WORK ON A HOUSING development began in early 2000 about a mile from where we lived. This was right around the time that my wife Lisa and I were starting to feel like we wanted some more room for our family. In addition, we were concerned about our current backyard. There was a swale—a shallow ditch—that ran the length of the yard, parallel to the house.
When we bought the house, there was grass in the base of the swale and nothing looked unusual.

MANY FOLKS—ESPECIALLY those still working—think retirement is “living the good life.” The truth is, unless you develop a solid plan for how to enjoy your newly available time, life after retirement can be filled with bouts of boredom, anxiety and even depression. My objective: Forewarn recent and soon-to-be retirees of the emotional dangers that lie ahead—and to suggest a road to a successful retirement.

Retirement isn’t a destination but a journey with three key stops.

THE TOPIC OF TRAVEL pops up occasionally on HumbleDollar, and I’ve even written about my own travels. The reasons for not traveling go from “can’t afford” to “no interest.” I can understand “can’t afford.” But the “no interest” is a mystery to me. The only budget we have in retirement is for travel. It’s funded with our Social Security checks.

When I was in school decades ago, my favorite subject was history.

WHEN I LAST REPORTED on our retirement journey, we’d decided to put our search for a second home on hold. Well, in the immortal words of Saturday Night Live’s Emily Litella, “Never mind.”
We looked at many properties in several communities earlier this year, but we didn’t find anything we wanted to purchase. We decided on a cooling-off period, while we pondered what our next step should be. We kept a casual eye on properties coming up for sale,

WHAT’S THE STATE of America’s family finances? The Federal Reserve just released its once-every-three-year look, in the guise of the 2022 Survey of Consumer Finances, which is based on in-depth interviews with some 4,600 families.
You can read the Fed’s analysis here. Below are some key insights from the latest survey:
Net worth. The typical (or “median”) net worth—meaning the value of all assets minus all debt for those American families halfway down the wealth spectrum—was $192,700 in 2022. 

LIKE MANY OF MY generation, I grew up in a family that never talked about money. I had some sense that I should save, but no sense of where to save. This made me susceptible to a lot of advice—both good and bad—that shaped my financial journey.
I married a teacher and I became a school-based speech pathologist. I knew we’d never be rich, but we would have a comfortable life. In those early days,

NO ONE SCHEDULES when the car battery is going to die.
Monday morning arrives after a full weekend. Bleary-eyed, I roll out of bed, make a steaming cup of coffee, and pull up the latest HumbleDollar articles on my iPad. My wife rushes past, gives me a quick peck on the cheek, and leaves to drive to her study group.
And then I hear the groan. Alas, the car won’t start. No power,

DO YOU EXPECT IT TO be warmer this winter in Minneapolis or in Miami? This isn’t meant to be a trick question. We’d probably all agree that it’ll be warmer in Miami. But what if I asked you to predict the precise temperature in either city on Jan. 1. This is a much more difficult question.
In his book Mastering the Market Cycle, investor Howard Marks uses illustrations like this to make an important point.

“GOD, GRANT ME THE serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference.”
No matter what our religious beliefs, we’re constantly bombarded with reasons to invoke the serenity prayer. There are so many things we can’t control: what our bosses decide, what acquaintances say behind our back, how stocks and interest rates perform. This lack of control can be a source of endless anxiety,

ALASKA FINALLY HIT the top of our bucket list. A number of friends had made the trip and returned with glowing reports of the scenery, wildlife and fresh seafood. Vicky and I each had our own No. 1 reason for the trip: She wanted to see whales, and I wanted to see the Northern Lights.
Alaska’s Inside Passage is often the destination for travelers headed to the 49th state. There’s a wide variety of ships that ply those waters,

WHEN I WAS BORN IN Iowa in 1973, my parents were renters—and they didn’t become homeowners until eight years later. Looking back, I can see that it would have been hard for them to buy a house. When my dad started at the factory where he worked for more than 30 years, it didn’t pay the best.
But as Bandag, the retread company he worked for, began to prosper under its founder Roy James Carver,

I READ QUITE OFTEN on HumbleDollar about the trials and tribulations of those planning for retirement—questions like when to retire, where to retire, what will my expenses be, when to take Social Security, how to minimize taxes, how much money to save, how much to spend.

I approached retirement quite differently. Even I’ll admit I’m not typical, and perhaps only questionably normal. I tend to set major long-term goals with modest attention to details.

I HAVE BEEN FIRED, downsized, restructured and laid off 10 times in my life. The first time was at age 16, when I worked for a McDonald’s-like hamburger joint, and the last time was shortly before I turned 70, when I was working for an insurance company as the manager of regulatory compliance.  
I can’t blame this on discrimination. I’m a white Christian male, five feet 10 inches tall, college educated, and of sound mind and body,

WHEN I TOOK OVER responsibility for my developmentally disabled uncle’s finances, following my father’s death in 2001, I inherited the stock broker that my dad was using. The broker was associated with a well-known financial company. I’d never used a broker before. Any investments I personally owned were held in my employer’s 401(k) plan.
The first time I met the broker, whose name was Jim, I took notice of the large and finely appointed office he had.

WHEN MOST PEOPLE retire, they have a good idea where they’ll live. It might be where they currently reside, or where they vacation, or a place near their children or grandchildren. Whatever the case, there’s usually a limited number of possibilities.
But what if you move to a new city for the last two years of your working life, never vacation in the same place twice, don’t own a vacation home, are childless and—upon retirement—sell your home,