I Kept a List of Purchases I Regretted, and Then Noticed I Was Still Defending Them

Two years ago I started a list with one rule: when I regret a purchase, I write the item, the amount, and one sentence about what I was thinking when I bought it. There are 41 entries. The total is £3,610. The interesting thing is not the total, and it is not the pattern in what I bought. It is what happened to entries over time.

Roughly a third of the entries have been amended by me, later, to be less negative. Not deleted — amended, with a second sentence explaining that actually it had been useful for something, or that I had used it more than I expected, or that it had been a reasonable decision given what I knew. In eleven cases I can now see that this was true. In the other three or so it plainly was not, and I was writing a defence.

I only noticed because the list was old enough to reread. A regret I recorded in March 2024 had a sentence added in July that said, in effect, this was fine. Reading both in 2026, the July sentence is a small piece of fiction, and I have no memory of writing it, and I certainly did not experience myself as rationalising at the time.

The mechanism is not mysterious and it has a name, and knowing the name did not protect me from it at all, which is the part I want to record. Having spent the money, I had an ongoing interest in the money having been well spent, and my mind quietly went and found reasons. It did not feel like finding reasons. It felt like remembering accurately.

What this costs beyond the original purchase is the lesson. A regretted purchase that stays regretted teaches you something about your own buying. A regretted purchase you have talked yourself out of teaches you nothing, and worse, it leaves you with a slightly inflated sense of your own judgment, which makes the next one more likely. Of my 41, the eight or so that I have rehabilitated without justification are all in categories where I have since made the same mistake again.

The practical change is small: the list is now append-only. I do not edit entries. If I later think a purchase was fine after all, I write that as a new dated line underneath, which preserves both versions and makes the revision visible as a revision. Since doing this I have added seven such lines, and rereading them, four are genuine updates and three are the same fiction, now legible as fiction because it sits under the original.

The second change is that I record the regret at a fixed interval rather than when I feel it. On the first of the month I look at the previous month’s discretionary purchases and ask about each one. Waiting for the feeling meant I only caught the sharp regrets, and the sharp ones are the rare, large, obvious mistakes. The persistent low-grade ones — a subscription I keep meaning to use, a tool that is fine and that I did not need — never produce a feeling strong enough to prompt a note, and in aggregate they are considerably more money.

I am describing my own habit and not recommending a way to manage money. But if you keep any record of your own decisions, financial or otherwise, I would suggest making it append-only, because the version of you that reads it is not a neutral party.