Over the weekend, I spent some time looking for money I may have forgotten about. And while I was at it, I checked for money some friends and family members may have forgotten about, too.. It's something I like to do about once a year. I'm not talking about the loose change that's sometimes accompanied by the rogue Cheerio hiding between the sofa cushions. I'm talking about unclaimed money. And this time, I didn't find any for us. But I did find several hundred dollars for so

Last week, I explained why my wife and I decided an Health Savings Account (HSA) paired with a high-deductible health plan made sense for our early retirement strategy. Once we made that decision, though, I realized I still had a long list of questions. Some were simple. Others sent me down rabbit holes through IRS publications and insurance websites. I wanted one place that answered everything. If you're considering opening your first HSA, these are the exact questions I res

The end of October marks a big milestone in our early retirement—the expiration of our COBRA coverage. COBRA can be a great healthcare option in early retirement, but it only lasts up to 18 months. After that, you’re on your own. So I started shopping for insurance on the ACA Health Insurance Marketplace recently—the logical next step. And that’s when I realized there was a major flaw in our early retirement plan. We knew buying insurance on the ACA Marketplace could get pric

Last week, I explained how my wife and I can use a Roth conversion ladder to access retirement savings before age 59½ without paying the 10% early withdrawal penalty. The downside? You have to wait five years before touching the converted money. Then I discovered another early retirement income strategy that skips the waiting period entirely. With Rule 72(t), you can begin withdrawing money directly from a traditional IRA immediately—without converting anything to a Roth IRA