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Hi, Friends!

This week I want to talk about something that does not get enough attention in most retirement conversations: the rules that exist to protect you, but only if you know about them before you need them.

Inside this edition, you will find two articles built around exactly that idea.

A provision in the tax code that allows qualifying workers to access their 401(k) before age 59½ without the 10% IRS early-withdrawal penalty an a rule that determines how much you can earn from work while collecting benefits before your monthly checks start getting withheld.

Two different rules. One shared lesson: the people who benefit most from knowing them are the ones who learn about them early enough to act.

I hope this edition gives you something useful and maybe something you can pass along to someone else who needs it.

Warmly,
Mike Bridges

FEATURED ARTICLE

f you are between 55 and 59½ and thinking about retiring, there is a legal provision that could save you thousands of dollars in IRS penalties on your own retirement account. There are also two mistakes that permanently close that door — and most people make at least one of them before anyone explains the rule.

This week, I walk through exactly how the Rule of 55 works, what disqualifies you, and what to do before you turn in your notice.

Expense receipts shouldn't require a search party

Adam spent 20 minutes looking for a $36 receipt. His finance team sent three Slack messages. Someone made a sticky note.

Ramp would have matched it automatically the moment he swiped. Auto-coded, in-policy, synced. Nobody had to ask Adam for anything.

This is what finance looks like when it runs itself.

Your team can be Adam. Or they can not be Adam.

Imagine opening your bank account and finding that a Social Security deposit you counted on simply did not arrive. No notice. No warning. Just a missing check — and a call to the Social Security Administration explaining that your work income crossed a limit you did not know you were supposed to be tracking.

This happens to working retirees more than most people realize. This week, I explain the 2026 earnings limits, which income counts, and the one running-total habit that prevents the surprise.

Little Known RMD Strategy Allowed by the IRS

For investors with $1M+ in retirement accounts, the tax code allows specific strategies that can reduce your tax exposure once RMDs begin—but only if used before then. 

The window is open for anyone within ten years of 73. A fiduciary advisor can review which may apply, at no cost.

The Hustle: Claude Hacks For Marketers

Some people use Claude to write emails. Others use it to basically run their entire business while they play Wordle.

This isn't just ChatGPT's cooler cousin. It's the AI that's quietly revolutionizing how smart people work – writing entire business plans, planning marketing campaigns, and basically becoming the intern you never have to pay.

The Hustle's new guide shows you exactly how the AI-literate are leaving everyone else behind. Subscribe for instant access.

YOUR OPINION MATTERS…

Give a Friend Smarter Money Tips

Someone you know could be overpaying for groceries, prescriptions, insurance, or everyday bills right now.

Share The O55 Report and help them start saving money every week.

If you’ve been wanting a simple way to keep track of your money each month without complicated apps or confusing charts, this one’s for you. The Budget Buddy is an easy, step-by-step tracker designed to help you see exactly where your money goes, what you can adjust, and how to stay in control of your spending.

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