I take what the author describes as "staring into the abyss" as a special case of playing devil's advocate: one where the contrarian view has significant and emotionally difficult consequences, and you're actually letting yourself feel the emotional weight of potentially choosing it instead of just playing with the idea.

For example: Imagine you go to an engineering college, and you start feeling like you might not like the idea of an engineering career. You could play devil's advocate by chatting with your engineering-enthralled friends about how fun it'd be to drop out of college and go to culinary school instead, but that's just talk. Staring into the abyss would be actually thinking through the financial, social, and personal implications of that choice, looking into culinary schools, and letting that dread and anxiety and excitement wash over you while you genuinely contemplate making the switch.

> If you want to talk about "staring into the abyss" though... to me that phrase evokes the casting of all reality into doubt.

In a more literal sense, yeah, I agree, that's what staring into the abyss is. I think here the author uses it as an effective way of saying "question the assumptions of your immediate reality".