It might come down to personality and experience, but I don't see how you can reduce the majority of these questions to a coin flip, even if they present difficult decisions. With questions like "should i propose to my girlfriend," "should i quit my job," or "should i quit smoking" if you haven't thought through this shit enough to know what the clear right decision is then... well i don't know what to say to you.

"Yes. Money has been a little bit tight lately, but at the end of my life, when I'm sitting on my yacht, am I gonna be thinking about how much money I have? No. I'm gonna be thinking about how many friends I have and my children and my comedy albums."
 

That's exactly what I was thinking. I think it also goes for stuff like "should i get a tattoo?" Too important to not reason through and let a coin make the decision for you.

I'm talking about liquid. Rich enough to have your own jet. Rich enough not to waste time. Fifty, a hundred million dollars, buddy. A player. Or nothing. See my Blog & AMA
 

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