If I need to tie it to decluttering and moving on, I'll say that if you struggle with decisions and worry about making the right choices, then you probably wrestle with fear and perfectionism, which perhaps carry over to other parts of your life.
SO, here is a fun 20 min. talk by a man named Jia Jang. Realizing he was selling out staying in his secure but unfulfilling job, he wanted to toughen up his skin as he pursued his real dream to be an entrepreneur. He tried out "rejection therapy" and gave himself 100 days to get rejected in all kinds of ways. He asked a cop if he could drive the police car...and the cop said yes. He asked a man if he could fly his private plane...and the man said yes. You get the picture.
And to paraphrase Jang, if you avoid rejection from others, you'll end up rejecting yourself for not being true to what you really want. Ouch. And scary. He also said that people are really nice and he didn't know that before.
Check out his 2013 talk on vimeo:
http://vimeo.com/70167462
Or just see how he fared at Krispy Kreme in Austin (using a hidden camera) when asking for custom-designed donuts:
