I read this as sort of an odd contradiction. A man who is chastising the reader, at least the one who has settled, for giving up on his dreams in an attempt to conform to his familial conditions. In essence, in order to be considered a successful non-conformer, you must conform to his ideals rather than that of your wife, or your child's, parents, boss's, or even your own.
As I think about this, having driven my 27 year old Accord to work again (Catywampus is like a fine Swiss watch!), and the minivan, wife, and four kids at home getting their education from Mom (and me at night), and don't think that I have "settled".
I have crafted my career, to the best of my ability, to give a mix of home time, money, and stability. These are my priorities. Likewise, having one income rather than two is one of my priorities. What this means, almost as necessity, is that a Ferrari or a 993 is not something which I could ever reasonably get. It also means that a minivan is a borderline necessity, if you consider it necessary to be able to drive all of your kids anywhere. Once there exists a minivan, and a car for getting to work and back, there is not a lot of extra on the table.
The author seems to think that unless you give up everything for an awesome car, that you have settled, as if all other priorities are simply noncritical in comparison.
In summary, I think that the real world is full of conflicting priorities, with limited resources (time & money) and balancing those. Now, it has been some time since I have raced at Lemons but I do believe that I do a pretty good job at maintaining some time and money for fun.
Now, I do understand the parallels he is making here. Sure, if you drive a Cayenne to the office every day, and your kids are handled with Mom, and you have plenty of cash, sure, do it in a Cayman or 911 instead. I get the point he is trying to make, but I believe, perhaps based on the rather generous economic situation the author has found himself in, that the real world rains down pretty hard on some of us, maybe even most of us.
Furthermore, if I give up my marriage, split custody of my kids, get a single bedroom apartment, and forget all other priorities to get that 993, am I now not settling in a much more catastrophic way? Sitting in traffic during the morning commute in a 27 year old Accord isn't much different than sitting in traffic in a Cayman, now is it?