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I WAS THINKING ABOUT Jonathan the other day on my morning walk, which happens more often than you might think. It’s hard not to think about him when you have HumbleDollar coasters in your living room and a HumbleDollar shopping bag in your car that you use for groceries. My wife confiscated the HumbleDollar cup I had been using for my morning tea, and it now has a new home in our bathroom holding her toothbrush and toothpaste. There’s even an apron somewhere in the house that Jonathan once sent to all the writers.
Ever since I started writing for HumbleDollar in 2017, Jonathan has influenced my retirement. I now own the Vanguard Total World Stock Index Fund (symbol: VT) in my investment portfolio because of his recommendation. He liked it for its “broad global diversification in one low-cost fund that covers virtually all publicly traded companies worldwide.” It struck me as a good way to simplify our holdings.
I didn’t just borrow some of Jonathan’s investment ideas; I also borrowed some of his words he used when editing my articles. I began peppering my writing with words like fret, upshot, and folks. He once told me, “While your grammar is occasionally a bit dodgy, you have a great ear for language.” I was too embarrassed to ask him what he meant by a “great ear for language.”
When I retired, I never imagined that writing for HumbleDollar would become such a big part of my retirement, and I’m grateful to Jonathan for that. I also didn’t think my retirement would be so fluid. I pictured something far more stable: remaining single, living in a one-bedroom condo, and fending for myself.
My life now is different.
I’m married and live in a three-bedroom home in another city. One of the biggest changes, however, has nothing to do with geography. It has to do with money—specifically, how financial decisions change when there are two people instead of one. I learned that lesson early in our marriage.
We got married in August 2020. That December, I woke up one morning and saw blood in my urine. I went to an urologist who ran a series of tests, but it took about a month to determine the cause.
During that time, I decided to consolidate our remaining investment holdings to make things easier for Rachel to manage in case something happened to me.
Most of our money was already at Vanguard, except for a 401(k) from my former employer that was invested in a stable value fund. It still held a significant balance. Without much hesitation, I moved it into a bond fund at Vanguard.
Not too long afterward, the bond market nosedived. The fund performed poorly—especially compared to the stable value fund the money had been in.
The upshot: I panicked—and paid for it. It wasn’t a good time to make a financial decision while I was under stress. Some of the worst money moves happen when emotions are running high—selling stocks at the bottom of a bear market or rushing to act after an unexpected windfall. More often than not, it’s better to wait until you’re clearheaded before making a decision.
At the time, I was also fretting about whether Rachel would qualify for my Social Security benefit, which is much larger than hers. You have to be married for at least nine months. I found myself counting off the days.
Another financial decision became more complicated simply because we were now a couple: what to do with the three properties we owned—my condo, Rachel’s house, and the house I had inherited.
Neither of us wanted to be landlords at this stage of our lives. We were excited about getting married and starting a new life together.
I decided to sell my condo during the pandemic, which wasn’t easy. Rather than wait, I accepted an offer of $380,000—$43,000 below the asking price.
Rachel decided to wait and rent out her house for two years. She didn’t get caught up in the excitement or rush into selling. As it turned out, that patience paid off.
When the for-sale sign finally went up, I would stop by the house to water the yard and rake the falling leaves. One day, a real estate agent and his client were there looking at the property. They kept asking me whether the price listed on the brochure was correct. Rachel’s agent had intentionally priced the house at the lower end of the range in hopes of creating a bidding war.
I told them they would have to talk to my wife and her agent because it wasn’t my house. The agent asked how long we had been married. When I told him two years, he nodded and said, “I get it. She wanted to wait until she was sure about the marriage before selling the house.”
Rachel laughed when I told her what he said. She wasn’t waiting to see if the marriage would work. She waited because selling a house is a major financial decision, and she didn’t see any reason to rush it.
Two years later, the timing turned out to be just right. The market had improved and the strategy worked exactly as planned. There were multiple offers, and the final sale price was well above what it would have been earlier.
At the time my wife sold her house, Zillow’s estimated price of my condo was $484,000—$104,000 more than I received. I don’t really know why I was in such a rush to sell. Maybe it had something to do with the pandemic, my mother’s recent death, my sister and brother-in-law moving out of state, or the stress of renovating our new house. It was an emotional time for me, and I was probably searching for some stability in my life.
