The file drawer
All milestones
16 files in five drawers. Inside each drawer they run in timeline order, earliest age first, with the after-a-death files last.
Final Expense
5 filesWhat the last bills are, who sends them, and the ways people set money aside for them.
- The letter of instruction: one document that saves your family a monthComes due: Age 50
Margaret "Peg" Ellison · filed June 29, 2026
- Final expense insurance: what it covers and what it doesn'tComes due: Age 60
Margaret "Peg" Ellison · filed October 12, 2026
- What a funeral costs in 2026, from FTC Funeral Rule price listsComes due: Age 65
Dev Okafor · filed October 5, 2026
- Preneed funeral contracts vs final expense policiesComes due: Age 70
Margaret "Peg" Ellison · filed September 21, 2026
- Burial vs cremation, line item by line itemComes due: Age 75
Dev Okafor · filed August 31, 2026
Late-Life Coverage
3 filesLife insurance that is still available after 60, 70 and 80, and the clauses that decide what it pays.
- Your term policy ends at 75: the conversion deadlineComes due: Age 65
Margaret "Peg" Ellison · filed September 7, 2026
- Life insurance after 70: what's still on the tableComes due: Age 70
Margaret "Peg" Ellison · filed September 14, 2026
- Guaranteed-issue life insurance and the two-year waiting clauseComes due: Age 80
Margaret "Peg" Ellison · filed September 28, 2026
Care Costs
4 filesPaying for help at home, adult day programs and the household changes that come with caring for a parent.
- Over-the-counter hearing aids, four years inComes due: Age 55
Margaret "Peg" Ellison · filed July 27, 2026
- Adult day programs vs in-home aides: the hourly mathComes due: Age 80
Dev Okafor · filed August 10, 2026
- Paying for a parent's care: the first-30-days checklistComes due: Age 85
Margaret "Peg" Ellison · filed August 17, 2026
- Moving a parent in: the household costs nobody budgetsComes due: Age 90
Dev Okafor · filed August 3, 2026
After a Death
3 filesThe paperwork of the first 30 days, in the order it tends to arrive.
- Veterans' burial benefits: what the VA paysComes due: Within 30 days
Dev Okafor · filed August 24, 2026
- Death certificates: how many copies, and who asks for themComes due: Within 30 days
Margaret "Peg" Ellison · filed July 13, 2026
- Closing a parent's accounts in the order that avoids frozen fundsComes due: Within 30 days
Margaret "Peg" Ellison · filed July 6, 2026
Longevity Math
1 fileMaking the money last as long as you do, worked as arithmetic you can redo with your own numbers.
- Longevity math: planning income to 95 vs 100Comes due: Age 95
Margaret "Peg" Ellison · filed July 20, 2026