How to Turn Your Greatest Insecurities into Your Greatest Assets: Interview with Brett McKay

Often in life, our greatest weaknesses can become our greatest strengths, if we are willing to do the work. This is true for Brett McKay, founder of The Art of Manliness, which he describes as a men’s lifestyle magazine that helps men become better men in all aspects of life from being husbands, fathers, citizens, and community members.

The Art of Manliness Today: An Interview with Brett McKay

Brett started The Art of Manliness because, in part, of his grandfather’s influence.

One of his favorite childhood memories is going to his granddad’s farm in New Mexico and spending time with his grandfather. His granddad was a jack of all trades, but master of many. He was a curious man who continued learning about the world around him and in the people in it until he died at the age of 101.

His grandfather’s tough mountain man skills along with his thirst for knowledge stuck with Brett into adulthood today — largely because Brett found those were things that were missing in culture and in his life.

One day while looking at men’s magazines he noticed they were all focused on similar topics: six-pack abs, the latest sex secrets, and other stereotypical “macho” man subjects. But no one was focusing on life skills as a father, a husband, and a citizen of the world. No one was helping men with topics like facing your greatest failure, how to know if you should marry the woman you are dating, and how to help you and your wife after a miscarriage.

Brett decided to do something about that, and while on winter break from law school, he began The Art of Manliness. In no time at all the web site found its footing and grew a considerable audience. Today it has spawned several books, courses and a podcast.

On this episode of The Portfolio Life, Brett and I talk about why the world needs you to turn your insecurities into assets, how he knew it was time to transition from his corporate legal job to becoming a full-time blogger, and what he does with his life when he’s not working to become the best man he can be.

Listen to the podcast

To listen to the show, click the player below (If you’re reading this via email, please click here).

Show highlights

In this episode, Brett and I explore:

  • How does his grandfather continue to influence his life today?
  • What was his childhood like in Oklahoma?
  • Why did he start his first blog, The Frugal Law Student?
  • What does his team look like today?
  • What is The Strenuous Life and where did the idea come from?

Every generation revolts against its fathers and make friends with its grandfathers.

Brett McKay

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The origins of The Art of Manliness

  • What did bare knuckle boxing from the 19th century have to do with the site?
  • What was his first article about on The Art of Manliness?
  • Why do a lot of men come to the site?
  • What personal lessons of his does he share with his audience?
  • The origins of the illustrations and images on The Art of Manliness.

Living life right now is where I get a lot of ideas.

Brett McKay

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On life after law school

  • Did he work in the legal world after completing his law degree?
  • How did he decide to take a risk on The Art of Manliness?
  • Why does he not claim to be an expert?
  • How did this web site fill a void in the marketplace?
  • Out of all the skills on the site, which are his favorite?


How have your early influences impacted your artistic career? Let us know in the comments.