Wise Words from Ira Glass; and where did my confidence go?

I came across this video on another blog and had to share. So much of what I've been feeling is addressed here in under two minutes.

[vimeo http://www.vimeo.com/24715531 w=400&h=225]
Ira Glass on Storytelling from David Shiyang Liu on Vimeo.

I was at a critiquing workshop on the weekend, and in the weeks leading up to it, I asked myself why I felt I needed to go, why after all these years of writing and critiquing I still struggled with editing my work. The answer that came to mind was that I felt I knew what I was doing, but I lacked confidence in doing it. I have good words, I have all the parts of story captured on the page, my writing instincts are dead on... but when it comes to the execution, I second guess myself. I start assuming the reader isn't going to understand what I mean (this is entirely the fault of bad critiques, by the way) so I over-explain.

At the workshop, I shared 5 pages with 4 other people including 1 multi-published, NYT-bestselling author, and with those 5 pages, the author wisely pointed out that I was both showing and telling, and then she told me to "have confidence in your writing" and to trust the reader to get it.

In 5 pages.

She captured exactly what I'd been feeling lately. I thought, "Whoa. This is bad. My lack of confidence shows on the page?? I have to do something about this." So, I came home and started hacking and chopping and reduced those 5 pages down by half.  I now have a sticky note on my monitor to remind myself to "trust the reader to get it." Those 5 pages are from the opening chapter, which may very well be rewritten. Again. Until I'm happy with it. And the prologue? I've thrown it out.

I don't have the first clue how to develop my confidence on the page-- there will likely be many more blog posts about this-- but I've decided my first act is to chop anything I've put in because I didn't feel the reader would understand. I suspect this is mainly a problem for first few chapters only.

Do you have any advice for me? Any suggestions on developing confidence?