The Obstacle Is The Way: The Right Mindset For Finding Success

The Obstacle Is The Way: The Right Mindset For Finding Success

Some people are paralysed in their tracks when they hit an obstacle in their lives, while others manage to thrive because of them. Ryan Holiday’s The Obstacle Is the Way: The Timeless Art Of Turning Trials Into Triumph doesn’t provide step-by-step instructions on accomplishing your goals, but it does offer a mantra and mindset that everyone can pursue.

This is part of Lifehacker’s new book review series. Not every life hack can be summed up in a blog post, so we’ve decided to review some of our favourite life-changing books for deeper dives into life’s most important topics.

Author Ryan Holiday is only 27, but he has worked in marketing, written for major publications like Forbes and the New York Observer, and been a media strategist for other authors. The Obstacle Is the Way is Holiday’s third book, and deals with failure, perspective, and having the mental toughness to carry on no matter what the circumstances. It’s a study and reflection on the philosophy of Stoicism, along with stories of great historical figures that realised that problems were merely a chance to grow stronger. By the time you finish it, you might just feel a little stronger yourself.

Who This Book Is For

This book is for everyone, and I mean everyone. We all have obstacles in our life. Whether you’re an entrepreneur, artist or student, this book is about seeing problems the right way. It cuts through the bullshit excuses you may have and delivers example after example of great people doing great things despite their struggles. This book is for everyone that wants to do something, but hasn’t yet.

This is also a motivational read for anyone that feels like they’re stuck and they have nowhere to go. Holiday makes it clear that this is “not a book of gushing, hazy optimism”, so cynics can approach knowing that this is not a head-in-the-clouds, follow-your-dreams lesson in looking on the bright side. If anything, I recommend you buy this book as a gift for someone who is constantly complaining, whining, or announcing that the world is out to get them.

What You’ll Get

This book is only about three things: perception, action and will. These three things shape your very existence, however, because these are the three things you are capable of controlling in your world. Holiday splits the book into three parts, with each part focusing on the three things you can control. Here are some of the lessons you’ll find in each section.

In Part I: Perception, you’ll learn:

  • To see events straightforwardly, as neither good or bad.
  • That you should focus only on what you can control.
  • That getting emotional or upset never provides you with more options to solve your problem.
  • To look at your problems from the outside.
  • To focus on the present.
  • And when you’re stressed, tell yourself that “I’m not going to die from this”.

In Part II: Action, you’ll learn:

  • To focus on the process, not the end result.
  • That persistence is key.
  • That “eureka!” moments don’t appear out of thin air; they’re solutions found after an exhausting number of attempts.
  • To have realistic expectations.
  • That action isn’t always about moving forward, but sometimes about choosing to make a stand.
  • That finishing is the most important thing.

In Part III: Will, you’ll learn:

  • To remember that “this too shall pass,” no matter what it is.
  • To build a fortress in your mind called your Inner Citadel.
  • To do a “premortem” on your ideas.
  • That constraints in life are actually a good thing.
  • To develop acceptance and cheerfulness.
  • To love what happens to you, good or bad.

Each chapter is a different lesson with stories from great people in history, including Marcus Aurelius, John D. Rockefeller, Ulysses S. Grant, Abraham Lincoln, Amelia Earhart and Steve Jobs. The stories range from inspirational to hilarious, but each does a solid job of helping explore Holiday’s key concepts.

One Trick You’ll Take Away

This book has a lot of fantastic ideas, so choosing one to share isn’t easy. My favourite section is on perception, and I think it’s one of the most important things you can work on adjusting. Holiday explains that your perspective is everything. Control is one of the major themes in this book and focusing on what you can control in every situation is key.

Telling the story of legendary baseball pitcher Tommy John, Holiday explains that you should Look for a “yes” in every situation:

Tommy John, one of baseball’s most savvy and durable pitchers, played twenty-six seasons in the majors… It’s an almost superhuman accomplishment. But he was able to do it because he got really good at asking himself and others, in various forms, one question over and over again: Is there a chance? Do I have a shot? Is there something I can do? All he ever looked for was a yes, no matter how slight or tentative or provisional the chance. If there was a chance, he was ready to take it and make good use of it — ready to give every ounce of effort and energy he had to make it happen. If effort would affect the outcome, he would die on the field before he let the chance go to waste.

So ask yourself, where is the “yes?” If there isn’t one, you’re better off focusing on what you can control. If you find a “yes,” give it everything you’ve got.

Our Take

This book has the wonderful ability of making you feel like a weak, worthless piece of crap while simultaneously inspiring you to get over your fears and focus on what you can control. Learning there’s no such thing as a new problem is a sobering lesson. Of course, not every obstacle is in our heads — and many are bigger than us — but The Obstacle Is The Way touches on that and does whatever it can to show you that problems are opportunities to get stronger. The book is a fairly quick read, and even though I’m a slow reader, I was able to plough through it in a couple of hours. In that short amount of time, however, I had the opportunity to reflect on expectations, failure, acceptance, and even death. The Obstacle Is The Way is a strategic manual for the war on apathy, weakness, and our own detrimental laziness.

By the end of each chapter you have a solid understanding of the different concepts, but on occasion Holiday can be overly thorough. It will vary from reader to reader, but I found that some chapters only needed one example to explain a concept. The other aspect of this book that some may have a hard time accepting is that there are few straightforward tips to grab and run with. It’s all entirely up to you to put everything you read here into practice. Put together an idea index while you go through it to make sure you don’t forget the parts that stand out to you the most. It’s not forgettable by any means, but there is no handholding or “step one: do this.” As well thought out as these lessons are, you still have to be the one to actually use them.

What Holiday has crafted is an approachable method for any who wish to change the way they think about the problems in their life. It never gets too wordy, the historical references are all well-known figures — or are at least explained well enough — and reading the book feels like you’re receiving a pep talk from the life coach you never had. An empowering reminder that even the most downtrodden can be capable of achieving greatness. The bottom line is this book forces you to realise that success is not a gift of any kind, but a path anyone is allowed to follow. There are no more excuses. You can either change the way you think, or stay stuck in the same loop of paralyzing fear and frustration.

This book is well worth the read. I honestly can’t recommend it enough, even if it’s just to gain a different perspective on things. It’s well-organised with each concept flowing into the next, and the lessons in these pages are invaluable. No matter what your outlook on life is, this book can help you look at your problems big or small in a very different light. There may be a few moments of, “ok, I get it, let’s move on,” but by the time you finish, whatever problem you had on your mind before you started will seem completely solvable.

The Cheapest NBN 50 Plans

Here are the cheapest plans available for Australia’s most popular NBN speed tier.

At Lifehacker, we independently select and write about stuff we love and think you'll like too. We have affiliate and advertising partnerships, which means we may collect a share of sales or other compensation from the links on this page. BTW – prices are accurate and items in stock at the time of posting.