This week, I hit the road for the National Association of Tax Professionals 2026 Taxposium conference. It was in Cleveland this year, and it did not disappoint. Even the extreme heat (more on that below) didn’t keep away my fellow tax pros, who were not only enthusiastic but also full of valuable insights on everything from the use of AI in practice to the importance of bookkeeping in tax practices. I spoke twice at the conference—once on legal developments in tax and again with former IRS Communications Chief Terry Lemons on the changes at the IRS.

The round trip from my home to the conference was about 800 miles, and we opted to drive. Among other things, it meant I got to stop by the world's largest coffee pot—an 18-foot-tall landmark in Bedford, Pennsylvania, built in 1927, large enough to hold 800,000 cups of coffee—and the world's largest quarter, a 20-foot-diameter 1,600-pound metal replica located in Everett, Pennsylvania.

I diligently recorded my mileage (we took a snapshot when we got in the car to start), which turned out to be great timing. This week, the IRS announced that, beginning July 1, 2026, the optional standard mileage rates will increase to 76 cents per mile for business use and 23.5 cents per mile for qualifying medical and moving purposes, citing the recent rise in fuel prices (the charitable rate remains fixed at 14 cents). Those rates are prospective, not retroactive. That means taxpayers now have two sets of mileage rates for 2026, with the original rates applying through June 30 and the higher rates applying to eligible miles driven on or after July 1.

Clearly, I love a good road trip. It’s fascinating to drive through small towns (Ohio and Pennsylvania have plenty of those) and catch a glimpse of days gone by, including some stores that have stood the test of time (and some that sadly have not). It’s a great look at how things change—and how they also stay the same.

That was the theme this week as we looked at some new tax proposals. According to Joseph Thorndike, proposals to tax artificial intelligence may sound novel, but the instinct behind them is not. In the 1920s and 1930s, lawmakers turned to special taxes to curb another disruptive business model: the chain store. National retailers such as A&P, Woolworth’s, and J.C. Penney used centralized buying, integrated distribution, and sheer scale to offer lower prices than many local merchants could match. Critics warned that the chains were destroying independent businesses, weakening communities, and sending profits elsewhere, and 28 states ultimately enacted some form of chain store tax.

The parallel to today’s AI debate is not exact, but it is instructive. Then, as now, lawmakers faced a technology-enabled economic shift that produced real gains while threatening jobs and established institutions. Taxes were used not simply to raise revenue, but to influence how quickly the new model spread and who absorbed its costs. The history of chain store taxes suggests that the central question for any AI levy is not whether the disruption is real, but what the tax is actually supposed to accomplish, which is fund worker relief, recover public costs, slow adoption, redistribute gains—or somehow do all four at once.

Old tax ideas have a way of resurfacing when the politics are right, and indexing capital gains for inflation is a good example. The argument—that taxpayers should owe tax only on real economic gains, not appreciation attributable to inflation—has circulated for decades, along with claims that the Treasury might be able to act without waiting for Congress. Steve Forbes argues that Republicans could turn the proposal into a winning campaign strategy by framing it as relief not just for investors, but for homeowners, small-business owners, farmers, and others holding appreciated property.........

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