After listening to this podcast and reading the associated article, I think I finally understand the difference between political and free market competition. The issue clarified was rent seeking, both how it is defined and why it is harmful. Robert Tollison, an American economist who specializes in public choice theory (wikipedia):

Rent seeking is the expenditure of scarce resources to capture an artificially created transfer.

Basically, it is harmful to give things away for free. This is because people will compete to influence your choice (of who to give to), but since you refuse to accept money, they will spend on things which do not increase your ability to conjure up more of the supplied good, e.g. a more convincing proposal or a more extravagant charity event. The surplus from the exchange is thus partly dissipated away. This type of behavior is known as rent seeking.

A few weeks back, I posted a talk on the collapse of the middle class. In that talk, rising education expenses were identified as a major contributor to the fiscal fragility of the middle class family. In this article from The Chronicle Of Higher Education, Marty Nemko talks about how much of a waste college is for many, despite greatly increased spending. Nemko writes

... most of those college dropouts leave the campus having learned little of value, and with a mountain of debt and devastated self-esteem from their unsuccessful struggles. Perhaps worst of all, even those who do manage to graduate too rarely end up in careers that require a college education. So it's not surprising that when you hop into a cab or walk into a restaurant, you're likely to meet workers who spent years and their family's life savings on college, only to end up with a job they could have done as a high-school dropout.

HT: EconLog

NYT article: A Different Kind of Homework for Singapore Students: Get a Date

In a successful, benevolent, conformist, paternalistic state, risk avoidance is an optimal strategy for personal success. However, those who succeed may come to apply this strategy much too widely. Having kids is a big investment entailing lots of risk, no matter who you are. It is a risk which managed society in Singapore has not yet formulated an effective insurance policy for.

The decision to enter a marriage and have children is a personal one, the expense and success of which are determined in large part by how your personal conditions for happiness are structured. If you were truly conformist, there would be no problem with settling, but I would guess that that is hard to jibe with the self-image of the young single professional. People underestimate the difficulty of being happy AND unique.