OK, the first thing I've learned is this--it is better to spend less time on crafting my request (in this case, my e-mail to Barry), less time reading and re-reading what I've written and less time pondering the wisdom of hitting the "send button." Each of those steps offers me an opportunity to NOT take the chance and the longer I spend on them, the more likely I am to not take the risk.
In the past I've used a glass of wine or two to provide me with the false courage necessary to say or do something that might risk rejection. I'm happy to report that I sent the e-mail fueled only with a few cups of coffee and the knowledge that I've just publicly promised that I would actually engage in this experiment for 30 days.
I've also learned that public promises help the project along. And that AFTER hitting the send button, there's plenty of time for regret.