Wilde said that most of us live lives of quiet desperation. It's a good observation, and in my opinion it's the best reason to do whatever it is we choose to do with our lives. You spend so much time on the job you hate, listening to the boss who treats you like shit, and wondering why you bother to get out of bed anymore. So if you want to spend your time writing the great American novel, building birdhouses, attending Star Trek conventions in animal-themed S&M gear, or touring the country in a van with a band no one has ever heard of to play before tiny audiences, so be it. There are always risks, ranging from simple embarrassment to bodily harm depending on the nature of your pursuits. Hell, having any pursuits at all is a risk. Why not get a second job or work harder at your first one instead of wasting your time telling jokes at the Comedy Pouch in Possum Ridge, AR or playing math rock at the 4th Street Vomit Bucket in the worst neighborhood in Newark? Well, not only are some things more important than being practical, but what could be more practical than doing whatever is necessary to make yourself feel like your life is worthwhile? It's OK to remind yourself that you're not quite as worthless as the world makes you feel, even if there are considerable risks and opportunity costs involved.
Life is glorious and vibrant and joyous at points, but it is essentially tragic. That's not a unique David Simon perspective. That's the perspective of anyone who contemplates anything as simple as mortality. You're gonna die, and everyone you love and care about is gonna die. Life is finite. Some of them are gonna die too soon, and some of them are gonna die with things unsaid and things unfinished. And if you look at life in a fair and accurate context, you see that it is often deeply tragic, regardless of how well or poorly you live portions of your life -- and certainly some people get luckier than others.