The Obstacle Is the Way
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Stoicism for the rest of us
Ryan Holiday

The Obstacle Is the Way — A method for excellence in any and all situations

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Harry Stebbings
Ryan, such a huge fan. I am 18 and your work is such an inspiration to the young generation! So, what was the hardest part about entering the workforce much younger than your peer group and what one moment would you say was the defining moment of your career?
Kiki Schirr
@harrystebbings holy shit, Harry, you're only 18? What will you being doing at 22, then? Taking over the world? :P
Ryan Holiday
@harrystebbings The hardest part is not other people, it's you. There's a reason that young people are typically made to wait and not put into major positions of responsibility. We don't know enough yet, we haven't been fully tested, it can go to our heads, we might be sensitive or not in control of our emotions, etc etc The reality is that these stereotypes are not totally untrue. We do have those weaknesses. The hardest part about being trusted earlier than other people is that battle against the sense. It's proving that you really were worth it and that you are different. It means putting up with bullshit. It means not doing the things you'd maybe like to do or naturally would do. It's that whole "be twice as good" thing. Not everyone is capable of it, but that's what it takes.
Mike Coutermarsh
hey! @ryanholiday, just bought the book :). q. Seems like you're crazy PRODUCTIVE. Are there things you do everyday that helps you to maintain energy, focus?
Ben Tossell
Hey @ryanholiday, thanks for taking the time! Big Fan :) Q. What is one thing you learnt that you thought the complete opposite beforehand?
Ryan Holiday
@bentossell That's a great question. I'm honestly a bit stuck on it. I'll tell you one thing I'm working on a lot now: I always thought that discipline was a matter of saying yes. Of being organized, of setting up rules, of sticking to things. Now I'm starting to see that not only is saying NO a big part of it, that often times discipline is a matter of doing nothing. Of waiting, of passing, of focusing really only on the important things. Even as I type this I realize how silly my old understanding was, but I guess part of me always that that I should be doing a million things all the time. Which is ridiculous and exhausting.
Kiki Schirr
Confession: I pirated Growth Hackers --but then I got so much value out of it that I felt guilty and bought it on Kindle. Since then I've legitimately purchased your other books (though I forced myself to stop reading "Trust Me I'm Lying" half way through because I was coming up with seriously devious plots as a side effect!) I have to say that "The Obstacle is the Way" is my favorite of your books, but I see it as a bit of a change in direction for you. What inspired you to write it? Did your time with Robert Greene play a part in your motivation? Thanks (and sorry)!
Ryan Holiday
@kikischirr I don't want to say I don't care about piracy but my theory is, if you make good stuff people will eventually buy it. So don't worry about it. In any case, TOITW was much less of a 'departure' than people thing. The first book offer I ever got was for a book about stoic philosophy but I passed on it because I wasn't ready (to be honest, I thought I was but Robert Greene astutely advised otherwise). I actually sold Obstacle immediately after TMIL came out. But then the idea for Growth Hacker came up and the book was released first. Really though the book was inspired by the fact that stoicism changed my life since I'd been introduced to it at 19 and I really really wanted to share it with people. Robert Greene is right when he identifies stories as being the best way to communicate an idea to people.
Kiki Schirr
@ryanholiday That's really interesting! Thanks for clarifying the timeline. I'm glad you and Robert Greene are still in touch--will there ever be another collaboration? One where both your names are on the cover?
Ryan Holiday
@kikischirr I would be obviously very honored and flattered if that ever happened. It'd be fun to talk about American Apparel some day. Really though, I'm plenty happy helping him however I can. I would be his research assistant again in two seconds if I had the time and if he would have me. Though my wife would probably kill me. It was just such an amazing opportunity to be directed to read these things and to be accountable to such a incisive, brilliant person. Half the things I'm proud of in TOITW are basically leftover scraps from research I did for assignments he gave me.
Stewart Rogers
1. Thanks for your honest opinion of "he with the dodgy toupee that shall not be named" - I like you already 2. I feel mildly compelled to state my age in this AMA, but I'll pass (P.S. I'm old) 3. Here's my question: if you were transported back in time to Day One, but you were able to take all your knowledge with you, what two things would you do first to gain the greatest impact?
