A friend of mine quit his job recently. He was good at his job. He made good money. He had autonomy over his schedule. He had unlimited vacation. His job had many of the qualities that we all think we want. But he quit anyway.

He had lost the sense of fulfillment in his work some time ago. He always had another “itch” that he wanted to scratch, but every time he worked up the nerve to consider quitting, the money or the offering of new incentives had a way of reeling him back in. It wasn’t that the money and incentives were SO GOOD that he couldn’t ignore them, but they were just enough to make the pain of staying a little less.

This “Do I stay or do I go?” dance has played out repeatedly in some capacity over the last several years. For years, though, the decision was always one requiring a huge leap of faith to throw away the comfortable, known quantity of the current path for one of potential excitement but filled with uncertainty.

But then…something happened that disrupted the equation and closed the gap of uncertainty between the familiar path and the new unknown. Suddenly, the familiar was less familiar and year’s of contemplating the unknown had in some way made it feel more comfortable…and what was once a giant leap of faith was now a much less intimidating step.

A case could be made that he was lucky. Lucky that a change in circumstance nudged him to make the change.

A case could be made that he was courageous. Courageous that he threw away the easy, comfortable path for the path of uncertainty.

The truth is likely somewhere in between, but what many people don’t get to see are the years of mental and financial preparation happening behind the scenes to put himself in a better position to take the leap when the time was right.

Quitting isn’t always the right answer, especially when it’s done emotionally or impulsively. But, sometimes quitting and change is the right choice in the long run when it’s planned, calculated, and well-thought-out.

Here’s what caught my eye this week:

MONEY: How to Teach Your Kids About Money (MintLife)
“There’s a specific conversation I frequently have with people around my age. As they get closer to middle adulthood and look back on everything they’ve learned about money, they start to wonder – why didn’t they teach us this stuff in school?”

LIFE: Men Have No Friends (Bonefide Wealth)
“Over the weekend my wife shared an article with me from Harper’s BAZAAR titled “Men Have No Friends and Women Bear the Burden” by Melanie Hamlett. It’s a stellar examination of the emotional lives of men if not masculinity itself. It details why so many men are terrible at making friends, expressing themselves to other men and why we believe that women are the only people we can turn to for emotional support.”

Simplicity, Clarity & Purpose in Money & Life

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