For thousands upon thousands of people, The Points Guy has been a go-to resource for maximizing their credit card rewards. But the Points Guy himself isn't a professional credit card salesman, and started his eponymous blog on a whim while working in HR at a bank. On this episode, Mike Lewis talks with Brian Kelly about how he found his way in the world of credit card rewards, and what it took to jump from a safe career to a burgeoning business.

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This episode is brought to you by Memory Rescue (memoryrescuebook.com) and Grasshopper (grasshopper.com/whentojump)

Jumps require a lot of work, time, and planning. But sometimes, the first step to making a jump can be to do nothing at all. This week, Mike Lewis talks with Manoush Zomorodi, the host of WNYC's Note To Self, about the powerful and positive effect of being bored.

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Arianna Huffington became a household name thanks to her groundbreaking internet publication. So it was surprising when she decided to jump from her namesake, the Huffington Post, to focus on, of all things, sleep. In this week's episode, Mike Lewis talks to Huffington about why she left the company she built, and what she's done to combat sexism in the workplace as a board member at Uber.

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Sheryl Sandberg jumped from the federal government to the burgeoning tech industry. Along the way, she's inspired countless women and minorities to fight for greater representation at the highest levels of the government and corporate America. In the first episode of When To Jump, Sandberg discusses her move from the government to tech, and why and when she made the jump.

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This week's episode is brought to you by TopResume (topresume.com/jump) and Hello Fresh.

Mike Lewis took a big risk: he quit his comfortable desk job in corporate America to play the professional squash tour. When to Jump features authentic conversations with people who chase their dreams, whatever they may be.