What's on Your Bookshelf?
“What’s On Your Bookshelf” is a personal and professional growth podcast exploring the intersections of passion, potential, and purpose - featuring multi-certified coach and leadership development consultant Denise R. Russo alongside Sam Powell, Zach Elliott, Tom Schweizer, Dennis LaRue, and Michelle King.
What's on Your Bookshelf?
109 - The Obstacle Is The Way: Introduction, The Obstacle Is Your Opportunity!
Obstacles don't block your path—they are your path. In our deep dive into Ryan Holiday's "The Obstacle is the Way," we unpack how ancient Stoic wisdom offers practical solutions for modern challenges.
The book provides more than inspiration; it delivers a framework for transforming life's inevitable roadblocks into opportunities for growth. We examine the remarkable stories of leaders like John D. Rockefeller, who found unprecedented success during economic depression by maintaining what Holiday calls "unflappable coolness under pressure." Rather than being paralyzed by circumstances, these historical figures developed the mental discipline to see opportunities where others saw only problems.
We share personal stories about leaders we've known who embodied this philosophy—from calm management during national crises to everyday resilience in business challenges. The four-step process Holiday outlines becomes our roadmap: objectively assess the problem, adjust your attitude toward it, apply creativity to transform it, and cultivate the inner will to persevere.
Our conversation reveals how this approach works at all scales—from small daily frustrations to life-altering challenges. We unpack the powerful parable of the king who placed a boulder in the road, rewarding the one person who took initiative to move it instead of complaining about it. As Benjamin Franklin wisely noted, "The things which hurt instruct."
This episode offers both philosophical depth and practical strategies. Whether you're facing professional setbacks, personal struggles, or simply the everyday obstacles of human existence, this timeless wisdom provides a path forward. The obstacle isn't just something to overcome—it's the very way to become stronger, more creative, and ultimately successful.
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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. Hi everyone, welcome back to another episode of what's on your Bookshelf. This is a Life and Leadership podcast where we are living out loud the pages of the books on our bookshelves. My name is Denise Russo and I'm here with my co-host, Sam Powell. We are just starting our newest book of the year, the Obstacle is the Way, by Ryan Holiday. Sam, it's good to be here with you today.
Speaker 2:It's good to be here with you too. I'm so excited. I feel good like getting back in the groove with this, with you. I'm talking week over week. So this is great, so happy to be here.
Speaker 1:Me too, Ditto. And it's so interesting because when we were starting to get ready for this book, friends, we were thinking like how are we, are we going to have enough time in the episodes to get through multiple chapters? So last week was the first one and we literally only got through the preface of the book, which is like four pages all said and done.
Speaker 2:So yeah, we're doing our best.
Speaker 1:So maybe for listeners who are new, sam, do you sort of want to help them understand how we actually do this, so that it's not really that we're teaching from the book, but share with the listeners what our attempt is at living out loud these books.
Speaker 2:Yeah, I like to think that everyone's just listening in on your and I personal development discussions. We had a family party over the weekend and I was talking to my uncle about this. He was like, oh, how's the podcast going? I was like, great, we're actually, you know, restarting up recording episodes now. Finally, and I said honestly, I just love doing this because it's such a good like it's selfish. I just love this like personal development, because we're reading these books and we're talking about how we're applying them to our life, what we, because we're reading these books and we're talking about how we're applying them to our life, what we think about. You know the concept, so we're not sitting here teaching you the book. Sorry, you're going to have to read it for yourself.
Speaker 2:We are really talking through what this is doing for us, for our perception and for what we're putting into action, which are the. You know how this book is broken down, right, what are we thinking? How are these thoughts changing what we're doing in our lives, and how does that then impact really who we are and how we show up in the world? And I don't know, this has been what a multi. How many years have we been doing this now. Wow, it's been a while and the books we've read have changed my life significantly. I talk about them all the time with clients, with family, with friends, with people, and you know this book so far is, no, no exception.
Speaker 2:So this one, the Obstacles of the Way, is really about not looking at obstacles as something that you have to overcome, but looking them as part of your journey, as just the thing. Like you know, take the emotion out of it and just the fact that, like I am in this situation and so what am I going to do about it at the end of the day. And that's really where we're at. We're at the introduction of this book. So last week we only talked about the preface, so now we're actually in the introduction and, um, it is know, it's really, it's really great.