What I’ve learned—both from Jonathan and from being married—is that good financial decisions usually come from patience, not urgency. When I feel anxious or pressured to act, I’m more likely to make a mistake. When I slow down, think things through, and listen—especially to my wife—the outcome is usually better.
Managing money well isn’t about always making the right move. It’s about avoiding the wrong ones—and knowing when to wait.
Dennis Friedman retired from Boeing Satellite Systems after a 30-year career in manufacturing. Born in Ohio, Dennis is a California transplant with a bachelor’s degree in history and an MBA. A self-described “humble investor,” he likes reading historical novels and about personal finance. Follow Dennis on X @DMFrie and check out his earlier articles.
I too enjoy your articles and this was another gem.
It’s always good to read a reminder of Jonathan’s guidance or encouragement.
I’ve been thinking about another HD contributor that I/we haven’t heard from in a while and was wondering if anybody knows what happened to David Garland – another contributor with a personal and an enjoyable style of writing. This may not be the best time to ask, but am curious.
Great to read another of your excellent articles Dennis. My only complaint is too few!
As to, “The fund performed poorly—especially compared to the stable value fund the money had been in.”
I put a significant amount of inherited cash into a Vanguard intermediate bond fund in 2020 as I knew the money was not going to be tapped for nearly a decade. At first I looked like a genius (earning 13K) until the bond market worst drop in US history. I sold at a capital loss of 21K two years ago and bought a short term bond fund as the remaining balance was about 5 years from funding a large percentage of our new deck project. I said to my wife that we will get it back 3K a year as a capital loss telling her two other things:1) don’t plan my demise for 7 years as otherwise she won’t get it back, and 2) there was no way I could predict the future.
As always, Dennis, your courage in sharing your deepest feelings and emotions is impressive. Many thanks.
Dennis – thanks for such a well-considered and appropriate post. I always look forward to and enjoy your writings.
I guess I started writing HD articles too late – I never received any HD swag! That sounds really cool.
Dennis, your “timing loss” isn’t as great as you believe. There are carrying costs to owning a home which would erode your loss, as well as unexpected capital repairs that pop up, which in some cases can be quite costly. Timing the sale of a home for maximum gain can’t be done- much like the buying and selling of stocks. Generally both assets rise over time, but knowing exact exit points for them is unknown.
Bill,
Fair points. Carrying costs and repairs matter, and timing is never precise. Thanks for your comments.
Dennis thank you for your many thoughtful articles over the years. Jonathan is smiling and so are we.
The last two times I moved, I felt some pressure to sell my home in what was a down market, and I occasionally looked at what those houses sold for when they were resold a few years later in up markets. The gap was pretty large. Did I give up too much? I console myself by thinking about the houses I bought with the proceeds of my sales. In both cases, I saw even greater increases in value with them, far outpacing what I supposedly had given up. You usually can’t have it both ways unless you can somehow find a way to sell in an up market and simultaneously buy in a down market.
Thanks for sharing this great article. There is no reason to beat yourself up for selling your condo when you did. If any of us knew how much housing prices were going to rise from 2020-2022 we would have bought as much property as we could. Together, the two of you did quite well.
I’m pleased to see that this appears to be an article instead of a forum post but curious about who made the decision to post it as one. I don’t recall seeing articles by anyone else besides Adam and Bogdan in a long time.
Thank you for your kind words. I sent the piece to Bogdan, and he decided to release it as an article in the newsletter.
I’m curious as to how that works. I’ve submitted a couple of things to Bogdan and never even received a reply. They must have been awful.
I noticed the same thing and am also curious. Anyway, it’s always great to read Dennis here.
Great article Dennis. I also think about Jonathan frequently. I have all the “HD” swag he sent to his regular contributors as well as a bunch of emails from him. His comments were always so kind and thoughtful and his ability to ‘gently’ edit my pieces was always appreciated.
Beautifully written, thank you Dennis.
Thanks for this, Dennis, seems to me exactly the kind of continuity Jonathan hoped for when he set forum posts as the website’s front page, so to speak.
Patience and avoiding panic (selling or buying) are virtues in financial life. And Jonathan repeatedly observed that in a diversified portfolio, it’s likely at least one thing is not performing well at any point in time. I was thinking of his gentle reminders today while looking at “year to date” earnings and longer term “unrealized gain/loss” in my accounts. When I got to the one that was down, I found myself tempted to sell it all and buy something else. (I admit I’ve done that in the past, locking in poor results. How could I even think of doing it again?!) The sale would have been an impatient act as this part of the overall portfolio is likely to improve, eventually. So instead I logged out, closed the computer, and took the dog for a walk.
