"Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart."
Luke 12:16-20, Seneca, or some time working in insurance might do just as well.
No matter how much you own and how much you've got things secured in your life, all you need is one gravel under your shoe and you can fall and hit your head so as to never go back to the life you had. Wealth, job, relationships... they can all be torn down should things go majorly awry.
Security is an illusion of control, and in life you never really have any real control.
The idea of 'security' should be represented as a spectrum, like white to black with grey in the middle. The ideas of perfect security or total insecurity— the white and black ends of the spectrum— only exist in our minds (Not in the real world.) Thats what you're talking about.
Don't focus on the extreme ideas- instead, think about the grey area of the spectrum with 'more security and more hassle' on one end, and 'less security and fewer hassles' on the other. Then you'll have a reasonable mental foundation to build your ideas on.
It's true that there are lots of things that we cannot control, regardless of money or power, but when we have more options we certanly have more control over our own lives and those around us. Money is a very effective way of increasing our options in life but there are other ways too, like having more knowledge or developing a skill, more meaningful relationships.