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The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph

Ryan Holiday · 5 HN comments
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Amazon Summary
#1 Wall Street Journal Bestseller The Obstacle is the Way has become a cult classic, beloved by men and women around the world who apply its wisdom to become more successful at whatever they do. Its many fans include a former governor and movie star (Arnold Schwarzenegger), a hip hop icon (LL Cool J), an Irish tennis pro (James McGee), an NBC sportscaster (Michele Tafoya), and the coaches and players of winning teams like the New England Patriots, Seattle Seahawks, Chicago Cubs, and University of Texas men’s basketball team. The book draws its inspiration from stoicism, the ancient Greek philosophy of enduring pain or adversity with perseverance and resilience. Stoics focus on the things they can control, let go of everything else, and turn every new obstacle into an opportunity to get better, stronger, tougher. As Marcus Aurelius put it nearly 2000 years ago: “The impediment to action advances action. What stands in the way becomes the way.” Ryan Holiday shows us how some of the most successful people in history—from John D. Rockefeller to Amelia Earhart to Ulysses S. Grant to Steve Jobs—have applied stoicism to overcome difficult or even impossible situations. Their embrace of these principles ultimately mattered more than their natural intelligence, talents, or luck. If you’re feeling frustrated, demoralized, or stuck in a rut, this book can help you turn your problems into your biggest advantages. And along the way it will inspire you with dozens of true stories of the greats from every age and era.
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All the comments and stories posted to Hacker News that reference this book.
The obstacle is the way (https://www.amazon.com/Obstacle-Way-Timeless-Turning-Triumph...) is also a good one on the Stoic philosophy, could serve as in introduction to Meditations
Camille Fournier literally wrote the book on Engineering Management so when she speaks, I always listen [1]. Every technology leader will reach a point where there are just too many problems to solve and OPP is a great mental model for prioritization.

OPP is also a forcing function for leadership. It forces true leaders to step up and make the hard choices.

If you're faced with OPP, here are a few things I found useful in my career.

## Do Important Work for Important People

The best way to be successful in any organization is to do important work for important people. Important work for unimportant people will get you no where. Same is true for unimportant work for important people.

Take a look at your OPP and ask yourself:

* Is this work for someone important?

* Is this work important to that person?

Both answers should be yes, otherwise it's just OPP.

## Let Fires Burn

Once you decide the work is OPP, then you need the courage to say no. You must let that fire continue to burn without it distracting you. Masters of Scale has a good episode on this topic [2]. Easier said than done of course. I found Stoic practices to be very helpful here [3].

## Customer Obsession & Ownership

OPP should always be evaluated through the lens of the customer. Bottom line, the customer is always the most important person and they trump all. True leaders are obsessed about providing a better customer experience and they're willing to pay the price in order to do so.

If you have OPP that's important work for someone important, but it's not important to the customer, then you may just have to let that one burn too. And once you make that call, you have to own it. Always take responsibility for the decision and defend it on the customer's behalf.

I've found Amazon's leadership principles to be invaluable when making these type of tough decisions [4]. It's no coincidence that Customer Obsession and Ownership are #1 and #2.

[1] http://amzn.to/2niWhO9 (Camille's link not mine)

[2] https://mastersofscale.com/selina-tobaccowala-let-fires-burn...

[3] https://www.amazon.com/Obstacle-Way-Timeless-Turning-Triumph...

[4] https://www.amazon.jobs/en/principles

itronitron
Organizations that clearly and regularly establish and communicate their priorities enable their members to easily make these assessments.
tempguy9999
I need to read the articles and the comments properly, but this

> It forces true leaders to step up and make the hard choices.

reminded me of a discussion on the radio about the mess of a situation detroit car manufacturing had got into. Someone summarised, saying that the bosses spent decades making easy choices instead of the right choices.

