The Midlife Money Playbook
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What Is an LLC, Really?
I have a friend who’s been doing consulting for years.
Apr 7
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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
3
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
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Gary Romano
1
The SAVE Plan Is Dead. Here’s What to Do Next.
A colleague’s daughter called me last month.
Mar 19
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Gary Romano
1
The $500,000 Difference: Why Starting Now Beats Starting Later
I was almost 30 when the math finally hit me.
Mar 17
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Gary Romano
1
When the IRS Has Questions (And You Have to Wait) — A Survival Guide
I approach taxes like a game.
Mar 10
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Gary Romano
1
1
BONUS PLAY: “When You Have to Raid Your Retirement”
Two trends are colliding right now—and if you’re in your 40s or 50s, you’re probably watching both.
Mar 5
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Gary Romano
1
Your Money Should Always Be Making Money
When I was in graduate school, I taught a class in public financial management.
Mar 3
•
Gary Romano
1
February 2026
The Recovery Assumption: Why Most Financial Advice Breaks in Midlife
About twenty years ago, I was having coffee with a friend.
Feb 24
•
Gary Romano
2
The Account That Lets Your Disabled Child Save Without Losing Benefits
A few years ago, I was helping a small business owner in her early 50s figure out a financial plan for her teenage son, who has a developmental…
Feb 19
•
Gary Romano
2
The Rules Nobody Told You: How Disability Benefits Actually Work
If you’re the parent of a disabled child and you haven’t started planning for their financial future, I need you to hear something first: you’re not…
Feb 17
•
Gary Romano
2
2
2
Part 2: Your 401(k): Pre-Tax vs. Roth and Where to Invest
This is Part 2 of a two-part series.
Feb 12
•
Gary Romano
1
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