Goins, Writer

On Writing, Ideas, and Making a Difference

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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To listen to the show, click the player below (if viewing this in email click here).


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.

About Jeff Goins

I write books and help writers get their work out into the world. I am the best-selling author of four books, including The Art of Work. Each week, I send out a newsletter with free tips on writing and creativity.

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  • Emily

    Hi Jeff, after reading this, it gave me the idea that learning from the people who are already in the industry would cost me some money because, as they say, nothing’s given for free these days anymore. I mean if I start to go after famous writers in their own right, wouldn’t they charge me for it?

    I just hope that people are willing to teach newbies like me who want to get into the industry as well, if I try to approach professional writers and learn from them on how they became who they are now.

    But, thank you for this information, as it is definitely valuable for me.

    • Hi Emily! I would have a similar concern. The best thing to do is just ask. Offer to assist them in a project or be a member of their team for an agreed upon time so you can learn from them in exchange.

    • Emily, you might be surprised at how many successful people are willing to share their secrets. Everybody likes being asked to tell their story. Make it about them, and you can’t go wrong.

  • Krithika Rangarajan

    Hey Jeff

    My trust in you is so complete that I bought Ryan’s book immediately after reading this article. I need to learn the art of ‘turning obstacles into opportunities’. (Of course, the 4.5 stars out of more than 200 reviews didn’t hurt either) Thank you for introducing us to another brilliant mind (and warm heart) 😀

    #HUGS Wish I could meet you – lol. You are an inspiration!


  • Great post Jeff, always enjoy reading, listening and learning from your blog. It looks like you and I had our thoughts on a similar subject 🙂 I just posted an article on my blog “The Positive Power of Obstacles”.

    • Thanks Kimunya. Great minds think alike. 🙂

  • I’ve always questioned whether I was “good enough” Jeff. The questions got even louder when the haters questioned my credentials. I was blessed to discover a blog like this that taught me that to be a writer I just have to write, that’s what I did. I found my voice and have continued to grind. It’s paid off because in addition to my blog and guest posts, I’m now a contributing writer for the Huffington Post 🙂 https://www.huffingtonpost.com/kimanzi-constable/ I stopped waiting for permission!

    • Excellent! How’s it going? What was the process? What did you learn?

      • Jeff, I’ve gotten more traffic in two weeks than I’ve had in three years and added 4,400 email subscribers. I got in through a friend that I met at Brendan Burchard’s Expert Academy. I’ve learned that all they can say is no. For so long I was afraid to pitch. I finally got over that fear and went for it anyway. As a result I was able to write for two other large websites. The Good Men Project gets 2 million visitors a week (https://goodmenproject.com/featured-content/7-choices-youll-regret-at-the-end-of-your-life-dg/) and Entrepreneur magazine! Once I stopped waiting to get picked exciting opportunities happened.

    • Awesome Kimanzi! I was stuck in the rut of getting the perfect product or writing done before I put it out. In the last couple of weeks, I installed a new theme for my blog, showcased my new coaching program to a leading artist in the country, and will soon be building a landing page to get people onto it. I have stopped being perfect and embraced the fact that I have to keep on going and my voice will build up. Thank you Jeff and Kimanzi for continuing to prod me on…

    • Denefield

      Thanks for sharing! I sincerely admire those who persistently chase after their goals. It’s so easy to give up, especially for the creative types, but it’s always harder to press through. Interestingly enough it is the latter that is the most rewarding.

  • Excellent episode Jeff! The roller coaster of pursuing our passions leaves us nauseous and wanting to jump on a less thrilling ride many times. But it is those times I lean on faith knowing if I was created on purpose for a purpose then I can make it happen. Obstacles may come but they all can be conquered with a chosen attitude to prevail. Thank you for always sharing and encouraging.

  • Katherine Elizabeth

    Hello, It is a fantastic blog post, Offered plenty important information within, These posts maintains the people interest on the web page, while keeping on writing a little more … all of the best!

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  • Stephanie Hilliard

    I have to admit that my approach to my writing career has been one of leading with the concept that “I am a writer, therefore I write”. For me, that means I tackle jobs that might be outside what I had originally envisioned and outside my comfort zone, such as movie treatments or webisode writing, even if at first it doesn’t pay the big money. What it does, much like with Ryan, is expand my horizons and teach me even more about writing. It also gets me exposure. At the end of the day, I am a writer. If there is a writing project that I can reasonably take on, I’m going to tackle it. Because you never know just where that road less traveled might take you.

  • Great podcast Jeff! I enjoyed listening while we were driving across South Dakota. I have just one question for Ryan. Ryan, you said you traveled to every country, what about countries like Transnistria, South Ossetia, and Abkazia; did you make it to those?

    • Caleb, are you referring to the interview I did with Chris Guillebeau? I believe he traveled to every single country in the world.

      • Ok, I feel a little foolish now! I guess the reason I got confused was because I’ve listened to so many of your podcasts recently Jeff!

  • sal

    “Ryan suggests that we go where there’s the least competition and be a pioneer”, I’ve heard a very prolific blogger who has said the opposite to this advice, but because I admire what you’ve done, i’m going to seriously consider the advice you endorse Jeff 🙂 great podcast!

  • Apprenticeship is very much so a lost art Jeff. But I feel like it’s coming back. Competition is getting so high.

    To humble ourselves and be willing to be taught again. Nothing in the world wrong with that. To submit yourself to one’s self in whom we trust. That’s complete self control at it’s greatest. Thanks Jeff for the exploration of our minds as we hear of the success of this young man.