My Biggest Money Blunders and How You Can Avoid Them

Note: I am not a financial advisor. I have not a single financial credential to my name. I am neither a CFP nor a CPA. My degrees are in English literature and Jewish Studies. I know nothing about your financial situation and even if I did, I am in no position to tell you what you should do with your money or your life. The following is for entertainment purposes only. You and only you should do you (perhaps with the help of a financial advisor whom you do NOT pay a percentage of your assets under management.

Like many I grew up knowing little to nothing about how to manage money or invest. My parents showed me the very basics. I had a savings account as a teenager (the balance was recorded in a little book that was updated when you when to the bank). I was taught that credit card debt was a most grievous sin and that you should spend less than you earn and that was about it. My parents had money trauma from the Great Depression burned into their DNA from their parents who had lived through it. The only thing they “invested” in were FDIC insured bank accounts and Certificates of Deposit. I learned through trial and often, as you will see, through error.

I got a checking account when I went to college and taught myself how to reconcile it from the directions on the back of the statement. I never gave investing a moment’s thought until at the age of 26 I had the opportunity to begin making contributions to my organization’s 403(b) retirement account. A rep from the firm came in and gave me and my co-workers a presentation on the various investment options offered and noted that she had all her money in the “High Growth Fund.” High growth sounded good to me, so that is what I did with the $20 per paycheck that came out of my salary. Later the organization also made a contribution on my behalf.

Thus began my little hobby of trying to grow a nest egg for a retirement date that seemed very, very far away. Early on I read a few books, like a Wall Street Journal primer on personal finance and The Only Investment Guide You’ll Ever Need, by Andrew Tobias and I tried a bunch of stuff some of which worked and much which didn’t. Here is a list of four worst money decisions I made and one more that while bad on paper, I am still glad I did. So (as they say on the YouTube vids) let’s get into it!

1. Buying Individual Stocks

Early on in my investment journey I thought myself a genius who could pick winning stocks. I tried many methodologies: value investing (buying companies the stock price of which is low compared to its earnings), growth investing (buying companies that seem to be growing rapidly), and the “walk around the mall and see where the teens are shopping” strategy. These were all abject failures. Most of these stocks I later sold at break even or a loss. Here are some of the stocks I owed at one point or another: Alcoa Aluminum, IBM, American Airlines, Lands’ End (before it was bought by Sears) and lots of others. Fortunately, I was protected from my abysmal instincts by the fact that I couldn’t invest in individual stocks in my 403(b) plans. I was restricted to my modest brokerage account and my Roth IRA.

Eventually, I learned that I had no talent for picking individual stocks and that I would never have access to the kind of information that large money managers have which give them a leg up. I realized that I would be better off just investing in mutual funds and leave the investing to those smarter than I. When I came to that conclusion, I sold all my individual stocks. Except one. I kept the one not because I expected it to do anything. The company was in shambles and looked like it might go out of business. The founder had been brought back in a last-ditch effort to save the company, but no one gave him great odds. I kept the stock because owning it was part of my identity. Perhaps the worst reason for owning a stock there is.

2. Using Actively Managed Mutual Funds

As I said, I finally realized that I should leave the investing decisions to those smarter than me and I began investing in mutual funds. Mutual funds are big pools of money and investors that buy lots of different things. Each fund manager has an idea or a philosophy that guides their decisions and if he or she is right, the individual investors make money. These are called actively managed funds. Well, it turns out I was wrong. Not about my conclusion that I was a horrible stock picker; I was quite right about that. I was wrong in thinking there were those who were better than I. It turns out over the long term (ten years or more) virtually no actively managed funds beat the market.

John Bogle looks at this in depth in his Little Book of Common Sense Investing. This book is one of the best books on investing and perhaps the only book on investing you ever need (sorry Mr. Tobias) but if you don’t have the time or patience to read even one, here is the take away: No actively managed fund will do better than the market as a whole in the long run so just buy the market as a whole. Enter passive funds. Passive funds surrender the decision making to an algorithm that simply replicates an existing index like the S&P 500. In other words, if you invest in an S&P 500 Index fund, you returns will replicate the performance of the S&P 500 year in and year out. Does that mean you will make money every year? No. It does mean you will match the performance of the market over time and in most lifetimes of investing that ‘average’ return will be sufficient to meet your goals assuming that you are saving and investing enough. And you will beat almost every kind of investment there is from bonds, to gold, to real estate. Eventually, I figured out average was good enough for me and I got out of active funds and into low-cost passive or index funds where I have been ever since. Low cost means that the company who manages the fund takes a very tiny amount for their work of managing the fund. For example, some of my funds charge just .06%. Compare this to many actively managed funds that can charge 1% or more. 1% doesn’t sound like a lot but over time paying 1% in fees versus going in your pocket can be tens or hundreds of thousands of dollars when you take compounding into account.

