nursery rhyme, where it's like I can't go over it, I can't go under it, I have to go through it. Like that there's just there is no way out but through. And to get through you have to be persistent. You have to just keep going, keep going, keep chopping away at it, keep hacking through the weeds, whatever it is to get through, and that persistence is boring sometimes, but it's the key to action right. Once you get moving, like we talked about last time, how do you keep going?

Speaker 1:

You persist. Yeah, this makes me think about. There was a story from thousands of years ago where there was this guy. He became a king and he was really struggling with something like down and out just a lot of controversy, lots of obstacles, people were trying to kill him. And he basically says in this one verse of a chapter of a book, that that he wrote that, even though I'm walking through a valley of a shadow of death like that even just sounds dark and scary I'm walking through this valley of a shadow of death Like that even just sounds dark and scary. I'm walking through this valley of the shadow of death. And then he says but I'm going to fear no evil because your rod and staff comfort me. And I always get stuck on that part of this particular verse which is about this experience this guy is having that how in the world would a rod and staff comfort somebody? So if you don't know what it is like, imagine if you're a shepherd and a rod and a staff are the things that a shepherd has to like prod the animal with and it's painful. It's painful to be prodded, it's not comforting at all actually. But in this case the guy was saying that this rod and staff comfort me while I'm walking through this shadow of death. He didn't say I stopped there. I said oh, woe is me. Oh, my life is horrible. I'm stuck in this valley.

Speaker 1:

The idea of even visualizing a valley is that a valley is down, but a valley also has an up. That's how you get out of it is you have to climb up, and there was this chapter in one of John Maxwell's books about the law of Mount Everest, which is sort of like you know, everything worthwhile has to go uphill. It's something that John teaches a lot. And if you don't like climbing mountains unless that's something that you do for fun most people don't want to go uphill. It's so much easier to go downhill. But if you have, I think he says, if you have, you're gonna have to correct me on this part, sam. But if you have, um, I think he says, if you have, you're gonna have to correct me on this part, sam. But if you have, if you have uphill goals but downhill habits, you're never going to go up, or something like that, yeah, something like that, uh-huh, yeah and um, I, as you're saying, this I'm thinking about.

Speaker 2:

So when I was in high school, I lived in Japan, and one of the pilgrimages that all Japanese people are supposed to take is to climb Mount Fuji. It's a holy mountain, it's the tallest peak in the country, and so I climbed it with my dad one summer when I was in college and it was one of those things that was so hard. Glad I did it. You could never convince me to climb another mountain in my life like ever, because it was this relentless, uphill, persistent battle and it's and like a lot of people climb this, like as far as mountain climbing goes, it's not that difficult, but like it's still climbing a mountain, like you are still walking uphill for a day, like it's just it's, it's rough and it's this switch back and forth where you're going up and up and up and up, like you're going back and forth, back and forth, back and forth, up and up and up. And for me, like I, one of the things I didn't expect is like the thin air kind of triggered my asthma and so for me it was like I would have to walk up to the end of one switchback and stop and rest and like get some deep breaths and then do it again and again and again and again for hours.

Speaker 2:

But I made it to that peak. I wasn't going to give up. But it was this like you said, like any goal worth pursuing is uphill right. Like you have to just keep going, keep going. And Ryan Holiday says like we will chisel and peg away at the obstacle until it is gone. Resistance is futile. Like you have to just keep at it. Like there's it's not pretty. A lot of times it's just this relentlessness that we're gonna chisel away at it.

Speaker 1:

Well, and sometimes you have to. While you're being persistent, you have to make some hard decisions, right? So this talks about in this chapter, about a general of an army that had to make some really difficult decisions. And when you think about this, there was a story a long time ago I can't even remember how old, but it's like a couple hundred years ago that there was this concept of something called burn the ships. Do you know what that? What that is? Yeah, I've heard of that.

Speaker 1:

So basically, the gist of it is is that there was it's it's a legend, I think but there was a conquistador, so another kind of army ish story, where it was talking about how these guys were going on this conquest to take over this area, and so the order that he gave his men was just simply well, burn the boats, burn the ships. So, in other words, he wanted them to realize there was no opportunity for them to turn back to whatever was behind them, so they had to go forward, they had to fight with everything they had. There was no option for failure. They had to win, whatever this battle was, and so burning the ships is kind of an interesting concept here of practicing persistence, when this book is talking about General Grant, where General Grant had to make some hard decisions, where he had to leave a bunch of supplies behind. The people had to learn. The troops that were with him had to learn how to live off the land, make their way up a river. They had to go through a lot of obstacles, but he was unstoppable, he was persistent.

Speaker 1:

And what I highlighted was a word I have never heard of before and curious if you'd ever heard this word. It says that Grant learned two things First, persistence and second, pertinacity.