Ryan Holiday
@therealsjr Hmmm. So if all the knowledge was the same, basically we're either talking about spotting and jumping on other opportunities or we're talking personal stuff/mindset. I have no regrets or no real unsatisfied needs so I don't think I'd handle the career part much different. I would tell myself to relax. I think I'd like to instill some patience and self-care in myself that I was lacking when I was younger. I know that's pretty common for young people. You're dying to prove yourself, you think you'll die if you don't. But the reality is, a lot of this is out of your control. If you can relax, if you can enjoy what's happening, you'll still have the same success but you'll actually appreciate it. It won't be so painful and costly.
Erik Torenberg
HUGE thanks to Ryan for taking the time to do an AMA! Amazing answers that we'll continue to resurface. Thanks everyone for participating!
Melissa Joy Kong
1. What mental model do you think best catalyzes one's personal growth? 2. What is the most common and detrimental logical fallacy you see people make?
Ryan Holiday
@melissajoykong Pragmatism is a favorite of mine. Of course, what I talk about in the book is the idea that you accept what comes to you and then make the most of it. It's a sort of an iterative, adaptive, resilient, mental model. I call it stoic optimism. In terms of fallacies...if only there were just one. The sunk cost fallacy is a big one. The confirmation bias is a huge problem.
Jeff Umbro
Hey @ryanholiday - can you tell us your favorite books of 2015 so far and anything forthcoming you're excited for?
Ryan Holiday
@jeffumbro I'm going to change your question a little bit because I don't really care WHEN books were published. Some of my favorite reads this year: The Hunters by James Salter A Night To Remember by Walter Lord The Epic of Gilgamesh The Sorrows of Young Werther by Goethe Facing Codependence by Pia Mellody Enemies of Promise by Cyril Connolly Ben Franklin by Walter Isaacson Creatocracy by Elizabeth Wurtzel
Jack Kaufman
Hi, Ryan! Big fan of your work. I have two questions for you today. 1. When it comes to manipulating the media and getting press coverage, what are your favorite tools for automating email outreach from a bunch of different email accounts to smaller blogs and news outlets? 2. Are you impressed by Donald Trump's manipulation of the media for the upcoming presidential election?
Ryan Holiday
@kaufman_jack Fuck. Donald. Trump. I only respect people who do things on purpose, not someone driven by some compulsion for attention and inability to consider the words that come out of their mouth. What is he even getting out of this? It's certainly not making him money. It certainly won't make him president. He's just a troll.
Eliot Peper
1. What is the most misunderstood part of stoicism? 2. Why are books important to the world? How has your love of reading shaped your life?
Ryan Holiday
@eliotpeper You know the word Epicurean? How we think it means a glutton for pleasure. A quick definition from Wikipedia is actually "Epicurus believed that what he called "pleasure" is the greatest good, but the way to attain such pleasure is to live modestly and to gain knowledge of the workings of the world and the limits of one's desires." Stoicism is misunderstood to an equal degree. It's supposedly a philosophy of fatalistic resignation and an appetite for pain. In reality, it is a formula for resilience and optimism and strength. It's a set of ethics that guide you towards the good life in a world that is unpredictable and often unforgiving. That's all. In terms of why books are important...I hate this question. It seems silly how often people ask me to make a positive use case for books, as though in all of human history there was some other thing more responsible for success, brilliance, creativity, progress, wisdom and relief.
Ryan Holiday
Looking forward to talking to everyone in a few hours. I love Product Hunt books and have been putting up submissions fairly regularly. For anyone who wants some other reading recommendations, I have a monthly list I do here http://ryanholiday.net/reading-n... and a list of 'books to base your life on' here http://ryanholiday.net/reading-l...
Erik Torenberg
@ryanholiday definitely subscribe to this. i have for years and have found lots of great reads from it.
Erik Torenberg
My pleasure to introduce Ryan Holiday for a Product Hunt AMA today at noon! (Ask questions in advance...:) For those who don't already know him, here's a quick bio: Ryan Holiday is an author of three books, including Growth Hacker Marketing, and he’s an Editor at Large at the New York Observer. He dropped out of college at 19 to become director of marketing of American Apparel, and has since advised writer and artist clients such as Robert Greene, Tucker Max, and Tim Ferriss and many more. We're grateful to Ryan's for giving great feedback and recommendations to Product Hunt Books. For more, check out Ryan on the Product Hunt Podcast: https://soundcloud.com/product-h...
Ryan Holiday
I'm trying to think of how this scenario could ever actually come to pass. But if I had an hour, I'd probably spend almost none of it on marketing and almost all of it on making the product better--running through all the things wrong with it and better positioning it for the market. Then I'd think of ONE place to launch it from....producthunt maybe?
