If we start lying to others about the state of our finances, we likely stopped telling ourselves the truth years earlier.
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.
Ed is a semi-retired physical therapist who lives and works in a small community near Atlanta. When he's not spending time with his church, family or friends, you may find him tending his garden and wondering if he will ever fully retire. Check out Ed’s earlier articles.
John Yeigh is an author, coach and youth sports advocate. His book “Win the Youth Sports Game” was published in 2021. John retired in 2017 from the oil industry, where he negotiated financial details for multi-billion-dollar international projects. Check out his earlier articles. NO. 54: WE NEED to be great savers to amass enough for retirement. But we shouldn’t get so good at saving money that, once we’re financially successful, we can’t bring ourselves to spend.
LOOK FOR INSURANCE gaps. Many folks agonize over whether their policies are too large or small. A bigger danger: not having coverage at all, because our life has changed but our insurance hasn’t kept up. Just had kids? It’s time for life insurance. Grown wealthy? Consider umbrella insurance. Working for yourself? You may need disability coverage.
NO. 50: WE LIKE owning assets we can see and touch—but that doesn’t mean they’re good investments. Go back a few generations, and folks put great value on art, jewelry, fine furniture and land. But most tangible assets haven’t been good investments in recent decades. Homes are the exception, but they’re also a big, undiversified risk that come with high costs.
NO. 37: IF INFORMATION is publicly available, it’s hard to make money from it. As soon as news breaks—whether it’s economic or otherwise—investors trade on the information, so it’s almost instantly reflected in stock and bond prices. True, you could get an edge by better analyzing that public information than other investors. But how likely is that?
NO. 54: WE NEED to be great savers to amass enough for retirement. But we shouldn’t get so good at saving money that, once we’re financially successful, we can’t bring ourselves to spend.
Released:
A SUMMARY OF THE 2025 ANNUAL REPORTS
Social Security and Medicare Boards of Trustees
“Based on our best estimates, this year’s reports show that……
The Old-Age and Survivors Insurance (OASI) Trust Fund will be able to pay 100 percent of total scheduled benefits until 2033, unchanged from last year’s report. At that time, the fund’s reserves will become depleted and continuing program income will be sufficient to pay 77 percent of total scheduled benefits……”
“As in prior years,
A recent post on the Forum raised the issue of dealing with a cut in Social Security benefits – hopefully an unlikely or very temporary event. However, something still worth planning for.
If the status of SS is not fixed, around 2033 benefits could be reduced by 23-24%. The Committee for a Responsible Federal Budget projects a 24% cut by late 2032 for retirees, equating to an $18,100 annual reduction for a typical dual-earning couple retiring in 2033.
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’m turning into my mother more and more every day. Back when I was taking care of her, she’d hand me her credit card whenever we went shopping. She’d say, “I’m not qualified to carry this anymore.” She was afraid she’d lose it.
Now I catch myself doing the same thing. When Rachel and I go out, I sometimes give her my wallet to toss in her purse. I’m scared I’ll lose it. Since I’ve retired,
I’ve been dabbling in AI. Began using precursor “Expert Systems” about 20 years ago, but the new apps are more generalized and interesting. I’m aware of the limitations and anyone who wants to use something like Gemini or ChatGPT should also be aware. They can (and do) generate false information with apparent confidence. This can deceive users. Such disinformation has been given the name “hallucination” or “confabulation” by AI experts. Interesting names for inaccuracy.
However, using precise prompts seems to improve the response.
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.
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- Tax-free growth when used for qualified education expenses
- High gift-tax contribution limits: $19K per contributor per year (indexed)
- New ability to convert up to $35K into a Roth IRA for the beneficiary
Cons- Relatively complex with penalties and taxes on non-qualified withdrawals
- Limited, state-approved investment options
- Risk of underutilization if the child does not pursue qualifying education
Caveats- Technology and AI could significantly reduce education’s cost structure in the future
- Roth conversions are capped at $35K lifetime
- The 529 must be open 15 years, and contributions must age 5 years before conversion
- Conversions require the beneficiary to have earned income (i.e. they could Roth anyway)
- Annual Roth contribution limits still apply (e.g., $7.5K in 2026), so completing the full $35K conversion would take five years
UGM Custodial Accounts Pros- Brokerage account where up to $2.7K of unearned income can be tax-free each year
- High gift-tax contribution limits: $19K per contributor per year (indexed)
- Broad investment flexibility — stocks, bonds, funds, etc.