Have you looked into Stoicism? It's got a lot of the Buddhist elements of learning to accept the present while also focusing on achievement. I think of it in some ways as a Western-friendly mindfulness approach. A Guide to the Good Life [1] is a great book on the subject, and in the past has helped me be more effective in life, while also being happier. I've also heard good things about The Obstacle Is the Way [2].

[1]: http://www.amazon.com/Guide-Good-Life-Ancient-Stoic/dp/01953...

[2]: http://www.amazon.com/Obstacle-Way-Timeless-Turning-Triumph/...

Scarblac
Marcus Aurelius has been on my reading list for years, but he never got to the top of the list. Maybe it's time to read something on this subject, like one of your suggestions, thanks!
Supposedly, The Obstacle is the Way is in the vein. I haven't read it yet; it's on my list this month though. Supposedly a fairly good read though. It's written by a big PR guy though so who knows.

http://www.amazon.com/Obstacle-Way-Timeless-Turning-Triumph/...

For an intro to stoicism you should start with Seneca's letters and Marcus Aurelius' Meditations before you jump into Guide to the Good Life (which I do not recommend, despite Derek's praise of it)

Also, check out the upcoming book 'The Obstacle is the Way' by Ryan Holiday - http://www.amazon.com/The-Obstacle-Is-Way-Timeless/dp/159184...

sramsay
Both amazing, but I think I prefer Epictetus' Discourses to either one.

I'm not a big fan of Guide to the Good Life either -- mostly because I think it takes a very profound (and by no means simple or obvious) set of ideas and reduces it to a kind of intellectual fad diet.

For something weightier, you might look at the works of Pierre Hadot (Philosophy as a Way of Life and What is Ancient Philosophy?), both of which contain excellent discussions of stoicism.

hvass
Check out Hadot's Inner Citadel if you haven't, also an amazing book.
benrhughes
A Guide to the Good Life has its issues, particularly around complicating simple ideas (for example, his "trichotomy of control" adds nothing at all the the basic dichotomy, other than confusion).

However, he does a good job of giving a basic introduction and framing for Stoic concepts. I think it's easier to digest the Romans (particularly the concise and acerbic style of Epictetus) if you are somewhat familiar with the subject. I got much, much more from Epictetus than I did from Irvine, but he is, I think, a valuable on-ramp.

I'm also not sure what the big deal is with Marcus Aurelius. Compared with The Enchiridion and even Seneca's letters, it's haphazard and dull. I'll give it another shot once I'm done with all of Seneca's letters.

Personally, I would start with Irvine, then the George Long translation of The Enchiridion (it's more poetic than the Carter translation, IMO). I'm about half way through Seneca's Letters, and while enjoyable, he takes a long time to cover the same insights as Epictetus.

(aside: on my 3rd or 4th reading of The Enchiridion, I wrote brief notes on each part, which you can find at http://thiscodinglife.com/dissecting-epictetus/intro)

wismer
Truly warms my heart to see there is some resonance on HN for the stoics. I came across Epictetus in a particularly low part in my life - it was this particular passage that nailed me - excuse the bad formatting/spelling. http://wismer.github.io/
hvass
I wouldn't start with Epictetus just because I think some of his lines can be easily misinterpreted, for example, the line about kissing your child and thinking about his death can really put people off.

I had the same initial reaction with Marcus, but honestly it might be because I didn't have the right translation (pick Gregory Hays's!!) and not enough background on the man. I would highly recommend watching this short series that mentions both Epictetus and Marcus: https://www.youtube.com/watch?v=nLD09Qa3kMk I truly think you'll see the Meditations in a different way after watching this. Also, Pierre Hadot has a very good (but scholarly) analysis on it in The Inner Citadel.

And for Epictetus, I always introduce him with the story of the Vietnam prisoner of war James Stockdale who in a way relied on stoic principles to endure the tortures he was inflicted. He wrote and lectured about the lessons there, Google him around.

benrhughes
Wow, that was a brilliant lecture, thanks! Part 1 is one of the best summaries of stoicism that I've heard.
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