Yes, us "oldies" seem better prepared with a Plan B in case Plan A fails. Life was harder back then and we didn't have all the gadgets, gizmos and facilities which make us lazy and reliant today.
I'm pretty paranoid and not only have a Plan B, I often have a Plan C too! Not just with means to buy things or pay for things, but also for route options when driving or using public transport - I always know alternative routes/options when a road on my planned route is closed or congested due to an accident, or when a train breaks down blocking the line, or bad weather causes widespread train cancellations. Not to the extent of worrying so much that I lose sleep, but just with a small amount of time researching alternative routes via google maps or the train booking apps, etc.
It's something I've hammered into our son throughout his teenage years whenever he's got a bit blase about how to get home after being out/away with his mates, what he'd do if he lost his phone or his wallet, etc.
It worked well a few months ago when he went to London for the first time ever (well he'd been as an 8 year old child!). He went on his own due to work - well a few others from his workplace were going, but they weren't in his department and he didn't know them, so he was effectively on his own! He doesn't live with us, so I helped him plan the trains, underground, hotel accommodation, etc., over facetime with him. Well, he didn't need much help to do that as he's pretty switched on himself with researching things etc. But where I did stick my oar in was with contingency planning, i.e. what he'd do if he missed his train, what he'd do if he got lost, what he'd do if the hotel was double booked, etc - not to scare the shit out of him, but to get him thinking of what he'd do. In the end, it turned out necessary as on the day he was coming back, it was severe storms and literally all trains north from Kings Cross to the North East were cancelled, well, as usual, not officially cancelled, but all marked as "delayed" and Kings Cross staff hadn't a clue what would run, when, if at all. We'd been through this, and we'd agreed he'd get himself to Euston and get whatever train he could somewhere "north", preferably at least to Crewe, and even better to Manchester, so that he'd have options to get from Crewe to Manchester and then Manchester to Leeds and onto the North East. He did that, and managed to squeeze onto a Manchester train, literally the last person on it and it was the last train of the day to Manchester - others were being turned away by platform staff as it was severely overcrowded! He was the only person in his firm who got home that night - the others either had to find hotels in London, or got themselves out of London by overground trains or shorter distance trains to midlands towns and ended up in hotels there as the trains started finishing late in the evening. They hadn't contemplated what to do in case of a major failure in the train network, and were too slow to work out alternative routes and ended up missing the "last" trains going to Manchester and being turned away from Euston.
I know some people will regard that as extreme paranoia, but I really don't think it's particularly wrong to think about what may go wrong and spend a little bit of time researching alternatives etc., so that you're ahead of the crowds when things do go wrong.