WE MET IN THE GALLEY, the cafeteria in Vanguard Group’s nautical lexicon. Jack Bogle shook my hand. My pulse raced.
I’d learned about Vanguard’s founder while working at Morningstar. I’d read about him in Jonathan Clements’s Wall Street Journal columns. And I’d devoured his first book, Bogle on Mutual Funds.
“Where’d you go to college?” he asked. “Good board scores?”
We sat down, tucked into our meals—some sort of industrial casserole for me,

IT PAINS ME TO SAY this, but I hurt—everywhere. I’ll start at the bottom and work my way up. My feet hurt, my knees hurt, my hips hurt, my back hurts and my shoulders hurt. One more thing: I can’t remember. My memory is in decline.

Cataract surgery improved my eyesight. Hearing aids mean my grandkids don’t have to be two rooms over when we watch TV together. Exercise seems to reduce my pain slightly and increase mobility.

AS AN ENGINEER and a believer in keeping things running, I haven’t owned many automobiles during my lifetime. Instead, my focus has been on extending each one’s longevity.
Among the maintenance and repairs I’ve undertaken: oil changes, spark plug and wire replacements, carburetor cleaning and adjustment, belt and hose replacements, distributor and timing settings, brake replacements (disk and drum), master and slave brake cylinder repairs, clutch adjustment, alternator repair, radiator repair, heater core repair,

“IS THAT INDIA or something? Where was that picture taken, Richie?”
“You’ll never guess, Stevie. Remember 266 Washington Avenue?”
“That brown brick, 114-unit apartment building in Brooklyn that Grandpa bought 75 years ago? Mommy said he saved for the down payment with money from the kosher butcher shop he opened after he got here from Poland. But didn’t we sell it in the 1970s? It looks like the Taj Mahal now.”
“Yeah, it’s obviously been spectacularly upgraded over the years.”
“How did you get the picture?”
“Robin and I were in New York last month and went to see it.

LIKE MANY AMERICANS, Sally found herself caught in a whirlwind of unexpected expenses and mounting credit card debt. It wasn’t lavish vacations or shopping sprees. Rather, it was veterinary bills for her aging dogs.
I conducted a credit-card debt-reduction workshop for Sally. Here’s a glimpse at her finances:

Her Mastercard balance was $12,970 at a hefty 17% interest rate.
Despite that, she had an exceptional credit score of 820.
She also had a $26,000 emergency fund.

WHAT DO WE MEAN BY an “enjoyable” retirement?

I suspect there are as many answers as there are retirees. But one thing remains a constant: the need for an adequate income. Given a choice, I don’t think many people would choose to live a frugal, barely financially sufficient retirement.

My father retired at age 66. I say “retired,” but the reality is one day the owner called him into the office and said he was no longer needed.

MY WIFE AND I TOOK a hiking trip last fall that included wandering through the foothills of the Ozark Mountains in Arkansas. The leaves were just starting to change colors, something I so badly miss living here in Texas.
I returned exhausted and sore, yet mentally energized and invigorated. For the majority of the trip, we were untethered from technology: no cellphone service during the day, no newspapers or TV distractions, no political talking heads,

YOUR CAR IS TALKING to your insurance company. You aren’t part of the conversation. Suddenly, though, your insurance premium shoots up 50%. Welcome to the brave new world where your car is spying on you.
In one instance, a Florida resident drove his Cadillac around a racetrack during a special event. His insurance subsequently skyrocketed—by $5,000 a year.
Has artificial intelligence taken over? No, but automobile companies have, and without our knowing it. Carmakers are spying on drivers and passengers,

JEFF, DAVE, JERRY, Glenn, John, the ElderBeerMen, and then Jeff again. Experts say a robust social network is crucial to a happy retirement. My life’s journey has revolved around a handful of friends who begin and end with the same good dude. 
I was a 15-year-old kid who didn’t like school, and I had the grades to prove it. I did, however, have two burning desires. I couldn’t wait to turn 16 so that,

BACK IN THE 1980s, I was working for an insurance company on Wall Street. This was when I was between marriages. There was a nearby bar and restaurant called Harry’s, located below street level. The bond market was going strong, so the bond salesmen with their fat paychecks were there, which meant the pretty young girls were also there.
The place reminded me of Cheers, one of my favorite TV shows.

BACK IN 1987, Nassim Nicholas Taleb was a trader on Wall Street. But unlike most of his peers, Taleb wasn’t pinning his hopes on a market rally. Instead, he’d positioned himself to benefit from a market meltdown. On Oct. 19, just such an event occurred. For no apparent reason—in the midst of an otherwise strong market—the S&P 500 dropped 23% in a single day. The result: Taleb made a fortune—enough to retire at age 27.

OVER THE PAST SEVEN years, HumbleDollar has become my professional life’s passion. Cancer means I have maybe another year in me—and then it’ll be up to you. My hope: The site will have a life beyond me.
On the site’s homepage, just below the latest articles, you’ll find a new feature dubbed Forum. Will HumbleDollar have a lively future, rather than fading into a dusty collection of old articles? That all depends on whether readers and writers embrace the Forum,

DO YOU REMEMBER the days before you could drive? You felt like you were on a leash. No freedom. No fun.
I have news for you: Those days could return.
One of the post-age-65 nightmares that we don’t talk about enough: Most affluent retirees live in the suburbs. Homes are miles from grocery stores, medical offices, movie theatres, restaurants and—perhaps most important—drugstores.
In the suburbs, the stream of city-based public transportation usually slows to a trickle.

IN AN EARLIER ARTICLE, I detailed how Charter Communications wasn’t so much my internet provider as my extortionist. I thought I’d dealt with it all in an equitable manner. But then, exactly two years after our relationship began, Spectrum abruptly increased the price it charged for internet access by 67%, from $29.99 a month to $49.99. I guess we didn’t have a relationship so much as a contract.
While I didn’t take too kindly to that,

I VIVIDLY REMEMBER my father explaining how small sums of money could grow exponentially. Using the example of a penny that doubled every day for a month, he showed how it could grow to more than $10 million. Indeed, as Albert Einstein didn’t say, “The most powerful force in the universe is compound interest.”
Many authors tout the benefits of saving beginning at a young age. Radio personality Dave Ramsey and his daughter Rachel Cruze,