In my (relatively short) life, I've always been far more happy in my periods of unemployment than when I was "gainfully employed." Don't expect a single person on HN to share this view, but there it is.
Which shows that happiness is not contingent on employment, but on bank account balance, which is not the philosophy a lot of people push when they say lack of work will ruin people.
I don't understand these people who can't find things to keep them occupied outside work. I don't have enough hours in the day to do all the things I want to do. Work is just 8 hours per day that I can't do those things.
I'm kind of the opposite, I just love laying around all day doing nothing but reading. I spent most of my time at my last job doing this, but surrounded by people, noise, and fluorescent lighting.
Plus, being able to attend events spontaneously and stay out as late as you want is pretty great.
I suspect that being a trust fund kid ruins it for you anyway. If you were born that way you'll have a harder time enjoying it because this has always been your baseline and you don't really know what life without is like. Now if you started out normal but became trust fund level rich, then I reckon there is a higher chance you'll actually appreciate it. So, don't feel bad, things feel more rewarding when you've earned them but not as much when they were given to you without effort on your part.
I envy you :) I always had this fear deep inside that I will run out of money and boom, poverty awaits (even now, that I have a more than decent salary).
With employment, there's usually a lower limit since there's a reasonable change you're able to eat and stay out of the rain.