edit: FYI -links in comment are literally just wikipedia definitions of the generations mentioned for those not too familiar.

So what happened? Well, we invented the Internet. Not in a Tim Berners-Lee way but in a "we can buy and sell you from petty cash" way. Gerry Yang? GenX. Sergei Brin? GenX. All the money the Internet ever generated it generated because of GenX. Which made the 'Boomers STFU right quick. Now nobody even really remembers the phrase "Generation X" because we're the guys paying the bills while the 'boomers start collecting more social security than they put in.

Is this cyclical? Does every generation think less of the next? Of course they do. The Lost Generation probably thought the The Greatest Generation were a lousy, no good group of wimps, until they saved the world. The Boomers thought the gen-x'ers to be lazy and complacent, but guess what... it's easy to "change the world" and "drop out" when mommy and daddy are flipping the bill (Boomers were the first trustafarians) until like you say, Gen-x'ers invented our new economy.

The point is, each generation thinks the next is worthless until the crux of them come of age and do something meaningful. It seems to happen with each generation. The Millennial's will have their moment to shine.

Your testimony about your wife's student loans mirrors our situation, I know we've discussed this in the past. One thing we had to do was to file taxes separately so that our loan repayment isn't effected by our household income but only her income. The system is extremely broken and the cost of higher education is no longer justified.

aside: We are currently debating some big questions in our household about finances and opportunity costs. Do we buy another house and put down 20% or do we rent? If we rent we have a large chunk of capital to invest in the market. Realestate doesn't have the ROI that it used to. Money is cheap right now, but still we are currently seeing a 16% return on some of our mutual funds, that's hard to say no to. We could rent and buy a rental property. We could rent a house and start buying a new rental every year. I'm thinking this may be the route to go. The rental market's good where I live. Side question: Do you use a property management company for your rental? If not, is it a pain being so far away from your property? Any horror stories about tenants or has it been good?

Back to the article:

I've never met someone who describes themselves as a "hipster." It's a pejorative, not a class of people.

-It's not a term of endearment. I have a cousin that had a great job in marketing for Kraft. He designed the labels and such of many every day products. He couldn't stand it anymore and has just recently bought a piece of property to start an organic farm in Michigan. He's MUCH happier. I think what we are seeing is a redefining of "success" that has less to do with monetary achievements and more to do with, I don't know how to say it... but maybe even spiritual achievements?

The "hipsters" are the vanguard and while you're looking down your nose at them, they're enjoying themselves.

-Well said.