If you didn't realize we are we are huge fans of Stoicism, so it was big honor to get a chance to interview one of the leading researchers and writers on the topic, Ryan Holiday.

In this interview, Ryan Holiday, author of The Obstacle Is The Way, answers our questions about practicing boldness, creative success and gives his advice on how to be your best self.

Helen: Many times when young people want to dive into a creative field, they receive advice to leave school and go get started. (I went to a small liberal arts school and majored in writing and all [ALL] of my writing professors told me to leave and start writing.) You dropped out of school at 19. Can you describe that moment? And would you advise someone else to do the same?

Ryan: Terrifying is the only word. On the way hand there is a huge stigma about dropping out of school and on the other a total glamorization. I don’t know what Mark Zuckerberg or Bill Gates thought when they left, but me, I was totally unprepared and scared. I was a kid just half way through school and I had an offer to leave and do a job that I would kill to have had upon graduation: working with talent in Hollywood and being a research assistant to Robert Greene on his next book. I felt like it was insane not to do it but...What if I failed? What if I’m making a huge mistake? What if I die? You know, my parents didn’t take it well and essentially disowned me at the time which certainly compounded those feelings. The reality of it--as I soon figured out--is that there really is no need for it to be so scary. You’re definitely not going to die, you probably won’t fail and if you do--guess what, you can always go back. It’s just very hard for humans to wrap their minds around the fact that things actually can go back to how they were before. You can go back to being a student. Just like if you leave your career to pursue something else, you can always go back and apply for a similar old job again.

"You’re definitely not going to die, you probably won’t fail and if you do--guess what, you can always go back."

Would I advise someone else to do the same? Knowing how scary it was for me, I would never push someone to do it. What I do encourage if for them to think really rationally about their position, motivations and goals. Are you leaving school because it’s the best way to get at certain opportunities or are you just running away? What is it that you can only do if you leave? Couldn’t you get a start on what you’re so desperate to do while you enjoy the safety of college? What have you done to prepare yourself for the discipline and self-motivation required to be successful post-school? What’s your backup plan? Etc etc. It’s really easy to get worked up at 18, 19 years old and think that what you’re facing is the unbearable, unfair, that you’re the first one to ever experience and all that. Of course, this is not true and stepping back can give you clarity and make either decision easier.

H: Do you think working in the creative spectrum requires a different type of bravery? If so, has facing your fears become any easier after certain successes?

Ryan: Of course, different in the sense that it doesn’t require physical courage or the same kinds of sacrifice. Pursuing a creative career is hard. Not as hard, or requiring the same bravery as say, being a soldier though. Or a social worker. Or emigrating. So I think creativity takes an important kind of bravery, sure, but I wouldn’t recommend going around and beating your chest about your own bravery for being a painter or a writer or a dancer. It’s not totally honest and it’s definitely not good taste.

"The most important kind of bravery a creative person can have is to do the work and all that it entails. The rest is secondary."

That being said, there’s a great quote from Ira Glass where he’s talking about how hard it is for young people pursuing creative careers where they have great taste but are still developing their talent. Waking up every day to work on a book that isn’t turning out as good as your mind wants it to be is brutal. Same with any artistic endeavor. It’s also brutal to wake up and work on a project that requires you to reveal parts of yourself or probe painful parts of your past. But at the end of the day, the only way you will ever find an audience or build a connection through your work is by powering through that and facing that fear. The most important kind of bravery a creative person can have is to do the work and all that it entails. The rest is secondary.

H: It's been said that fear is a state of mind. In your book The Obstacle Is The Way, you talk about reframing obstacles into opportunities. What has that realization changed for you?

Ryan: I would say it’s the single most profound realization I’ve had in my life. Basically stoic philosophy says: We don’t control what happens to us, but we do control how we respond. And they say that by focusing our energy exclusively on that response, on making it a virtuous one, we find the path to happiness, freedom and purpose.

It’s a very big idea but it’s also a small and practical one, right down to how you handle traffic, a rude guy at a store, bad news, whatever. In my experience, I’ve not yet found a situation where it doesn’t apply and it doesn’t provide a path forward. Computer eats my answers to these questions you’ve asked--it’s easy, I know what to do. Big opportunity falls in my lap--easy, I know what to do and I know how to stay humble and clear headed about it. I fall and get injured--not necessarily easy or desirable, but I do know what to do about it.

And I illustrate that in the book with stories. Edison’s factory burning down and telling his son to go get his mother “because they’ll never see a fire like this again.” Eisenhower seeing the counteroffensive at the Battle of the Bulge as the opportunity to win the war and not something to fear. This is what stoicism is about. It’s a practical philosophy--it’s made for people trying to live their lives. The idea of “The Obstacle Is The Way” which I built the book around.

H: I loved your summary of writing advice from Dear Sugar (Cheryl Strayed has something for all of us, doesn't she?). Do you have any advice of your own?

Ryan: For writing? A couple: make commitments. Have people that you owe work to--ideally under a contract or a job description. You have to get your hours somehow and often times, left to our own devices, we’ll just work on the same thing over and over again, never ship it and never grow. I’m better because of the blog posts I did, the press releases I had to write, the book contracts I signed. Second, write the things that only you can write. That’s not to say you can’t or shouldn’t be influenced by other people but why on earth would you try to produce work like what someone else is doing? They’re always going to be better at it than you. There are stories and perspectives and a style inside each person that is totally their own. Find it, hone it, and deliver it to the world.

"Find the standard you want to live your life by and hold yourself to it."

As a person? Be a good person; do what you love. Take care of your mental health and sanity. Focus on self-awareness and dispassionate analysis of yourself. Don’t let your crazy--and we all have it--hold you back from the opportunities that you want and deserve. Find the standard you want to live your life by and hold yourself to it. And don’t be afraid to make big changes: move across the country, cut bad people out of your life, take risks, sign up for stuff, quit things that suck. That’s how you end up light years ahead of where you ever thought you’d be. Life should be punctuated by big events.


Helen Williams is the Community Love Director at Holstee. She is passionate about cooking and writing which pair well together on her vegetarian food blog, green girl eats. She's strives, every day, to be less sorry

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