3. Thinking It is Always Better to Buy Than to Rent

In 1988, believing that we were “throwing money down the drain by renting” my wife and I bought a one-bedroom condo (really a coop). We bought it knowing that we were planning to have children soon. The price was too good to be true (We later learned why. Coops were very hard to finance and therefore to sell) and we grabbed it thinking we’d sell it for a tidy profit in a year or two and move up to a house. Two years later with one child and another on the way and a coop we couldn’t sell, we bought a house and rented out the coop. Being a landlord was a huge pain and went on for years until we finally sold the thing at a loss to a nonprofit housing corporation. Renting can often make more sense than buying unless you are pretty sure you are going to stay put for seven to ten years. We’ve been in our current house 25 years and even now after considering the interest we paid on the mortgage, the cost of maintenance, and the opportunity cost (of investing) I am not sure it was a good decision from a purely financial perspective.

4. Jumping In and Out of Bond Funds and Chasing Yield

For most of my working life, I invested only in equity funds, that is active or index funds which bought stocks rather than fixed income investments like bonds. But as I got into my 50s it seemed prudent to add some bonds into the mix. At the beginning I bought an index bond fund without really understanding how they work. What didn’t realize was that as interest rates rise the value of bond funds fall and vice versa. As interest rates rose in the mid-2010s, I saw the price of my bond fund fall and was rattled I was buying bonds to avoid volatility! What I didn’t understand was that though the price of the fund was falling it was because it was paying larger and larger dividends.

So, I sold the bond fund and built a CD ladder instead. Of course, as soon as I did that interest rates reversed and each time a CD rolled over it was generating less interest than before. Finally, during Covid when rates sank to near zero, I was getting close to nothing and looking longingly at the bond fund which had soared and was still paying more than 3% annually. Finally, I understood the pros and cons of bonds fund. As my CDs matured I bought back into the index bond fund and am staying put! It was an expensive lesson. As long as you are buying and holding, an indexed bond fund will match the return of its index and do as well as individual bonds over time with a lot less effort. If you don’t need to sell it anytime soon, the short-term price fluctuations shouldn’t worry you.

5. Paying Off My Mortgage Faster Than I Had To

My last mistake wasn’t exactly a mistake. That is I knew while I was doing it that it didn’t make financial sense and I did it anyway. The spreadsheet said no. My brain said no. But my instincts told me to do it anyway. I paid off our home faster than I had to.

We bought our current home in 1999. At the time, I had quit my well-paid full-time job to go to graduate school. I was working about 3/5 time making a fraction of what I had been making at the trade association. My wife was also working part-time as she had been since the kids were born. We could barely afford to make the payments on the house. But a year later I returned to full-time employment and as interest rates continued to fall, we refinanced our mortgage not once but twice. After the second time our interest rate was around 4.5 percent. It was a decent rate and after deducting the interest from my taxes, the effective rate was probably in the threes or even twos. My investments were generally returning way more than that so what I did made no sense. I paid off my 30-year mortgage in less than 15 years.

We made the last payment on our Mortgage sometime in 2013 and it was accompanied by an incredible sense of freedom. The next year, I quit my job (again!) and took another paying a fraction of what I had been making. This time there was no financial stress. On paper it had made more sense to keep paying the scheduled payment and invest the difference, but the sense of freedom after making the last payment was worth whatever it cost me. I am in no way saying this is the right move for everyone, but I have no regrets. We’d still be paying that original 30 year note today if we hadn’t accelerated the payments. Instead we’ve been mortgage free for 12 years.

In spite of these missteps, we came out alright. I retired (mostly) at 58 and my wife two years later. I guess we did more things right than wrong. Here are a few mistakes we didn’t make.

• We never borrowed except for a house and our first few cars (those were low interest factory incentive loans we paid off quickly). We never had any credit card or any other consumer debt.

• We never paid someone a percent of our assets to manage our money.

• We always lived well below our means saving at least 20 percent of our income (in later years up to 50 percent) and maxing out our retirement accounts every year that we could.

• We avoided “lifestyle creep” and live today pretty much the way we did when we were young and broke and yet I can’t think of anything that I want that I can’t afford. (Lack of imagination?). Small luxuries are everything. For many years, travel meant sleeping in a tent. Today we sleep in our minivan!

