Business, Careers & Money

Taking a Career Break

Recommendations from Matt Yao, Former Product Manager at Cash App

Matt was a Product Manager in a past life, but left his job to pursue a career break which turned more into a career transition. Matt wrote about his experience with quitting his job. Through his three creative projects, he aims to forge nourishing conversations with the self, inspiring individuals, and society (which includes our environment).
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Book

The Pathless Path

The Pathless Path

Paul Millerd

In February 2022, I was mid-way into this book when I decided that I would, at some point, quit my job without another one lined up. This felt like a tectonic-sized decision and the book is what gave me permission to explore the unknown.

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Podcast

Infinite Loops

Infinite Loops

Jim O'Shaughnessy

Infinite Loops explores a multifaceted set of topics covering work, philosophy, meaning, entrepreneurship, culture, arts, and more. Although not explicitly about career or quitting your job, I find that the guests' backgrounds reflects less traditional paths which serve as leading examples for what might happen if you just follow your curiosity. I'd recommend the David Perell, Paul Millerd, Tom Morgan, Will Storr, David Senra, and Visakan Veerasamy episodes to get started.

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Film

Past Lives

Past Lives

Romantic Drama

I had the opportunity to watch this film at Sundance Film Festival and came in with zero expectations. I didn't know the director, lead actors, or even the studio name. While the story and film itself deserves all the accolades it will end up receiving, I'm recommending this because of the themes interwoven throughout. Throughout life, we could've gone in many directions and yet we're here in the present. How do we reconcile the past, present, and future to make any sense at all? That's what this film explores.

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