“You’re nobody here at $10 million,” [Gary] Kremen said earnestly over a glass of pinot noir at an upscale wine bar

I can’t say I’m all that sympathetic to people who got themselves onto a money treadmill and now feel that they can’t get off it. You always have a choice, and if you think you don’t, it’s because you’re not looking in the right places for options. If your role models are the folks with a net worth of $50 million, then yeah, you’re a schlub for only having $5 million. Perhaps you might try spending a little time with people whose net worth is only $500 thousand instead? Is that too demeaning for you? Those people, after all, can’t afford a nanny for the toddlers and new Acuras for the teenagers. They might even — dare I say it? — rent their homes and join the Y instead of a country club.

Is that too much like “admitting defeat”?

Cry me a freaking river.

Here’s where I come from on this: I went to a very exclusive private school when I was growing up, and my family was on the lower end of the income spectrum for the school. Kids didn’t have ipods and multi-function cellphones and $200 Gucci sunglasses back then, but some things were the same; many of my classmates had brand-new cars, designer jeans, shopping sprees at Bloomingdales, and spring break skiing trips to Aspen. I didn’t. I’d like to say that it didn’t matter, but that would be a lie. Of course you’re going to feel bad if some people in your peer group have stuff you don’t. What’s important is how you deal with it.

If you’re lucky, you take away the lesson that ‘stuff’ doesn’t necessarily make you happy, that somebody is always going to have more stuff than you, and to be happy with the stuff you do have. If you’re less lucky, you walk away with the ambition to get all that stuff, and then some, when it comes time for you to raise your own kids. And thus, a new generation of overworked treadmill-walkers is born.

Any accusations of sour grapes aside, there’s also a business lesson to be drawn here. I was interested to see that one of the subjects of the article earned much of her wealth from being an early member of the team at Handspring (and later a senior staffer at Palm). One wonders if that company’s ever-increasing inability to deliver products that people wanted might be linked to their own staff’s disconnection from what life for “normal” people is like.