it is a bit luck based, but with a jam it's kind of the only way. The way your changes are calculated is: percentage chance of winning for
easy - skill level + 20
medium - skill level
hard - 70% of skill level
there's also mediocre chance which is always 10%.
your experience seems, from my playtesting, to be an outlier: i found that i lost every time i clicked randomly and tended to win when i thought about it from playtesting. I'm sorry things didn't work out like that for you and maybe once the jam is finished i'll rework that entire system. thanks for your critique!