Social Security
He’s 66, Divorced, and Paying Child Support — Now the 2032 Social Security Deadline Is Keeping Him Up at Night
Eddie Jennings, 66, is banking on Social Security — but the CBO now projects the…
Social Security claiming age
19 articles
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…
Health
Her Insurance Changed at 63 and Her Prescription Bill Nearly Tripled — Now She’s Racing the Medicare Clock
At 64, Gina Haddad watched her monthly prescriptions jump from $187 to $514 after an…
Health
He’s 61, His Roof Is Leaking, and His Rent Just Jumped 30% — What Nolan Dupree’s Story Reveals About Retiring on Social Security
Most retirement advice assumes you get to retire on your own terms. You pick a…
Health
He’s 63 With No Retirement Savings and a Wrecked Credit Score — Now Social Security Is His Only Plan
The window for the most consequential Social Security decision a person can make — when…
Social Security
I Almost Claimed Social Security at 62 — The Math That Changed My Mind
The letter from the Social Security Administration arrived on a Tuesday in March, and for…
Social Security
She’s 42, Has $38,000 in Student Debt, and the 2026 Social Security Changes Just Made Her Retirement Feel Unreachable
The email landed in my inbox on a Tuesday morning in late January 2026. Brenda…
Health
Her Co-Signer’s Default Cost Her $23,000 — And Now Her Retirement Timeline Has Collapsed
Roughly 26% of Americans between the ages of 40 and 55 have less than $50,000…
Social Security
No 401(k), $47,000 in Student Loans, and a 13-Year-Old to Raise: A Truck Driver Faces Retirement at 55
Roughly 57% of Americans between the ages of 45 and 54 have less than $100,000…
Health
He Has $680K Saved and a Paid-Off Home — So Why Can’t Warren Jeffries Stop Losing Sleep Over Retirement
The first thing Warren Jeffries said when I sat down with him at a coffee…