The Obstacle is the Way: A Craftsman Book Review - Craftsman Founder

The Obstacle is the Way: A Craftsman Book Review

Ryan Holiday’s new book, The Obstacle is the Way ($3.99 eBook) is a life philosophy non-fiction book from someone I greatly admire. Ryan Holiday is the guy behind Tucker Max and the head of marketing for American Apparel. You may or may not like Tucker Max or American Apparel ads, but you have probably heard about them both, which means he gets results. In fact, Ryan’s previous book, Trust Me, I’m Lying was an expose of modern marketing techniques. If you remember the Paul Graham Sexism Scandal just a few months ago, Ryan Holiday predicted it in his “Trust Me, I’m Lying” book. He explained why that kind of thing not only happens, but will continue to happen. It is a fascinating read and made me a huge fan of Ryan in the process.

About the Book

At 224 pages long, this book is over before you know it. The book is about Ryan’s take on modern Stoicism. It is full of fantastic and timeless advice that helps you get perspective on things. Although the advice is generic, all of it applies strongly to anyone who strives to move from just a startup founder to becoming a Craftsman Founder:

To perceive what others see as negative, as something to be approached rationally, clearly, and, most important, as an opportunity—not as something to fear or bemoan.

A startup founder faces many obstacles:

  • They run out of money
  • Have trouble raising venture capital
  • Have trouble growing
  • Have to layoff staff
  • …and many other trials

It often feels impossible on first blush. A Craftsman Founder relishes in these problems because to one who takes startups as a craft, there will always be another startup where you can take the lessons learned and apply them and get better. Every challenge, no matter how hair raising, is just an opportunity to learn. And often learning requires you to try many times. So you want to be challenged.

Too often we react emotionally, get despondent, and lose our perspective. All that does is turn bad things into really bad things … Focus on the moment, not the monsters that may or may not be up ahead.

Buddhists call this “making a problem out of a problem” or putting a head on a head. Eckhart Tolle says “The greater part of human pain is unnecessary. It is self-created as long as the unobserved mind runs your life.”

Being present and aware of the here and now is critical to the survival of any entrepreneur. While others flail and thrash, you must execute cooly and coldly towards the vision you know to be true.

George Clooney spent his first years in Hollywood getting rejected at auditions. He wanted the producers and directors to like him, but they didn’t and it hurt and he blamed the system for not seeing how good he was.

If you have ever tried to raise money from venture capitalists, you know EXACTLY how George Clooney felt.

You don’t convince people by challenging their longest and most firmly held opinions. You find common ground and work from there. Or you look for leverage to make them listen.

This is a much more eloquent way to sum up my recent blog post about startup marketing.

Admiral David Porter, who was with Lincoln in his last days, described it as though Lincoln “seemed to think only that he had an unpleasant duty to perform” and set himself to “perform it as smoothly as possible.”

This also rings true to anyone who has had to do startup layoffs or letting someone go.

Certain things in life will cut you open like a knife. When that happens—at that exposing moment—the world gets a glimpse of what’s truly inside you. So what will be revealed when you’re sliced open by tension and pressure? Iron? Or air? Or bullshit?

Startups will cut you open like a knife. They will bleed you to the core. A Craftsman Founder is driven by this, it is their motivation. They want to see what they are made of. They want to show themselves what they are made of. There are very few occupations that provide this kind of self-evaluation. Often people find it in other ways like skiing off mountains and surfing 30 foot waves. Startup founders get to find out what they are made of as part of their day job.


I give it 5 out of 5 stars. Ryan Holiday has written a manual for surviving startup life. For thriving. This passage really sums up the point of the book to me.

The goal is:

Not: I’m okay with this.

Not: I think I feel good about this.

But: I feel great about it. Because if it happened, then it was meant to happen, and I am glad that it did when it did. I am meant to make the best of it.

If you aren’t scared to death as a startup founder, then you are missing out on something unique and special. The point is not to be fearless. It is to do your best when you don’t know what the right thing to do is. It is to face all of your fears and insecurities and do it anyways.

You do not “conquer” your fear. You embrace it. You let it power you. It is your rocket fuel. You use fear as a compass to guide you. You feel great about being scared to death and still executing anyhow.

Buy the book. Read it frequently, when times are good and especially when times feel bad. When the world feels like it is against you, pick up this book and find inspiration to power on.

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Lucas Carlson

About the Author

Lucas Carlson

Lucas Carlson is a hands-on consultant, author and entrepreneur. He helps founders discover opportunities for growth, both for their companies and for themselves. He was the CEO and founder of AppFog, a popular startup acquired in 2013 after signing up over 100,000 developers and raising nearly $10M in venture funding from top angels and VCs.

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