Book Recommendation #2: Outwitting the Devil by Napoleon Hill

You don’t have to hang around the entrepreneur community for very long before hearing the expression “fail fast”. In fact, in the world of fast-growing startups, there’s a strange obsession with failure.

It’s not uncommon to be told that you’re, “not failing enough.” Or perhaps that, “failure is an asset.”

Crazy right?

Well here’s the thing: if you truly want to be successful you’re going to need to embrace failure. To understand success, you need to understand failure.

Outwitting the Devil

Napoleon Hill spent 20 years of his life interviewing some of the world’s most powerful, successful men. The results of these interviews culminated in his classic business books, the Laws of Success and Think and Grow Rich.

But during this journey, he paid an equal amount of attention to failure as he did success. He wanted to know what stopped people from achieving. Why were some people always down on their luck? Why was it that only a lucky few managed to break free from their limitations and realize their dreams? What holds the rest of us back?

Why you fail— and how to prevent it.

In the book, Hill conducts an imaginary interview with the Devil (failure). Through the interview, the Devil explains what makes him so powerful, so hard to elude.

But perhaps most important, the Devil also explains how he might be outwitted; he explains what it takes to beat failure and come out on top.

Among the massive, value-packed list of takeaways, these are three of my favorites:

1. There is an epic battle between love and fear constantly being waged in our minds. As the Devil explains, fear is what makes him stronger, and allows him to control people. To outwit him (escape failure) you need to focus on love— loving your family, your customers, and yourself. I love how this ties perfectly into the business idea of giving value to the marketplace (love) and taking risks (ignoring fear).
2. The mind is nothing more than the sum total of one’s habits. Personally, I’ve found that good habits lead to success, destructive habits to failure. The Devil (failure) makes it very clear how he grows more powerful as we adopt more destructive habits.
3. Think for yourself. The Devil explains that wields more control over those that live their lives without critically examining their own actions. However, he suggests that the best way to outwit him in this area is to develop a strong critical thinking muscle through habit, “Form the habit of reaching definite decisions on all subjects.”

Naturally, this only scratches the surface of the lessons to be learned in the book. The interview itself is a fairly quick read, and because of its conversational format it’s quite easy to consume too.

Of all of Hill’s books, you may find yourself coming back to Outwitting the Devil most often. After all, you’re more likely to encounter failure first, before experiencing success. Prepare yourself for the worst with some of the best advice on failure ever written.

PS. The real value in this book comes from Hill’s interview with “the Devil”. The book is annotated by Sharon Lechter, but personally I found that the annotations distract from Hill’s message. Feel free to skip over these annotations if you find they’re disturbing your rhythm.

This is just one book review from a series. Click below to see the full list:

If you’d like to receive recommendations straight to your inbox (and learn what book we’re reviewing next, a full week in advance) enter your email below to subscribe to the blog. You’ll receive blog updates through a weekly email, and you’ll have a direct line to me if you ever have any questions about this whole bootstrapping thing. See you on the inside!