Very interesting game! I tried several runs to explore the different possible paths. If you plan to expand the game, you could add more events throughout Gary's life. For instance, in one of my runs, he managed to work until he was 100 without any consequences, which felt a bit odd ^^'
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Thanks for taking the time to check this out! Yeah, I'll see about expanding this idea. There's already so many things I wish I had done a bit differently but game jam pressure will force you to deliver whatever you got. There is consequence for working past retirement age - Gary loses happiness every year - but if he's got a really good relationship/family or loves his job, then it sort of cancels out. If I had more time I would've playtested it to get it balanced.