The short answer
The yearly paperwork comes around on a calendar. Taxes, insurance renewals, Medicare choices and property tax each arrive at roughly the same time every year. Put them on one page, month by month, and decide who helps with each.
This chapter explains how things usually work in the United States. It is not legal, tax or financial advice, and the rules where you live may differ. Before you act on anything here, check it with one of the people named at the end of the chapter.
What to do
- Write each yearly job on The year's jobs, in the month it comes due.
- Write who helps beside each one.
- Mark October 15 to December 7 on the calendar, if you have Medicare.
- Set up one drawer with a few plain folders.
- Start a folder for this year's tax papers today.
- Read each insurance renewal, and ask your questions, before it renews.
- Choose a few months to look at your credit reports.
What can wait
- Sorting his old files beyond what the tax preparer needs. Ask the preparer which of his papers they want, and leave the rest in their box.
- A perfect filing system. A drawer with a few labels is enough to start.
Who can help
Free tax help: VITA or TCE at 1-800-906-9887, and AARP Foundation Tax-Aide at 1-888-227-7669.
Local, one-on-one Medicare counseling at no cost: your SHIP, at shiphelp.org.
A helper, or a librarian at your public library, can look up either one with you.
The rules, phone numbers and web addresses in this book were checked against the agencies’ own pages in October 2026. They change, so check anything you rely on with the office itself.
From Book 4: Everything They Handled
This page has the short answer and the closing lists from chapter 10. The full chapter explains, in plain words, what exists, what to ask, and who can answer. The book covers months 1 to 9.
Hear when the next book is out
Five or six short emails a year at most, and a note when a new book is out. Each one is about something that tends to come up in the first two years. You can unsubscribe whenever you like.