The Midlife Money Playbook
Subscribe
Sign in
Home
Notes
Archive
About
Latest
Top
Discussions
Quarterly Estimated Taxes: The September 15 Deadline Is Coming
When I first did contracting work in my mid-20s, I learned this lesson the hard way.
Jul 28
•
Gary Romano
1
The $40,000 Surprise Nobody Warns You About
A friend of mine was in his late 50s when he got laid off during the Great Recession.
Jul 21
•
Gary Romano
1
1
The $250,000 Mistake I Made at 30
When I was about 30, I changed jobs and had a 401(k) with about $25,000 in it.
Jul 14
•
Gary Romano
2
1
Mid-Year Financial Check-In: Are You On Track?
I do a financial review twice a year — once in the first quarter to make plans, and again over the summer to make sure I’m hitting my goals and…
Jul 7
•
Gary Romano
1
June 2026
Life Insurance at 50: The Math Has Changed
When I turned 50, some of my term insurance was expiring.
Jun 30
•
Gary Romano
1
Special Edition: Trump Accounts Are Open — Should You Put Money In?
Whenever I have the opportunity to personally test these things, I like to.
Jun 24
•
Gary Romano
Not All Unexpected Money Is the Same
Many years ago, I had a grand-aunt pass away.
Jun 23
•
Gary Romano
1
When Leaving Money Does More Harm Than Good
There’s a cruel irony in how benefits work.
Jun 16
•
Gary Romano
1
Medicaid Planning: What You Need to Know Before You Need It
When most people hear 'Medicaid,' they assume it doesn't apply to them.
Jun 9
•
Gary Romano
1
The $300,000/Year Problem Nobody Wants to Talk About
My father had a good long-term care policy in the mid-90s.
Jun 2
•
Gary Romano
1
May 2026
What to Do Before Your Kid Leaves for College
We haven’t been through the college send-off yet, but we’re starting to think about the search with Ben, who’s 15.
May 26
•
Gary Romano
1
1
The Vacation You Can’t Afford (And How to Know the Difference)
Karen and I enjoy vacations.
May 19
•
Gary Romano
1
This site requires JavaScript to run correctly. Please
turn on JavaScript
or unblock scripts