Speaker 2:He starts this with a story, he starts this that he carries through, but it's really getting you into that mindset of you. Know, he says that it's that really. What are we missing here? Like, it's simple, a method and a framework for understanding, appreciating, acting upon obstacles as liferows at Us. So, as we think about what this book is really talking about, that's what this is. It's giving us this framework for really understanding and appreciating these obstacles that come into our path and then acting on them in a way that serves us, serves those around us, and this is a collection of stories about how people have done that and how that really comes into life, and so you get to hear our stories I actually love that you just mentioned that about the framework, because in my book I put a star and I wrote the word sam after it.
Speaker 1:Because I know that so and for me, I really like the simplicity of it because the bottom line is, whatever we face in life, we have a choice. Number one is you can be blocked and have obstacles and have sort of this what if, with a question mark, like, well, what if I fail, like the eeyore syndrome? Or? Number two, you could advance through or over them and look at the exclamations in your life like, well, what if I succeed? What if I'm a better person because of it?
Speaker 1:The very first part of the intro even talks about this through a story about Rockefeller, john D Rockefeller. That he was a very, very successful person, and whether you believe he was a good person or bad person is not the point of the book. Whether you think that he got rich off the backs of other people or not is not the point. The point is is that he looked at obstacles that were around him, which was a depression time. It was a time of a lot of obstacles. It was a time where there were a lot of people that were stuck inside of the obstacle, that weren't overcoming them, and he looked at that as the opportunity that if I could go the way that nobody else is going, what might that be like.
Speaker 1:And so, indeed, this is like a framework and a method, just like another one of our books from the past Atomic Habits with James Clear, which was about how we could talk about all these stories about how other people were good at habits or good at change, or good at obstacles or good at being happy or good at whatever the thing was we were talking about.
Speaker 1:But the practicality of a method and a framework is how you can do it too. Maybe not exactly the way they did it, but how you could do it too. And with this book, I think that at the 20,000 foot level, what it is is that the framework is about attitude and approach, that if you fix your thinking and your beliefs and then you look at your actions or inactions, so the attitude and the approach, then you're going to be able to review, I suppose, and adapt your results. Be able to review, I suppose and adapt your results. And if you don't like your results, then all you have to do is change the way you act or react and believe or not believe, and think about those things yeah, yeah.
Speaker 2:And that's what he really sets this book up is that it's a book of ruthless pragmatism and stories from history that illustrate the arts of the relentless persistence and indefectible ingenuity. And he said so. It's not just. How can I think this is not so bad? No, it's really willing to get yourself into the situation that this must be good. This is an opportunity to gain a new foothold. So it's not. This is so. This is not so bad. Right, oh, the situation I'm in is not that bad.
Speaker 2:Or, oh, other people have it worse, or whatever it's, I can make this good right so it's really taking that like passive point of like things are happening to me, to things happen through me, right, and it really is me taking action.
Speaker 2:That changes the story of how this is. And he uses Rockefeller as as a really good example of regardless of situation and again, like I think I said this last time but like you know, rockefeller was in this time of history where there was, you know, like just a lot going on in the world. And we also live in a time and I think everybody always lives in a time where there's a lot going on in the world. We just don't recognize it because we're not in the other times, but there's always a lot going on in the world and it's and sometimes it feels so helpless, right, like how am I going to affect change? What could I do about things? But the point of this is that you have a lot of power. It it is not that things happen. You know that this is not so bad. It's that I can make this good.
Speaker 1:I think that what you're describing to what's important is, this is not just about positive intelligence, even though we both love and appreciate positive intelligence and study that in our own coaching philosophies. This is about character development is what I would say in the beginning of the book, because he talks about Rockefeller, but then he lists a whole bunch of other leaders as well and points out some of the character traits Cool-headedness, self-discipline, demonstrated relentless drive for self-improvement intelligence. He even talked about things, though, that weren't just about some of those more driven activities. He talked about the people side as well, like when he talks about President Lincoln and says those character traits were things like humility, compassion and endurance. It's about developing yourself as a good leader.
