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

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 off-the-grid through entrepreneurship, the arts, or kite-surfing-mountain-climbing-veggie-juice-fasting in Bali. To make the point, these performance provocateurs cite historical badassery such as Spanish conqueror Hérnan Cortés who, upon landing the fleet in Mexico, demonstrated his commitment to the mission by torching his ships. …

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 trip never happened. But lockdown did, and the momentum born from seven years of full-time grinding, open mics, and doing all possible gigs went straight down the toilet. I was scared and pissed off. But after a week or so, I realized something — all the clubs were closed, so…

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 have 15 years left until retirement,” he shared solemnly. “I work most weekends, and every morning, I have to drag myself to the office. What am I going to do?”

Since I started my podcast about the connection between money, work, and meaning, I’ve received many emails from people like…

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 display of swagger. The showboating would have been no big deal except that when she landed, Jacobellis fell on her backside while Tanja Frieden of Switzerland zoomed past to win the gold medal.

This kind of showy blunder happens all the time in sports. NFL players DeSean Jackson and Danny…

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 a happier life. Again and again, the same answer keeps coming up: “Lower your expectations.”

The first few times I heard this advice, I refused to accept it. “Low expectations” sounds defeatist. It sounds like giving up on happiness altogether. But over time, I’ve realized that the gap between their…

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 ‌have‌ ‌in‌ ‌common‌ ‌is‌ ‌that‌ ‌repetition — at‌ ‌the‌ ‌scale‌ ‌of‌ ‌years‌ ‌of‌ ‌your‌ ‌life — is‌ ‌the‌ only path ‌to‌ ‌proficiency.‌ ‌Similarly, the actual number of hours may vary, but that’s not the point. In‌ this ‌controversial model,‌ “10,000‌ ‌hours”‌ ‌plays‌ ‌the‌ ‌same‌ ‌symbolic‌ ‌role‌ ‌as‌‌ ‌“40‌ ‌years‌ ‌in‌…

What watching my kid play baseball taught me about life

Filtered image of a young kid hitting a baseball with a bat.
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. Your pulse soars and hands tense as you wonder whether they’ll triumph or return to the dugout in defeat.

Last season, my parental nerves grew increasingly agitated when my son adopted the strategy of not swinging in hopes of earning a walk. While it worked often, his coach pushed him to be more aggressive so he could gain the confidence…

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 scan indicated all was good. So he ordered a slew of tests and an ultrasound, which he scheduled for the next afternoon.

After I left my samples and departed the office, I spent the next 24 hours Googling “stomach pain” while contemplating my imminent death. The internet suggested I had…

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. Because not working is the ultimate dream, right?

A few months later, I found myself sitting on the couch, shoving Pirate’s Booty into my bored face, and enduring constant heckling from the annoying neighbor between my ears. That brain, lacking work’s daily responsibilities and long-term goals, cried out for a purpose: “We should be famous,” Brain…

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 after several months back home, things weren’t gelling socially quite the way I had hoped. So I called my former leadership coach, Alpesh Bhatt, and confessed that I just wasn’t finding the community I had hoped to rediscover. Al, who seemed to know me well from the first day we…

Paul Ollinger

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