How can anti-poverty programs encourage people to work?

Oren Cass, Gov. Mitt Romney’s domestic-policy advisory during the 2012 presidential campaign, outlines the inherent tension between welfare and work in this article (subscription required) for National Review:

By some measures, the War on Poverty has already succeeded. If the goal is simply to guarantee that every American has access to food, providing an average of more than $3,000 of food stamps each year to households in need is a nearly unqualified victory. If the goal is access to medical care, a Medicaid program spending an average of $7,000 each year for a family of three represents extraordinary progress. Indeed, counting the full range of federal benefits as “income” to low-income households leads to a substantial reduction in the poverty rate.

But simply transferring enough resources to someone so that he is no longer “poor” treats only the symptom; it does not move him toward self-sufficiency or a foothold at the bottom of an economic ladder that could lead to better opportunities. To the contrary, it hinders that process. Therein lies the paradox at the heart of anti-poverty policy. Every dollar spent to reduce the suffering of an impoverished person reduces the incentive for that person to improve his own condition by earning an income—not only because the need has become less pressing, but also because the system will in fact punish him for any success by taking the dollar away once he earns one of his own. The “handout” is locked in perpetual battle with the “hand up.”

One could say, “So what?” Why not just spend the money to ensure everyone’s needs are met, and let work be its own reward? For one, fiscal constraints preclude the possibility of further expanding benefits for the further-expanded pool of beneficiaries that this approach would attract. But even if one were prepared to undertake the taxation and redistribution necessary to implement such a policy, the result would undermine societal values of individual responsibility and self-reliance and impede the upward economic mobility that is possible only for those who enter the work force in the first place. Thus the conservative emphasis on work requirements and other incentives to move people into jobs. And thus the effectiveness of welfare reform in the 1990s, one of the great conservative policy successes of recent decades.