fast-paced
hopeful informative inspiring reflective medium-paced
challenging hopeful informative inspiring reflective fast-paced
slow-paced

Long Story Short: Ryan Holiday, a self-proclaimed modern day philosopher, combines the feats of the successful with the mindset of the Stoics to enlighten readers on harnessing obstacles for success.

Reductive at best, offensively out-of-touch at worst.

The least offensive problem with this book is that it's unclear who it's written for. Is it for entrepreneurs? Business leaders? Is it for personal development? Who knows! Holiday sure doesn't. The content of the examples is inconsistent, as are the explanations of how to apply the philosophy.

Speaking of the examples, not only are they conveniently diluted, the vast majority are about white men. There are a handful of examples of black men; one of a white woman. There is no other minority represented with any significance in the entire 200 pages. Holiday couldn't research and include one BIPOC woman who overcame an obstacle? Instead, he focused on about 20 different leaders of war (there is SO much war talk).

Holiday was in his mid-20s when this was published, and it's hard to believe anyone at that age would have a true grasp of the obstacles life can throw at a person. It is clear he hasn't had a lot of hands-on experience with true adversity and doesn't understand (nor cares to understand) privilege. He makes constant remarks about people being soft while pushing an agenda that if you just work hard enough, you'll have power. And why is power the end goal? He doesn't say, but his words drip with toxic masculinity (he honest to goodness calls someone effeminate) and 2014 gym bro #NODAYSOFF mentality.

Holiday also claims that Abraham Lincoln simply thought away his depression and that Theodore Roosevelt exercised himself out of having asthma. He talks down about people who have had to move back into their parents' homes - calling them whiny complainers who play video games all day.

If this had been any longer it would have been a DNF. Unfortunately for me, these were the longest 200 pages of my life - made longer by my 81 annotations as I researched what appears to be more than Holiday did for this book. I'm disgusted with myself for spending money on this in 2019.

Enjoyment: 1/5
Craft: 1/5
Overall: 1/5 

Clear and concise. A good opening salvo of basic stoic thought.

Probably a 2/5
informative inspiring reflective medium-paced

Taking the reader through a practical and extremely balanced approach for handling failure, The Obstacle is the Way is a must-read for anyone who has struggled with crippling self-doubt, self-pity, and ennui. Through the wisdom of the Stoics and the example of history, Ryan Holiday reminds us that even great setbacks and obstacles are not the end of the world. Rather, they can become the fuel for a life well-lived. If we so choose.

As someone who feels deeply and places great value on emotions as a creative and relational force, I confess I held a bit of a grudge against Stoicism before reading this book. Not anymore though. In MBTI terms, a Stoic is a person whose Fe is controlled, and therefore channeled into healthy and constructive paths, by his Ti. A Stoic does not lose his head over the challenges, pains, and sometimes utter brokenness that life throws at him. Rather, because he takes a moment to assess the situation, he keeps a cool head and overcomes the obstacles that stand in his way. This cannot be done without feeling. Passion is necessary to fire any vision. But passion alone kills. When thwarted, unbridled passion can lead to depression, self-obsession, and pettiness. There must be something greater encompassing that passion to make the vision come to life no matter what obstacles are thrown in its way. This something is the cool-headed logic and determination of the Stoics.

I just lost a bet by admitting how good this book is, but so be it. Reading this was a humbling experience. It forced me to re-examine myself and my choices with honest eyes. I'm grateful to have read it and would recommend it to anyone seeking to discipline their mind. It's not a book of specific steps to take, and if you're looking for a self-help book you might feel like Holiday does no more than throw around trite platitudes. The aim of the book is not to give specific instructions, though. It's just a broad reminder that if we really want to live well, we better get to it. It resets the button on self-pity, and that alone makes it worth reading.

DNF - it was too much surface level motivation. You can do it because these people did it! Doesn’t take into account or even discuss the depth of why people don’t, can’t, or unable to achieve or work through things at any given time.
informative inspiring reflective medium-paced