Learn the rules before you decide.
Plain-English guides, one per Case File topic. Each one shows where its numbers come from, links to the official source, and ends with a free calculator you can use on your own figures.
Social Security
The biggest check most households will ever get. Learn the rules before you choose.
When to claim Social Security: 62, 67 or 70?
What each claiming age pays, the break-even ages, and what a surviving spouse lives on. Worked example with Linda's numbers and a free calculator.
Read the guide · 4 min →Social SecurityWhat happens to the Social Security check when one spouse dies
A surviving spouse keeps the larger of the two checks, not both. How survivor benefits work, the age 60 rule, and why the higher earner's claiming age matters.
Read the guide · 3 min →Social SecurityWorking while collecting Social Security: the earnings limit
The 2026 Social Security earnings limits ($24,480 and $65,160), how much is withheld, what counts as earnings, and what happens to the withheld money.
Read the guide · 3 min →Social SecurityIs your Social Security taxable? How the 50% and 85% rules work
How provisional income decides whether up to 50% or 85% of your Social Security is taxed, the thresholds ($25,000/$32,000 and $34,000/$44,000), and a worked example.
Read the guide · 3 min →Retirement accounts and taxes
How the tax rules around 401(k)s, IRAs and Medicare actually fit together.
Roth conversion: the three checks to run before you convert
Can your cash pay the tax, is today's rate lower than later, and does the conversion cross a Medicare line? A worked example with a $53,800 tax bill and a free calculator.
Read the guide · 4 min →Retirement accounts and taxesRequired minimum distributions: when they start and how much
RMDs start at 75 if you were born in 1960 or later (73 if born 1951 to 1959). How the amount is figured with the divisor of 24.6, the penalty, and what to plan for.
Read the guide · 3 min →Retirement accounts and taxesThe Medicare surcharge (IRMAA): the income lines that raise your premium
How income-related Medicare surcharges work in 2026: the $109,000 and $218,000 lines, the two-year look-back, the extra Part B amounts, and how to appeal.
Read the guide · 3 min →Home and cash
Paying off the house, and how much cash is enough.
Pay off your mortgage before you retire? Five questions to ask first
Should you pay off the mortgage before retiring? Where the money comes from matters most. Worked example: paying from a 401(k) nets $1,482; paying from the paycheck saves $13,355.
Read the guide · 4 min →Home and cashHow much cash cushion do you need near retirement?
How to count your cash cushion in months of spending, why under six months is a warning light, where to keep cash safely, and why it matters before you pay off debt or convert.
Read the guide · 3 min →Stay safe and check the facts
How to test a money claim, and how to spot a scam before it costs you.
How to check a money claim in five minutes
Seven questions to test any money advice, video, ad or bulletin: the year, the source, the missing costs, who gains, and how to try it with your own numbers.
Read the guide · 3 min →Stay safe and check the factsMoney scams aimed at people over 50: the warning signs and what to do
The common scams that target older adults, the five signs that give them away, how to protect yourself, and exactly where to report one if it happens.
Read the guide · 3 min →New to all this?
Read in this order if you like: when to claim Social Security, then how it is taxed, then the Medicare surcharge, then Roth conversions. Those four connect, and most money mistakes after 50 live where they meet.