I often write about mistakes I’ve made. Why change now? Looking back over my 76 years and the many poor money decisions I’ve made, it’s a wonder I’m in better financial shape than the Social Security trust fund—and yet I am. Here are 10 of my more memorable decisions:
1. In 1961, when I started working at age 18, I got hooked on the stock market. With little money and earning a bit more than minimum wage, I focused on penny stocks, hoping for that big killing. I’m still hoping.
Read: What’s happened to value stocks?
2. College was never mentioned in my family. Around 1964 and still an office clerk, I realized I was going nowhere without a degree, so I enrolled in night courses. Before earning credits, I was required to take two years of courses I hadn’t had in high school. After one semester, I quit. I enrolled again in 1969, after a stint in the army. It took me nine years at night, while my wife and I raised four children—with her doing most of the work. Not the best way to get an important piece of paper. College was paid for by the Department of Veterans Affairs, employer benefits and me.
Read: This is how fast Americans are spending their stimulus checks — and what they’re buying
3. My wife and I married 10 months after our first date, much to the consternation of my parents. During eight of those months, I was away in the army. The following year—with me still in the army—was one of significant financial stress. I was based in Alabama and my wife was on her own in New Jersey. I was trying to send home a little money each month, which meant I barely had enough to telephone my new wife every few days.
4. We became pregnant a month after I got out of the army. My wife stopped working and didn’t return to part-time work until our youngest child was in high school. That meant even more financial stress.
5. Even before we were married, my financial planning faltered. In June 1968, I was home on leave. Anticipating the need to buy an engagement ring, I sold some stock at a loss of $7.50 a share. But the jeweler told me not to pay until September, when I was next on leave. By then, I could have paid for the ring with the profits from the stock I no longer owned.
Read: These 16 money wasters are why so many Americans can’t save for retirement
6. In part because of my own college experience, I told my children they could go to any college where they were accepted. Did I mention the four are five years apart? The net result was one, two or three kids in private college for the next 10 years. In 1988, my oldest entered a five-year program at Carnegie Mellon with an annual cost of $40,000, figured in 2020 dollars.
7. My strategy for paying college costs was blind faith. First, I borrowed from my 401(k) and quickly decided that was a bad idea. Next up: depleting some modest mutual fund assets. Then I began writing monthly checks on a variable interest rate home-equity loan. The first time the interest rate increased, I panicked, rushing to remortgage the house at a fixed rate of 9.75%. To help pay for all this, I started a very small side business updating people on employee benefits—something akin to the blog I write today.
Read: How to start a blog in retirement
8. Fulfilling a dream added to my financially hazardous moves: In April 1987, the year before college expenses started, I bought a vacation home on Cape Cod. Yup, that’s what I would call an irresponsible move. But, between renting it most of the summer and the tax advantages of doing so, it worked out.
9. I’ve written about my latest near fiasco: Simply put, to buy our new condo, I took out a large short-term mortgage at 5.37% that turned out to be not so short.
Read: 5 cheap and easy places to retire that you’ve probably never thought about
10. This one hasn’t materialized yet, but I’m thinking it may have something to do with being confined at home and my growing skill at online shopping. The upshot: There’s a new grill is on its way, along with an array of steaks from Omaha.
Amazingly, over many decades, it’s all worked out. What could have been several disasters weren’t. Unfortunately, many people aren’t so lucky with such risky financial moves, so I don’t recommend the Quinn strategy.
My comfortable retirement is not the result of FIRE-level savings and certainly not the result of exceptionally skilled investing. Rather, I attribute it to working for the same company for nearly 50 years, vesting in a defined benefit pension and accumulating a 401(k)—a trifecta that’s a near impossibility in the 21st century.
Oh yes, that plus being frugal or, as my spouse would say, cheap.
This column was originally posted on Humble Dollar. It was republished here with permission.