This One Question Changed Tim Ferriss’s Life

When I asked myself the same question, it changed mine too.

Written BY

Brian Pennie

Brian Pennie is the author of 'Bonus Time', a memoir about his fifteen-year struggle with heroin addiction. Since overcoming his demons, Brian now shares his story worldwide with his work as a motivational speaker, all whilst attaining a PhD at Trinity College Dublin.

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May 18, 2020

This One Question Changed Tim Ferriss’s Life

Tim Ferriss is a highly successful author, podcaster, entrepreneur and investor. He has written five #1 New York Times bestselling books, and the success of his podcast, which recently exceeded to over 400 million downloads, has seen him named “The Oprah of audio” due to its influence.

In 2017, however, as he turned 40, several of his close friends died in quick succession. It was a harsh reminder that time is a non-renewable resource, and life’s big questions started bubbling to the surface.

  • - “Were my goals my own, or simply what I thought I should want?”
  • - “How could I best reassess my life, my priorities, and my place in the world?
  • - “How can I be kinder to myself?”

Overwhelmed by the gravity of his personal interrogation, he asked himself one more question.

“What would this look like if it were easy?”

Tim had previously convinced himself that if he wasn’t pushing boundaries, he wasn’t trying hard enough. But this question made him wonder: “What if I reframed things in terms of elegance instead of strain?”

That morning, he began journaling on this question — What would this look like if it were easy?

With ‘this’ being anything, ninety-nine per cent of the page was useless, but one idea, one seed of possibility, jumped out:

“What if I assembled a tribe of mentors to help me?

What followed was his most recent book, Tribe of Mentors, where Tim reached out to his dream list of interviewees and asked them the very questions he was struggling with himself.

The result of this book is a deconstruction of the tools, routines, and tactics from 130 of the world’s top performers. This book is a masterpiece on the secrets of success and happiness, and if life is getting you down right now, the chances are you will find a solution in there.

In 2018, I was struggling with a problem myself. I was 4 years clean after 15 years of chronic heroin addiction, but with a newfound love of learning, I’ve fully embraced the lessons learned as my greatest asset.

I was now doing a PhD on the nature of human suffering, and lecturing in a university on the neuroscience of mindfulness and addiction.

I had also developed a programme that helped me to navigate my life, and in 2018, I began sharing this programme in schools around my country. Some kids listened, many did not. This was the problem I was struggling with.

I knew I was sharing life skills that worked — I was living proof of that — but how could I get these kids to engage?

I was reading Tribe of Mentors at the time, and fascinated by Tim’s question, I began asking myself: What would this look like if it were easy?

I threw down everything that came to mind, and all sorts of silly things found themselves on the page. “What if I could implant the lessons in their heads?” “What if I was a sports star or a celebrity?” “What if I could get into their heads, I could work backwards from there?

Then it came to me: “If I was sharing life lessons from their heroes, they might listen to me then.”

It couldn’t believe I missed it. My answer was the same as Tim’s. I needed a tribe of my own. With that, I set out to build my tribe. I reached out to many of the leading performers in my country — in sport, business, and the arts. The response rate was 81%, and I got interviews with everyone who responded.

Over the course of the last two years, this question has completely changed my life. Not only do I use what I learned to engage the kids in my school talks; it also launched the corporate speaking career I have today, and I’m writing a book about the tools I learned on this journey.

You can never underestimate the importance of questions. The problem is — they must be the right questions.

“What would this look like if it were easy?” is a great question, and it works in many situations, but it’s important to arm yourself with a battery of great questions. (Here is a link to 7 more to help you to think about life.)

Your future tomorrow depends on the questions you ask today. So the next time your feeling stuck in life, make sure you’re asking yourself the right ones.

Further Reading
How to Radically Improve Your Life
With just three words.
June 6, 2020
Six Habits of Deeply Miserable People
Psychologists say these are the giveaways to watch out for.
June 3, 2020