The Obstacle Is The Way — Ryan Holiday
I am excited that my book The Obstacle Is The Way has been selected as May’s selection for the Product Hunt Book Club! I’ve written a Medium post to give you a quick introduction to the book and to facilitate discussion and conversation. Please let me know what you all think!
I was recommended this book a few months back by a mentor of mine, along side The War of Art. Read them both; War of Art felt like disjoint, macho bravado to me (all “grr, punch your resistance in the face”), whereas Obstacle actually made sense. Especially for someone with depression, any philosophy that allows you to accept things will be broken and still give hope is a huge deal. I’m actually incorporating it into a talk I’m giving later in the year, since the whole approach of “yea, shit sucks, let’s work with that fact” will probably resonate really well with my slightly cynical target audience.
So, yea. If I had a little “stamp of approval” it’d be on this book. ☺ — Zoe Landon
That’s very kind of you. Thank you. The War of Art is one of my favorite books — and was actually quite influential in the writing of Obstacle. I definitely urge you to give it a second chance. It’s worth it.
Hey Ryan, thanks for the great book and introducing me to stoicism ☺. When it comes to practicing stoicism, how has it manifested in your daily routines? — Bryan Lee
My daily routine is a little bit different than it might be if I were something other than a writer (and indeed it was when I had a job I had to go to). For instance, I don’t have to make time to read in the middle of the day. Or go for a walk. When I am struggling with some moral issue or working something out, I don’t write a note to myself like the stoics would, I write and publish those things online. These are sort of part of my job.
BUT a couple things I think are important:
I write in a journal each morning.
-I get up early, when it’s quiet and reflection is easier and there is less distraction.
-I do intense physical exercise at least once a day — because this is what the human body is intended for
-I got to therapy approximately once per week where I rigorously review and work on myself
-I try to read something philosophical or stoic before bed most nights
-I have a 200+ year old bust of Marcus Aurelius next to my computer. I have two 3D printed ones too…They are helpful reminders.
Hi Ryan, thanks for the AMA! Funny to see your approach, as I was recently thinking about what cynicism from Diogenes could bring to entrepreneurship ☺ Mostly about self-sufficiency, and how to focus on reducing needs rather than expanding resources, which could be a prime for any startuper.
Despite stoicism inheriting from cynicism, its self-sufficiency concept is quite different, iirc — something more in the stance of detachment. Do you think this could apply as well to entrepreneurship, and if so, how? — Olivier El Mekki
Diogenes would probably be a little disruptive to entrepreneurship. From what I understand, he lived in a clay pot and loved to masturbate in public. He’s a genius for sure, and I love his one liners, but that’d still be hard to overcome.
There is a line in Juvenal where he says that “there’s only a shirt between” the Stoics and the Cynics. Essentially meaning that the philosophies are very similar but the Stoics did not have the same disdain for luxury and the trappings of society.
In any case, to answer your question perhaps a better word than detachment is indifference. In stoicism we see a lot of the ethics focusing on doing the right thing for the right reasons — with an indifference to the results. Help a friend because you want to help a friend, not because you want something out of it. Work hard to build your company because it’s fulfilling your potential and improving the world, not because you need to be famous, important or rich.
> Diogenes would probably be a little disruptive to entrepreneurship. From what I understand, he lived in a clay pot and loved to masturbate in public. He’s a genius for sure, and I love his one liners, but that’d still be hard to overcome.
Sure, it’s not the part we could focus on ☺ But then, there’s the whole “dropping everything that is not necessary” part and the cosmopolitanism, which is surprisingly close to the nomad trend among entrepreneurs.
The ethic perspective you develop is interesting. I’ve always wondered if true success as a person can actually happen if you’re looking for it. But past wanting to be personally successful, there is also the desire for our company to be successful. Do you think company success can be achieved as well without actively looking for it (that is, without pondering how to make the company successful, and only think about what it could bring to the world)?
There is a line from Viktor Frankl that happiness cannot be pursued it must ENSUE. I think that’s a great way of looking at it.
Now to get really practical and blunt: It really is possible to will certain kinds of success into existence. Brute force and energy will get you there. The problem is that once you arrive you realize it’s never going to be what you thought it was going to be.
Thank you so much Ryan for doing this AMA! I have 2 questions-
1) when evaluating your choices (ie. Where will I find the good or bad?) that lead you to action, how heavily do you weigh the good/bad for the society? 2) When applying Stoicism to entrepreneurs, who would you say is the best at leading by action today?
