TWO THINGS HEAVILY influenced my financial life. The first was my short stint after college as an internal revenue agent with the IRS. The second was getting married and having five children.
Result: I’ve spent most of my adult life as a tax-averse junky using retirement accounts to get my high, so much so that there’s a risk our retirement-account withdrawals will put us in a much higher tax bracket than when we made our contributions.
AUTO INSURANCE HAS been getting more and more expensive in recent years. There are many reasons: New cars cost more, extreme weather, folks seem to be suing more often, and so on.
Our daughter Brenda called me, asking if I could look over her auto policy to see if there was a way to lower her premiums. We have our car insurance with the same company. On the company’s website, I came across something called “Safe Pilot.” Many insurers have similar programs.
IT’S ONLY BEEN relatively recently that mankind has come to rely on banks, brokerage firms and investment companies to build wealth.
Tangible property—land, gold bars, houses, livestock and so on—was the standard of wealth just a couple of centuries ago. The Bible frequently cites cattle to signify someone’s wealth. If folks had “cattle on a thousand hills,” they were a billionaire in that era. Wealth was something that you could physically lay your hands on.
I’M A SUCKER FOR those “10 best” lists. But are they accurate?
What if you had the best job in a poorly rated company? Would that be better than the worst job in a well-rated company? What if you move to a bad neighborhood in a well-rated city? Would that be better than an excellent neighborhood in a poorly rated community?
You get my point. Even among the worst, you can find some real gems.
I HAVE A SIDELINE writing stories for a local newspaper. Every now and then, even in a small rural community, you’ll find folks who blow your mind. One such individual is a retiree named Junius R. Tate, who goes by J.R. and who spent his youth in Washington County, Kentucky.
Tate hiked the Appalachian Trail, which crosses 14 states from Georgia to Maine and is roughly 2,200 miles long. It takes a determined hiker about six months to complete.
FOR A FEW YEARS early in my career, I was an internal revenue agent for the IRS. I audited the tax returns of small businessmen, drug dealers, doctors, lawyers, a professional basketball player and everybody in between.
That was 43 years ago, when the IRS was much bigger relative to the population. One result: A larger percentage of the population were subjected to audits.
I saw and heard a lot. Some people would put dogs,
MORE THAN 40 YEARS ago, I was an agent for the Internal Revenue Service. During training, we learned about auditing individuals, corporations, subchapter S corporations, Schedule C businesses, partnerships and probably a few other areas that I’ve since forgotten. But there was one area we didn’t touch: trusts.
That puzzled me, so I asked the trainer why. His response: “You aren’t smart enough to audit trusts.” He told me that how trusts operate might change drastically based on slight differences in wording.
HERE’S A RECIPE FOR disaster: a good internet connection, plenty of storage space, lots of time on your hands—and credit cards.
Impulsive shopping has a name, oniomania, and the above recipe makes it all too easy. If you have a credit card, research suggests you’ll spend significantly more than if you were paying with cash or a check. The availability of 24/7 online shopping makes it just that much worse.
Here are eight signs—besides the pile of packages outside our front door each day—that tells me impulsive spending has reached our house:
1.
MY DAD LIVED TO BE age 92 and my mom is going strong at 95. I was involved with my father’s care as he struggled with dementia, and I continue to assist my mother, who still lives independently.
Helping an elderly family member? Here are 16 important lessons that I’ve learned.
1. Don’t be blind. My dad started developing dementia five years before his cognitive ability totally fell off a cliff. No one in the family wanted to recognize his deterioration,
HERE’S ONE OF THE most important lessons I’ve learned in retirement: Bad health will limit what you can do—or feel like doing—no matter how much money you have. Good health is the biggest determinant of how rich and fulfilling your retirement years will be.
You and you alone are responsible for your health care. It’s not your spouse, your children, your friends or your doctors. It’s you. Nobody should have to beg you to see a doctor.
HOW’S YOUR FRIENDSHIP account balance looking? I spent my life watching my bank account, and taking great pleasure as it grew and grew. I never cared much for what I could buy with the money, but I loved the feeling of security it offered.
Friendships, meanwhile, took a back seat. That was pretty much normal for my family, and maybe it’s more normal for most folks than we like to admit. We have a tight little circle that includes family,
I SPENT ALMOST 43 years either on active duty or in the reserves for the Navy and Army. Yes, I’ve been around.
The following is my list of the top 17 items—including some pertinent financial details—that might surprise those who have never served in the military.
No. 1: Our primary mission is not to fight wars. Instead, it’s to be so big, so bad, so mean, so well equipped, so well trained and so well led that any potential enemy in its right mind wouldn’t want to fight us.
I’VE SEEN FINANCIAL advisors do great work and I’ve seen them do poor work. Which brings me to my late father’s experience.
Dad was a heck of a small businessman. Starting in 1956, he and his partner sold and serviced radios, televisions, appliances and furniture. Forty years later, he sold the business to four of my brothers.
By the mid-1960s, Dad had accumulated what was for him a small fortune. This was the time of the stock market’s so-called go-go years.
THIS IS MY SIXTH STORY for HumbleDollar. You don’t know how happy you’ve made this old hick from Kentucky feel by taking the time to read my stuff, let alone comment on it.
I’ve done and continue to do a lot of dumb things in my walk down life’s path. I hope to share most of them to give you something to think about and maybe avoid on your own. Today,
I’VE MADE A LOT OF investing mistakes in my time. In fact, if I ever wrote a book on investing, the title would probably be Don’t Go There, It Sucks.
