HI RYAN, DON’T FREAK out because I’ve written an actual letter rather than an email. No big news here, no emergency, we’re fine. I just have something that’s been percolating and I want to share it with you.
Ry, it’s become clear learning about investing is not where you’re at right now. I’ve tried to think of what I might have done to turn you off. We know I was depressed and withdrawn for much of your childhood,

IF YOU KICK AROUND Wall Street for long enough, you’ll witness all kinds of investment fads—special purpose acquisition companies, cryptocurrencies, meme stocks, to name just a few. Each bubble differs, but the eventual comeuppance always feels brutally familiar.
But there aren’t just fads among investments. There are also fads among investment concepts. But while naïve investors tend to get caught up in investment bubbles, it’s the brainy types who fall in love with investment concepts,

FRANK CAPPIELLO and Carter Randall were longtime panelists on the television show Wall Street Week with Louis Rukeyser. Panelists typically worked at investment firms, with their affiliations displayed on the screen. At some point, Cappiello and Randall retired. On the screen, each was simply identified as an “independent investor.” At least one regular guest, John Templeton, also achieved this listing after retiring from running the Templeton Funds.
That “independent investor” label intrigued me then and does to this day.

WE TRIMMED THE TAXES we owed on investment gains in 2021 by using losses we’d realized during 2020’s stock market swoon. Now, 2022’s market decline has allowed us to repeat this process, once again offsetting capital gains with tax losses that we’d earlier harvested.
My wife and I haven’t just saved on taxes, however. The sales have also allowed us to reposition our taxable portfolio away from active management and toward more of an indexing bent.

IF YOU PUT DOWN less than 20% on a conventional home loan and you’re still paying private mortgage insurance (PMI), do what I did: See if you can get those pesky PMI payments eliminated.
I purchased a home in September 2017 for $341,000. The interest rate was near 4% and I put down roughly 10%. Why not put down 20%, so I could avoid PMI? My thought: If I can borrow money at an interest rate below 5% and get a reasonable rate of return elsewhere,

OVER EIGHT MILLION Americans have said “so long” to the U.S., heading overseas to work or retire. These expats—short for expatriates—most likely have eight million different reasons to leave our shores for life in another country. My wife’s cousin Chuck and her brother John are among them.
John had his eye on living abroad when he took his first engineering job with Litton Aero Products, where he helped support aviation customers in the Middle East.

I STARTED WRITING for HumbleDollar almost five years ago—and it’s become a big part of my retirement.

Some folks have likened me to Andy Rooney. It’s a comparison I’ve happily embraced. I try to offer pointed opinions leavened by a measure of humor. Here are my 10 favorite articles that I’ve written for the site.

Choosing Badly (April 24, 2018). This was my first piece for HumbleDollar. Employer-sponsored 401(k) plans are underutilized and misused.

IN JANUARY 1987, I was an unmarried junior Coast Guard officer just beginning the flight stage of U.S. Navy flying training. I decided to see a financial advisor who’d been recommended by friends.
This wasn’t just any advisor, but rather a retired Air Force lieutenant colonel and fighter pilot. He worked for a firm whose advisors were comprised mostly of retired military officers, and they marketed their services primarily to military officers. If there was anyone I could trust,

I BEGAN BUYING Series I savings bonds in 1999. At the time, you could purchase them at a local bank and receive paper bonds. Amid 2022’s spike in inflation, those early bonds that I bought were—for a six-month stretch last year—yielding an annualized 13.08%. Not bad for a low-risk investment.
One drawback to buying savings bonds: the limit on how much a person can purchase each year. When I began buying Series I savings bonds,

THE BEST DESCRIPTION for my career would be “corporate vagabond.” I moved the family six times to five different states over 42 years.
Because we never settled down in one place, my wife and I spent 15 years visiting potential retirement locations. We visited sprawling metropolitan areas, small towns, retirement communities and the town where we both grew up. We also considered the areas where we’d lived, but nothing appealed to us.
One evening,

HOPE SPRINGS ETERNAL for mega-cap tech, meme stocks and cryptocurrencies. And the bond market is starting to party again, too. True, the financial markets have pulled back in the two trading days since Friday morning’s strong jobs report. Still, year-to-date performance has been startling.
Investor’s Business Daily reported recently that just 10 stocks, including Apple, Amazon, Tesla, Alphabet (parent of Google), Nvidia, Microsoft and Meta (parent of Facebook), have accounted for half of the S&P 500’s 7% year-to-date rally.

“I WOULD SAY TO the House, as I said to those who have joined this government: I have nothing to offer but blood, toil, tears and sweat. We have before us an ordeal of the most grievous kind. We have before us many, many long months of struggle and of suffering…. You ask, what is our aim? I can answer in one word: victory. Victory at all costs—victory in spite of all terror—victory, however long and hard the road may be,

WALL STREET WAS stunned Friday morning by the strength of the jobs market. While technology company layoffs have lately hijacked the fear-mongering media’s narrative, the truth is that the employment picture is quite strong.
With a 517,000 gain in net employment last month, along with ebbing wage growth, the “soft landing” crowd is one big step closer to winning the battle against the recession prognosticators. True, January’s jobs jolt is merely one data point.

IT’S HUMAN NATURE to be impressed by things that sound sophisticated or seem complex. In the world of personal finance, this certainly applies to the planning tool known as Monte Carlo analysis.
Its roots go back to the 1940s, when it was developed by Stanislaw Ulam, a physicist working on the Manhattan Project. Today, it’s a popular way to assess the strength of a proposed retirement plan. If you’ve seen presentations indicating that a financial plan has a particular probability of success,

I’M AMAZED BY the opinions expressed by some retirees about the Medicare premium surcharge known as IRMAA, short for income-related monthly adjustment amount. Is it really unfair for higher-income older Americans to pay larger premiums for Medicare Part B and Part D? Many people think so.

IRMAA was part of 2003’s Medicare Modernization Act and took effect in 2007. The threshold at which IRMAA kicks in for a couple is four times higher than the median household income for Americans age 65 and older.