I’m not a Dresden Dolls fan, and before listening to the interview she did on Tim Ferris show I had never even heard of Amanda Palmer. But what she talks about in her book (also available more condensed as a TED Talk) struck a chord with me. How difficult it is to ask, and how valuable it is to learn. 

From what I’ve seen, it isn’t so much the act of asking that paralyzes us—it’s what lies beneath: the fear of being vulnerable, the fear of rejection, the fear of looking needy or weak.
— Amanda Palmer, The Art of Asking

I was raised to be independent and that has been a huge part of how I define myself. Asking anything from anyone affected me on a scale from slight discomfort to physical pain. 

Just calling a friend to see if they want to hang out could feel like I was demanding too much. Having to ask for help when I was in real trouble, even worse. If I can't do everything by myself, what was I even worth? 

Yeah, I know, super healthy. I should probably point out that I have come a long way since those years of extreme anxiety. 

Whether it’s in the arts, at work, or in our relationships, we often resist asking not only because we’re afraid of rejection but also because we don’t even think we deserve what we’re asking for.

The Art of Asking is part a biography of an artist, with all that it entails. But reading it is also like having an honest conversation with a friend. Much of it feels obvious, but you know, sometimes you need to hear it in someone else's words for it to connect. 

And, some parts hits really close to home.

The problem was that I craved intimacy to the same burning degree that I detested commitment.”

”There’s really no honor in proving that you can carry the entire load on your own shoulders. And … it’s lonely.”

”And when you’re afraid of someone’s judgment, you can’t connect with them. You’re too preoccupied with the task of impressing them.

If asking makes you uncomfortable, or if you're struggling with vulnerability, this might be a good read for you. 

Asking is, at its core, a collaboration.