Would you turn down a job to keep your teeth?

In the U.S., for better or worse, healthcare is inextricably linked to employment and income. So this week I want to talk about healthcare and how the very system that's supposed to help people heal often traps them in homelessness instead.

I have a good friend I'll call "Steve." Steve spent more than ten years living on the street. During that time, his teeth took a beating. That's not unusual. Many of our neighbors experiencing homelessness struggle with malnutrition, lack of dental hygiene, and limited access to bathrooms, toothbrushes, or even a good night's sleep. Add to that the impact of coping with trauma through addiction, or relying on cheap food high in sugar, and the result is often devastating dental problems.

For Steve, the consequences were more than cosmetic. Missing teeth made it difficult to feel presentable in job interviews, and painful infections made everyday life harder. But he was determined to rebuild his life step by step. He started working with one of the few dentists in New York City who provides the level of care he needed and accepts Medicaid.

That's when he ran into a heartbreaking and frustrating dilemma. I asked Steve if he had found any job opportunities, and he told me he had, but he couldn't accept them. Why? Because earning just a little more would push him over the Medicaid threshold. If that happened, he would lose access to the dental care he desperately needed and could never afford out of pocket. 

In both New York and New Jersey, an adult generally qualifies for Medicaid only if they earn about $1,800 a month or less—that's roughly $21,600 a year. For a family of four in New Jersey, the limit is about $3,700 a month. Go even a dollar above those amounts, and you risk losing coverage. That's the reality: the income cutoffs for America's most basic healthcare safety net are so low that anyone working even a modest full-time job can quickly become “too rich” for help, while still far too poor to afford private insurance.

So Steve made a painful calculation and remained homeless longer in order to finish repairing his teeth. He wanted the health, comfort, and long-term dignity of a smile he could be proud of more than a short-term paycheck that would cost him his healthcare.

This is the gap that so many fall into. The thresholds for government support are so convoluted and so low that they exclude people who are still in deep need. And once someone qualifies, any progress toward stability can become a penalty. The system is designed in such a way that moving forward can mean losing the very resources that make recovery possible.

Steve is just one story, but we see this all the time at City Relief. People want to work, they want to move forward, but the safety net is riddled with holes that actually punish progress. It's not laziness. It's not a lack of ambition. It's a trap built into the way support is structured.

This is why compassion matters. When we encounter our neighbors on the street, we often see only the surface. But behind those stories are choices no one should ever have to make, like stay homeless or lose healthcare. Hide pain or risk stability. Work hard and get punished for it.

And yet, people like Steve keep going, step by step. That perseverance is worth honoring—and worth responding to with empathy, not judgment.

With gratitude,

Josiah Haken

City Relief, CEO