"The more willing you are to have awkward conversations and put yourself in awkward positions, the more successful you will be" is the one statement every single one of my entrepreneur friends or mentors have all agreed on. This seems like an exercise to put yourself in the MOST awkward position so much that it will cease to matter entirely. Brilliant. STICK WITH IT!
Love what you're doing with the 100 Days of Rejection Therapy. Your blog is my home page until you've finished your quest!
On the front page of Reddit I see....
Would be more interesting to negotiate something possble, like asking to buy something at a premium from the #1 guy. This was asking people to hand over something valuable for no reason.
I am constantly walking on a fine line between asking for something completely impossible (can I get your house for free?) and asking something too easy for a yes (can I give you $5?). The whole idea is that there is a 95% chance I get a no, so I can expect it and be genuinely surprised if I get a yes.