015: Turning Obstacles into Opportunities: Counterintuitive Advice from Author Ryan Holiday [Podcast]

You know the feeling. You’ve just created something special, and you’re afraid to launch it. What if no one cares? What if no one reads my blog post? What if no one buys my book? What if I fail?

Photo credit: John Lodder via cc
Photo credit: John Lodder via cc

Ryan Holiday has been there. He always wanted to be a writer but early on realized it wasn’t enough to just write well about a great idea. He needed to understand how to present that message first to a publisher and then to an audience.

In this episode of the podcast, Ryan shares how he used what he didn’t know as an opportunity to grow.

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You can also download it at iTunes or on Stitcher.

The lost art of apprenticeship

Most of us think that to be a writer or an artist or anything, we need to just study our craft. We imagine (or dread) going back to school to get another degree or having to spend years practicing before we can start doing it for real. But Ryan Holiday chose another path.

He realized he could learn a lot more about writing and marketing books by studying at the feet of people doing exactly what he wanted to learn. Instead of learning theories, he decided to get more practical experience.

So Ryan packed up his pride and started reaching out. He met an author who was working on a book and saw an opportunity. Ryan loved to research, so he offered his help for free, agreeing to do whatever the author needed in return for the opportunity to learn.

He created an apprenticeship for himself.

Lessons learned

As Ryan worked with more and more successful people, including Tim Ferriss and Robert Greene, he started studying their approach to obstacles. Rarely did they get tripped up by impediments in their path. Instead, they invariably turned those barriers into opportunities.

We can do this, too.

Every day, each of us faces the difference between how we want things to be and how they really are. What makes us succeed or fail is how we respond to those differences (you can tweet that, if you want).

After years of learning, here’s Ryan’s advice on what to do with obstacles:

  • Worried no one will care about what you’re writing? Know your audience. Write the book they want to read, and trust people will buy it.
  • Afraid your work isn’t worth what you’re charging? Be generous. Bundle content and offer great bonuses and see how people want to return the favor.
  • Scared your message will get lost in a crowded market? Experiment with new things. Do what no one else is doing yet. Pioneer something. Being first to a new market is a great way to establish yourself as a leader

Are you struggling?

If you’re one of those who struggles to reach your goals, if you feel like no one will read your blog or buy your book or fund your startup, then you might find some ideas to try in Ryan’s book, The Obstacle Is the Way.

The suggestions might be counterintuitive and might take some effort, but I encourage you to pick it up and try something different. You can get it here from Amazon, or get it free when you sign up for Audible, the audiobook resource I use (note: those are affiliate links).

As for me, I’m still finding ways to grow and learn, too. Ryan suggests that we go where there’s the least competition and be a pioneer. That’s what I’m trying to do with this podcast. If you’re enjoying it, I’d love for you to leave an honest review, tweet about it, or share it with your friends on Facebook.

You can also subscribe by copying and pasting this URL into the podcast player of your choice: https://feeds.feedburner.com/ThePortfolioLifeJeffGoins

What is standing in the way of your success? How could you turn that into an opportunity? Share in the comments below.