The five-year rule on Roth earnings is one of the most important and most misunderstood rules in retirement accounts. Even after 59½, Roth earnings aren’t tax-free unless the account has been open for at least five years. Contributions come out anytime — earnings have their own timeline.

After the long Labor Day weekend, I was able to see my son off as he returned to base. My wife, one of our kids, and our 3 grandkids were there too. I didn’t need time off, I don’t need to make up the time, I didn’t need permission, I just did it! I like being…

Withholding on IRA distributions is a choice, not a default. You decide what percentage gets withheld for federal taxes, or whether to pay estimated taxes quarterly instead. Getting this wrong doesn’t feel like a mistake until April. Getting it right is the kind of thing that only happens if someone told you it was a decision…

This is what an actual Tuesday looks like for me now, two months into retirement. Morning I don’t get up as early as I did when I was in the 9 to 5. When I was working, I would get up around 6 AM and leave the house around 6:30 AM. That has slipped a…

Everyone talks about retirement like it’s the finish line. Nobody really tells you what the first thirty days really feel like. So here is how mine went — the good, the weird, and the stuff that genuinely caught me off guard. The first week The first week I approached Monday morning as I did for…

Mike here — welcome to the first post of Life After 59½. About a month ago, I retired from my IT career. Not at sixty. Not at sixty-five. At fifty-nine and a half. If you already know what that number means, you are aware of it’s significance. If you don’t, that’s exactly what this post…