The Midlife Money Playbook

The Midlife Money Playbook

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The Recovery Assumption: Why Most Financial Advice Breaks in Midlife
About twenty years ago, I was having coffee with a friend.
 • Gary Romano
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…
 • Gary Romano
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…
 • Gary Romano
Part 2: Your 401(k): Pre-Tax vs. Roth and Where to Invest
This is Part 2 of a two-part series.
 • Gary Romano
Part 1: Your 401(k): What It Is and How to Make the Most of Your Employer’s Contribution
This is Part 1 of a two-part series.
 • Gary Romano
Do You Actually Need a Trust? (Let’s Do the Math)
A reader sent me a question after the estate planning post, and it deserves a full answer — because the honest response might surprise you.
 • Gary Romano
Social Security for Couples (and Ex-Spouses): The Benefits You Might Not Know About
Comedian Bill Burr has a bit about what he calls the “drop dead years” — men between 49 and 61 who might suddenly die for any reason.
 • Gary Romano

January 2026

Why “Invest Instead of Paying Off Debt” Rarely Works (The Real Math)
Before you take on debt—or keep debt you could pay off—do the real math.
 • Gary Romano
Four New Tax Deductions You Might Already Qualify For (And the Gotchas That Could Trip You Up)
Tax season is my favorite time of year.
 • Gary Romano
How to Think About Debt (A Framework That Actually Helps)
Debt is history.
 • Gary Romano
When to Take Social Security (The Timing Decision That Could Cost You Thousands)
The decision of when to start taking Social Security could be worth tens of thousands of dollars over your lifetime—or hundreds of thousands if you live…
 • Gary Romano
How to Hire Your Kids (The Tax Strategy Most Side Business Owners Miss)
Pay your kids for legitimate work in your business, deduct their wages, and fund their Roth IRA — legally. Here's exactly how to do it right in 2026.
 • Gary Romano
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