Boomers Trade · Andrew James

The schedule so far

Same time yesterday, and the day before that.

Every letter I have sent, newest first. One move on the schedule read as arithmetic, and the business already standing in front of it. Nothing gets reshuffled here either.

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The box on your statement nobody reads

This cohort borrows less on plastic than its children do, and pays for it longer.

8/8/2026

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4 min read

Nobody makes you insure a paid-off house

Premiums are up 46 percent since 2021, and the lender that used to enforce coverage is gone.

8/7/2026

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3 min read

The withdrawal you do not get to choose

Private assets are walking into retirement plans, and the table still wants cash in December.

8/6/2026

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4 min read

Medicare will not drive you to the doctor

Coverage for the trip fell to 24 percent of plans this year, right as the cohort starts needing it.

8/5/2026

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3 min read

Help at home now costs more than the room

Forty four hours a week runs $6,673. The median assisted living community runs $6,200.

8/4/2026

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4 min read

Retirees have lost 14% of their buying power

The yearly raise is real. The grocery bill just keeps getting there first.

8/3/2026

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4 min read

America's fastest-growing job cannot find takers

The reason sits on the pay stub: sixteen dollars an hour to lift, dose, and show up at six.

8/2/2026

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3 min read

The fastest-growing borrower just turned 65

Bill that will not wait now runs at a rate a pension never planned for.

8/1/2026

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2 min read

The one bill Medicare still won't pay

Original Medicare has skipped dental since 1965, and a cash-pay clinic built its whole model on the gap.

7/31/2026

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2 min read