How To Simplify Your Life

The Art of Questions

Brian Pennie, PhD
The Startup
Published in
6 min readSep 25, 2018

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“Our life is frittered away by detail. Simplify, simplify.” — Henry David Thoreau

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 over 300 million downloads, has seen him named “the Oprah of audio” due to its influence.

In 2017 however, as he turned 40, several people in his close circle 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 much of life have I missed through underplanning or overplanning?”

“How could I be kinder to myself?”

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

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

By journaling on this question, one idea jumped out from the page…

“What if I had a tribe of mentors to help me answer these questions?”

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Brian Pennie, PhD
The Startup

Change is possible. I write to show that | Recovered heroin addict turned doctor. www.brianpennie.com