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EP 4: Obstacles Are Good, Passion Is Dangerous, & Other Things You Didn’t Know with Ryan Holiday

May 7, 2018


Who’s on This Episode

Ryan Holiday

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EP 4: Obstacles Are Good, Passion Is Dangerous, & Other Things You Didn’t Know with Ryan Holiday

Welcome to the Do It Scared podcast! In every episode of this podcast, we’ll talk about how to face your fears, overcome obstacles, and create a life you love!

Today, I’m thrilled to bring you a conversation with Ryan Holiday, one of my favorite authors. He’s here to talk about what you can do to avoid being your own worst enemy, turning trials into triumph, why it’s so important to keep your ego in check, why passion can actually be a little bit dangerous, and why obstacles are actually a good thing.

Ryan liked college, which makes it more interesting that he dropped out of it. He made this choice because he had the amazing opportunity to do things that made it worth it to pursue them instead of continuing in school. This is just one of the risks that led him to where he is today. As part of our conversation, we’ll talk about the role of risks, even when they don’t work out.

We’ll also talk about Ryan’s books and the philosophy he shares in them. One point he makes in his books is that ego is an unhealthy belief in our own importance, and the root of almost every problem or obstacle that we face. He explains that ego is belief, while confidence (which is important to have) is based on real evidence.

Passion, too, can be dangerous. It’s important to like what you do and be excited about it, but Ryan would rather have an extremely talented person who’s not passionate than an extremely passionate person who’s not talented. If this surprises you, you’ll enjoy listening to this episode, where Ryan explains the reasoning behind this stance.

He also shares his perhaps-surprising perspective on obstacles, which is that they’re a good thing! Obstacles, he explains, create scarcity. He offers the example of the Olympics; if it were easy to get in and there were no obstacles in the way, everybody would take part and nobody would be in the audience. Ryan will offer some practical tips on how to shift your perspective to start seeing obstacles as advantages.

We’ll also chat about what gets Ryan fired up, why his new book Conspiracy is the hardest thing he has ever had to write, whether he’s a perfectionist, and much more! Tune in for lots of great insight from this bestselling author who has contributed to changing my life, and who can help you change yours too!


[02:12] – Ruth talks about a couple quick points before digging into the meat of today’s episode. To get the Do It Scared manifesto, either text MANIFESTO to 44222, or visit this link!

[02:56] – Ruth introduces today’s amazing podcast guest and lists some of her favorites of his works.

[04:00] – Ryan gives a brief overview of his life story, explaining how he got into being an author and how he made the decision to drop out of school.

[07:02] – What are some of the hardest lessons that Ryan has had to learn either in business or in life? And what did he take out of the experience?

[08:45] – Ryan speaks about Stoic philosophy as it relates to his perspective, linking it to his previous example of dropping out of college.

[10:43] – We hear about what Ryan did after dropping out of college, when he was on a track that was going in a great direction.

[13:11] – Ruth switches over to talking about two of Ryan’s books: Ego Is the Enemy and The Obstacle Is the Way.

[15:20] – What is the difference between healthy confidence and an unhealthy ego?

[17:08] – We move onto talking about passion, with Ryan explaining why passion alone isn’t enough.

[19:52] – Ryan differentiates between passion for the work itself as opposed to passion for being seen as a specific kind of person, or the results of the work.

[21:13] – Ruth brings up the topic of obstacles, a subject on which Ryan has an entire book.

[23:58] – What are some practical things that you can start doing right away to look at your obstacles as an advantage?

[25:48] – Ruth takes a moment to talk about her daughters and the phase they’re going through.

[27:28] – What other practical things can we do to start turning our obstacles into advantage?

[28:29] – Ryan talks about his routines, which are based on various factors like when his son wakes up or whether he’s on the road.

[30:17] – What is Ryan working on right now that he’s fired up about?

[33:28] – Ryan finds marketing different than what he normally does as a writer, and thinks it’s important to have different skill sets.

[34:58] – We learn that Ryan is a perfectionist in some setting and not others. His bigger problem is that he wants things to make sense.

[37:52] – Ryan isn’t a huge goal-setter, but he focuses on the process every day.

[40:06] – What is the best piece of advice that Ryan has ever received, and why?

[42:08] – Ryan talks about how he practices self-care in his life and his business, and what he does to protect his confidence.

[44:28] – Ruth reminds listeners to download the manifesto for this episode, and invites listeners to contact her with any questions or feedback.