Wasn't any kind of masochism, I guarantee it.
Fuck-you contrarianism, maybe... I've long suspected I come by it honestly.
Oddly enough, I actually felt kindasorta "relieved" at the 1995 generation revision.
My dad had been an armchair JW scholar back in the day, so through him, I knew WT eschatology backwards and forwards, and as a result, followed current events.
Problem was, I'd realized by then that a significant number of particular mundane-slash-real-world geopolitical circumstances had to be in place first for a lot of the benchmarks in ol' Freddy Franz's end-times script to actually be able to take place in a realistic and plausible context...
...and since the Org had (previously) promised that the End would essentially come by the conclusion of the 20th Century, I correctly grasped that we were effectively running out of time for all those things to fall into place before the semi-scheduled "End".
Switching up the definition of "generation" seemed - for all intents and purposes - to buy the Org a little more time to still be "right" (for me, anyway, 'cause at the time, I still had dog in that fight).