I know the 1st question is a source of endless debate, but is good/ bad the same as right/wrong? — Virginia Barnett
What the stoics try to remind us over and over against is this concept of “what injures the bee, injures the hive.” An example off the top of my head. You build a company that is immensely profitable for you, but externalizes a good deal of its costs onto the world (and thus making it worse). A lot of web publishers fall into the boat. They publish media that is cheap to produce but expense for society (it’s cheap, shitty, untrue, etc etc). All of this leads to a general decline in our culture — the culture that those same entrepreneurs live in. I guess I would ask then: What exactly is the point? You make a lot of money personally so you can afford to live in a bubble that blocks out the shittiness of the world that you helped create?
I suppose my point here is: Helping yourself at the expense of other people is very often a one step forward, two steps back scenario. In which case, it’s rather self-defeating.
What has been most interesting/surprising thing you’ve learned since releasing the book? — Erik Torenberg
1) Writing a book about stoicism is a bit inconvenient if you’d ever like to complain about anything ever again. People are always trying to make me ‘live up to my own words’ which is a total pain.
2) Just how many people have followed the precepts in their life but didn’t know that there was a word or a philosophy for it. It’s been really cool to connect with those people and reintroduce them to a philosophy they already KNEW but couldn’t articulate.
3) Just last week I read a new passage in Marcus Aurelius’s Meditations — one I have read dozens and dozens of times — that I never realized better articulates my own thesis better than I could have hoped. Funny how that works.
“–But there are external obstacles…
Not to behaving with justice, self-control, and good sense.
–Well, but perhaps to some more concrete action.
–But if you accept the obstacle and work with what you’re given, an alternative will present itself–another piece of what you’re trying to assemble. Action by action.”
Ryan how have you used these ideas in your work life? — Andrew Warner
I would say there is not a day that goes by that I do NOT use them. From beginning to end, there is something in stoicism to think about.
Starting with this line from Marcus: http://ryanholiday.net/motivation/
ending with this line from Epictetus:
“As you kiss your son good night whisper to yourself, ‘He may be dead in the morning.’ (the point being to practice and anticipate misfortune instead of pretending that it could never happen to you. To enjoy the things you have as you have them)
Why are your hands covering your face in you profile photo? — Andrew Warner
One of my favorite musicians Jackie Greene did it in a photo once and I’ve always liked the photo. A photographer at American Apparel took a version of it for the back cover of my first book, Trust Me I’m Lying and I use it for a lot of stuff now. My wife and I did a version at our wedding too. It’s my favorite.
Are you still working on a book with Cash Money? — Ross Simmonds
This is going to sound weird, but I don’t know. I’ve spent a lot of time with Birdman and Slim and I’ve written the intro but obviously their world has been in a bit of a state of flux recently. I’m basically just waiting for word from them (and some other minor contract details) and haven’t gotten any quite a while. I’m still excited about the book and their story. I think they are two of the most underrated entrepreneurs in the history of the music industry.
Whoa. can you hint anymore about their story? Been a ton of music entrepreneurs — why them? — Erik Torenberg
In 1997, Birdman had offers from every major label to buy Cash Money (basically the same thing that Russell Simmons and Puffy both got offered). Instead of selling, he and his brother signed a distribution deal with Universal — a $30M advance with a 85/15 royalty split in his favor. Cash Money has since sold something like 500M songs. Just think about the acts that have graced their roster: Juvenile, Lil Wayne, Nicki Minaj, Drake, Kevin Rudolf, Big Tymers, Rich Gang, DJ Khaled, etc etc They are the most successful independent label in the history of music.
When Jay Z rapped “own your masters, slaves!” he was talking about something that Cash Money has done from day one. Every other hip hop mogul has gotten rich from all the ancillary products — clothing, clubs, headphones, beverages etc. Birdman and his brother Slim (who is the quiet one) are worth about $500M almost entirely from music. And that’s just what their worth now — Michael Jackson’s estate (which was comprised mostly of copyrights to famous songs) has made something like $700M since his death. Same growth will happen for Cash Money…except the guys are in their 40s.
Wanted to first thank you for the books you’ve written. “Trust me, I’m Lying” has completely changed my outlook on media and made me much more aware of how to see how the media manipulates. That being said, if you could wave a magic wand and make any change to the way that media is done, what would you change and why? — Daniel Kao
I’d bring RSS back as a major consumption/delivery mechanism. Ideally, with some sort of paid subscription component too. I wrote a piece on the first part of that for Medium a while back:
