(Edition 15)

Dear Friends,

Money questions start to sound different. They’re less about “how do I build more?” and more about how do I use what I have, wisely, calmly, and without regret.

This edition focuses on three real-life decisions many seniors are quietly navigating. First, we look at side income that actually matters — not pocket change, but work or activities that can realistically bring in a few hundred dollars a month and make retirement feel less tight. These aren’t trends or hustles. There are practical ways people your age are using experience and skills they already have.

We also break down the Rule of 55, a rule many people have heard of but few truly understand. Used correctly, it can offer flexibility. Used carelessly, it can create problems. We explain what it is, who it applies to, and why timing matters.

And finally, we talk honestly about so-called “bad” financial habits, THAT small things you keep because they make life enjoyable, social, or manageable. Not every expense is a mistake. The real goal is knowing which ones are worth keeping and which ones quietly work against you.

With gratitude and a whole lot of hope,
Mike Bridges
Founder, The O55 Report

The heart of The O55 Report is all about helping people, providing ideas, tips, and hacks on how to be financially smarter.

About 2-3 weeks ago, I called my cell company because I thought it was a bit too high. I was paying $94.00 per month for cell service. After spending about 15-20 minutes on the phone, I was able to reduce the bill to $52 per month. I am including the script that I used to lower that bill. That is a $1,008 saving over the contract. That’s $1,008, Folks. Would you like to have that added to your budget? Let me show you how and what to do, and let me know how you did.

When people talk about side income, it’s often framed as small change — a little here, a little there. But for many adults over 55, the goal isn’t pocket money. It’s a meaningful monthly income that can ease pressure, stretch savings, or create more flexibility in retirement. This article looks at real ways seniors are earning extra money using experience, skills, and time — without chasing trends or burning out.      

Most money advice focuses on cutting, canceling, and doing without. But life after 55 comes with a different reality: routines, small comforts, and social habits often matter more than ever. This piece takes a practical look at the “bad” financial habits many people keep — not because they’re careless, but because those habits support quality of life. The goal isn’t guilt. It’s understanding which habits are worth keeping and which ones quietly cost more than they give back.

If you’re 55+ and thinking, “I’m done working… but I’m not 59½ yet,” the Rule of 55 can be one of the most useful (and most misunderstood) retirement rules in the U.S.

It’s an IRS exception that can let you take money from a workplace retirement plan without the 10% early-withdrawal penalty, if you leave your job at the right time and follow the right steps. You’ll usually still owe regular income tax on what you withdraw.

What’s your biggest Financial Challenge?