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

I got really excited when I finished filing our 2025 tax return last week. You might assume it’s because we’re getting a huge refund. Nope. The real reason I was excited? My tax optimization spreadsheet actually worked. Last year, I shared a spreadsheet I built to estimate how much long-term capital gains we could realize while staying in the 0% capital gains tax bracket . I had tested the math every way I could think of. But until you actually file a tax return, you never

I’m so excited to share a new spreadsheet I recently created to estimate tax liability and optimize long-term capital gains (LTCG)! I know this sounds like an odd thing to get excited about—but hear me out. Since retiring earlier this year, early retirement tax planning has become a major focus for us. We have more than a decade before we begin to collect Social Security. And without steady paychecks, we’ll be relying solely on our savings and investments. Of course, we’d li

In my last post , we talked about how long-term capital gains stack on top of ordinary income when calculating your federal taxes. We also looked at the magical unicorn of tax brackets: the 0% long-term capital gains bracket. This “stacking” concept doesn’t just help reduce your taxes today—it can also shrink your tax bill years from now by intentionally using the 0% tax bracket. And that’s where capital gains harvesting comes in. Yes, “harvesting,” as if we’re out in a fiel