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I DON’T FIT THE USUAL profile of a HumbleDollar reader. I don’t have what I’d consider a high net worth, nor am I a college graduate. Still, I hope my story shows it’s possible to reinvent yourself.
Around 1920, my dad’s family moved—with few belongings but a willingness to work—from Tennessee to northwestern Ohio. My dad met my mom while working at Hostess Bakery, and he later worked at Willys-Overland, welding together Jeeps during World War II. I was born a decade later, in 1952.
I remember my dad coming home from work on Friday, after stopping at the bank to cash his paycheck. He and Mom would get out the Dome Budget book to prioritize which biller got what. Still, the first allocation was always a deposit to their savings account.
My generation was the first to grow up with TV. During Saturday morning cartoons, we kids were inundated with toy commercials. I remember telling my dad that I wished I could have this or that toy of the week. My dad’s colorful answer is something I carry with me to this day: “Well, Dan, shit in one hand and wish in the other, then tell me which one fills up first.”
My first job, at age 16, was as a bag boy at a local supermarket. Eventually, I worked in the beverage department, and I used my connections there to get a job, first with a soft drink distributor and later with a beer distributor. I’d also been going to college to pursue a business degree. But I never cared much for school, and I was earning more than my college-graduate friends. I let those two facts justify one of my life’s worst decisions: dropping out of college.
For 30 years, I worked hard on the beer truck and earned a good middle-class income. Of course, the income of my college-graduate friends eventually eclipsed my wages as a driver-salesman. So much for my justification for quitting school.
I always had this thing about numbers—and about money and saving. In 1984, Money magazine published an issue with a fill-in-the-blanks exercise to help readers determine if they were on track to retire when they wanted and with enough money. I did the exercise and became hooked on retirement planning.
Three decades into my career, two things happened that changed my life: one involving my marriage and the other my job.
My wife and I got divorced after 25 years of marriage and after raising two amazing daughters. We split our assets equally and went our separate ways. I was ordered to pay spousal support, which continues to this day.
Meanwhile, the pain of job-related arthritis became more frequent, and plantar fasciitis had set in as well. I felt like I was on the verge of total disability, so I left the beer business behind.
One son-in-law, who happens to be a financial planner, was impressed with my knowledge of his world. He encouraged me to become a registered representative. I studied for and passed the various exams for the life insurance, health insurance and Series 6 licenses.
This did not work out well for me. The main goal of the company I joined was to sell insurance products, such as variable annuities and variable universal life insurance contracts. Don’t get me wrong: I like annuities and life insurance. But when you add that word “variable,” you lose me. Those variable insurance products have killer high fees and, in my opinion, aren’t suitable for most people. I just couldn’t sell them, so I left.
Life took two more turns. In my time as a beer-truck driver, I’d picked up rather unlikely skills. I became active in the union, and I was doing all its financial reporting to the Department of Labor and the IRS, and also handling payroll.
After leaving the insurance company, I began preparing income-tax returns to make ends meet. It turned out that I was good at it, and friends I’d made while selling insurance began sending me clients—lots of clients. I was a one-man shop with low overhead. I had about 650 clients when I sold the practice in 2022─the year I turned 70─to a buyer who was both a tax attorney and a CPA.
Meanwhile, after my divorce, I was middle-aged and unsure about my future marital status. I became analytical about the type of person I’d want as a romantic partner. She would be an intelligent and independent woman who didn’t need a man to survive, and someone who shared my philosophy regarding saving and spending.
I figured I’d remain single for a long time. I was wrong again.
A few years into single life, I bought a house and became fast friends with a neighbor, Chris. She worked for an accounting firm, so we had a financial background in common. Turns out that we checked each other’s boxes. That was 21 years ago, and our relationship remains awesome.
With the combining of our lives came economies of scale. Still, we didn’t change our lifestyle. Instead, Chris began contributing 20% of her income to her 401(k) and maxing out an IRA. I was maxing out my SEP-IRA, IRA and health savings account. Both Chris and I were piling up regular taxable account savings as well. We’ve achieved our goal of a seven-figure net worth, and that doesn’t include home equity.
Chris retired at 64 and began her Social Security benefit. I started Social Security when I sold my business last year. Because I waited until 70, my benefit is some $50,000 a year. Chris’s amount is about $25,000 a year. With our home and cars paid off, and no consumer debt, we live well on our Social Security benefits alone.
