Diligent savers are admirable. Even more admirable: Retirees who transform themselves from great savers to happy spenders.
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. Check out Dan's earlier articles.
Adam M. Grossman is the founder of Mayport, a fixed-fee wealth management firm. Sign up for Adam's Daily Ideas email, follow him on X @AdamMGrossman and check out his earlier articles.NO. 26: WE SHOULD strive to spend our days as we wish—by using our dollars to escape today’s chores that we dislike, while also saving for the ultimate prize: full financial freedom.
NO. 104: SHIFTS IN investor sentiment—as reflected in the stock market’s rising and falling price-earnings ratio—become less important as our time horizon lengthens. Instead, for investors who hold diversified stock portfolios for decades, what matters is the stock market's starting dividend yield and subsequent growth in earnings per share.
HUMAN CAPITAL. If we’re early in our career, our most valuable asset is usually our human capital—our ability to pull in a paycheck. That paycheck allows us to service debt, provides the savings needed for retirement and frees us up to invest in stocks. But as retirement approaches, we should aim to pay off all debt and shift maybe half our portfolio into bonds.
NO. 32: WE REVISE our memories to make ourselves look better. Suppose we believe we’re smart at managing money, but then we panic during a market decline. The result can be the uneasy feeling known as “cognitive dissonance.” To escape our discomfort, we might revise our memory—and decide we stood our ground and perhaps even bought more.
NO. 26: WE SHOULD strive to spend our days as we wish—by using our dollars to escape today’s chores that we dislike, while also saving for the ultimate prize: full financial freedom.
Perhaps what we should be debating is which is the most important line on the tax return. I can tell you that most would say line 34, “this is the amount you overpaid, or line 37, “this is the amount you owe. I contend line 24 matters most, “this is your total tax”. Rarely, and I mean well under 1% of the time, did a client ask me how much tax they paid. As a matter of fact,
I still help prepare tax returns for pay. As such I am required, among other things, to annually renew my preparer pin number.
I recently received the following from the IRS in a email –
We have updated the Tax Professional PTIN System sign-in process for tax return preparers who have a Social Security number (SSN). You will now sign in using ID.me, a technology provider that conducts identity verification and credential management for access to IRS online services.
The new U.S. tax legislation extends today’s relatively low tax-rates that were implemented in 2017. While this tax legislation includes some new nuances that may impact retirees, the main tax-rate impact for Roth conversions has been extended for 2026 and beyond. Here are four reminders of the benefits and challenges with Roth conversions. “Roth on.”
Who should Roth:
https://humbledollar.com/2020/05/to-roth-or-not/
How Roth conversions can impact Medicare premiums:
https://humbledollar.com/2023/04/that-28000000-tax/
Rothing can lower future taxes especially when considering the widow’s tax after the first spouse passes and estate tax impacts:
https://humbledollar.com/2023/01/securing-lower-taxes/
Rothing may not gain ground on future RMD tax obligations due to growth in tax deferred accounts:
https://www.theretirementmanifesto.com/my-biggest-surprise-in-retirement/
I get a lot of questions from W-2 employees asking, “How can I save money on taxes?”
Many people know that business owners have a lot of flexibility to lower their tax bill, but what about W-2 workers? I’ll skip some of the more “obvious” strategies, like:
401(k)
Backdoor Roth
HSA/FSA
Here are some other ones you might want to think about:
Commuter benefits
Some companies offer pre-tax commuter benefits that can be used for transportation expenses such as transit passes or parking.
TAX EFFICIENT FUND placement is an often underrated topic. The goal of the tax efficient fund placement is to minimize taxes within your investments, and select the right account for those investments.
But how much does that actually matter?
Vanguard’s research finds that a thoughtful asset location strategy can add significantly more value than an equal location strategy. The value added typically ranges from 5 to 30 basis points of after-tax return, depending on circumstances (e.g.,
On April 30, Kitces posted an comprehensive article regarding the Tax Cuts and Jobs Act (TCJA) describing in detail where the congress is currently at and what steps are necessary to extend and/or change the the TCJA before the current tax law sunsets at the end of 2025.
https://www.kitces.com/blog/tax-cuts-and-jobs-act-tcja-sunset-budget-resolution-reconciliation-salt-cap-qbi-deduction-congress-republication-house-senate-bill/
I agree with the conclusion of the article to currently “wait and see” before taking action until I have a concrete expectation of what the individual income tax rules will look like in 2026.
