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Regarding #2: Having worked hard is nothing to regret. I (like to think that I) work hard. I love what I do. I work to make money. Money I use to accomplish some of my goals. Do I feel bad that I work to make money? Hell no. I do business with other people on a voluntary basis. I've never put a gun to a person's head and forced him to pay me. Instead I produce products and deliver services other people value and are willing to pay for. My clients are able to buy those products and services because I offer those things for sale. If I didn't do that, my clients wouldn't be able to buy those products and services. So, by working hard and making money, I'm helping my fellow man.
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