Speaker 1:We've gone through enough books now, sam, that talk about how you start with yourself before you lead others, before you lead the strategy. In fact, we have a special edition or an exclusive edition podcast series that just recently is coming out that features Zach Elliott, who we're going through books that are written by military veterans, and one of the books that we started with is called Extreme Ownership, and it's all about that that you have to start with owning up to things yourself before you could lead other people and before you could lead the strategy or an operation. And one of the things that Ryan Holiday points out in this intro is he says that bad companies are destroyed by crises. Good companies survive them, but great companies are improved by them, and so when I read that, I started thinking about my gosh, the avalanche of companies, including government entities, that are laying off people right now, including government entities that are laying off people right now and what is going to be their legacy as they get to the other side of this. Because this book talks about how the obstacle being the way is simple, but it's not easy, because you could have mental obstacles, physical obstacles, emotional obstacles, perceived obstacles, but you can always turn the obstacle into an advantage, and it really one of the stories that sticks out for me, sam is well, there's two, because I mentioned last week I wanted to talk about a leader that I had that is extraordinarily good at saying Freud, which is a word the author used to describe Rockefeller, which was somebody who has unflappable coolness under pressure.
Speaker 1:Rockefeller, which was somebody who has unflappable coolness under pressure, and the time of my career was during the time of 9-11. And I was working for Planet Hollywood and I had this boss named Steve Cook, who is still one of my greatest friends and mentors today, and he was the manager of this particular location in Atlanta and I'll never, ever forget. I think all of us that were adults around the time of 9-11 won't forget where we were, what was happening and these things that surrounded the moments when the United States changed. And in that day we were in the restaurant getting ready for the morning, to get ready for another day, and at the time I was working in sales and marketing for the restaurant, so I wasn't a server or on the front line, if you will. I was in the back and we were just getting ready like any other day, and we had all the televisions on, waiting for customers to arrive. And then suddenly the world became silent and it could have been, I suppose, very easy for there to arrive. And then suddenly the world became silent and it could have been, I suppose, very easy for there to be chaos and disruption when that happened.
Speaker 1:But Steve was cool, calm, unflappable, unlike years before that, when I was in 11th grade, I had just moved to Florida and my very first week of school I was in Spanish class. I was on the second floor of a building and it was sort of like a motel sort of a school, because in Florida all the doors are like on the outside of a hallway and then you go into the classroom, but it's not like a giant building that's enclosed, like when you live up north where it's cold. So the teachers all said, hey, great opportunity, today there's a space shuttle going up and a teacher is on board. So we're going to go outside because from where we are we can see this shuttle go up into the air. So we went outside.
Speaker 1:It was my first week of school and we watched it go up and I'll never forget that incident either. I saw the two plumes. I didn't know what was happening. It was the first time I had seen a space shuttle live and in person. But then we suddenly saw gray snow falling from the sky and there were teachers running around frantically trying to get students back into the classrooms. The televisions were all positioned to the news and it was a much different experience. It was that there was this terrible thing that had happened and the teachers had to think quickly about how to calm students down from something that just we experienced in real time, right in front of ourselves. And yet then I can also think about and I'm sure we could dive deeper into it, but I'll take a breath here that I've had other leaders in business that were on one side or the other of that fence, of how they endured things like massive layoffs or economic downturn, or even acquisitions and mergers and things of that sort.
Speaker 2:Yeah, and I really I'm a firm believer that leaders have to be the steady, stable force for the world around them, like, right, like they need to be the you know, like the post on the ship of this, like with the sail. Right, they need to be the thing that is grounding everybody, that's keeping everyone together. And I think that when I think about self-leadership, it's that same thing. You've got to build a part of yourself that can hold steady to your calm, your values, your, you know the things that are most important to you in life in the midst of storms, right, you've got to be that really strong thing that kind of holds things together and like, and it makes such a big difference to your experience and to the people around you. If you can be that and if we think about all the obstacles, right, the storms will come, but you have to be ready to take action. Right, you have to be ready to be that in that moment. But that doesn't some people, it comes naturally to right. Those people are just kind of naturally calm in chaos. But for most of us, it's a skill you have to develop, it's a thing you have to practice. Right, you practice it in small, safe spaces, day in and day out, have to practice right. You practice it in small, safe spaces, day in and day out. And he says in the book like most of us aren't faced with, like huge, big, life-altering challenges day in and day out, it's, you know, it's just things we have to simply endure, it's basic situations. And so in those moments it's where we can really start to build these skills up of figuring out how to be that presence. And again, like I, again, we go back to like that, mogada, solve for happy. Like you got to set your expectations that the storms will come, the obstacles will come.
