When you are tough on yourself, life is going to be infinitely easier on you.
It might interest you to know that the 1828 Noah Webster Dictionary identifies the optimist in complimentary terms, but says nothing about the pessimist. The word 'pessimist' was not in our vocabulary at that time. It's a modern 'invention' which I believe we should 'dis-invent.'
Money is not the most important thing, but when you need it, there are few substitutes. So while I like the things money can buy, I love what money won't buy. It bought me a house but it won't buy me a home. It would buy me a companion but it won't buy me a friend.
It makes no difference where you go, there you are. And it makes no difference what you have, there's always more to want. Until you are happy with who you are, you will never be happy because of what you have.