‘What was I thinking?’ The big-ticket items people regret

livemint.com:

While it may be true that money can’t buy happiness, that doesn’t stop people from trying. And then wishing they hadn’t. Many of us have had a big-ticket expenditure that we later come to regret.

Maybe it’s something meant to convey status, which we realize later did nothing of the sort. Maybe it was to fulfill dreams of a luxury lifestyle, only to discover that we’ve bought a bottomless money pit. We asked Wall Street Journal readers to share their stories of pricey purchases that ultimately led to disappointment.

Below are some of their stories and reflections—with some free advice to their younger selves. “It was back in day of wingtip shoes, white shirts and red ties," says Bryan Desloge, who began his career at IBM in 1984. And like many rookie employees, Desloge wanted to fit in.

“I bought suits. I took my earring out. I cut my hair and I registered in the Republican Party," he says.

To complete the look, he paid over $7,000 for the wristwatch of his dreams—a Rolex Submariner. It was a hefty sum, considering he was making roughly $18,000 a year. Now 64 and retired, Desloge says his younger self saw the stainless-steel watch as a status symbol.

“The older guys had nice dress watches already, while I wore a Casio or a Timex." Just two years after buying the Rolex, however, Desloge realized the timepiece was impractical for him. “The Rolex is great, but I don’t want to look at a clock face," he says, “and the glow-in-the-dark hands are hard to read at night." Desloge, who lives in Tallahassee, Fla., recently tried to give the Rolex to his son, who turned him down. So it remains tucked away in favor of a Garmin smartwatch, which has a fitness tracker, alerts and email, among other features.