Every time I tried the game (using OP's described steps) I "lost all hope and quit". I thought that was the joke / funny commentary: that all paths through the game involve you ending up losing. Didn't know there was a path to actually win the game until reading the HN comments. So I kept trying it over and over doing the same steps and finally won once.

I guess that's an even funnier commentary on how it's pretty much entirely luck based.

I actually got the PhD so it’s not all ways leading to failure — just accept when your advisor offers you to take time off.

i won on my first try at just under 6 years and my hope never got below 65 i think, maybe i got lucky

I think you need to "Slack Off" more than once when your hope is low.

I wonder if there are other issues you can get e.g. if you slack off too much but your hope is still low, it just stops working.