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- My continued employment as a delivery driver would likely have left me on Social Security Disability (SSDI) by age 55.
- I was very interested in personal finance, and knew many people in that field who would help me get my foot in the door.
- I had acquired bookkeeping, payroll, and tax prep skills through my involvement with my local union, though I never pictured myself as the type to sit behind a desk, in a dimly lit office, crunching numbers beneath the glow of one of those green shade banker’s lamps.
- As a last resort, I could fall back on my truck driving skills, using my commercial drivers license to get a job hauling ‘no-touch’ freight of some sort.
- Last but not least, I needed a place to live. “Hello, mom and dad, I need my room back”. Sleeping on the twin mattress I gave up 25 years earlier, was not part of my plan.
- I was determined not to let my occupation as a beer truck driver dictate my future job prospects.
Where did I want to be?- Where to live? Living with the folks was never meant to be a long term thing. After three months of that, I signed my first ever apartment lease as a lessee, as opposed to a lessor. That lasted two years, until a very large increase in the rent caused me to buy a duplex, and become a lessor again.
- Where to work? I continued my work as a delivery driver for three more years. My position as the local union president, and my five paid weeks of vacation actually kept me off of the truck much of the time. That enabled me to tolerate the maladies that would eventually force me out of that job. Having absolutely no desire to spend the balance of my life languishing on SSDI and a minimal IRA balance, I set off on the path to becoming a financial services guy. That did not work out, and if you want more information on that, here’s a link.
- To make ends meet, I turned to my last resort; driving a truck. Piloting an 18-wheeler was not how I envisioned my remaining working days. And although the freight was ‘no touch’, driving 600 miles every day in a Kenworth tractor is still pretty hard on your vertebrae. But sometimes you have to do what you have to do to survive and to keep your eye on your finish line. My heart goes out to full time drivers, that job is no walk in the park.
- And what about love? My preference was to be in a relationship, but not any relationship. I wanted a good partner, I wanted to be a good partner as well. What qualities would I look for in a new partner? Independent, established, confident, and nice. Was I asking too much?
Making it All Work Finally, preparation collided with opportunity. In other words, I got lucky. Remember when I told you I didn’t picture myself as ever being a bean-counter? Two established financial services guys set me up with free office space and began funneling tax prep clients to me. What began with me preparing taxes for about three dozen of my union brothers, instantly turned into over 100 clients. There I was, a bean counter of sorts. I kept that truck driving job for several more years. And remember that duplex I bought after the rent spiked at my apartment? Well, there was this girl living next door. Enter Chrissy. We became best friends. She is no longer my neighbor. She is now my spouse. Of course, at the time we met, aside from being a nice guy, I wasn’t much of a catch. Man, she took a chance on me. As my client count went up, my days driving the big-rig went down. When the client count got to about 400, I retired forever from driving. No more trips to Chicago, Des Moines, Snow Shoe PA, or Jersey City. Chrissy and I began pounding 40% of our gross pay into savings. It would take until I was 70, but working together, we got to a place each of us only dreamed we would be. By living within our means, and keeping lifestyle creep to a minimum, we surpassed our goals. Chris retired at 64 and helped me during my final three years as a tax preparer. Lucky for me, Federal Wage and Hour never found out that I violated the minimum wage laws by never paying her in the first place. I sold the practice at age 70. I prepared 650 tax returns in my final year. It’s important to note that during our journey, we did not starve ourselves of food nor fun. We counted 27 trips during our first ten years together. Chris was great at finding great deals to various destinations in the Caribbean, and we turned several of her business trips into mini vacations as well. It’s important to prepare for the future, but have some fun along the way as well. I hope this piece inspires someone who is still on the road, dealing with similar obstacles, and wondering if there was a way around them.The IRA Decision That Affects Your Kids
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