The Midlife Money Playbook
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Building a Retirement Paycheck, Part 1: Which Account Do You Touch First?
She wasn’t in any shape to handle them herself.
Sep 8
•
Gary Romano
1
Your Hospital Bill Is Negotiable (And Might Be Erasable)
Your Hospital Bill Is Negotiable (And Might Be Erasable)
Sep 1
•
Gary Romano
1
August 2026
When You Become the Responsible Party for an Aging Parent
I was the responsible party for my mom in her final years.
Aug 25
•
Gary Romano
1
How the Rich Actually Got Rich (And Why Instagram Has It Backwards)
Recently, a friend told me I was doing it all wrong.Thanks for reading The Midlife Money Playbook !
Aug 18
•
Gary Romano
1
1
Planning for the Survivor’s Penalty Before It Happens
Every six months or so, Karen and I review our finances together.
Aug 11
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Gary Romano
1
The Tax Surprise That Hits When Your Spouse Dies
My dad died at 59, soon after retiring.
Aug 4
•
Gary Romano
2
1
July 2026
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
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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
1
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