I've Already Started my Taxes for Next Year

I had a pretty quiet weekend again this past weekend. Boring, too. How boring? So boring that I started my taxes. ...And I don't mean my taxes that are due April 15. I started next year's taxes. The ones for 2026 that aren't due for another 15 months!

Why start so soon?

As I've mentioned before, I start my taxes a year in advance. Obviously I can't fill out forms yet. I mean, I won't have the numbers for at least another 12 months... and even the forms won't be available until around this time next year! But what I do start a year in advance are estimates.

I like to know in advance approximately what I'm going to owe for taxes. With that knowledge I can adjust my withholding rates, if necessary, and also pay quarterly estimated taxes accurately. My goal is not to be surprised by a big balance due or refund come April— whether that's April 2026 or April 2027. A big balance due can mean penalties owed to the IRS... and a big refund means I've lent them money at 0% interest! Either way, ugh.

Working on these estimates now for the tax return I'll file 15 months from now already has proven worthwhile. As I plan to retire soon this year I'll be shifting from earning significant amounts of money in wages to getting most of my taxable income from dividends and capital gains. That has tax implications. Dividends and capital gains are taxed lower than wages. There's an interesting edge case where some dividends and cap gains can be taxed at 0%. That provision never applied to me before because my wages were always too high. I worked through that edge case in my planning this weekend. It lowered the tax I expect I'll owe by several thousand dollars. Hooray! And by knowing that now I know not to overpay on quarterly estimated taxes and give Uncle Sam a big, interest-free loan. That makes my advanced preparation a double win.

Oh, the Place We've Been. We Bought a New Map!

Yesterday I wrote about Oh, The Places We've Been and the pin map we hang on our wall. Before the holidays I realized that we hadn't updated our map in a while. We needed to add several more pins for places we've been! But our supply of pins was out.

Okay, no problem, I figured. I can jump on Amazon.com and find probably a bazillion different kinds of map pins. But then a funny thing happened.

When I searched for map pins my results also included matches for pin maps. It's kind of an anagram, right? Mathematical property of commutation? 🤣

Some of the pin maps were really nice. Some of them were basically like the DIY project I put together on my kitchen table over 25 years ago except... nicer than DIY. As much as my AAA-map-stapled-to-a-cork-bulletin-board still has sentimental value to me I decided I was ready for an upgrade. I checked with Hawk— because while I started the project we have updated it for 25+ years— and $250 we had a new, custom map in a hardwood frame on the way.



The new map arrived in December, before the holidays. It was like a birthday present for me. A present for the birthday which I otherwise didn't celebrate and received no gifts for. But there was a problem. The custom legend, which you can see toward the lower right of the map in the pic above, was wrong. It was only a slight mistake, but it was still there. I considered whether to keep the map as-is because the error was so small. But at the same time I knew that every time I looked at it— every time, daily, for the next 25+ years— I'd see that error. My spirit sank.

Fortunately the maker was really cool about fixing the problem. I sent a brief note explaining the error and asking what we could do. She immediately accepted responsibility for the mistake (her team had botched the custom message in the legend) and said she'd print and send a new one after Christmas.

Indeed, the new map arrived around New Year. And it was perfect. My spirit once again soared.



Now all we'd need to do was move pins from the old map to the new one. Hundreds of pins, all marking places we've been (in the USA) over the past 25+ years. It'd be another project, a labor of love.