Hmm. On the one hand, it's clear that plenty of people are clueless when it comes to talking about their income (lots of quotes of these 'poor' bankers can set anyone's teeth on edge), but it's not completely unreasonable for them to be feeling the pinch. Yes, it's their fault to the extent that one should never rely on bonus salary to fund required commitments - no one is disputing that.
But - I do think that it's not completely unreasonable for someone making $350k to be feeling a pinch in their cashflow. A lot has to do with where they live - housing costs are astronomical there - and their choice to send children to private school. I'll agree it's a choice, but it's hardly an unreasonable one - most parents would like to provide the best education possible for their children, so I can't fault them for them sending their kids to one of the best (albeit most expensive) schools.
It's easy to live on a fraction of his income if you're living somewhere with low housing costs and you're willing to use public education. But I know from personal experience that you need a lot of income to support a family in other circumstances. Figure a cheap private school (or, for that matter, childcare for younger kids) will set you back about $25k/child, plus extracurriculars and summers (add another $5k or more?). If you have a family of 3 kids (not uncommon in the US), that's $90k in post-tax income right off the bat. Housing costs in areas which pay high incomes (mostly CA, NYC area, Boston, a few other places) are quite high - you can easily end up paying $10k/month for even fairly modest accommodations, between mortgage, property tax, and upkeep (that banker had a 1200 sq ft house, which is hardly huge). So you're now talking over $200k in post tax money just for your education and housing. That's not talking about transportation costs, food, entertainment, vacations, etc. Even fairly modest requirements can push your spending pretty high if you live in an expensive enough area. If you save at all for retirement, figure you're taking another 10-15% bite out of your paycheck, and pretty soon you're not looking at that much money left over from a $350k salary.
I am NOT suggesting that these people are poor, or that we should feel bad for the plight of the poor benighted banker. I'm just saying that it's not unreasonable to have money concerns even on that kind of salary - and that said concerns are not driven by greed or a lavish lifestyle, but by a fairly understandable set of choices (prioritizing education, living in a home near work). My wife and I combined make somewhere around the 95th percentile in household income in the US (very roughly - I haven't looked up the latest data). Obviously we're not poor, but we're hardly rich either. It'll be years before we can afford a home (and we're currently shoveling a huge amount of cash into a rental), and we have no idea how to pay for children once we have them - it'll cost $20-30k just to send them to a decent daycare, let alone actual schooling. We don't take lavish vacations, go out of the town a lot (except for cheap/free events), or anything else. It's not unreasonable for high earners to feel the pinch of a budget. The ire directed against the 1% is a bit misplaced - the people who are really 'megarich' are in the 0.1%; most of the 1% are people just trying to get by, especially in more expensive areas.