In the first of two rounds of interviews, 12 Social Security Administration (SSA) beneficiaries, all of whom professed a desire to work, discussed their perspectives on barriers to employment. Two years later, 8 of the 12 engaged in a second round of interviews. Only 1 of the 8 participants had succeeded in becoming self-supporting. After a review of the literature concerning the effects of SSA procedures in discouraging beneficiaries from seeking full-time work, the authors tell the stories of these participants and then analyze the findings using a phenomenological framework. They conclude by positing suggestions for how to improve outcomes for SSA beneficiaries in the future.