MBA2524 Must Read: The Obstacle Is The Way by Ryan Holiday – REVISITED
2 Feb 2026 · 29 min
Omar Zenhom revisits Ryan Holiday's The Obstacle Is the Way, breaking down three core ideas: how you perceive problems, taking decisive action, and building resilience. He uses real examples like a Webinar Ninja outage to show how obstacles become opportunities for entrepreneurs.
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Welcome Back to the $100 MBA Show. I'm your host Omar Zenholm, and today.
We'Re revisiting a book that I first.
Spoke about here on the podcast back in 2015 when I first read it.
This is such a good book.
It's such a great book that I wanted to talk about it more now that time has passed. You know, it's been over nine years since I read that book, and it's.
Time for me to kind of give you perspective.
I've changed a lot in nine years. I've learned, I've grown, and this book has proven to be useful and insightful through those experiences. So what's today's must read and what is this book that I'm revisiting? Well, it's called the Obstacle is the Way by Ryan Holiday.
This book is probably, I would say.
Top 20 books of all time I've ever read. I know that's a big claim, but it's hard for me to say it's.
Not because the theme, the stories, the.
Takeaways that you get from this book is incredible. I think Ryan Holiday really won me over as an author with this book. When I first read this book, I really decided that that's it. Next time Ryan Holiday publishes a book, anytime he publishes a book, I'm going to buy sight unseen. And that's exactly what has happened since then. And I've spoken about a lot of.
His books on the show, but this one in particular, we're going to go into detail.
I love this book for so many reasons, and this is why I wanted to talk about it in detail today. I want to give you some prime examples in the last nine years, how this book has taught me so many lessons and how its lessons has shown up in my life over and over.
We're also going to provide a worksheet for today's episode.
So if you want to download that worksheet, if you want to kind of make use of the knowledge we're going to be sharing today and put into practical action, go to 100mba.net worksheets and over there you'll be able to download.
It free of charge. Let's dive right in and talk about.
This book, the Obstacles Away. One of the things I love about this book is how much it emphasizes.
How most successful people in history have turned their greatest challenges into their biggest triumphs. This is a pretty big concept and.
We kind of know this on the surface. Yeah, you know, struggles are gray and they help us grow and yeah, yeah, yeah, blah, blah, blah.
Right. No, this book really gives you a different perspective. The Obstacles Way teaches us that when you have an obstacle in front of you, when you have a challenge in your life, when you have a challenge in your business. Right. It's not there just to be difficult.
And okay, if you could pass this.
Challenge, you deserve to be successful. No, it's actually a gift. It's actually the way you will solve and improve things. It's actually the way that you're going to add value to your business. And I'll explain in today's episode.
It's actually really, really profound.
I first read this book 2015, which was a year into my journey building Webinar Ninja.
I launched in 2014. Webinar Ninja was my software company that me and my co founder built and grew to over 30,000 customers and then finally got acquired recently by Proprofs, which was an incredible step in my career as an entrepreneur, changed my life drastically. But a year into that journey, I.
Found that the principles in this book.
Helped me tremendously to navigate the challenges that that I face with growing that software company. Ryan Holiday, the author of this book.
Shares insights from stoicism, which is a.
Concept and a philosophy we've heard about many times.
But it's more than just stoicism. It's about the idea of resilience.
It's about understanding human nature and how.
To turn obstacles into opportunities.
And I've applied those lessons in my business, in my personal life, and it's.
Helped me in ways I can't even describe.
There's so many times where I am going through something, something I'm learning something, I'm, you know, struggling with something. And this book comes to mind. I tell myself the obstacle's the way and it helps me tremendously because it reminds me of all the lessons I learned that I'm going to share with.
You today before I get into the.
Three things that I want to take away and share with you in this book. And now there's a ton of value. These are just the three things that helped me the most. And there's a lot more. I highly recommend you pick up this book like, this is a no brainer. Buy this book right now.
Okay?
It's worth its weight in gold. It's really, really amazing. And if you want to learn more about the books that we Recommend, just go to 100- MBA-NET READ. We have all our book reviews there, all the must reads that we recommend.
So let's break down. What are the three things I believe.
Are like the key insights from the obstacles away and how it helped me in my entrepreneurial journey and how I.
Hope it can help you as well. The first one is perception. Seeing obstacles as opportunities. Okay. This is such a profound, profound idea where when you have a challenge in your business, when you have a challenge in your life, this challenge, this obstacle, is actually an opportunity. It's actually a chance that's a given to you. It's not as horrible as you may perceive, right? No doubt it is horrible.
I am thinking about a painful time I had in my business in my.