Speaker 2:

I had not and I tripped over it when I saw it, but I like it.

Speaker 1:

It says, whatever it is, is that it was an incredible asset, and his main asset as a leader, so you think about this, is Ulysses S Grant, known as a historical figure, that he was known. His assets, his most important assets, were persistence and pertinacity.

Speaker 2:

Yeah, and I think that there's a lot of people like they go on to say, like a story about Thomas Edison, about how Nikola Tesla said that if Edison needed to find a needle in a haystack, he wouldn't proceed at once to simply examine every straw after every straw until he found the object. And it's that. And I think that it's those types of people that, like, we don't see that work right. We see that Edison invented the light bulb, but we didn't see that it was number whatever. It was something like crazy number of things that work right. We see that Edison invented the light bulb, but we didn't see that it was number whatever, it was something like crazy number of things he tried.

Speaker 2:

Right, it's like number 982 or something crazy, right, like it's this relentlessness of like I'm going to just keep going, keep going, keep going. And I like that Holiday says here too, like the thing standing in your way isn't going anywhere, you're not going to outthink it or outcreate it with some world changing epiphany. And I love that because for me, I like to I think I said this last time it's like I like to make a plan for a plan, a lot right, like sometimes it's like, oh, if I just think about it. If I just like design it, just right, if I get the system just correct, like right, then I can, can, I can get it done, but like it's not going anywhere, you still have to do the thing, you still have to get out there and still get after it, and so you have to do it over and over and over again until the light bulb comes right, until it works, until the thing that you've been searching for happens, or you break down the barrier or whatever.

Speaker 1:

It's not going anywhere here's interesting thing, even about the light bulb story, is that there were light bulbs before the last one he created that probably worked. But he kept going and imagine this. Imagine if, when he created those, that they just stopped after that and said, yeah, the light bulb works, we never need to improve it. Now there's all sorts of light bulbs light bulbs that change colors, light bulbs that you can use your phone to turn on and off, light bulbs that have timers, light bulbs that don't hurt your eyes, you know. So what if people just stopped at whatever the last thing was?

Speaker 1:

So the persistence to me says that you never really settle, and not to say that you shouldn't be happy with success, but that your success. I think the way that John Maxwell says it is that once you've tasted significance in life, then success never satisfies. And so the idea meaning is like what is it about what you're trying to accomplish? Or do that actually matters If it's something like you're trying to be? Or do that actually matters If it's something like you're trying to be persistent because you want to raise at your job? Why do you want to raise If you want a promotion at your job? Why do you want a promotion If you want a certain thing that you want to purchase like my son is very persistent about a very expensive thing that he wants and he's persistently asking me to pay for it. But I've talked to him about you know what are you going to do to earn it. And if you persistently really want something bad enough, then you will do what it takes to get what you want.

Speaker 2:

Yeah, absolutely Absolutely. And I we're working on that with my son right now. He really wants something and he's got a whole checklist chart that we work on and he is after it every day. There's like I don't know seven things on this list that he has to do and it's like showing responsibility and you know all these kinds of things and, uh, he's after it, I mean, every single day. But it's this persistent thing. And I was talking to somebody and they're like oh my gosh, I can't believe, like you're still doing this weeks later, that you started it. And I was like he's got a goal, he has a solid why statement, right, like he knows what he's after and knows what he wants.

Speaker 2:

And I think that, like Simon Sinek has the book, start with why, right, like when you're starting action, when you're getting in motion, having that, why I'm doing it, why this is important to me, that big picture view helps you persist, I think, because persistence is boring. There's a point where you're like I'm sick of doing this, right, like why am I on the treadmill every day? Like, forget it, like this is dumb, but it's. I want a healthy, active body, right, I want to be an active person and so therefore, I understand why I'm persisting. I always want to.

Speaker 2:

I have clients goal setting. I always always make them write down. When they write down what they're trying to achieve, I always make them write down why they want it, because I tell them it's going to get hard, you're going to want to quit and when you get to that point, I want you to come back and read this why statement. I want you to come back and understand why you're after the thing that you're after, because you, if not, if you don't keep your eye on that prize, you're going to abandon a lot of things in your life. A lot of paths are going to be left unfinished because you just lost track of why you were doing it.

Speaker 2:

Or, if you need to pivot right, same thing, like, hey, this is why I was originally doing this, but that reason is now different, or things have changed in my life and so now I know it's time to abandon ship. Right, like last time you were talking to us about people that you had known, who had been laid off and changed jobs and things like this, and it's like they'd stayed with, stayed in a place they didn't really want to stay in, and it's like they lost that. Why statement why am I doing this? I'm doing this to collect a paycheck only then, fine, but that's not it, right. That's that I need to pivot and I lost track of what my big picture is.

