As long as they're not mooching off other people or constantly complaining about situations they have control over then I don't care about how they live their lives. 

I do believe it's good to encourage academic success through high school so a person WILL have more options. They don't need to have a 4.4 GPA and have a loaded schedule full of AP classes, just perform moderately well at the bare minimum. If they want to dive straight into the workforce after HS that's fine, but if they have a decent enough academic background they'll have a choice to attend college if they decide to do so.

I'm aware there are high school drop outs who were able to land awesome jobs. That's cool, good for you, however there are many dropouts who aren't as fortunate to obtain such amazing job opportunities or end up regretting their decisions much later in life. 

As long as someone is happy and isn't being corrosive to society then it's all good!