I’m a Kentucky hillbilly and, yes, that’s hillbilly talk. Another local colloquialism is, “Careful, or you’ll end up like Scrambo Hill.” I don’t know who Scrambo was. But apparently, he resided around our parts at one time, and you don’t want to end up at the bottom of the barrow like him.
IT TOOK FIVE FALSE starts to write this column. Each time, I’d inundate readers with information. So, here’s a sixth try.
Have you ever seen those questions to financial advisors on the internet that say, “I have [insert dollar amount]. Can I retire?”
How the heck could the advisor give a reasonable response? To answer the question, it takes more than simply knowing how much you have in the bank. You need a lot of personal and financial information to make the decision to retire.
OUR FIVE KIDS SPENT a collective 24 years in college. All five have bachelor’s degrees, and three also have master’s degrees. The youngest graduated May 2023. Only one child qualified for non-merit aid—a $300 Pell grant.
My wife and I didn’t give them money for college. We don’t live near a major public university, so four of the five had to live on campus. Here’s what prepared them for college and how to pay for it.
AS I WROTE THIS STORY, the word count kept climbing and climbing because it has more twists and turns than a detective novel. It was so long I was afraid no one would read it, not even my mother. So, here is a condensed version of what I wanted to say.
The hardest transition for some folks as they reach retirement is to go from a saver to a spender of what they’ve saved.
THIS IS MY FIRST article for HumbleDollar. I’m new to the site, but not new to writing for the public and, indeed, I’ve contributed regular columns to some small newspapers.
My life has had more twists and turns than going down a Kentucky country back road filled with hillbillies, of which I am one. Kentucky is either the poorest state in the country or next to it by any measure you want to look at.
Comments
It's a great article. I have to admit I have such trouble following it. I've done well in the market but have such a terrible desire to endlessly tinker with my portfolio with narrow focused EFT's trying to beat the market. It's a fool's journey.
Post: Going to Extremes
Link to comment from July 26, 2025
Read you great article in the AARP Magazine this month. You know your Number 1 advice on worry less is also my number one problem. I worry so much about my children on things I can't control in their lives while my own life, as I wind down, seems to be pretty well set. I always thought that if everything in my personal life was set then I would not have anything to worry about. Not in my nature unfortunately. Sort of takes a lot of enjoyment out of retirement even though most of my worries never happen. It's like paying interest on debts you don't owe.
Post: Four Thoughts
Link to comment from March 1, 2025
I've done well in the market by sheer dumb blind luck. I would have done great if I had had the ability to listen and follow someone like Johnathan early and often. I thought too much of my own opinion and acted accordingly to my later regret.
Post: Taking It Personally
Link to comment from February 8, 2025
I used to read Jonathan's "Getting Going" column in the Wall Street Journal all the time. I especially liked his two highly humorous columns called "Excuses, Excuses: How We Save Face" and "More Great Moments in Steet-Speak". I know the titles because I cut them out close to 40 years ago and later added them to my computers as pdf forms. I give them to folks every so often as well. They are so incredibly true and incredibly funny because they are so true. Every so often I read them and chuckle to myself no matter how many times I've read them before. True yesterday, true today and will be true tomorrow. That is great writing. My real regret in investing is that I wished I had followed Jonathan's advice on indexing instead of chasing a highly forgetable pile of actively managed funds and then held them through thick and thin. I would be a much richer man today.
Post: Money Grows Up
Link to comment from January 18, 2025
You are so right about dollar cost averaging into investments. I do use it as an emotional crutch now that I am not employed and putting money into my retirement account. It is not the most effective but it helps me mentally to stay in the market during bad times.
Post: Spending It
Link to comment from January 11, 2025
Life is an adventure. But as a matter of faith I can't help but feel that the real adventure begins after life.
Post: No Regrets
Link to comment from September 7, 2024
I eagerly wait for each of your columns. My mother is currently 96 and my dad died at 92. But I lost two brothers to cancer at age 64 and 68 and nearly lost a niece with three kids at 46 to cancer as well. The strange part was cancer didn't really run in our family and these three led extremely healthy lives with no smoking, very little drinking and were actually thin. One brother had never been sick in his life if you can believe that up until he got cancer. Yet it came. My greatest wish is if it comes for me that I can be as strong as you are. It makes it so much easier on the family and I don't want to unset them. You are truly amazing and I will remember you for as long as I live.
Post: On the Clock
Link to comment from August 17, 2024
This is such a great article. I am in the same boat on many fronts concerning tax deferred accounts. Also I am POA on my widowed 96 year old mother's account that holds stocks that I would rather be out of but holds enormous capital gains subject to step-ups in value at death. On one hand she could die at anytime at her age but on the other hand I feel that she could very well go way pass 100. I feel that there are better ways to invest the money but worry I will cause a large tax situation that would not happen if she dies shortly after the sale.
Post: Driven by Taxes
Link to comment from July 20, 2024
Warren Buffett. Unfortunately it took me to my 60's to try to follow all the wisdom that I read for years that he gave out free of charge.
Post: Who has had the greatest influence on your financial thinking?
Link to comment from June 6, 2024
Trying to get my spouse interested in our finances. She is annoyed whenever I bring it up.
Post: Which financial tasks do you find most irksome?
Link to comment from June 6, 2024