There’s nothing wrong with spending money—as long as it’s spent on things that deliver plenty of happiness.
After spending more than two decades building a successful landscaping business with his twin brother Nicholas, Andrew Clements retired in 2015 with a new appreciation for what matters most. Born in England, his essays draw on a life that has included growing up in England and Bangladesh, entrepreneurship, caregiving, family loss and travel. A regular HumbleDollar contributor, he enjoys tellingstories that remind readers life’s richest lessons often have little to do with money. Andrew is the older brother of HumbleDollar founder Jonathan Clements, whose life and legacy have inspired some of his most personal writing. He lives in Florida with his husband, Joey.
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. IBTG (2026) through IBTK (2030+)IBDR (2026) through IBDV (2030+)IBHE (2026) through IBHG (2028+)BSGR (2027), BSTS (2028), etc.BSCQ (2026) through BSCZ (2035+)BSJQ (2026) through BSJY (2034)BSMQ (2026) through BSMZ (2035+)MYCF (2026) through MYCO (2035)MYHA (2027) through MYHE (2031)MYMF (2026) through MYMK (2031)VBCA (2027) through VBCJ (2036)NO. 53: STRIVING toward our goals is usually more satisfying than achieving them. Yes, we should think hard about our goals—but we should also ask whether we’ll enjoy the journey.
NO. 37: WE ATTRIBUTE our winners to our own brilliance, a phenomenon known as self-attribution bias. Meanwhile, we blame our losers on others—the neighbor, financial advisor or TV pundit who suggested the investment. This makes it harder to learn from our mistakes, while boosting our self-confidence and increasing the risk of future missteps.
MAKE END-OF-LIFE decisions. Ponder who should make medical and financial choices for you if you’re incapacitated. Draw up powers of attorney that reflect those wishes. Add a living will, detailing what life-prolonging medical procedures you want taken. Decide whether to donate your organs. Specify what sort of funeral you want. Choose an executor.
DICTATOR GAME. In experiments, a “dictator” is given money or some other prize and gets to decide how to split it with another person. If a dictator’s goal was maximum financial gain, he or she wouldn’t give anything. But in experiments, dictators typically share part of the prize, suggesting they’re concerned with fairness and perhaps with how they’re perceived.
NO. 53: STRIVING toward our goals is usually more satisfying than achieving them. Yes, we should think hard about our goals—but we should also ask whether we’ll enjoy the journey.
I’m three months retired today, my goodness the time has flown by!
When I managed my own business I always collated business figures into a quarterly report for better performance monitoring and to help give me a feel for how things were going. I guess the urge to do so is still ingrained within me, and I thought I’d do a similar but more holistic exercise with a first quarter retirement report for the quarter ending 07/31/25.
My wife started her professional career in 1979, and I in 1980.
I previously wrote an article on Humble Dollar where I tried to research the points covered below by Mark Miller who is considered one of the nation’s leading experts on retirement and aging. In a recent article on Morningstar’s website he warns of the effects of the bill recently signed into law. He writes that if congress does nothing to shore up Social Security the trust fund is projected to be emptied by 2032,
I like Wednesday now; it’s my favorite day of the week. When I was organizing everything before selling my business and retiring, I was so uptight and stressed about sorting out a cash flow stream for our everyday spending. I decided to pay ourselves weekly, reasoning it would make things easier to track what we spent this way. If you think about it, it’s a silly thing to do. It’s not like it was a surprise to me what we spent;
IF YOU’RE IN YOUR early 60s and retired, you probably have a lot of financial questions on your mind. The next few years may be among your lowest-income and lowest-tax-paying years. Your salary and bonus years are behind you. Social Security and required minimum distributions from your IRAs and 401(k)s have not started yet. You are hearing advice about doing Roth conversions during this low-tax window, and the arguments are compelling. You may also be thinking about consulting or part-time work to stay active and bring in some income.
MY RETIREMENT HAS been wonderful so far. Honestly, sometimes I have to stop and remind myself how lucky I am. Rachel and I have our health and enjoy each other’s company, which is not always true when a couple retires. However, there are four things that concern me as I reach my mid-70s.
Loneliness
I tried calling Mark, my old high school friend, a couple of weeks ago, and I haven’t heard from him.
NOT TOO LONG ago, Treasury Inflation Protected Security (TIPS) was a relatively obscure investment for safe long-term fixed-income investments. For the first twenty years of the new century, consumer prices were mostly stable or rising at a too-slow-to-notice rate. Why bother with anything related to inflation?
Sadly, persistently low inflation made us complacent on the biggest long-term risk of bond investments — the insidious unexpected inflation that robs us of the purchasing power of our “safe” investments.
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- Market Status: The market leader and pioneer in target-maturity bond ETFs.
- Product Lineup: Covers virtually every major sector of fixed income with annual maturity dates running up to 10+ years out.
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- U.S. Treasuries:
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- Municipal Bonds: Extensive national and state-specific (e.g., California, New York) muni suites.
- TIPS (Inflation-Protected): Target-date Treasury Inflation-Protected Securities.
2. Invesco (Invesco BulletShares)IBTG(2026) throughIBTK(2030+)IBDR(2026) throughIBDV(2030+)IBHE(2026) throughIBHG(2028+)- Market Status: The second major pillar of the space, boasting large liquidity and long historical track records.
- Product Lineup: Robust annual maturity lineups running through 2035 and beyond.
- Asset Classes Offered:
- U.S. Treasuries:
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- Municipal Bonds:
3. State Street Global Advisors (SPDR MyIncome / SSGA My20XX)BSGR(2027),BSTS(2028), etc.BSCQ(2026) throughBSCZ(2035+)BSJQ(2026) throughBSJY(2034)BSMQ(2026) throughBSMZ(2035+)- Market Status: A newer entrant that distinguished itself by offering actively managed target-maturity ETFs (rather than purely passive index trackers).
- Product Lineup: Focuses on active credit selection to optimize yield and reduce cash drag during the maturity year.
- Asset Classes Offered:
- Corporate Bonds:
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- Municipal Bonds:
4. Vanguard (Target Maturity Corporate Bond ETFs)MYCF(2026) throughMYCO(2035)MYHA(2027) throughMYHE(2031)MYMF(2026) throughMYMK(2031)- Market Status: Entered the target-maturity landscape with low-cost index options.
- Product Lineup: Focuses on investment-grade corporate bonds with explicit target years.
- Asset Classes Offered:
- Corporate Investment Grade:
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