Still, lots of people do “all the right things” and still find themselves scraping by. Credit must be given to a large amount of luck as well. For example, that one stock I held on to when I sold everything else and moved into index funds, as you’ve probably already guessed, was Apple. I bought a handful of shares shortly after Steve Jobs returned to the company as it teetered on the brink of disaster. I reinvested the dividends and even added to my position a few times. That little gambit resulted in the highest return of anything I invested in over the last 38 years -- far out pacing the S&P 500.

Stupid. Irrational. Dumb. Luck.

The world’s a narrow bridge; fear nothing.

The Bread that Launched a Revolution and Turned Me into an English Major (Updated for the 21st Century Baker)

“A recipe doesn’t belong to anyone. Given to me, I give it to you. Only a guide, only a skeletal framework. You must fill in the flesh according to your nature and desire. Your life, your love will bring these words into full creation. This cannot be taught. You already know. So please cook, love, feel, create.”

— Edward Espe Brown, The Tassajara Bread Book

In 1980 I was in my second semester of freshman English. My professor, Richard Morton, was having us read Walden by Henry David Thoreau. I had been struggling to write papers that ever got more than a C+ from Dr. Morton who was a notoriously tough grader. That’s when an idea hit me. I would bake a loaf of bread and write about it in the style of the first chapter of Walden. In this chapter, “Economy,” Thoreau goes into meticulous detail about how he built his famous cabin in the woods by the banks of Walden Pond near Concord, Mass. He even includes a list of materials that lists the price that he paid for nails.

I would do the same only for a loaf of bread instead of a cabin. Of course, I had never baked a loaf of bread before. But no matter, I could follow a recipe – if I could get one.

The Guilford College library did not have a bread cookbook and there were not many bread cookbooks on the market in 1980. Beard On Bread comes to mind. But the book that began the home bread baking revolution had been published ten years earlier and was still the go to for home bakers looking to get into bread: The Tassajara Bread Book by Edward Espe Brown, a Buddhist monk and communal baker at the Tassajara Zen Center in California, which gave the book and the bread its name. I found a new copy at the bookstore across the street from campus ($4.95) and with a $10 withdrawal from the Wachovia Bank ATM, I bought everything I needed to make the bread including all the ingredients and two loaf pans with money left over. (I documented the costs in my paper in homage to Thoreau.)

My all-male dorm didn’t have a proper kitchen, only the women’s dorms had those. So, I camped out in my friend Lindsey’s room making the bread in her dorm kitchen late into the evening and hiding out in her room during risings. Males weren’t allowed to be in female dorms after midnight so the whole operation had to be super stealthy. As luck would have it, Lindsey’s roommate had returned to campus that January only to immediately withdraw from the college. Lindsey had the room to herself, which meant there was no one to disturb as the baking project carried on to nearly 2 am. Lindsey was fast asleep when I packed up my pans and crossed back to my side of campus.

The bread was a success by which I mean it was edible. I made two loafs and gave one to Dr. Morton along with the paper (Lindsey and I split the other loaf.) I got a B+ on the paper, the best grade I had gotten from him to date though I was never sure if it was the writing or the bread that had earned the grade.

During the subsequent summers, I made Tassajara bread again and again. For many years, it was the only bread I made. The recipe calls for 100 percent whole wheat and it is sweetened with honey and enriched with butter or oil. It makes a pretty dense loaf but it is quite tasty especially fresh from the oven.

After graduation, I lived in Albany, N.Y. for about a year and during that time I worked in a retail shop six days a week. I had only Sunday’s off from work and I invariably made Tassajara bread on that day. I’d make two loafs every week, cut each in half, freeze the halves and defrost as needed. I lived mostly on sandwiches during this time and two loaves got me through the week. I never bought any commercial bread at all.

Later I moved on to fancier breads, bagels, challah, and the occasional sourdough but that copy of The Tassajara Bread Book with its stained, yellowed, and ragged pages has moved with me a dozen times. Last week, I got into my head to make a loaf for auld lang syne and I drew the tattered brown and orange volume from the shelf.

One hurdle was that I now bake by weight and the recipe is for volume measurements. I decided that as I baked the bread, I would convert the recipe to weight and then rewrite the recipe for you! So here it is. It tastes just as I remember it. Feel free to add a cup of raisins if you like (I used to always do that) and eat it with the best butter you can find. Kerrygold Grassfed Irish Butter is an excellent choice.