Head right now, and it was really, really bad.
I don't want to go back to it, but If I'm being 100% honest.
That struggle, that hard time had an opportunity in it. And because I took that opportunity, I was able to get past it and be better because of it. So the first part of this I.
Want to kind of convey is change your perspective.
How you perceive obstacles can significantly impact.
How you respond to them, right?
When something bad happens to you, right. How you respond to them is everything, right?
How you respond to that bad event, that horrible event, that difficult, challenging event.
How you react is everything. That's who you are. That's your life. The actions you're about to take will determine what will happen next. Okay? So by viewing challenges as opportunities to grow and learn and turn these things around, see these setbacks as challenges that you can overcome and become something better. One of my favorite quotes by Jim.
Rohn, who's the like, like the godfather.
Of personal development, is don't wish it was easier, wish you were better. Let that sink in for a moment. When things go wrong in our lives, in our business, our Knee jerk reaction is to be like, why did this happen? How did this happen? Why me? And we wish it just never happened. But really what we should wish for.
Is that when something happens like that.
We'Re like, no problem.
I can handle this.
I'm strong enough, I'm experienced enough. This is a no, not an issue. I can take care of it.
Right?
So for example, when we faced technical difficulties at Webinar Ninja, we had a moment where we had an outage and it was not caused by the servers.
Or AWS or one of our service providers.
It was our fault.
There was a bug in the software and we had to fix it.
Right now when this happened, it's a horrible time, right?
Because everybody's, you know, not having a great day. All hands on deck.
We're kind of scrambling to fix this.
So customers are not suffering for too long.
We find out it is a bug.
We now identify the problem, we now need to quickly fix it.
But after we kind of band aid.
The solution and was able to get back online and serve our customers, we.
Discovered the reason why this bug creeped in is because of the system that we have built to deploy code was not solid. This is in our early days, is.
Probably within the first 18 months of our company.
And we changed the way we deploy.
Code, the way we create code, how we common code, how we qa, do.
Quality assurance, everything got better and faster. We actually deployed co faster and updates came to our customers faster. If it wasn't for that challenge that was really horrible in that day, or believe me, bad day, okay, I didn't.
Feel so great that day.
But that obstacle allowed me to learn how to get better very quickly. If that thing never happened, if that bug never creeped in, we would never actually analyze our current system of deploying code and we would never get better. And we would never deploy code faster, and we would never be a better.
Company and be able to launch new.
Features as fast as we did. So in a way, that was a blessing.
You know, they say a blessing in.
Disguise, but this would not be a.
Blessing if in the moment I was.
Just like, this is horrible.
Start blaming everybody, start yelling, get angry. And then when we fix it, we're like, okay, fine, it's fixed. That's fine. Let's move on. Let's hope that never happens again.
No, as soon as the challenge happened.
Because I read this book, I was like, okay, obstacles away.
Where is the opportunity here? Let's take a look. What can I learn from this? How can we improve upon this? How can we become something better because of this?
And that's what kind of got the.
Discussion with me and the cto, and.
We were kind of like, okay, how can we get on our feet and figure this out and make sure that we're a world class company even though.
We were a small team?
There's a quote from this book that you're gonna love. I absolutely love it. And I'm gonna just read it to you right now. That relates to this topic and this, this takeaway. So here it is.
Choose not to be harmed and you won't feel harmed. Don't feel harmed.
And you haven't been.
If you don't choose to say, this.
Is gonna hurt me.
This is horrible.
I hate this.
Right? You won't feel horrible, right? You won't feel like this was an attack on your life, right. If you don't feel harmed, and then it wouldn't have been a harm. The harm will not exist, okay? Because you'll just see this as an incredible opportunity. Thank goodness we had that bug because it just made us better.
Okay. Love that quote.
The second takeaway I want to share.
With you from this book.
My favorite takeaway is this concept of action. Taking the right steps, Specifically taking decisive action. Instead of being paralyzed by obstacles, take clear and decisive action to move forward. Break down the problem to, like, manageable.
Steps and then tackle them one by one.
So many of us get overwhelmed when.
A problem happens, when a fire occurs in our business, when a challenge in our life happens. You know, somebody gets sick, somebody is.
Hurt, somebody has a financial situation that's devastating, right? It's shocking, it's overwhelming.
It's like, I don't know where to start.
I don't know what to do.
I want to give up.
That is natural. Allow yourself to feel that pain for a bit. It's okay, all right?
But don't let it last too long. For me, it's about maximum.
I give myself two minutes, right?
120 seconds.
This is my system where it's like.
Okay, I get to feel the anger.
I'm upset. Da, da, da. And then I take action. Two minutes have gone by.
