Retirement questions, answered plainly
Notes on the decisions that come up in the three years either side of a retirement date.
For the decisions in front of you
Pension Decision Analysis: Chicago Suburbs
One packet, two elections, both permanent once payments begin. What gets modeled, and what a calculator cannot tell you.
Tax-Aware Retirement Planning, Chicago
Illinois exempts most retirement income. Three things it does not reach, and why the work moves to the federal side.
Fee-Based Retirement Advisors Explained
Fee-based, fee-only, commission. Every model carries a conflict, including the one that claims not to.
Seven steps, and recommendations are fourth
What a CFP Does for Retirement
Not picking investments. The seven steps, the analysis nobody sees, and the document that decides a bad month in advance.
Three credentials built for drawing, not growing
Designations That Signal Retirement Income Expertise
What each one actually requires, where the broad credentials fit, and what none of them tell you.
Pension Decisions: Lump Sum, Annuity, and the Survivor
Two choices on one form. The survivor election is irrevocable, and the lump sum moves with interest rates.
Using a Health Savings Account in Retirement
It pays Part B and Part D premiums but not Medigap. After 65 the penalty disappears.
Capital Gains in Retirement: Harvesting, Losses, and Basis
The zero percent band, the wash sale trap, and the one thing Illinois still taxes a retiree on.
Financial Advisor Designations: What the Letters Mean
FINRA lists them and endorses none. A designation is education, not registration, and the two get confused.
Long-Term Care Costs: What Medicare Does Not Cover
Medicare pays for getting better. The help most people eventually need is a different category entirely.
The Social Security Tax Torpedo, Explained
One dollar out of an IRA can drag up to $1.85 onto your return. Your bracket is not always the rate you pay.
The 4% Rule and What It Actually Tells You
A 1994 study of historical worst cases. It was never a spending plan, and the assumptions are the part worth knowing.
New Federal Deductions for Retirees, and When They Expire
One ends after 2028, the other after 2029. In a high property tax state the second one is the larger.
Medicare Late Enrollment Penalties and IRMAA Appeals
Two of the three penalties last for life, and COBRA does not protect you from them. Plus the form that fixes a retirement-year surcharge.
The Illinois Estate Tax: What Retirees Should Know
A threshold that does not move, that a spouse cannot inherit, and that many estates cross without owing anything federally.
Social Security Claiming Decisions for Married Couples
The higher earner's claiming age sets the survivor's income. Why couples usually need two claiming ages, not one.
Twelve earlier articles, published between August and mid-September, live in the archive. The subjects still hold; the figures in them are dated.
Browse the archiveThe material on this page is for informational purposes only and is not individualized investment, tax, or legal advice, or a recommendation to buy or sell any security or insurance product. Consult your CPA or attorney before acting on anything described here.
Tax rules, Medicare premium tiers, and enrollment deadlines change and are indexed annually. Confirm current-year figures with a qualified professional.
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