Esteban Aravena
Hi @ryanholiday Q: Besides all the growth hacking and writing, what do you for fun? What do you do to relax and balance everything?
Ryan Holiday
@esbvn I wish I could upload a picture but the view behind my computer monitor is a farm with a lake and I can watch my pet goats prance around. For lunch, I cooked myself a steak and read on the porch. When this AMA is over, I am going to go fishing with a friend that's come over. I might do some target shooting too. I feel very fortunate to have a little slice of the American Dream here in Texas.
Bakz T. Future
Hey Ryan, Bit more of a tactical question: any suggestions on running a multi-outlet pr campaign? Reaching out to multiple outlets at once to promote the launch of something and maybe booking your schedule full to speak at conferences, events, etc? Would love to hear your feedback - I'm a huge fan! Thanks!
Brent Summers
Hey Ryan, If you had a million dollars on the line and had an hour to teach someone about how to grow a company, how would you spend that time?
Micah Baldwin
@ryanholiday what's the once thing you wish people know more about you, and what's the proudest thing only you know about.
Ryan Holiday
@micah That's a very cool questions. Honestly, my life is pretty public and I like writing about it so there is less than you think. I suppose I am very proud of my relationship--it's been 8 years now with my wife. She's been with me since the beginning. Not everyone gets to meet her but when they do they seem to *get* it.
Anarghya Vardhana
Thanks for being here Ryan! 1. How do you / did you find your passion, and do you think that changes over time? How do you know what is the ONE thing that drives you when you are several interests? 2. How can people in positions of privilege (whether due to race, gender, socioeconomic, etc.) and leadership create safe spaces and openness for those who may not benefit from those things, specifically in the world of tech? Thanks!
Ryan Holiday
@anarghya503 1) I found my passions by following and learning from really great mentors who had found theirs. Our paths have differed to certain degrees but it was in their model and with their support that I was able to explore and take risks and learn. 2) The answer to this question is to pay forward what I was talking about in answer #1. I also somewhat bristle at the concept of privilege. We're ALL advantaged and disadvantaged in various ways. It's absurd to think these things can or should be ranked. The idea should be to: recognize talent when you see it, help the people that you can, empathize with everyone.
Arran Ferguson
Hi Ryan, I'm 18, i read Growth Hackers and it changed my whole opinion on marketing. I've just joined a new Tech Startup and handling a lot of the marketing side and is there any essential growth hacks you would recommend? I love all your books and well all your written material, Thanks, Arran Ferguson
Ryan Holiday
@frame_arran Aaron Ginn put it very well when he said that growth hacking is a mindset and not a toolkit. I try to direct people to that little proverb when they ask me for specific tactics. You wouldn't say to Napoleon "what's a good way to win battles" because every battle is different and even individual battles only matter as part of the larger strategic goal. Does this make sense? The specifics of your company--your resources, your market, your budget, your goals--that are going to determine what the essentials are for you. But even realizing that as a marketer your job is to GROW a company, already puts you ahead of most of your sadly ignorant and worthless peers.
Arran Ferguson
@ryanholiday @frame_arran Haha, that is useful and good advice. I very much like your proverb and will undoubtedly find myself using it in the future
Ignacio Alonso
Hi @ryanholiday big fan of your work: 1. What would you recommend to not forget to apply the stoicism principles of the book in everyday life (it's hard to remember to focus, take action and consider my will when a lot is going on) ? 2. How did you manage to learn what was needed for you to get the American Apparel job at such a young age and how did you choose what to focus on to get more results in your education?
Ryan Holiday
@allnacho This passage from Marcus Aurelius is pretty damn good. "“When you wake up in the morning, tell yourself: the people I deal with today will be meddling, ungrateful, arrogant, dishonest, jealous and surly. They are like this because they can't tell good from evil. But I have seen the beauty of good, and the ugliness of evil, and have recognized that the wrongdoer has a nature related to my own - not of the same blood and birth, but the same mind, and possessing a share of the divine. And so none of them can hurt me. No one can implicate me in ugliness. Nor can I feel angry at my relative, or hate him. We were born to work together like feet, hands and eyes, like the two rows of teeth, upper and lower. To obstruct each other is unnatural. To feel anger at someone, to turn your back on him: these are unnatural.” In terms of AA, for me it was all about connections. Robert Greene was on the board. He got me an entry level position with the CEO and then I helped create my own job there.