Speaker 1:

Life is meant to be lived for so much more than just settling. So I'll tell you I looked up the word while we've been talking about what does pertinacity mean? So I'm going to tell you the first definition, which is great for coaching, which says pertinacious means adhering resolutely to an opinion, purpose or design and, perversely, being persistent. So that is basically saying you're going to be resolute about this thing. Persistent, so that is basically saying you're going to be resolute about this thing. Now don't tell your son the second definition. So the second definition of pertinacity is to have a mix of courage, conviction and a little stubbornness.

Speaker 2:

That's all right. I'm okay with him being stubborn in things he's pursuing. I think that that's a good thing. Right Like I, I like this. I'm gonna start using this word all the time in my life with, uh especially with clients Like we need to get a little pertinacity.

Speaker 1:

We have to figure out how to pronounce it first. Yeah, exactly.

Speaker 2:

I'm going to look it up and listen later, um, but yeah, I think that that's it. Like there is a stubbornness to working through things and to you know, and to moving. But I think that, like, this next section that he gets to is called iterate, right, so we talked about the practice of persistence, but iterating is things aren't going right all the time, like yes, I'm going to relentlessly pursue, but I also have to change course, kind of, you know, agilely right, like I don't think agile is a word Agile-ish, I don't know, but whatever, when things don't go right, like when you're in pursuit of a goal and you mess up along the way or you hit failures along the way, how do you adjust in time, right, how do you move? How do you, you know, switch a little bit right, like my son's after this goal, and he's working towards it. But he's checking this list and like, okay, one of the things is simple, right, he is in school, so homework, he has to do his homework every day and he has to do it without fight, without an attitude, and he has to do it complete and correct.

Speaker 2:

But there are days when, like you, don't feel like doing your homework right. There are days when, like you're gonna take the shortcut on it. But then what did you learn? What do you have to do next time? Right, like he realized that he can't do homework as the last thing of the evening because he's in no mind for it. So now he changed that up. He comes home first thing, he does his homework, gets it done, gets it out, it out of the way. He's got the right mindset, got the right action for it, and then he just doesn't want everyone's the rest of the evening, right? So it's this like you change as you hit the problems and you adjust in time, because if you relentlessly pursue without looking around, you're going to end up missing something.

Speaker 1:

What's really important about what you just said is that your son realized when he's at his best like, in other words, if his mind is at his best right when he gets home from school to do the homework and get it over with so that he can go outside and play or whatever he knows that that's when his brain and thinking is going to be at its best. And the way the book describes it is it says you need to master persistence and resistance, is it says you need to master persistence and resistance. Persist in your efforts but resist into giving into distractions, discouragement or disorder. Because the reality is, if you are moving, you likely will encounter obstacles. You will, even if you think about you could be on the smoothest sailing road, like Route 66, but it doesn't mean that you won't face some sort of obstacle on your drive. Even if you think the road is smooth and flat and open, something will happen. Flat tire run out of gas, something else happens. There's something in the road. Who knows? But you will be faced with an obstacle road. Who knows? But you will be faced with an obstacle.

Speaker 1:

And the point here is to be able to look at whatever your path is, understand that you're going to have to make some maybe detours along the way, or maybe you're going to have to reroute yourself in some sort of a way and then look at that and the iteration comes first by assessing right Like you change something, because you have to assess what needed to be changed, like what went wrong here, what went right here, what would be like we used to use this at work, a process called even better.

Speaker 1:

If so, this thing we did might've been good, but it would have been even better if dot dot, dot. And it's just kind of like when you give that coaching question that you're mentioning in the other episode about it and when somebody says, if you don't know the answer, um, what would you say if you did know the answer? It's like the same thing to say if you think something is good, well, what would make it even better if I did whatever you might think. Well, I already did it the best I could. But usually people will still come up with more ideas of it could have been even better if I had whatever.

Speaker 2:

Right, yeah, and I, I love that. And what you're saying, right, is like it's inevitable that we're going to hit those problems, but learning from them and moving from them is really what's key. And he says in here, like, right, we can acknowledge that anticipated temporary failure certainly hurts less than catastrophic permanent failure. And it's really in the context of like, why, like, why am I embracing failure? Like, failure hurts, I don't really want it. But he's almost saying like if you can anticipate that you're going to fail all the time, it doesn't hurt as bad.

