Comedian. Host of the Crazy Money podcast. Proud former Facebook and Yahoo! sales person/leader.

Your Spraying and Praying Isn’t Helping You

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Dear Podcast Publicist,

Thanks for your email. Before I reply to the enticing proposition to interview your creepy client with dubious credibility in his purported field of expertise, allow me to acknowledge the necessary and critical symbiosis between publicists and media properties.


Cortés had second thoughts. You will too.

Is this image a little too ‘on-the-nose’? (iStockphoto)

Quit your job.

That’s what the cult of potential-achievement wants from you. They dare you to pull the ripcord, probing on their podcasts: “What would you do if you weren’t afraid?” (thus implying that anyone with a steady paycheck is a corporate cream puff).

Modern ninjas, they preach, live awesomely…

What to do when your professional career becomes a grind

Illustration: Dora Godfrey/Medium

Bob stared at his iced tea and grilled salmon salad. A senior partner at a regional investment bank, he earns a very substantial income. He had asked me to lunch “just to catch up,” but I suspected he harbored a more urgent agenda. And here it was.

“Paul, I still…

As the pandemic inches toward completion, here’s an important message: You’re not done yet

Photo: John M Lund Photography Inc/Getty Images

Heading into the final stretch of the women’s snowboard cross race at the 2006 Winter Olympics, American Lindsey Jacobellis held a commanding lead over her competitors. As she ascended the second-to-last jump, Jacobellis looked back to confirm her lead, flew into the air, then grabbed her board in a celebratory…

The struggle to attain a deeply meaningful life may be an issue of language

Illustration: Dora Godfrey/Medium

Over the past two years, I have conducted more than 100 podcast interviews with best-selling authors, prominent academics, and other high achievers about the connection of money, happiness, work, and meaning. In each of these conversations, I make a point to ask these thinkers how each of us can lead…

Paul Ollinger

Why 10,000 hours doesn’t guarantee the success of your dream

Illustration: Dora Godfrey / Medium

In‌ ‌his‌ ‌2008‌ ‌bestselling book ‌Outliers‌,‌ ‌Malcolm‌ ‌Gladwell‌ ‌delivered‌ ‌to‌ ‌the‌ mainstream‌ ‌the‌ ‌theory‌ ‌that‌ ‌gaining‌ ‌mastery‌ ‌of‌ ‌any‌ ‌craft‌ ‌requires‌ ‌10,000‌ ‌hours‌ ‌of‌ ‌dedicated‌ ‌practice — as he calls it, “the magic number of greatness.”

The‌ ‌trade‌ you’re in doesn’t‌ ‌matter‌ ‌much‌, he argued, ‌because‌ ‌what‌ ‌all‌ ‌skill-based‌ ‌pursuits‌…

What watching my kid play baseball taught me about life

Filtered image of a young kid hitting a baseball with a bat.
Photo illustration; Image source: Shoji Fujita/Getty Images

“Never let the fear of striking out keep you from playing the game.”

— Babe Ruth, Babe Ruth’s Own Book of Baseball

Watching your child play baseball can be a highly stressful experience, especially when they get up to bat. …

Meditating on our fleeting mortality might sound like a downer, but the ancient practice can help us find more tranquility while we’re here

Photo illustration; Image source: Westend61/Getty Images

A couple weeks ago, I felt a dull ache in my abdomen. It wasn’t painful, but it was persistent and, since the belly houses several mission-critical organs, I decided to get it checked out. My doctor seemed puzzled by my nonspecific symptoms, especially since a recent colonoscopy and upper GI…

Paul Ollinger

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