Hey Giles, I think there’s a strong bias towards overestimating and being over-worried about pushiness. This is what you’d expect given that humans have evolved to have hyperactive social threat detectors. I don’t think that people would regard asking once a year as objectionable—a year is a long time, and giving every year (e.g. every holiday season) is a widely recognised practice. And this worry doesn’t even apply when it comes to sending out emails for your first fundraiser—it doesn’t make sense to let worries about using up ‘asks’ stop your from making even your first ask!
Hey Giles, I think there’s a strong bias towards overestimating and being over-worried about pushiness. This is what you’d expect given that humans have evolved to have hyperactive social threat detectors. I don’t think that people would regard asking once a year as objectionable—a year is a long time, and giving every year (e.g. every holiday season) is a widely recognised practice. And this worry doesn’t even apply when it comes to sending out emails for your first fundraiser—it doesn’t make sense to let worries about using up ‘asks’ stop your from making even your first ask!