It's easy to forget this place is populated with upper-middleclass skilled professionals that probably haven't lived economically precariously in years, if ever.

For some folks out there, planning ahead is "will I have enough money for groceries next paycheck?". There are cheap phones, and I agree that folks are careless. But there is also a concerted effort to encourage this kind of behavior because the economy is built on this kind of dumb consumer spending and debt.