- Few restrictions on how funds may be used for the child’s benefit
- Potential for low taxes on capital gains, but subject to marginal “kiddie tax” at parent’s rates until tax-independency or age 24
Cons- Higher income or capital gains could trigger the kiddie tax at the parents’ marginal rate
- Assets count as the child’s for financial-aid purposes
Caveats- Custodians have some ability to spend down the account for legitimate child expenses if the child is a wild-child in the later teen years
Coverdell Accounts Pros- Tax-free growth for qualified education expenses
- More flexible investment choices than most 529 plans
Cons- Low contribution limit: $2K per year plus income limits restrict who can contribute
- Essentially irrelevant today given the expanded options within 529 plans
Trump Accounts Pros- $1K government seed deposit for children born 2025–2028
- Contribution limit of $5K per year in 2026, indexed to inflation
- Parent employers may contribute up to $2.5K per year (also indexed)
- Tax-deferred growth with Roth-conversion opportunities beginning at age 18
- No earned-income requirement for Roth conversions
- Roth conversions are ideal in low-income years starting after age 18 once the child has transitioned to tax-independency of parents or at age 24 when “kiddie taxation” ends. Early tax independence could even be a combined Roth plus student financial-aid strategy
- Potential to convert large account values over several years at relatively low tax rates (potentially marginal 10-12% tax-rates, but averaging less due to the standard deduction).
Cons- Investment options limited to low-cost indexed stock funds (not necessarily a drawback)
- Penalty-free withdrawals must wait until age 59½, but the accounts could be advantageous even including penalties
- Limited custodian control and intervention possibilities if the teen is a wild-child
Caveats- If Roth conversions are not undertaken during the child’s low-income years, a UGMA invested to capture long-term capital gains tax-rates may outperform a Trump Account taxed at ordinary income tax-rates
- Watch this space as future adjustments or eligibility changes are possible
In effect, the 529 is a two-decade college savings program having some complexity and withdrawal limitations; the UGM is a reasonably flexible, 18-30-year college or house downpayment savings program; and the Trump account is a somewhat inflexible, sixty-year retirement accelerator. Resulting Playbook Here is our family’s intended playbook for tax-advantaged accounts in the grandchild's name:- Parents’ retirement account fundings remain their top priority - 401K’s at a minimum up to the match, HSAs with their triple tax advantages, and Roths as long as eligible within income limits.
- A Trump account has already been initiated to secure the free $1K government seed contribution – grows to potentially $2.6K at age 18 after penalties and taxes.
- Limited 529 funding has also been initiated to start the 15-year clock for potential later Roth conversions.
- The family’s next priority is to fund the Trump account which starts at $5K later this year. Maximizing the Roth conversion opportunity will require ~$116K of contributions (at 3% inflation) over 18 years which we grandparents intend to help fund. I estimate the Roth converted Trump account could grow to ~$2 million of tax-free money at age 60 (6% growth) assuming early-age Roth conversions, and the Wall Street Journal projects as much as $3 million (link likely paywalled).
- The subsequent priorities are to start UGM taxable account and 529 account contributions in parallel to perhaps initial levels of about $35K each. This may take our family some years depending upon available resources for contributions.
For the UGM account, a balance of $35K should capture a sizeable chunk of the annual $2.7K tax-free income limit by investing in high-yield income alternatives. For the 529 account, $35K aligns with the Roth conversion limit. On a personal note, we had extremely positive UGM outcomes with our children. We saved taxes for two decades, and each child used the ~$60K balance as down payments on their first house shortly after college. Due to the 529’s withdrawal rigidities and potential technology impacts, we are unlikely to fund the 529 to the max.- We will skip Coverdells as the alternatives offer ample savings opportunity in the child’s name ($200K+).
- Depending upon spare resources available for gifting, we can always reassess future contributions.
That’s our plan, and we’re sticking to it…. until something changes.The reality of Social Security and Medicare- My real life experience.
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