I've got a confession to make.

I’ve never been the smartest guy. 

If you had a bell curve of intelligence, I’m probably smack dab in the middle of it - but what I do have is hustle when I’m passionate about something. 

I did okay in high school—just well enough to get into a business degree at university, where I learned one of my life's most important lessons that wasn’t on the syllabus.

In my first year, I treated the campus like a drive-thru—in for class and out just as quickly.

My real life was a mix of skateboarding, chasing girls, and believing success would just fall into my lap. Because here’s what I figured:

You only need 50% to pass - you could literally get half the stuff WRONG and still get through.

Then came Accounting 101. 

Like my other classes, I didn't apply myself, and the results proved it.

But this time, it was really going to set me back. 

When I logged in to check my final results, I’d failed the class.

This wasn't just a red mark on my transcript; it felt like a red flag on my life plan.

I don't know what I was expecting to happen when I stopped taking class seriously. It seems stupid in hindsight, but that result was a shock - it hit me in the guts. 

Failing in university made me question my identity. Should I just give up? 

And that wasn’t even the hardest punch.

I still had to go home and tell my Dad I’d failed. 

I’ll tell you how that went in a minute.

But first, I want to tell you about this book I later discovered that gave me the tools to put failure in perspective. 

The book was Ryan Holiday’s The Obstacle Is the Way, and I'll share the three most impactful lessons from this book that reshaped my approach to life’s challenges.

In hindsight, that conversation with my dad was such a turning point in my life.

So, what is the book even about? 

Stoicism. A philosophy with the principal teaching that there are two aspects of life: the events that occur, and the stories we tell ourselves about these events. 

The events are beyond our control - they're the unpredictable waves of life.

But the stories, the meaning we attach to those events – that's where our power lies.

Part 1: Everything Matters, Be Exceptional

So, it's winter - just past 6am in the morning, and I’m doing my run up the local hill. 

A storm the night before left the trail in ruins. And there is one choke point where a large tree has fallen, scattering branches across the path. 

On my way up, I tip-toed through the debris, and I knew all these branches might be difficult for other people to get through. 

But I left. I had my run to finish and my own goals to think about.

On my way back down the path, I run back through the debris, and then, in an instant, I’m airborne.

You know those moments when everything moves slowly, and you know you’re about to get hurt? It was one of those moments. I had tripped on one of the branches.

After my short flight, I tumbled a few meters down the hill, cartwheeling like a rodeo clown. 

I got up, winded, and look around to check if anyone saw me fall. 

My pride was wounded, but my hands were also bloody, and my knees were throbbing.

I started limping home.

Then it hit me. Nature had just reminded me of a lesson I thought I knew: 

“How you do one thing is how you do everything.” 

By passing those trees and not doing anything about it, I was setting a standard.

Sort of like walking past rubbish at the beach. Yeah, I didn't make the mess, but by not doing anything about it, I set the standard of an unclean beach because I tolerate it. 

I should have cleared those branches when I first saw them. So, I turned around and cleaned the mess so it was safe for others.

And I share this story because, unfortunately, there are a lot of times in my life where I have fallen short and let myself and other people down. 

By failing that accounting class, I let my future self down. But this stoic philosophy has since taught me to at least try to be exceptional in all that I do, from the smallest task to the biggest challenge. 

Sometimes it's easy to think you know the answer in the book, but it's a whole other thing to do it in practice.

Part 2: Philosophy Comes from the Battlefield

Another confession to make - for too long in my life, I thought all the answers I needed were in books. 

I prided myself on reading a book a week and taking down all the lessons.

Don’t get me wrong, there's a lot to learn from books. But if all the lessons were in books, then all the world's billionaires would be librarians.

But true philosophy doesn't happen in the quiet corners of a classroom; it's practised on the battlefield of life. 

Which can be messy, chaotic, complex, all that stuff not easily summarised in words. 

The textbook answer was to go to university and get good grades, but I really struggled with this when I was no longer tied to the daily schedule of 8am to 3pm that would keep me in rhythm with my life. 

I was free to do whatever I wanted at all times. 

Get up whenever I wanted, play basketball until the sun went down, go to the beach because it was sunny, or binge-watch The Mighty Boosh because it was raining. 

The freedom of unstructured time made all these distractions loud and up close in my life.

I lost the battle with constant trade-offs and decisions of my time every day.

