The Obstacle Is the Way: 6 Key Lessons in Stoicism & Winning in Life

The Obstacle Is the Way by Ryan Holiday

You’re powerless to control most things!

However, the few things that you do control are also the things that will ultimately determine where you’ll go in life. That’s one of the key points that Ryan Holiday’s book “The Obstacle Is the Way” goes into.

Today I’ll share 6 lessons from the book.

Note: Think of this as a book review or a preview for The Obstacle Is the Way. This is not meant as a replacement for the book, as I truly believe there is power in reading the book and stories in its entirety!

Get the book or audiobook on Amazon.

Lesson 1: It’s Not What Happens to You, It’s How You Respond!

This is one of the main ideas of the book as well as modern stoicism.

Oftentimes people blame where they are in life by the things that have happened to them and use that as an excuse. They don’t realize the true power that they truly have!

Let’s take a look at an old stoic quote:

“Objective judgment now in this very moment. Unselfish action now at this very moment. Willing acceptance now at this very moment of all external events. That’s all you need.”

Marcus Aurelius.

That quote is your personal power!

No matter what ever happens to you, no matter what external event, you always have 100% control over your attitude, your beliefs and your choices.

For example:

Let’s say that in the upcoming economic crisis, your business goes under and you get into a dire financial situation. If you look at that and you decide it’s a sign that it wasn’t meant to be, things will only get worse!

How most people react to problems
This is how most people react to a problem.


You could also decide that this is a lesson to learn, that many others have the same thing happen to them, and that this is an opportunity to build things up again even faster and better.

Your choices dictate your future!

Sure, unfortunate things happen to everyone. Things that you cannot control. But beliefs, attitude and choices regarding the situation is what separates those who recover and thrive quickly, from those who stay stuck forever!

If you focus on things you cannot control, you’re on a downhill path!

Which brings us back to the title of the book: The Obstacle Is the Way.

As Ryan Holiday likes to point out, your obstacles are really just lessons for you to learn. They are opportunities for you to learn from past mistakes and to grow as a person.

The opposite can also be true:

Something good can happen to you, say getting a big inheritance, and you react by getting complacent. In this case your response could mean your own downfall in the long run.

It’s never the circumstances that determine your future!

It’s your actions, your beliefs, your choices and your attitude!

The Story of Thomas Edison

At one point, Edison’s lab and workplace caught fire.

They all escaped and watched this weird fire.

Due to all the chemicals and other things inside, that were quickly catching fire, there would occasionally be clouds of different kinds of smoke and colors of the fire.

He then turned to his son and set:

“Quick, go get your mother. She’ll never see a fire like this one ever again in her life!”

And so, they watched his life’s work go up in flames like it was some kind of show.

He enjoyed the moment, rather than breaking down.

Afterwards, he went and got a loan from Henry Ford, got himself a new lab, and within a couple of weeks, his business was up and running again!

All because he didn’t get deterred by the situation, and responded to the situation in a way where he bounced back, rather than staying down, which many people would have chosen to do instead.

Lesson 2: The Way You Think About Failure is Critical

People do not like failure!

Just the thought of it alone can freeze people in their tracks sometimes!

Think about not sending that message on a dating app (fear of rejection), being hesitant to apply for a better job, try out a new hobby, sport, or start that business or project you’d like to start.

All because you fear failing!

That’s the critical part.

If you think that failing at something is a bad thing, you’ll go through lengths to avoid it. In other words, you’ll spend months planning while you should have been doing, or worse: you don’t even get started at all!

I want you to look at failure as feedback!

If you made your 100 step plan, and you fail at step 3, the other steps become irrelevant. Your fear of failure has caused you to procrastinate, waste your effort, and because of your attitude, you’re now likely feeling stuck or like a failure!

How about this instead?

You realize that failing is an inescapable part of success, you get started right away with the things you know how to do, steps 1 and 2. Now when you meet an obstacle at step 3, you’ll think of it as a sign that you need to make a change in the plan to move forward.

You welcome failure as something positive!

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By not being afraid to fail, you allow yourself to take action! You allow yourself to make progress, get the feedback to adjust, and reach your goals way faster than you ever could otherwise!

Lesson 3: There’s an Objective Reality & Your Subjective Reality

Part of the book’s philosophy is objectivity.

In order to make the right choices and recognize the lessons and opportunities in the things that happen around us and to us, we need to first look at those things objectively.

That’s often not what we do though…

We often look at things emotionally and often think about things as if they are worse than they really are. That is the subjective reality, the one we create ourselves inside of our own heads, which is mostly based on emotion.

You need to take a break!

Just like I talked about in my review of “The Subtle Art of Not Giving a F*ck“, sometimes what you need more than anything to solve a problem, is to get out of your own head!

You need that break, to step back and calmly observe.

Let me illustrate with an example

Let’s say you’re in a relationship of 4 years.

And suddenly it ends.

It can definitely be a heartbreaking thing, and it’s not uncommon for people to feel down about it for weeks or months. To feel like their world just crumbled down or that “they’ll never find happiness like that” again.

That’s the subjective part.

It’s the emotional side of us that takes over and turns a “bad” situation into something way worse. We often are our own worst enemy because of the way we think and create even bigger problems!

