This TedTalk by self proclaimed rock star, Amanda Palmer, is a really enlightening take on asking, and the baggage that comes with it. Nearly her entire career has been based upon asking for help and receiving it.
This goes beyond the music industry – asking is powerful in any industry. If you are unsure how to progress in your field – ask. Ask someone you respect. Ask someone who has done it. Ask them out for lunch, buy them a meal and gather all the information you can from them, and thank them heartily. You’re not weak, or wasting their time. You’re asking for their help – and they are willingly giving it to you. This is an equal exchange. You’re not cheating. It’s okay to ask for help. And it is okay to get help. That’s what people are for. Helping each other.