Scarcity and attachment to material things

Lately, I feel like I cannot hold the frequency of fear anymore. Sometimes, an overwhelming fear of survival used to take over - and I would feel bad for days - but now it just seems like I cannot be bothered. 

As I gave the first things away today (some books), I was confronted by this feeling of regret - regretting that I didn't get money for them, regretting that maybe I gave them away too soon... there's a bit of the fear of being used and abused in there, and fear of not saying how I feel 100%, not daring to appear selfish or mean or inconsistent. 

I feel like if I knew I had all the money in the world, it wouldn't matter. Things are just things, replaceable [less so in the case of crystals, which I would NEVER sell if I could take them with me around the world], readily available, and ultimately not meaningful. 

But since I do not currently physically own all the money in the world [yet!], maybe that's why I still have some attachment to the things I've got, or to their material value at least. 

Someone once said that when you give money to a beggar, the difference between you and him on a very profound level is that you know that there is more from where that money came from. You know you can easily replace the £1-2-5, or £1000, but for him the value of it is much more than to you. Which is why I feel like the more you give (money), the more you will receive. But having that first, initial trust that things will come your way one way or the other is the hardest step to make. And if you give with regret, you will only attract regrets, which is a low vibration by definition. Or if you feel guilty towards yourself that you gave, then that obviously doesn't help either. 

Plus, we've been deeply programmed since infancy, and through out the ages, to fight for our right to survival. To fight for food, kill for food, and die of hunger if we didn't protect ourselves. Those years of deep conditioning are still operating on a subconscious level sometimes in our lives. 

So, can we feel safe without the comfort of money? Can we really be that fierce, and trust that things will always turn out ok, even if we do not plan out for rainy days? Can we take a leap of faith and trust that the universe will take care of us, that those years of struggle are behind us, that we can give freely without fearing the non-return? Can I?