The most telling predictor of whether an ex-offender will reenter the community as a law-abiding and productive member, or whether instead he or she will return to jail or prison, is employment. Former inmates with steady jobs have fairly high success rates. For those who can't find work, prospects are dismal.
It stands to reason, then, that society would do what it can to ensure that former inmates get jobs. The benefits are reaped not just by the freed inmates, who can put incarceration permanently behind them, or their families, who can have their loved ones and their breadwinners at home instead of locked up in distant cells where they can provide little familial, and no financial, support. It's obviously also better for communities to have their residents holding down jobs, paying their taxes and spending their earnings locally than shuttling back and forth to jail and, when in the neighborhood, having idle time and empty pockets.
But in fact society makes it hard, both for people returning from jail or prison and for those who have lived responsibly for many years after being incarcerated but who then lose their jobs and must go back into the employment market. A felony conviction, no matter how long in the past, carries a stigma that makes job-hunting exceedingly difficult. Employment forms often include a box that asks: "Have you ever been convicted of a crime?" Check the box, and the application most likely goes to the bottom of the stack or into the trash. In large companies or public institutions, those applicants are generally blocked by lowest-level bureaucrats or by human resources software before they can even make their case to decision makers, who can put any criminal history in its proper perspective.