Tassajara Yeasted Bread by Ed Brown Updated for the Modern Baker (I’ve tested this; it works.). If you prefer the old school volume recipe — well the book is still for sale! It costs $18.61 now.

Makes Two Loaves

You’ll need:

850 grams of Whole Wheat Flour (any kind but I like King Arthur)

680 grams of warm water (it should feel warm but not hot on your wrist. 98F/37C. If the water is too hot, it will kill the yeast, and you’ll end up with matzah). (note: the method I used for calculating the amount of flour was by taking the water volume in the original recipe (3 cups) and converting it to grams. Then I reverse calculated the amount of flour to arrive at an 80 percent hydration which seemed right for an all whole wheat dough. Actually the original recipe calls for 6 cups of water, but I cut the recipe in half years ago because four loaves of bread is a lot to bake at one time unless you’re feeding a monastery!)

17 grams of salt

8 grams of instant yeast (packet or jar)

75 grams of honey

50 grams of a neural vegetable oil

A cup of raisins (or as many as you want)

2 aluminum loaf pans

A kitchen scale that measures in grams

Place the water in a large bowl or the bowl of a stand mixer and add the yeast.

add enough flour to make a thick batter the consistency of pancake batter.

Mix with a large spoon 100 strokes OR mix with your stand mixer until smooth.

Let rest for 15-30 minutes.

Add the honey, the oil, the rest of the flour and the salt, and the raisins if using. Mix with the mixer or by hand until you have a shaggy mass. Let rest for five minutes.

Now knead by hand or with your mixer for about five min. Rest for 10 minutes and knead again for five minutes. Repeat the knead and rest once more. The exact times aren’t that important.

The dough should be smooth and elastic. Sparingly add a little more flour if you need to prevent the dough from sticking to you fingers and the counter or kneading board. Form into a ball and place into a large bowl or (better) a Cambro until the dough is doubled in size. Gently push the air out of the dough and let it double again. This is often call “punching down the dough” but no need to get aggressive. No one likes someone who punches down.

Generously oil two bread loaf pans. Split the dough into two equal pieces (use the scale or just eyeball it.) Roll each dough into a tight smooth loaf the size of your loaf pans and place them into the pans pressing the dough into the corners.

Cover the loaves with a damp towel and allow them to rise for the final proofing. You want to see the dough cresting the tops of the pans. This will take 30 minutes to an hour depending on how warm the dough and your kitchen is. When you think the dough has maybe 20 minutes to go, pre-heat your oven to 375 degrees F/190 C.

Optional: brush the tops of the loaves with a beaten egg and add seeds if you like. Poppy, sesame, or caraway. Slash each loaf with a couple of diagonal slashes using a lame or a serrated knife. This allows the loafs to “bloom” and expand in the oven during the first 15 minutes of cooking before the crust sets.

Place the loaves on the middle rack and immediate lower the temperature to 350F/175C.

Bake for 35-40 minutes until the loaves give a hollow sound when thumped or (more accurate) when an instant read thermometer registers 190-200F/90-95C.

Let them cool for 10 minutes then remove from the pans. Use a knife to loosen around the edges of the loaves if needed. Let cool completely before slicing. If you plan to slice and freeze. Let them sit overnight and slice the next day. They will be much easier to slice. Otherwise slather with butter, jam, honey, cream cheese, or Nutella and enjoy. I used to make a peanut butter and banana sandwich for breakfast and eat it strolling up Central Avenue on my way to work in the store.

Best bread ever? I give it a solid B+.

Oh and that roommate of Lindsey’s, who had so disliked Guilford that she had only stayed one semester, baked Tassajara bread with me the following summer and married me seven years later. She’s a hell of a good baker herself.

Did you have a copy of The Tassajara Bread Book? Share your memories below.

The world’s a narrow bridge; fear nothing.

No Bad Lands or Dogs

Returning home from our road trip to Alaska in 2022, it occurred to me that there were just two of the United States that I had not visited. I had never so much as set foot in either North Dakota or South Dakota. It may not be surprising that I had missed these. They are far from population centers and don’t host as many national conferences and meetings as Florida, California, or Illinois. Barbara had visited South Dakota but not North so when we found ourselves with a window of opportunity between the High Holidays and the onset of serious winter, we decided a quick road trip of 5,000 kilometers was in order.

With our window limited to just three weeks and much distance to cover, we made a beeline for Fargo without much faffing about. Just four days after pulling out of our driveway, we arrived in Fargo ND having camped our way through the intermediary states. Neither Fargo nor Bismark a few hours further down the road had a lot to capture our attention but another day found us in Theodore Roosevelt National Park.