It's time to take action.
Here's an example. When we encountered that big bug I.
Just mentioned in our software, I stepped away from my computer. Me and my partner in life, Nicole.
We really were frustrated.
What is going on?
This is ridiculous. And it also, we felt overwhelmed. Who do we contact first? Who do we, what do we do first? Do we send a message to the customers? Do we talk to Our team do.
We put a notice up on in the software. It was a lot in one second.
So we just gave ourselves two minutes.
To be like, okay, this is horrible. We hate it.
This is not good. Right? And then we follow the instructions of the obstacles away and say, okay, what are the steps we need to take?
Forget about the order right now.
What are the steps?
Well, one, we got to fix the bug. Okay. Two, we have to notify our customers what's going on. Three, we got to make sure that the person that is going to help us fix the bug, somebody on the team is notified, and then they can tell their team. Four, we need to communicate a plan of action to the customer so they know when this is going to be back up. Five, we're going to do kind of.
A debrief and a postmortem to find.
Out what happened, and we're going to learn from it.
Right? We wrote down just, like, really quickly.
It took us like, maybe two minutes to write that down.
Three minutes.
And then we put a quick order. Okay, first we do this, this, this, this, this. And then we divvied up the task.
And then we took action.
Okay, what's relieving about this? What's great about this is you give.
Yourself time to be emotional, you give yourself size to feel the pain, and then you spring into action, and you spring into, okay, what do we do here?
Here's what I'm gonna do.
So what you're gonna do, and we.
Just go for it.
And you're just busy taking action.
You kind of don't have time to feel anymore.
Okay.
You're just doing what you got to do to solve the problem and learn from it. There's a quote from the book that is fantastic and encapsulates this perfectly, and.
It says, action is the solution and the cure to our predicaments, which is.
Incredible because a lot of us, we just want to sit down and just be like, oh, I give up. I don't want to do this anymore. This is horrible.
Actually, any action, just taking action, learning, discussing, talking to your team, just taking a step forward is going to allow you to just plan and be a little bit more strategic. And already, as soon as you start taking the first steps, like, as soon as I spoke to my team, as soon as I learned that, okay, this is what's going to happen, these are the steps that we're going to take.
To fix the bug, we're going to then communicate to the team. And then I communicated. You know, when I say the team.
The greater team customer support.
We tell all the departments, okay, heads up, this is what's going on. And then communicate to the to the customers.
As soon as we started doing some of these actions, it started to feel better and better. Still felt horrible, but it didn't feel.
As bad as that initial moment.
Started to feel like there's some light that things will get better, that this pain will be over soon and it's not that bad. We can take care of it.
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Takeaway number three it's all about will, really, in business.
How much will do you got? And this book really talks a lot.
About building resilience and inner strength. You really need to spend time as an entrepreneur developing your inner fortitude. Because this game, this life, this entrepreneurship thing, it's not for the weak. It isn't one of my favorite quotes from a book called Shoe Dog, which.
Is the memoir Phil Knight, who's the founder of Nike, this is one of my favorite quotes of all time. And I actually write it in my journal sometimes to remind me of this quote.
And here it is. The cowards never started.
The weak died along the way.
That leaves us.
And I love that quote because it.
Reminds you that this business stuff, you know, it's not for cowards.
It's not for the weak.
It's the people that can persevere and keep moving forward.
I talk about all the time at the end of these episodes. I encourage you to do that all the time because I know that's what it takes. I know that's the kind of attitude you got to have in order for you to be a successful entrepreneur.
Building resilience, building inner strength. It's just crucial. It's just crucial for you to be.
Able to overcome these obstacles that you will face.
They're coming, okay?
If you haven't faced them yet, they are coming and they will continue to come.
Because that's just the nature of doing incredible things, achieving significance, achieving something that's.
Valuable in the world.
It's just not going to come easy. There's going to be things in your way stopping you, and you're going to.
Have to overcome them just like in.
A video game, right?
And you got to beat that boss at the end of the level so that you can continue, right?
But you will continue if you keep persevering. So you gotta embrace these challenges as a part of your journey. You just gotta accept it. You gotta accept that, hey, this is.
Gonna be hard, it's gonna be tough.
It'S gonna be painful. And that's just a rite of passage. That's just how it is. And once you just admit to that, if you just commit to that and say, okay, that's just how it is, I have to just accept it.
And I know that's normal and I.
Know that that is actually what everybody else that I look up to, all the wonderful entrepreneurs and biographies I've read.
Have done, then I'm in that club.
I'm in the club that perseveres.
Okay?
So one of the things I want to share with you that's personal for.