Speaker 2:And he says in here there's an old zen story about a king who people had grown soft and entitled, and I loved this little story, but he didn't like that. His people, you know, were working this way and so dissatisfied he had hoped to teach them a lesson and his really his plan was really simple. He was going to put a large boulder in the middle of the main road and completely block the entrance to the city and then he waited to see what happened with people and what they did to do it Right. And some people were, you know, you know, just angry, giving up, like, oh, this is just blocking it Right. Like a lot of people just came up and like, nope, like this, I can't believe this is happening. This is, what is this? This huge things. In my way it's blocking what's happening. And then he said, after several days a peasant came along and he didn't turn away. Instead, he strained and strained and tried to move it. Then he had the idea and he scrambled to the woods and found something he could use as a lever and he moved the boulder out of the way right, and beneath the boulder the king had put a couple of gold coins and it said, and with a note, and the note said the obstacle in the path becomes the path.
Speaker 2:Never forget, within every obstacle is an opportunity to improve one's condition. And I love the parable and I just thought like I could just envision this in my mind. People like coming up to this giant rock and being like what the heck? And? And then there's somebody who comes along and says, okay, well, I'll just move it, right, we're going to improve this situation. And if you, if you really take that into, like, just the small things like these are the things I always encourage people when I'm coaching them about, like these little obstacles that are getting their way. It's like, oh, my goal between our last session and this one was x, and I didn't do it. And I was like, well, tell me about the obstacles, tell me about the things, and what are the levers we build that move those little things? It's like, oh well, you know, this popped up and this popped up, it's like, well, then you have to accept reality that this isn't gonna change.
Speaker 2:I had a client who, um, worked in sales and, uh, he was like, oh yeah, you guys, I got caught with, like, month end activities and you know, I didn't. I just didn't get done the things that we had talked about that I wanted to get done. And I said do month end activities happen every month? It's like, yeah, and I was like, and do they get worse at the end of every quarter and then at the end of every year? And he was like, yeah, and I was like, ok, we get to accept that reality. Right, this is, this is part of the path for you, right? And so this nice system you're trying to define for yourself that gives you this work-life balance that you want, has to look different in those weeks. Right, like it's the reality of it. What's the little lever we put in place that makes that work right, that gets that, you know, not out of the way, but part of the path.
Speaker 1:There is, based on that, a really good quote in here that the author has from Benjamin Franklin. That can help your salesperson, it could help anyone in any industry, it could help us seduction, I guess we could also add. Sports involved, involved resolving vexing problems with a potent cocktail of creativity, focus and daring. When you have a goal, obstacles are actually teaching you how to get where you want to go, carving you a path, and so the benjamin franklin quote says the things which hurt instruct. And it got me thinking about this story I had heard recently about Steph Curry so you may appreciate this, being a basketball player and fan yourself, sam that there was this story that had come out from him about when he was younger, maybe around 11 years old or something, and he was already a good player at that age. And so his dad, obviously very accomplished player and was trying to tell him that your obstacle is the way you stand or from where you shoot the ball when you're trying to get a shot, whether it's a three-point or otherwise, even though now he's known as obviously one of the greatest of all times in doing the three-point shots. So the dad basically instructed him, gave him the tools, like we're given this book, which is the instruction, if you will, of how to improve his obstacle, which was he was missing. He was missing the shots. Missing the shots, he was getting frustrated and every day he'd be exhausted from practicing and he'd kind of go into his mom and complain like it's just not working, it's too hard.
Speaker 1:And his mom was the one that basically was part number two, which was like the will and the like fortitude of it, and so she said to him look then quit or don't, and kind of left there, and so he, being the type of person with the tenacity and character that he had, clearly not only didn't quit but he overcame it. Because, again, this is not about just solving the obstacle, it's about not just surviving the obstacle, it's about thriving and flourishing. And so the book talks around how you don't quit but quitting is a choice. So the book talks around how you don't quit but quitting is a choice, and that one of the greatest ever being Steph Curry, which is not in the book, it's just a story I was thinking about is that he didn't take any shortcuts. He flipped the obstacle into something that has now made him be the most successful ballplayer of potentially all time doing what he does, because he took that obstacle and changed it around.
