DrLefty

WHEN I WAS A YOUNG adult, my parents sat me down and explained that I might at some point inherit money from my grandfather’s trust, which had also helped put me through college. My grandfather passed away in 1984, and his wife—my father’s stepmother—became the trust’s beneficiary.
My father was an only child. The trust stipulated that, if his stepmother died before him, he would receive two-thirds of the trust, while my two siblings and I would share the other third.

I’VE DECIDED UPON MY retirement date: July 1, 2025. We just passed the one-year countdown point, so I thought I’d share some of my ideas and plans for my final year in the workforce.
This countdown idea, of course, isn’t original with me. Indeed, there are apps that you can put on your phone to count down the time until retirement. I was primarily inspired by a retirement blogger named Fritz Gilbert. He’s way more decisive than I am.

MY ALL-TIME FAVORITE movie is the Coen brothers’ 2000 classic, O Brother, Where Art Thou? At one point, Holly Hunter’s character, Penelope, declares, “I’ve said my piece and I’ve counted to three.” Her estranged husband, played by George Clooney, understood from long experience that once she had “counted to three,” her mind couldn’t be changed.
Last summer, I wrote an article that explored the decisions my husband and I are working through about our retirement date and location.

MY LATE FATHER SPENT his entire career, from the time he dropped out of college to marry my mother until the day he died at age 61, in the insurance business. My father was also a huge fan of the San Francisco 49ers, our hometown NFL team.
Last year, the 49ers cruised through the playoffs, led by the team’s dynamic young quarterback, Brock Purdy. But then, in the NFC Championship game against the Philadelphia Eagles,

A LOT HAS BEEN written, here at HumbleDollar and elsewhere, about the “when” of retirement. Not surprisingly, there are strong opinions.
For example, I’m a member of a Facebook group where the overwhelming consensus is, “Don’t work one single day longer than you absolutely have to.” Of course, many people don’t have the luxury of choosing their ideal retirement date because life intervenes: They get let go from their job or experience health issues that dictate the answer to the “when” question.

I’M NOT SOMEONE WHO enjoys spending money on luxury travel. I’d never pay cash for a business class airline ticket or a hotel suite. Nonetheless, on a recent trip to Spain with my husband, we flew business class and had suites in all four hotels we stayed at.
We also visited lounges in every airport before our flights, had access to executive lounges at two hotels where we could get free meals, snacks and cocktails,

THE PROLIFIC MR. QUINN recently wrote that people who were irresponsible in one area of their life, such as failing to return shopping carts, also tend to be irresponsible in other areas, like managing their finances. He’s probably right. Still, I’ve had times when, even though I’m a “responsible person”—I’ve had a successful career, my kids lived to grow up, and so forth—I nonetheless had pockets of disorder in my life.
For me, the two biggest areas of chaos were managing money and maintaining a healthy diet and exercise regimen.

“I’D BE HAPPY TO JUST come here every year,” I told my husband. We and our two daughters had arrived on Maui 72 hours earlier. It was May 2000—and our first trip to Hawaii.
We’d signed up for a timeshare presentation in return for discounts on tours and activities. By the time we got to the meeting, I’d fallen head over heels in love with the place. The timeshare salesperson had an easy time persuading me to buy.

MY HUSBAND AND I WERE late bloomers when it came to estate planning. Though we took care of the basics when we became parents, such as purchasing term life insurance and naming a guardian, we never had a professionally executed will and trust until 2016, when we were in our late 50s.
Observing my in-laws, now in their 80s, made us realize how important it was to get our own estate-planning house in order.