Your dad's diary habit is the part I kept thinking about. I used to lose track of small food orders too, and they added up exactly the way you describe. Tracking for a full month before judging anything feels like the honest part, most people quit after a week. Did the quarterly balancing change what you cut, or just when you spent it?
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I am so in love with this habit. I have been doing it for almost 20 years now and it has made a huge difference in how I handle money