Twenty-nine articles on the real questions pre-retirees ask me at workshops — Social Security, Medicare, taxes, annuities, long-term care, retirement income. Real numbers. No sales pitch.
Retirement Income & Withdrawals · 5 articles
The first five years of retirement decide the next thirty. How to structure income so a bad market doesn't sink the plan.
The 4% rule was never a law. The danger isn't on the way up — it's on the way down. Sequence-of-returns risk in plain English.
Read →Sequence-of-returns risk peaks in the 15-year window around retirement. Two real 2022 cases — one ran out, one was fine — and what made the difference.
Read →Three buckets — cash, income floor, growth — built so you never sell stocks in a down market to pay the grocery bill. Sizing, contents, refill rules.
Read →The conventional "taxable first, tax-deferred next, Roth last" rule is incomplete. Modern tax-aware sequencing that saves real money over 30 years.
Read →A retiree who walked away on January 1, 1966 did everything right and still ran out. Their 30-year average return was normal. The order is what got them.
Read →Annuities · 4 articles
I sell annuities. I also dunk on the bad ones. What each kind does, what they cost, and the contract clauses that trap people.
What each kind does, what they cost, what surrender schedules to avoid, and the rule of thumb for how much of your money should ever go into one.
Read →A 73-year-old found out he had a 14-year surrender schedule five years after he signed. What to look for — surrender, MVA, bonuses, rider fees.
Read →Three boring places to park money you don't need for five years. The 2026 rates, the tax differences, and the right tool for the right job.
Read →VA sales have collapsed since 2007. The reason is fees. The good news: they still occasionally make sense in narrow situations. The honest 2026 picture.
Read →Medicare · 4 articles
What changed in 2026, the seven-month window you can't miss, and why Massachusetts has a Medigap rule the rest of the country envies.
Part B jumped to $206.50, the Part D out-of-pocket cap rose to $2,100, IRMAA shifted, and MA still has a Medigap rule the rest of the country envies.
Read →The cleanest path into Medicare is the seven-month window around your 65th birthday. Miss it without coverage and you face a lifetime penalty.
Read →MA is one of only four states with year-round, community-rated, guaranteed-issue Medigap. That single rule changes the entire Medicare decision.
Read →A single dollar of extra income in 2024 can trigger thousands in extra Medicare premiums in 2026. IRMAA brackets are cliffs, not slopes.
Read →Long-Term Care · 3 articles
Traditional LTC is fractured. Hybrid products have replaced it for many. Medicaid has a five-year look-back. The four ways to fund the risk.
The numbers on long-term care are sobering. Traditional LTC is fractured. In MA, nursing home costs run well above the national average.
Read →Hybrid LTC products combine insurance with a return-of-premium feature, so the premium isn't "lost" if you never need care. The honest 2026 picture.
Read →Medicaid is the safety net for households that have spent down assets. The five-year look-back means planning starts at least five years before need.
Read →Tax Planning · 4 articles
Roth conversions in your sixties, QCDs after 70½, RMDs under SECURE 2.0, and what Massachusetts actually taxes.
The handful of years between retirement and RMD age is the window where Roth conversions do their most damage to future tax bills. The math and the IRMAA trap.
Read →Once you're 70½, give directly from your IRA to charity — excluded from taxable income, counts toward RMD, avoids the standard-deduction problem.
Read →RMDs used to start at 70½. Then 72. Now 73. By 2033, 75. SECURE 2.0 changed the rules for anyone with a traditional IRA or 401(k).
Read →MA isn't tax-friendly, but it isn't the worst. What the Commonwealth actually taxes for retirees — and where MA is more generous than you'd think.
Read →Getting Started · 1 article
The five years before you retire are the most consequential planning window in your financial life. The order to make the moves in.
I run free workshops a couple of times a month at libraries and community colleges around southeastern Massachusetts and Rhode Island. Same plain English. Live Q&A. No sales pitch — ever.
See Upcoming Workshops →Real feedback from local pre-retirees who came to a Forbes Retirement workshop, class, or consultation. Shared with permission.
Social Security · 8 articles
Social Security: The Decisions That Lock In Your Lifetime Income
When to claim, how the rules really work, and the myths that get people to claim five years too early.
When to Claim Social Security in 2026: The Honest Math
The 2026 numbers you need, the four decisions that change your lifetime income, and why "going broke" headlines lead most people to claim too early.
Read →The Social Security Earnings Test, Untangled
If you claim before FRA and keep working, the earnings test withholds part of your benefit. Most people think they lose the money. They don't.
Read →"Social Security Is Going Broke" — What the 2025 Trustees Report Actually Says
The headlines say Social Security is going broke. The math of claiming early to "beat the cut" is a losing trade. Plain English version, with the numbers.
Read →Spousal, Survivor, and Divorced: The Three Benefits Most People Miss
Three Social Security benefits most pre-retirees never claim — or claim wrong. Real stories, plain-English rules, and the widow's switching strategy that still works.
Read →The Tax Torpedo: How SS Taxation Catches Most Retirees by Surprise
A zone where each extra IRA dollar makes more of your Social Security taxable, creating effective marginal rates of 40%+ — even in the 12% bracket.
Read →When NOT to Delay Social Security to 70
The conventional wisdom is to delay to 70. The math is right for most retirees, but not all. The specific situations where claiming earlier is better.
Read →WEP and GPO Are Gone — If You're a MA Teacher, Cop, or Firefighter, Read This
The Social Security Fairness Act of 2025 repealed WEP and GPO retroactive to January 2024. MA public-sector retirees got the biggest checks.
Read →Working Past 65: The Earnings Test, Medicare Timing, and the HSA Trap
Working past 65 changes three planning questions at once: when to claim, when to enroll in Medicare, and what happens to your HSA. Three rules, one coordination problem.
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