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If you want to retire in comfort, retire your debts first.
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.
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?
EXPECTATIONS. Investment losses are most distressing when they’re least expected. For instance, many investors expect their stock portfolios to fall occasionally by 20% or more. But they’d be horrified if their money-market mutual fund—which they consider a haven of safety—“broke the buck” and slipped 1% from the standard $1 share price to 99 cents.
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.
BEFORE THE YEAR ENDS, I wanted to cover a great concept – tax-loss harvesting. It’s a strategy to lower your tax liability by selling investments and repurchasing a similar one. The loss can be used to cancel out gains from other investments, which helps reduce the taxes you owe. Or you can use up to $3,000 of those losses each year to lower your taxable income if you don’t have any gains.
Here’s the key goal of the tax-loss harvesting strategy:
Swap assets into similar,
As a result of reading HD, I have become fascinated with certified financial planner videos on YouTube, some are pretty good, others not so much.
Often one thing strikes me as ironic. Some presenters look more like they will be starting college in the fall, than experienced experts and none of them look anywhere near retirement age – maybe they will FIRE, but I digress.🤑
My real curiosity is when they show a spreadsheet to see if a hypothetical couple can afford to retire.
The Joint Committee on Taxation today posted their analysis of proposed changes to the current tax code. The 400+ page document is long but certainly easier to read than the tax bill that posted yesterday 5/12/2025.
Nothing final here but I think it will give a flavor to what may be coming in 2026.
https://www.jct.gov/publications/2025/jcx-21-25/
Due to the COVID-19 pandemic and a spike in unemployment federal tax law was modified and the Employee Retention Credit (ERC) was born. The ERC was a refundable tax credit for certain eligible businesses and tax-exempt organizations that had employees and were affected during the COVID-19 pandemic. The business, tax community and the Internal Revenue Service continue to deal with compliance aftermath of the ERC.
On March 20, 2025 the IRS updated their frequently asked questions about the employee retention credit in the section headed “Income tax and the ERC”.
Like most Americans I pay taxes, income taxes both federal and state, sales taxes, property taxes and for fifty years, payroll taxes and I’m still, at age 81, paying income, sales and property taxes – plus assorted other miner taxes and fees on goods and services.
Like any normal person, I think it would be nice not to pay taxes and keep all my money. But unlike too many of the uninformed people ranting on social media these days,
The Missouri legislature recently passed a wide-reaching tax bill that includes ending the capital gains tax. The House passed the legislation 102-41. Since it had previously been approved by the Senate, it now goes to Gov. Mike Kehoe.
Rep. George Hruza, R-St. Louis County said this is one of the best things the legislature could do for Missouri.
Now I’m not sure it really is the best thing the legislature could do in a state that is #5 in the country in “gun death rates,”
Dickie and his magic beans
R Quinn | May 6, 2026
Jonathan’s Advice for 2026 Graduates
Jonathan Clements | May 7, 2026
Saving for Grandchildren
ArticleJohn Yeigh | May 2, 2026
- 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.
R Quinn | May 4, 2026
First Place
Jonathan Clements | Sep 6, 2024
A Life You Build
Jeff Peck | Apr 19, 2026
Retirement Toys
Mark Crothers | May 4, 2026
Living On Autopilot
Mark Crothers | May 6, 2026
Sundry Memories of Mom
D.J. | May 7, 2026
Starting Up
Andrew Clements | May 7, 2026
Tax Foundation Podcast Episode on American Financial Literacy
Randy Dobkin | May 7, 2026
Investing Fundamentals: A Simple Guide for Beginners
W.D. Housley | Apr 24, 2026