Speaker 2:

And that reminded me of the how of happiness or no solve for happy, where that was like the whole happiness equation of if, if my expectations are aligned appropriately, then I stay in balance of happiness more often. And so it's. If you assume you're going to fail, if you assume you're going to fail, if you're assume you're going to have to iterate, it doesn't stop your action, right, it doesn't slow you down and you don't get, like you don't get, you know, cut off or you know defeated by these failures that are inevitably going to happen to you, right, you just learn from it. You ask those questions that you just asked, right, like what do I have to ask myself how could this be even better? And move forward, right, like, just keep going, it doesn't right. This is all about movement, all about action, all about momentum, and so it's really just anticipating that's going to happen and move, you know, make the small adjustment, keep going.

Speaker 1:

I wonder if some of it is about taking the emotion out of it, because when you think about failing it's tied to some sort of a feeling and if you're stuck in that feeling maybe that prevents you from progress. And the way that the book and the author describe it is he's talking about when businesses maybe have a failure but they don't take it personally. So he says that great entrepreneurs are never wedded to a position, they're never afraid to lose a little of their investment, they're never bitter or embarrassed and they're never out of the game for long. They might slip, but they don't fall.

Speaker 2:

Yeah, and I love that. Right, like, think about it, like slipping, like, yeah, I slipped back a little bit, yeah, like I, you know it was a one step backward, but if I learned from it? Right, like John Maxwell's book, sometimes you win, sometimes you learn Like if I win, if I and the win here is if I learned from it and if I learned from it, then I can move forward. But I expected the slip right, like I'm not. And when you said, like I wonder if it's, you know, taking the emotion out of it, I think it's putting space between yourself and the failure. It's not that I'm a failure, it's not that I have failed, it's that this thing we were doing didn't go, like it failed. But that's okay. There's another path, there's another way to push forward, and I think you're right it's. It is taking the emotion out of it and to me it's creating that space between your identity and the actions that are happening around you.

Speaker 1:

I love that you mentioned John's book. Sometimes you win, sometimes you learn. And that book, I think, came from really an older book which was my very first John Maxwell book called Failing Forward, and when this person gave me the book I thought what a strange title for a book. Like I don't want to fail and I don't want to move forward in my failures.

Speaker 1:

But Ryan Holiday says that the way to guarantee we don't benefit from our failures is to never learn from it. So if you think about whatever that thing is like you said, it's not that you are the failure, and that thing that happened may also not have been a failure. It's like saying if you were a team that lost a game, does it mean you failed or does it just mean that the other team was more victorious? It doesn't mean that you failed. And if you go into the locker room and really study what happened in that game, you might find that you were the weaker team in some area, or you might find that the other team just happened to be stronger, and those two things are not synonymous.

Speaker 2:

Yeah, and he really encourages us to look here as these failures, these slips, these moments, these obstacles as feedback and they give you precise instructions on how to improve. It's trying to wake you up from your cluelessness and I love that right. And if you think about it as this opportunity to learn, right, to fail forward, then I just think of myself as, like I'm clueless in this area. I don't know, I don't know what's going to work and not work, so let's fail forward. Right. Like let's trip forward a little bit. As long as I'm moving in the general direction of how I want to go, I can always adjust and say, okay, I will trip less if I do this and the goal eventually is to not trip at all. But along the way, you got to learn how to do that.

Speaker 2:

Right, I have a five month old at home. Like all the little things she's learning as she goes, right, like I think about kids learning how to roll over and sit up and crawl. Like there's a lot of falling down as you're doing it. But as we ingrain those lessons, like I can stand up out of a chair just fine. Right, like I don't trip walking across the floor, but I sure did a lot, you know, 40 years ago, but you know it's, it's that that. I just loved that. Like I happen to be clueless about this right now and this is just going to be my instruction guide. This is gonna be my perfectly placed instruction guide for the thing I need to learn right now, because it's the thing I'm tripping over right now.

Speaker 1:

Yeah, I mean, it's everything about action. That's what we're talking about in this section of the book. So we've just finished talking about practicing persistence, iterating and changing when things change or when we think things didn't go the way we want, and so all of that is good as you're starting out, but I have a suspicion that next week is going to be one of your favorite chapters.

Speaker 2:

Yes, it is. It's called follow the process, and you know I love to design a process and a system. So, yes, ma'am, I am so here for next week, and especially in the context of action, right, what's the process that gets us in action? And, yeah, I cannot wait to talk about that with you.

Speaker 1:

Yeah, I'm looking forward to that as well, because, following that, we're going to be talking about what your role is in these actions and how you do it the right way, so we hope that you'll join us again next week. This has been a great time, as always, together with you, sam, and for those of you listening. If you're getting value from this, we sure would love to hear from you, and we would equally love for you to share these episodes with others that can get value from it as well. The book is the Obstacle is the Way, by Ryan Holiday. My name is Denise Russo and, on behalf of my friend and co-host, sam Powell, this has been another episode of what's On your Bookshelf.