Me when it comes to this topic is whenever you experience the ups and the downs in business, and you experience.
It over time, what you start to realize is it's never a good idea to be too up or too down. You want to stay in the middle a little bit in terms of the way you feel. Now, this doesn't mean like, don't celebrate.
Your wins or don't enjoy your time when you're having a good time or when things are great, or you know, have fun with your team and have.
Team retreats and celebrations. No, have fun. Enjoy it, but enjoy it because you know it won't last forever.
That's what I mean.
I mean, when things are great in your business, when things are going well, know that at some point you're going to have to challenge yourself to move.
The next level in your business.
To challenge yourself and put yourself out.
Of your comfort zone, to beat the.
Competition, to, to move up just in your value to the marketplace. Okay? And I'm going to give you an.
Example in a moment.
You know that in order to do.
That, things are going to get harder. Okay? So if things are good and fun and enjoyable right now, and you know, maybe it's cash flow, maybe it's accolades, maybe it's write ups, whatever in the.
Media, that's wonderful, enjoy it. Because you know, that it won't be.
Fun all the time.
So enjoy those moments because there will be sour right after the sweet.
That's what I've learned. Okay. And that's okay. One of the things I learned is.
That there's the seasons of the weather, right? The seasons that we know, like, we have summer, we have autumn, we have winter, we have spring. It happens every year without fail for.
You know, thousands and thousands and thousands of years.
Okay, so what does that teach us about life? That there's going to be another winter coming up. Right. And after winter, there's spring.
And spring is a chance for you to have an opportunity.
This is when you plant your seeds. Right after winter comes spring.
And this is exactly what obstacles always talk about. It's an opportunity. And then the summer comes and it's.
Sunshine and things are great and you're having a good time and things are starting to grow. And then you reap your harvest in the fall. Okay, now I'm getting my dividend, I'm getting my bonus. I'm raising my salary. I'm having a better life. But then you're going to get hit with the winter again. It's just the nature of life.
And one of the things I want.
To say is that sometimes you're going to reach the fall and you're not going to reap that much. You had a bad season, right. The crop didn't grow right. And sometimes that happens and you're gonna learn, why didn't it happen? Did the weeds get my crop? Was it the insects?
Was it just I didn't water it enough?
Whatever. You're gonna learn from that mistake, and you're gonna try to do better next year. But some years you're gonna have an incredible harvest, and you're gonna be like, wow, this is incredible. Don't feel bad about it because you know that sometimes you're not gonna have.
Right. Don't feel guilty about having a good, you know, season or a good reward.
From your hard work and your business.
Because, you know, that's not always going to be that way.
Okay? So that's what I've learned when it.
Comes to the idea of resilience is.
This idea of being, you know, a.
Bit stoic about this, you know, very relevant to this book.
Right? Be a bit stoic about it. Understand that. Yep. I enjoy these highs, but when I hit low, I know I'm expecting it. It's coming. I know it's going to get tough. Okay.
That's what I want to kind of convey when it comes to this topic.
A great quote from this book is the impediment to action advances action. What stands in the way becomes the way.
I love this quote.
So that winter is actually a good.
Thing because it's going to allow you to have an opportunity in spring.
So let's take these principles and see.
How they can be applied to your business.
We talked about, number one, perception.
View the market and its challenges and its opportunities.
What are the opportunities out there in the market? Instead of fearing competition or market changes, see them as opportunities to innovate to zig while everybody's zagging, right? And differentiate your product and differentiate your offering, okay? Use customer feedback to improve your offerings and stay ahead of your competition, right? Learn what people complaining about about your competition or saying, oh, I wish this.
Product or service did this.
One of my favorite things to do when it comes to this is three star reviews. Read three star reviews of books, of products, of software. Whatever market you're in, I'm sure there's.
Customer reviews somewh when it comes to.
That product or service or your competition, right? Read the three star reviews because they're gonna be fair.
They're gonna tell you, hey, you know, this is what I like, this is.
What I don't like, or this is.
What I wish it had.
These are opportunities for you to grow.
And to get ahead.
2. When it comes to action, implement incremental.
Improvements in your business.
Always think about what is one little action I can do today to improve my business, right?
Improve my marketing, improve my sales, prove my customer support, improve the product itself, improve my branding, right?
Break down these bigger ideas and challenges into smaller tasks that you can take action consistently.
One of my favorite things is this podcast. I publish this podcast three days a week.
I've been doing it for 10 years, okay?
I have over 2,500 episodes. I have over 2,500 episodes. And one of the reasons why I.
Do it is because it forces me to be consistent with my marketing, with.
My content, with my branding. And every time I step up to.