Albert Einstein said, "The only source of knowledge is experience." And I think what he meant was that true knowledge comes from personal experiences rather than mere information gathering. 

Reflecting on the journeys of the great stoics and people in business, it's evident that their greatest lessons were often learned in moments of defeat when they were passing through the valley of despair. 

Because here's the thing… sometimes, things are completely out of our control, which is actually the third big lesson I picked up from the book.

Part 3: Building Immunity to External Pressures

As the youngest of four children, I was born into a world where I was always looking up and trying to catch up with my older siblings.

They were always more developed and capable than I was, which led me to feeling behind in life and not good enough. 

I remember this one summer in the 2000s I watched a movie called Click. 

Adam Sandler finds a remote control that gives him the power to pause or fast-forward through scenes in his life. 

Man - I wanted that remote so bad.

I would have fast-forwarded my development and the areas of my life that felt boring.

But what happens in the movie is that the remote takes control, leading Adam to miss out on significant portions of his life. 

He fast-forwards through years, missing out on the growth of his children and watching his marriage deteriorate. 

The lessons I saw in that movie and felt in my heart were precious because my first year of Uni was full of pressures. Pressures of the boredom of class, pressures of distraction of sports, and pressures of comparison or wanting to fit in with my friends. 

I wanted to skip all those classes and just get to the end.

But here's the thing.

The chaos seems like it’s around us. But it more often isn’t.

It's just in our head. 

What I mean by that is it's only in our mind that we have the perception of chaos. 

Now, I wish I was better at this… but I'm not. 

I still struggle, even with the stupidest things like being stuck in traffic or having to line up for something. I can literally feel my blood boiling. My wife laughs at me. "How does someone so focused on the principles of self-development, she says, get so frustrated about having to stand in a line for 5 minutes?"

She’s right. 

I have to remind myself. I can choose to remain unaffected by the external environment. 

It's not about avoiding these situations or wishing they were different. It's about accepting them and finding peace amid the chaos. 

I find with young kids I’m constantly tested in my ability to stay unruffled by the world around me. This lesson isn't easy, and I'm still a work in progress.

Now, I didn't know this stuff at the time, but those three lessons of:

1. Everything matters
2. Philosophy comes from the battlefield
3. Building an ability to be immune from external pressures

These were all things I had to learn in 2008, but I didn’t have the right frameworks to interpret them until I found that book by Ryan Holiday. 

Which brings me back to the story about me failing at Uni and having to tell my dad.

My dad's an immigrant from Poland. He arrived in Australia by boat in 1952. 

Like many immigrants, he and his own dad struggled after moving to this new country, financially and culturally.

He worked hard his whole life to give me a good education. And here I was goofing around and getting a fail. 

I’d failed before, in many things. But this time was different. 

This was me, supposedly a grown-ass man, out on my own in the world, repaying the hard work he’d done for me. I hadn’t just failed class. I’d failed him.

When I summed up the courage to tell him, he wasn’t angry - in fact, few things ever got him angry. Somehow, he’d already found a way to control his response to life’s pressures like the stoic philosophy I spoke about earlier. 

He was calm. But he’s my dad. I could tell he was disappointed. He looked at me and said, 

"What are you going to learn from this failure and how can you make this a great turning point in your life?"

I don’t think he knew about stoic philosophy, and he definitely hadn't read Holiday’s book, but he was capturing the lessons here - setbacks are opportunities. 

The event had happened. I had failed Accounting 101. 

I was not where I wanted to be in my life. And now it was on me to give the situation its meaning. 

Like an archer shooting for a target, I needed to take this feedback that I'd missed and use it to improve my approach.

What I realised from that conversation and a few weeks of despair is that failure wasn't the end, but the opportunity to start a new chapter where I showed up for my future self. 

Failure turned out to be the best thing that could have happened to me at that point in my life. I really focused on this event and created change in my life. 

I applied myself and, soon enough, the results started showing up on the scoreboard too. 

So now when I fail, it hurts, but I smile through it. And I share this because, if you found this post, maybe you're going through some failure yourself. 

I don't know what your situation is, but I do know that you have the power to give it meaning. 

Finding lessons in failure is your opportunity to forge a stronger, more resilient version of yourself.

The Obstacle Is the Way taught me how to deal with failure, and it's been one of the most helpful books I’ve read. 

But there are 11 others with stories and lessons that have been just as meaningful and useful.

If you want to find out what they are, you can check out here.