Every essay
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Free tax filing is never quite free, and the word is doing pricing work
Every year the word 'free' does an enormous amount of work in tax software marketing. Here is what it actually describes, and why the irritation it produces is mostly a matter of sequencing.
Nobody sits you down and explains quarterly taxes
Going freelance changes a lot of things. The one that ambushes people is learning that tax is not an annual event, and that nobody is going to tell them.
Your refund is not a bonus. It's a receipt.
A large refund feels like winning something. I want to make the case that it's closer to getting change back from a shop, and why that reframe changed how I think about the whole year.
A shoebox and a spreadsheet: only one of them answers a question
Plenty of people run two parallel record-keeping systems without ever admitting it. Here's what happens when you audit which one is actually doing any work.
Chasing every deduction costs more than it returns
There's a genre of advice that treats deductions as a game you can win with sufficient diligence. Here is what that game actually costs the person playing it.
The withholding form deserves ten minutes of your year
Most people fill this in once, on their first day, distracted, and then never look at it again. I think it's the highest-leverage ten minutes in the whole calendar.
Tax software is a user-experience problem wearing a maths costume
The calculations were solved decades ago. Almost everything that makes filing unpleasant is an interface decision, and interface decisions have authors.
What I'd tell a twenty-two-year-old about their first paycheck
Not the compound interest lecture. The other things — the ones about paperwork, defaults, and the gap between gross and net that nobody warns you about.
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