What happens when the policies designed to help people struggling with addiction and homelessness actually make it harder for them to recover?
Tom Wolf knows this crisis from both sides.
After a surgery and a prescription for opioid pain medication, Tom developed an addiction that eventually cost him his job, his family, and nearly his life. His addiction progressed from prescription opioids to fentanyl, ultimately leaving him homeless on the streets of San Francisco and cycling through the criminal justice system.
Today, Tom is eight years into recovery and has become a leading advocate for changing the way California—and the country—responds to addiction and homelessness.
In this episode of We Have A Problem, Kaylyn sits down with Tom for a candid conversation about what he believes we’re getting wrong.
Together we discuss:
- How a legitimate opioid prescription after surgery led Tom into addiction
- Why Tom believes housing alone isn’t enough to solve homelessness when severe addiction is involved
- How California’s assistance and harm-reduction policies can unintentionally enable continued drug use
- Why America’s response to the fentanyl and overdose crisis is failing so many people
- The debate over permanent supportive housing vs. recovery-oriented and drug-free housing
- Why accountability—and even Tom’s own arrests—played a pivotal role in getting him off the streets
- Why Tom believes compassion should mean helping someone move toward recovery, not simply making active addiction safer
- The complicated debate surrounding harm reduction, treatment, personal autonomy, involuntary intervention, and recovery
- What San Francisco’s experience can teach the rest of America about homelessness and addiction policy
Tom’s perspective isn’t theoretical. He’s lived the very system he’s now fighting to change.
His argument is simple but controversial: keeping someone alive is essential—but the ultimate goal should be helping them get their life back.
So where is the line between compassion and enablement? Does providing housing without requiring recovery actually solve homelessness? And what should society do when someone suffering from severe addiction is no longer capable of choosing recovery for themselves?
This is a conversation about addiction, homelessness, fentanyl, public policy—and what it really means to help someone.
We Have A Problem... So let's talk about it!
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