Three properties, likelihood you’d miss the momentum/peak on at least one of them. Good thing it went better for the house.
Thank Dennis for all your articles.
Nice article Dennis. It brought a smile to my face. My wife is wearing the HD apron as she is baking a Guinness Chocolate Cake for company tomorrow. I often think of Jonathan and Elaine and wish the best for them.
I remember your article about selling your wife’s house ad the bidding war. We used that knowledge when looking for a home a few years ago, and avoided getting caught in a bidding war.
Rick,
It’s always good to hear from you. I’m glad the article brought a smile to your face—and the Guinness chocolate cake sounds wonderful.
Guinness, chocolate, cake? That’s like the holy trinity of my vices doing a three-way merger…and somehow I’ve never heard of this vision of loveliness. The audacity. The betrayal. I need to hunt down a recipe for this immediately—purely for research purposes, obviously.
Here you go – Guinness Chocolate Cake from County Wicklow.
Thank you. May your giving hand never fail.
Great article Dennis. Patience is a virtue and I usually step away from making significant financial decisions. It usually pays off! Jonathan is often in my thoughts as well. I was with my mother this past week and she is coping.
Nicholas,
Thank you for your kind words. Patience is indeed a virtue. I’m glad you were able to spend time with your mother and wish you both the best.
Simple, wise message. I think Jonathan would have concurred!
Nice article, Dennis. Thanks for sharing.
Dennis, I likewise often think about Jonathan. I greatly value the personal interactions I had with him in the course of contributing a few articles. Having him as an “editor” was a thrill as well as a great learning experience.
These days whenever I write some long winded letter, post, or email, he’s still right there to remind me to shorten, simplify, and get to the point!
Thanks for your article Dennis.
Like you, I currently own the ETF Vanguard Total World Stock Index Fund (symbol: VT) in my investment portfolio because of Jonathan’s recommendation after researching the investment and thinking about the logic of owning the entire world in a single fund as my core equity investment. I started my ownership of the Vanguard Total World Stock Index Fund (symbol: VTWAX) in the mutual fund class and in 2026 chose to convert to the exchange traded fund class. I found this conversion process at Vanguard to be simple and seamless.
Agree, the mutual fund to ETF conversion process Vanguard offers is easy to do. I recently decided to do a VSMAX to VB conversion (Vanguard Small Cap blend fund).
We have Vanguard Total World in our Roths, but in our traditional have Vanguard Total (US) Stock (VTI) and several bond funds as well as cash. Years ago I read a Christine Benz article in Morningstar’s that recommended this distribution in retirement accounts as the Roths may never be touched while the traditional is being used for living expenses. When I need to raise cash I take it from the “winners” thus also rebalancing at the same time. When your source of cash is either a target fund or a world fund you can’t separate the winners from the losers, but each as a percentage of the whole fund.
Thanks for sharing Dennis. If there is anything I’ve learned the hard way it’s that making real estate decisions without time on your side can lead to bad outcomes.
Indeed, just like you, it is hard to not think about Jonathan. His words, as well as yours, definately influenced what it means to save, spend, and retire.
This article is a gem, Dennis. Tidbits of wisdom, such as “cool your jets”, “chill out”, and “hold your horses” come to mind.
Denis – Thank you for sharing your experience and wisdom. You have a great writing style and hope you continue to find the time to contribute to Humble Dollar. Best Regards
Great article, Dennis. I never knew there was HD swag! Love it. Chris
Hey Dennis,
Jonathan would be proud of this contribution.
When Jonathan said your writing has a good ear — I suspect he meant your conversational manner delivered in humble tones.
Ideal for this space.
Mike
Mike,
Thank you for saying that. Jonathan’s encouragement mattered to me, and I’m glad the piece felt at home here.
Dennise, thanks for the great article. If I adjust an old saying to ‘Decide in haste, repent at leisure,’ it pretty much sums up your cautionary tale. Although, I have to say, that realtor at your wife’s home was definitely thinking about the original version! I always look forward to reading your thoughts and hope you have time to contribute more.