Then there’s the objective reality:

Yes, your relationship ended, but before you’ve been happily single for years. You’ve had relationships before, so if you want to you can start dating again, and get a new relationship with someone who’s an even better match.

On top of that, you’ve got your health, home and job.

The objective reality isn’t so grim!

Once you can take that step back and look at the situation objectively, you’ll be able to break out of destructive thinking and get moving forward again.

Lesson 4: The Question to Ask When Facing a Problem

This goes back to the idea of thinking of problems as lessons.

There’s an old quote I like:

Everything happens for a reason. But oftentimes the reason is simply that you have made stupid choices!

Let me tell you a story of an old job I had:

After finishing high school, I didn’t know what to study, so I decided to work for a while while I figure that out. It was a job in a factory, and while the job itself was pretty easy, it’s easy to mess things up with the heavy machinery.

And that’s what happened.

During one of my shift, I messed up some of settings, causing issues with the products. Someone else quickly realized it, but at that time, the damage (in products and lost time) already was way more than my annual salary!

I was scared as fuck when I had to see the boss!

I was scared that I might lose my job over a mistake that was 100% my fault. But instead of that, he asked what I did wrong, and then he asked what I learned from the experience.

And I was sent back to work.

And guess what?

Since I learned this the hard way, I made sure to double-check, and I’ve never made the same mistake again! For the company, my mistake was like an “investment” in my education.

Here’s why I’m sharing the story:

I want you to ask yourself the question that my boss asked me:

“What did I do to end up in this mess?”

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Whenever you find yourself in any bad situation, ask yourself what you have done to end up in that situation. Of course, in a lot of times it won’t be 100% your fault, but you will always have played a significant part in it!

For example:

Let’s say the stock market crashes, and you lost a fortune.

Of course, the market crashing isn’t your fault. But if you didn’t diversify your portfolio in different asset classes or didn’t learn about investing and markets, then that’s your contribution to the problem.

Those are the things you did (or rather didn’t do) to get you in the mess.

So when you ask yourself what you did to end up in the situation you’re in, you’ll have to reverse engineer what you did and didn’t do. Once you do that, you’ll figure out what mistakes you make.

You can then learn the lessons and move forward!

Lesson 5: Think About the Worst Case Scenario

There’s a great quote from Dwight D. Eisenhower:

Plans are useless, but planning is indispensable.

Dwight D. Eisenhower

It might seem like a paradox, but it’s not.

Remember the example I used earlier of planning out 100 steps and having things go bad at step 3? When that happened, the plan you made became obsolete.

However, the process of planning itself is an exercise so that you can adapt!

Ad that’s where this lesson comes in:

Generally, being positive and optimistic would be better, but occasionally, you should ask yourself what the worst case scenario is, and how you would react if that worst case scenario came to be.

Think about things like:

A project is due soon, and a key person quits, you lose your job, business or source of income, issues in an important relationship, or anything going majorly wrong in a significant area of your life.

What’s the worst case scenario in those areas?

What you want to do now is think about what the signs would be just before it goes down. From there on, imagine how you would react when the worst case scenario would actually happen.

It’s about being prepared.

When you think about the worst case scenario and your response, you’ll avoid freaking out and freezing up when something inevitably goes wrong! You’ll be able to act better because you’ve imagined a similar situation.

Think about situation in a war.

You make a plan, but things don’t go your way, and you’re not under attack. If the ones in command get overwhelmed, the team might die. So they’ll have thought of multiple scenarios beforehand and what they’ll do if they happen.

And if other things happen then what they imagined, this exercise has them more prepared to react anyway.

Try it yourself sometimes.

Lesson 6: Your Story Is Everything

The story you tell yourself matters.

Depending on how you interpret things happening around you, you’ll experience a completely different world. Your story can shape your subjective reality in a way that helps you, rather than break you down.

For example:

If you get fired, you might feel like (part of) your world is crumbling down. However, imagine the same situation, but now you handed in your letter of resignation 10 minutes before the talk where you would be fired.

You’d probably feel empowered instead in that case!

In the second example you tell yourself the story of how you’re making a change for the better. About how you’ll move to a better career for you. Or how you’ll finally be able to do what you couldn’t while working your past job.

Same situation, different story.

Different stories, different feelings, attitudes and outcomes.

It’s not really that easy though.

When something happens that wasn’t your choice, it can be tough to turn it into a constructive story. This is one of the cases where the previous exercise can really do miracles for you!

When you have a plan for the bad situation with which you can turn things around, it’s way easier to see the situation as a sign for you to go ahead and do the thing you might have been putting off for too long already.

Another example:

If a relationship ends without it being your choice, it’s easy to tell yourself a negative story.

However, what if you turn it into something like:

This relationship has been a significant part of my life and helped make me a better person. I’m happy to have met and been with him/her and hope they will find their way to true happiness as well.

Which story do you think will have a better ending?

Parting words

Avoiding problems, or thinking they won’t come is stupid!

They’re inevitable!

The reality is that there are things which you cannot control: external events and other people. But what you can control is your attitude, your response and your choices.

The obstacle really is the way!

Adversity and problems are there for you to solve and get over. They are the lessons that you should be learning in order to get to the next level in your life and something that should be embraced.

If you live life trying to avoid failing, you’ll always keep on playing small!

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