The Midlife Money Playbook
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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
Why $1,500 Can Matter More Than $1 Million
When I was young, my father was laid off.
May 12
•
Gary Romano
3
2
1
What Insurance Do You Actually Need?
I’ve found most people buy insurance reactively—a friend dies and suddenly they want life insurance, they buy a house and get homeowners insurance…
May 5
•
Gary Romano
April 2026
The Gig Work Bridge—Building Income Between Jobs
If you’ve built up some financial runway (see Part 1) and started working your network (see Part 2), you have options.
Apr 28
•
Gary Romano
1
The Job Search After 40—What Nobody Tells You
Whether you know it’s coming or not, getting laid off is a hit in the gut.
Apr 21
•
Gary Romano
1
1
You Just Got Laid Off—The Financial Checklist
The first 72 hours after a layoff are disorienting.
Apr 14
•
Gary Romano
1
2
What Is an LLC, Really?
I have a friend who’s been doing consulting for years.
Apr 7
•
Gary Romano
1
March 2026
The Only Index Fund Advice Most People Need
Most people who aren’t investing don’t have a motivation problem.
Mar 31
•
Gary Romano
1
2
4
The Conversation You Need to Have With Your Aging Parents
Before you can help your aging parents financially — or step in during a crisis — you need to know where everything is.
Mar 24
•
Gary Romano
1
The SAVE Plan Is Dead. Here’s What to Do Next.
A colleague’s daughter called me last month.
Mar 19
•
Gary Romano
1
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