Vain?

How do I know when to stop, when exactly to stop being delusional about life and get a grip on the reality that's screaming at my face? How do I know I'm not being an idiot doing the things I'm doing, believing in the things I believe in? 

Hello there, I'm 'the Earthian'.

And I'm not the one with answers to these questions, but as of now, as of this moment, all I can say without sounding like a prat is that lessons are best learnt when we try and not when we analyze scenarios. At some point we have to try, if we lose, we lose but we'll only know if we try. There's also the factor of playing it safe and playing it rough, and the best way to tackle this circumstance is by understanding your circumstances and what you can afford to do, and decide how you play. An important aspect is removing your emotions and sentiments from the decision making for they often lead to decisions that aren't necessarily good for you though momentarily satiating. Ponder.

Love, peace.