What to do with our savings? I admit I struggle with how much I can safely give away. I’m making progress by donating automatically and monthly. I have a handful of charities I support, such as St. Jude Children’s Research Hospital, the USO—short for United Service Organizations—and public media.
Now that I no longer have earned income and am older than 65, I could file a motion to have the spousal support I still pay reduced to zero. But if I did, my daughters and their husbands would have to help their mother financially. That’s not a burden that I want them to shoulder. Instead, I’ll pay spousal support for as long as possible. At least I get to deduct the alimony on Form 1040. It’s also my goal to leave a sufficient sum to the kids so they can continue to take care of their mom.
As I enter the foothills of old age, I just want my kids and seven grandkids to know how much they’re loved and to be happy. I hope that they’re able to learn from my experiences—both the hits and the misses.
For 30 years, Dan Smith was a driver-salesman and local union representative, before building a successful income-tax practice in Toledo, Ohio. He retired in 2022. Dan has two beautiful daughters, two loving sons-in-law and seven grandchildren. He and Chris, the love of his life, have been together for two great decades and counting.
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As someone that married, divorced and remarried the same woman, the thing that hits me the most is you continuing to pay your spousal support. The generosity in saving your kids from doing it is inspiring. I do a lot of things more for my wife and kids including paying off the house so that should something happen to me, my wife always has a place to live. Thank you for sharing.
I thoroughly enjoyed reading your most fascinating life story! Thank you for writing it. You should be proud of the multi-faceted career that you built rather than spend any time regretting dropping out of college, IMO.
You have quite a story to tell from beer truck driver, registered insurance rep, union leader, financial & payroll reporting, to building an income tax prep business with 650 clients. As a retired CPA, I am very impressed with the one-man income tax prep shop that you built out of thin air.
I couldn’t find the exact quote or adage to cite, but what impresses me most is not where a person starts out in life or even their final destination, but how far a person travels during their journey. By any related measure, I would say that you were the epitome of a successful life.
enjoyed reading a summary of your life. Wishing you the best
I enjoyed your article Dan. Thanks.
I have known a few people whose first marriage ended as the result of either divorce or death of the first spouse and who were then fortunate to find love in a second chance relationship. Financially your higher wait till 70 social security benefit will disappear for Chris if you predecease her if you are not married. I know that financial fact is only one of the many factors that go into deciding to chose to remarry but if she does outlive you a decision to tie the knot would be a $25K a year lifetime gift.
We actually married 7 years ago for that very reason. That logic also enabled her to retire and take her benefit a few years earlier.
Nice story Dan! Sounds like your Dad was a character.
Dan, welcome to HD and thanks for a great article. Your story is inspiring and fascinating.
I’d be interested in how you set up your tax preparation business. Did you become an enrolled agent with the IRS, and did you need any other certifications or insurances?
Unfortunately the tax prep business is like the wild west in that almost anyone can hang up a shingle. That explains why there is so much fraud potential. I am not an EA, though that would have been my plan had I been younger. I did pass the exam for the discontinued Registered Tax Return Preparer program, which was the IRS’s attempt at regulating the business. I participated in the IRS Annual Tax Return Program which required 15 CE hours each year. I carried errors and omission insurance as well as a standard business owners policy and cyber insurance.
I think you are a lot like the folks in the HumbleDollar community and are a great example.
You worked hard, set goals, stuck to your goals, were prudent and fair with your money, accumulated a nest egg. You educated yourself about money.
If more Americans followed your example, there would be far fewer retirees complaining about a 3% SS COLA.
Now you have the retirement you earned.
Word of caution, don’t be too free with that nest egg, some day SS alone probably won’t be enough.
So true Mr. Quinn. I’d love to help the kids with college tuition but can’t imagine a quicker way to drain our piggy bank.
Excellent article, Dan. In ways our lives took a similar path, but I have you by one year in age! I flunked out my first time in college because I cut too many classes and didn’t study; I was not ready out of high school! I eventually went back to college, got my accounting degree and became a CPA. It provided a good living, and we always saved and avoided debt, paying off mortgages and car loans as quickly as possible. We collected my wife’s SS when she reached FRA, then took mine when I reached 70. Several sayings come to mind, “it’s not what you make, it’s what you keep,” and “those who understand interest collect it, and those who don’t, pay it.” Thanks!
Ha, that’s another of my dad’s favorite comments; “don’t tell me how much you make, tell me how much you saved”.
This is Chris Great article, Dan. Thanks for joining HD to write. I found your story inspiring.