I've just discovered that my favorite personal finance book has a blog! This entry covers holiday spending; my approach was slightly different, but I'm in roughly the same place.
We have 4 family birthdays in October, 1 in November, a friend's birthday in December (she's pretty much the only friend to whom I give an actual present), and then of course the holiday gift-giving. So I started thinking about the holidays a few months ago.
Where I did things a little differently is I first estimated how much I was willing to spend on each person, and made that total number my budget. Then I started putting any extra money from 5-week month paychecks (and anywhere else) into the Presents line item, and started shopping.
As author Nagler suggests, sometimes I went slightly over but other times, slightly under so it has worked out well (so far). I have crossed off nearly everyone on my list and still have money in the Presents line item.
The only place I went over was in planning celebrations for the girls' birthdays so I did use some from savings to cover that, but since Presents is now a permanent line item in my budget, I am improving my chances that I won't have to do so next year.
My sister reminded me about ExpenseRegister, which I'd stopped using a long time ago. Then I realized that it was the easiest way to meet my next goal of tracking. I was trying to do it by keeping a log book, but I was forgetting to do so on a regular basis, or wouldn't have it with me when I wanted to do it. Since ExpenseRegister can be accessed from anywhere (and it does not keep any personal account information), I can easily add expenditures and run reports to see how I'm doing.
This doesn't mean I don't still obsess and worry and fret about money and what will happen if my next car service costs $1,000. I still have a long, long way to go. But I'm not so much worrying about the holidays this year, which is totally a first for me!