Holiday shopping challenged me as well, thinking about the recipient as an individual with , things they like to do, teams they root for, and their elements of heritage, all of which can be translated to small gifts.
Circumstances change over the years, both for me and for the normal function of the world. The gift list is much smaller, challenge of staying in budget much higher. Stores are now open Sundays, a novelty in Boston when I first started this. I no longer have to go to work on usual workdays and I am now rather attentive to not shopping on shabbos, now that there are ample other opportunities, though my regard for other Jewish elements may have waned. And my dinners have become more grand, served at my house, leaving me with quite a lot of dishes to do.
While we have on-line access to purchasing, it does not pay for items under $10. For birthday gifts of larger cost that need transport, it's the way to go, for shipping on my own, I keep the gift selections light.
Black Friday has itself changed. Stores now open in the evening on Thanksgiving. They used to open at 4-5 AM the following day, with steep discounts. The ads would come in a large newspaper edition, and still do. I would target one or two items, either for myself or for my wife's birthday gift, set out before dawn for Value City, of blessed memory, make a bee line for what I want to get, pay for it and be on my way before rosy-fingered dawn came over the parking lot. No reason to do that now. I don't need anything, don't particularly want anything, and wife's birthday gift is better expressed as an experience over a product. The retailers have figured this out. Stores open either at 6 o7 AM, the early bird discounts leave me unimpressed. I wash dishes instead.
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