Wow, what a parculiar woman.

I think you need to have a clearer and more secure picture of what it is you're putting you money into, so that when it comes to having to put money where it needs to be you're more confident. You can do this by making a little Pros vs Cons list. Will it be beneficial in the long run? Will you be happy with what you've soent it on? Is it worth it? Can you earn the money back? etc.
(Sorry if I'm rambling and am completely off topic :S)
Good luck!