Musings about early retirement with no fixed address

Category: Early Retirement (Page 6 of 6)

Finding the Courage to Quit

Deciding to embark upon retirement in our early 40s can be a scary prospect. As many, many people like to point out, there are numerous risks associated with that decision. The stock market is due for a crash. Our money may have to last 60 years. Economic signs point to a recession. The uncertainty of self-inflicted trade wars, foreign policy, government dysfunction, and [insert current event here] means that the future is bleak. We could be forced to go back to work with a huge resume gap or work a crappy job when we’re old. Quitting in our peak earning years means we’re giving up money and safety when it’s the easiest to amass both. And that’s just the tip of the iceberg.

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A Random Day Off

As someone who loves to travel, I have always cherished each and every vacation day.  I view them as precious gifts. They are definitely not to be wasted, misused, or arbitrarily cashed in.  Using one at home means that I can’t stay that extra day in France or Mexico or Vietnam. As such, I can’t remember the last time I burned a vacation day that wasn’t connected with a trip.  But considering that I will have no use for these in the very near future, I broke my rule the other day. For the first time in at least a decade, I took a random weekday off for no real reason.  And it was glorious.

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The Year of the Dragon

Growing up we didn’t eat out often, but when we did my family liked to go out for Chinese food.  In particular, my grandpa Herbie was fond of it. I’m not 100% sure if my dad liked the food as much as we did, but he was always willing to go because it allowed him to crack the joke that “if you fart, you’re hungry again” after the meal. When you add in the fact that it was reasonably priced, tasty, and of course came with free cookies, it checked all of the boxes to keep both the adults and the kids happy.

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A Series of Fortunate Events

It was the winter of 2003, just before Christmas, and the decorations were out in full force along the Magnificent Mile.  All of the stores displayed the top gift items of the season in their impressively decorated front windows.  Street musicians and carollers filled the air with festive tunes. I was still a young man, fresh out of college, only 18 months into my career.  Each weekday I exited the subway and walked down the iconic Michigan Avenue to my cubicle on the 19th floor of the John Hancock building, where I had gotten a job working for the 3rd largest insurance brokerage in the city.  And I was about to be laid off.

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What Did You Want To Be When You Grew Up?


I have a hard time remembering exactly what my answer to this question was when I was a kid.  I’m sure a frequently repeated answer was professional basketball player. When I was young, my dad was a high school basketball coach so we watched and played A LOT of basketball.  Unfortunately, my growth spurt stopped at 5’11”, my jump shot never quite developed as much as I’d hoped, and since I’m not quite as quick as Isiah Thomas, the NBA ceased to be an option.

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