Speaker 2:Yeah, yeah, yeah, I love that and I think that you know this quote from Ben Franklin is perfect the things which hurt instruct. And if I think about like right, what we learned as we talked about just human behavior, I'm thinking back all the way to Atomic Habits, when we did that. I like that book and all the things I learned from that like forever altered my life, and I quote that more than anything else I think still to this day. And it you know he talked about how like human behavior is.
Speaker 2:We're only ever doing two things Like we're either moving towards pleasure or away from pain. And you know, this is where you know, like the John Maxwell book of sometimes you win, sometimes you learn right, it's when you're losing you're learning. Right. When you're in pain you're learning. Like we need that pain as the motivator to do something, Because if there is no pain, then we just stay the way things are right, like when we aren't feeling any ill-advised. You know health effects from our lifestyle. We don't change it until something happens right and then it's okay. Now I got to change my life right. We don't. We had a party here at my house over the weekend. We don't clean our entire house until a bunch of people are coming out and there will be the pain of the shame of having a dirty house and having people trip over stuff if I don't pick up the toys that are everywhere.
Speaker 2:More you know. More specifically, have my son pick up his toys that are everywhere. Right, like it, we don't. We don't make changes. It is just in our basic nature to stay at a state of rest until something makes us move, and that thing that makes us move is pain. The thing that makes us move is you know the things which hurt and if we do them right, we use them as lessons, as we use them as moments to learn and to make the changes that we need to make to become the person we need to become.
Speaker 1:Absolutely Well, as we talked about earlier, it's. This is simple. It's not easy. Here's maybe a thing for you to take away as a listener, and what I know that we'll take away ourselves for this week, which is that he outlines the author outlines a process, and the process he says is three steps, but it's actually four steps, and so that process is that you can overcome obstacles in these four ways.
Speaker 1:Number one look at how your specific problem is Like. What is the problem? We talked about this last time Like, think of something that you feel is an obstacle for you right now. Number two he sort of combines this into the number one, but I'm going to call it number two, which is what's your attitude about it or what's your approach around it. Again, it's hard. Like if you're laid off from your job. It's hard.
Speaker 1:Hard if something happened and you are in the midst of a change with your relationships. It's hard, but you look at the problem. And number two is what's your attitude or approach to it? Number three is how much energy and creativity do you have inside of you that's kind of like your gumption, I guess, or your result to actively break down the issue and turn it into opportunities. Remember, it's not about positive intelligence, it's about creativity and the resolve to doing something about the thing you don't like. And then number four is finally, cultivating and maintaining an inner will that allows you to handle difficulties, because you're not going to just solve that thing overnight, because if it was that easy, then everybody would be able to solve all their challenges that easily.
Speaker 1:So look at your challenge for this week. How is your attitude about the challenge? How much energy do you really have to get around it and what's your will to be able to do that? And I will say in closing, as we wrap this episode up it is always easier to move through that if you engage with a coach, and if you don't have one, don't know how to get one, don't understand what coaching is or how it can benefit you. We implore you, we invite you, we encourage you to message us and we'll help you. And if we can't help you, we know coaches from around the world and can help you find someone that's a good fit. Next week we're going to talk about perceptions, which is part one of the book, but before we do, sam, is there anything else to leave our listeners with for today?
Speaker 2:um, I think you know he ends this with. He ends the introduction with saying these obstacles are actually opportunities to test ourselves, to try new things and ultimately, to try them Right. The obstacle is the way, and I I love that thought process, right, and that's really what this, this whole rest of this book, is about is, you know, using those and, like you said, through that step process, right, it's about that objective judgment, your perception on things, which is where we'll go next week, and so there's this is broken down into a number of different ways to look at perception and things like that. So it's an interesting thing. But, you know, I think begin with that thought process is, you know, what is this judgment we've got on the situation right, what is happening around us and how do we use that to move forward, and so I'm looking forward to talking about that with you next week.
Speaker 1:Ditto. Thanks, friends, for being here with us today. My name is Denise Russo, On behalf of my friend, sam Powell. This has been another episode of what's on your bookshelf.