Break it up, by being the anti-you..
If you play the logical, TAG game most of the time, you'll survive until the latter stages. But, like you said, it is boring at times.
The anti-you is an unpredictable player, an interesting player. The player who might take that bold chance. Might or might not survive, but is a player, out to win, whatever it takes.
And when the anti-you is taken out before the latter stages, he/she doesn't feel bad for losing early stage.
The feeling is one of relief, no more game stress, but at least you went down swinging, trying to hit a homer, win the game. No bunting, folding, playing it safe.