I can’t say enough about the quiet beauty of this park which receives a fraction of the visitors of Yosemite or the Grand Canyon. And in late October, the number of guests drops to a trickle. With water and other services already shut off for the winter, we had our pick of campsites inside the park. Just $5 per night with a Golden Age Park Pass. ($10 for youngsters).

Theodore Roosevelt National Park, N.D. Vastness and solitude.

The park has a northern and a southern unit. The northern is even less visited then the southern. There were greeted with dark skies filled with stars, a waxing moon, and even a comet! The temperatures in the Northern Unit dipped to near freezing at night but we were cozy and warm in VanGo! under a thick down comforter. A warm hat and wool socks helped keep the extremities warm as well.

Comet Tsuchinshan–ATLAS as captured by iPhone from Theodore Roosevelt National Park

One of the main attractions of these parks are the large number of bison that roam ad libitum throughout the park. These massive creatures are mostly quiet and chill but visitors are warned to stay at least several bus lengths away from them. They can get ornery if they feel you are in their personal space. On a day hike we encountered one just a few feet from the trail and had to stray deep into the brush to give him a wide swath. He took little interest in us.

The parks other attraction is its stunning geology including giant egg-shaped formations called concretions. These formed underground and were exposed when the sedimentary rock around them eroded. Even geologists are not sure exactly how they formed.

Where Mother Earth lays an egg. 

Feeling there was still more to see, the pressure of time pushed us south into the other Dakota. This was my last state. I celebrated with a photo at the Geological Center of the United States and used the rest room at the visitor’s center there.

In South Dakota we visited Custer State Park, Badlands National Park, the Black Hills, Mount Rushmore, and the Crazy Horse Memorial, which was begun in 1948 and is still being sculpted out of a mountain face today with at least another 50 years of work left to go. When complete, it will be many times the size of Mount Rushmore. Fun fact: Crazy Horse’s visage is the work of the imagination of the sculptor. No known photograph of Crazy Horse exists.

I got mine back but quickly misplaced it again. 

Our son and his space dog Laika met us for the weekend in Custer and we splurged on an AirBnB for the four of us. Asher wanted to see Mount Rushmore, where we had gone a few days earlier. Unfortunately (for Laika) dogs are not permitted on the viewing plaza. I waited with her outside, while Barbara and our son visited the monument. People love a dog! I was approached dozens of times by men, women, and children who wanted to say hello to Laika! People also wanted to know what kind of dog she was. I replied that she was of the breed canus nonspecificus, which seemed to satisfy the curiosity. Laika enjoyed the attention, which perhaps compensated for her missing the stone visages of Washington, Jefferson, Lincoln, and the pince nez’d Theodore. She didn’t say one way or another.

Boy love him some dog. 

All too soon, it was time for Laika and her boy to head back west and for us to begin the long journey home. As we headed back east, we stopped in Chamberlain, S.D. home to the Dignity of Earth and Sky sculpture and the South Dakota Hall of Fame. There I was surprised to see L. Frank Baum claimed by South Dakota as their own. I knew that he had lived in New York State and in California but hadn’t realized he had lived in S.D. as well. The Hall of Fame honored him for his role in the women’s suffrage movement of which I had also been largely unaware. I should have known: His Dorothy and Ozma didn’t tolerate any mansplaining from the know-it-all and decidedly male Wogglebug. (Incidentally, Ozma may have been the first trans kid in children’s lit transitioning from male to female in The Land of Oz (1904), the sequel to The Wizard of Oz.)

Not So Bad Lands for Big Horned Sheep

Finally, we stopped in Mitchell, S.D. to visit the “World Famous” Corn Palace. The interior of the building is not very remarkable. Most of it is taken up with a basketball arena. But the exterior is a façade of images made of corn cobs and is changed every year.

The Castle Corn Made

Leaving there, we plowed into Iowa and sped toward home and obligations.

Friends upon hearing my new boast about having been to all 50 of these United States often ask if I have a favorite. I don’t. There is not a place in this country, indeed on this planet that doesn’t host its own special and unique sources of beauty and wonder. We found Dakotans to be warm and friendly, the culture interesting and engaging, and the natural beauty of those states breathtaking in its vastness and solitude. Like many spots I have visited, I left there with a sense that there was much still to explore yet all too aware of the strong likelihood I will never return.

The world’s a narrow bridge; fear nothing.