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

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…


I’m finally ready to start treating it that way

Photo: Drazen_/Getty Images

In early 2020, my fledgling stand-up comedy career was finally finding its footing. I had started working the road for a large chain of clubs and had booked upcoming gigs in New York City, where I had meetings with influential industry gatekeepers scheduled on March 17.

Of course, that NYC…


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…


How Tony Hsieh’s death demonstrates our need to work

Tony Hsieh, 1973–2020 (Photo — Charlie Llewellin)

After two decades grinding away in the corporate world, I quit my job at 42 years-old. I didn’t have a plan, but I did have some money and decided I would use it to live a life free from the stress of professional employment. …


If there’s one thing the pandemic taught us, it’s that life is local. Research from the World Happiness Report backs this up.

Photo illustration; Image: FilippoBacci/Getty Images

A few years into my marriage, my young family relocated to my childhood hometown of Atlanta. After a couple of decades moving all over the country for a series of new schools or job opportunities, I felt it was time to pick a place and put down some roots.

But…

Paul Ollinger

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