The microphone, I am telling myself, okay.
How can I get better? How can I do it better than last time? And I've been doing that for 10 years and luckily I've gone a bit better, so I can't even listen to episode one through 300 or something.
And then lastly, cultivate resilience. You want to encourage a culture of resilience in your business.
I'm going to give you a couple examples.
Number one, we tell our team members when they join us that one of.
The requirements of being part of our.
Team is that you have to be willing to change. You have to be willing to improve. I like to use the word change because improve sounds so positive and people.
Don'T even think about what if that improvement is something that's uncomfortable, something that.
I'm not really interested in, or maybe something that triggers my insecurities, okay?
So I like to say you gotta.
Be willing to change because a company's gonna change, you gotta change with it. That includes me first, right? As the founder. I need to change and improve as the company changes. Because what happens is if you don't change, then we're gonna have to say goodbye, right? Because you're not changing with the business. And that's what happens. That's actually the number one reason why.
We'Ve ever let go of anybody in.
Our company, is that they just didn't change with the company as it grew.
You know, one of the things that.
We encourage everybody is to grow with the company. That means you grow, improve your skills, add more value, because the more valuable you are to the company, the more likely you're gonna stay with us because we need you. Okay? So that's the first thing. The second thing is they have to understand that what we do in the business because we can't keep doing the same thing and want different results, right? If you want exceptional results, you gotta do exceptional things. That means you gotta keep challenging yourself. An example is this podcast, okay, this was an audio only podcast for nearly 10 years.
And then I sold my company, Webinar Ninja. I said, okay, I wanna fully focus on this podcast, fully focus on this brand, the $100 MBA, and help as.
Many entrepreneurs as possible. I wanna reach as many people so they have a better path to success.
An easier path to success than I did. I had it pretty rough because there.
Was limited information when I was starting.
Out, okay, 20 years ago.
So one of the ways to achieve that is to reach more people in different mediums. So with different mediums like video. And I said, okay, this means we're.
Gonna have to do videos now, right? This means a lot of challenges for me. I have to grow, I have to learn, I have to figure this out. I have to understand cameras and angles and scripts and understand how to cover things in a concise fashion, just in audio, but now in video. So there's a lot to learn.
There's editing, there's post production, there's how.
We'Re going to market this information. We're going to have to build A team around all this change, okay?
So this is a big change. But I know that if I don't change, if our business doesn't change what it does, it will continue just to get the same results. I want more results, right? I want to reach more people. I want to have more impact. And I'm getting a certain number of.
People and I'm getting a certain, you know, type of impact or level of.
Impact with just the audio.
But I know that if I go.
Video as well, things will change. And as hard as it is, I know it's going to be difficult, but.
I got to be resilient. I got to challenge myself. I got to put myself outside the comfort zone that I've been in so.
That I can grow. So that's a real world example of.
Me exercising these principles in my business.
So, to recap my favorite takeaways from.
This book, the Obstacles Way highly recommend you pick up this book.
Okay.
Is you identify the obstacle as an opportunity. Right? The obstacle is the way, right?
It's how we get better, right? If you're struggling to convert leads into customers, this is a chance for you.
To figure out why.
Maybe your product needs to change. Maybe your customers that you're attracting need to change. Maybe you're attracting the wrong customers. This is an opportunity. Number two, change your perspective. Right? List the ways you can challenge this opportunity. Change how you approach it, right? How you feel about it. Number three, take action, okay? Just break it down. Take those actions, okay?
And of course, through all of this, you want to build that resilience and.
Knowing that the winter will come. But enjoy those springs, enjoy those summers.
And when you reap that harvest, don't.
Feel guilty if it's a good one.
The Obstacles Away by Ryan Holiday is.
A timeless book for turning your challenges in business, in life, into opportunities. There's so much to learn from this book.
And again, if you want the worksheet that goes along with today's episode, go to 1-000- MBA and you can download.
It there for free. Thanks for tuning in to the hundred Dollar MBA show.
Hope you found this episode valuable. And if you want more valuable episodes like this one, we have over 2,500 business lessons in our archives over on.
Our website at100mba.net until next time, keep moving forward.
I've said it so many times, but it's so true.
Business is about staying alive.
It's about surviving.
It's about just seeing another day so that you can keep going. So if you're in business and you're still operating and you're still turning a profit, any profit, right? Or even just kind of making it happen. Pat yourself on the back. It's okay. You are still in the game. You're still in the arena. You still are able to fight another day.
Right?
And that is a blessing in itself.
Okay?
So keep moving forward. Keep getting better so that your results get better. All right.
I'll check in the next one.
Take care.
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