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You may be right. Certainly, "asking" has been a success factor for people using Gittip, which is fine. For myself, I like not overtly asking for money too much, because then the gifts I do receive feel that much more genuine. :-)

What if instead of normalizing asking (pull), we normalized generosity (push)?

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I know asking is hard, and uncomfortable, but I feel like you are coming up with excuses to avoid the hard and uncomfortable thing. But I also suspect you know you have to do uncomfortable things to make this succeed. Asking/pulling extends the network, pushing does not. Certainly you aren't the only one reluctant to ask, but I think there's room to experiment with creative ways to ask, ones that will feel more authentic to you.

Also I'm going to pull out the Lesson In Humility card.

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