Health
At 51, Bernice Castillo Pays $1,847 a Month for COBRA. Now She’s Racing the Clock to Social Security — If It’s Still There
Phoenix barber Bernice Castillo pays $1,847/month for COBRA — more than rent — while carrying…
self-employed retirement savings
8 articles
Medicare
A 45-Year-Old Mechanic Ran the Social Security Numbers and Now He Can’t Sleep at Night
Most retirement advice assumes you have a steady paycheck. It assumes your income lands in…
Health
He Built His Shop for 18 Years. Then the Cars Changed — and a Milwaukee Mechanic’s Retirement Plan Unraveled
With the April 15, 2026 federal tax deadline less than three weeks out, self-employed workers…
Social Security
His Auto Shop Survived 18 Years. Then Computerized Cars Arrived — and Now He Has Nothing Saved at 52
Roughly 40% of self-employed Americans have no dedicated retirement savings — no IRA, no 401(k),…
Social Security
Robert Kowalski Fixed Cars for 18 Years. Now the Cars Are Too Smart — and His Retirement Savings Are Nearly Zero at 52
Have you ever been good at something your whole life, only to watch the world…
Social Security
He Ran His Auto Shop for 18 Years. Now Modern Cars Are Gutting His Revenue — and He Has Nothing Saved at 52
The deadline that Robert Kowalski keeps circling back to is August — when his oldest…
SNAP
He Ran His Auto Shop for 18 Years. Computerized Cars Cut His Revenue 30% — and Now His Son Needs $45K a Year for College
The deadline Robert Kowalski is staring down is not printed on any government form. It…
Social Security
He Has No Retirement Savings at 52, a Failing Shop, and a Son Starting a $45K-a-Year College
Roughly one in three self-employed Americans has no retirement savings whatsoever, according to data from…