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If you've just arrived, this is the order I'd read them in — roughly from "I just started earning" to "I have opinions about tax software."
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
Common questions
Are you a tax professional?
No. I'm not an accountant, attorney or licensed adviser. I'm someone who files their own return, reads the source documents, and writes about what I find confusing. For anything that applies to your actual situation, talk to a qualified professional where you live.
Which country do you write about?
My own experience is mostly with the United States system, so examples lean that way. The arguments about paperwork, defaults and product design generalise; the specific rules do not. Always check the rules where you live.
How is the site funded?
Display advertising, and occasionally affiliate links that are disclosed on the page where they appear. Advertisers have no say in what I write. Full detail in the Advertising Disclosure.
Do you accept guest posts or sponsored articles?
Not currently. If that ever changes, anything paid for will be labelled as sponsored at the top of the page, before the content.
How do I tell you something's wrong?
Email me. I correct factual errors in the text and add a dated note at the foot of the essay saying what changed. See the Editorial Policy.