The first one that comes to mind is trying to find someplace in an unfamiliar area without GPS, or course, but without even a map. Maybe, if you were lucky, you had decent directions. Otherwise it was trial and error, stopping and asking locals, calling the destination and saying “I’m next to a Denny’s on Hwy 17, am I anywhere near the right place?”.
Hell, finding a pay phone (that worked) was sometimes a chore. Now, of course, it’s impossible but mostly unnecessary.
Writing letters. I never wrote letters because I hated the amount of time it took, and I felt that the cost of a stamp required more than just a few lines; but when I was away at college I was obliged to write fairly long and fairly frequent letters home. If I had had email, it would have been so much easier.
Shopping for something specific. If I needed something I would have to go to a store that might carry that thing, and if they didn’t, maybe they would have some idea of who did. You could do this on the phone, of course, but that wouldn’t work if you didn’t know the right name for the thing you wanted (something for the kitchen, say, or some kind of hardware). Now you can just throw a few search terms into Google and you’ll probably get at least one hit that will help you narrow your search down and find tons of retailers who sell whatever it is. (The flip side of this is that stores seemed to carry more variety then; now a lot of stores seem to carry lots of the top 10 popular items, and expect you to find anything else online.)
Comparison shopping. You pretty much had to go physically store to store, and remember what you saw at the other stores and how much it was.
Music on LPs was a pretty dodgy experience (in my opinion). As soon as you opened and played a record, it was used and the more you played it the more used it got. I’ll say this for digital, it may lack that last 0.5% of nuance, but it sounds as good the 100th time you play it as the first time.
Listening to music on the go - I was a kid when the first cheap small transistor radios came out, AM only. We thought that was so cool. Later there were boom boxes. Later still were the first Walkman models, with cassette tapes. I had a reel-to-reel in the 60’s, but I was so glad when cassettes came along because they were actually portable (I never had 8-track so I can’t speak to that).
Dealing with emergencies away from home (see finding a working pay phone above).
When I was a kid we had a party line for a while. There were times you couldn’t make a call when you needed to, because someone else was on the line!
Traveling - you could submit yourself to the tender mercies of airline reservation phone numbers, or use a travel agent. Both sucked.
Restaurant reservations required you to call, often wait on hold, and then talk to someone who treated you with contempt and didn’t get the reservation right.
I’m sure there are lots more, this will do for now.
Roddy
p.s. sorry if you wanted stories, my memory doesn’t work that well any more