Episode 12 - Civil Disobedience as a Leadership Strategy: Housing Works' Charles King on Using Every Tool at Your Disposal to Influence Change

Apr 14

Charles King built Housing Works, one of the country's most effective advocacy organizations, not by mastering one form of influence, but by knowing which form to deploy and when. Whether he's chaining himself to a commissioner's chair, lobbying the capitol, or eulogizing a community member’s funeral, his operating principle is the same: it's all advocacy — just in front of different judges.

After 35 years leading Housing Works, Charles' model offers a masterclass in how conviction, versatility, and proximity to the people you serve translate into durable, systemic change.

How do leaders choose the right form of influence for each situation?

Charles King has been arrested more than 300 times. No, he’s not a reckless driver or a wanton burglar. He uses civil disobedience as a deliberate choice; one he makes alongside lobbying legislators, filing lawsuits, running social enterprises, and officiating funerals.

The goal is always the same. It’s just the venue that changes.

"I like to say it's all advocacy. It's just in front of different judges." – Charles King, co-founder, president and CEO, Housing Works

A sit-in in a senator's office isn't a tantrum, it's a filing. A cannabis license application isn't a pivot, it's a brief. For Charles, it’s all about owning a toolkit – and having the judgment to know which tool the moment requires.

If you’re a leader trying to drive change inside organizations, industries, or systems that resist it, this is the core question you should be asking:

Are you fluent in more than one form of influence? And do you know when each one is – and isn't – the right call?

What is the Housing First model, and does it actually work?

Housing Works was founded in 1990 in direct response to a deputy commissioner's deposition testimony that homeless people living with HIV were "better off in the shelter" because they would be "less of a menace to others."

Charles and his co-founder Keith Cylar set out to prove him wrong with a simple and, at the time, radical idea: house people first, without requiring sobriety as a condition of entry. Let them live in the dignity of their own apartment. Then see what happens.

"When we move people into our supportive housing who are actively using drugs, within a year to 18 months, about a third stop using drugs altogether." – Charles King

Another third reduce or regularize their use enough to carry out daily life. Even the third with the most chaotic use are now doing it privately – not on the street, not leaving syringes in public spaces, not cycling through emergency rooms.

The name itself was a provocation. Housing Works. Not "Housing Helps" or "Housing Supports." The name was a direct rebuttal to the deputy commissioner's testimony. That statement of philosophy would become a proof of concept. In 2021, a study found that housing first programs decreased homelessness by 88% and improved housing stability by 41%, compared to treatment first programs.

Today, Housing Works employs more than 1,300 people, generates nearly $200 million in annual revenue, and houses thousands of people across its network of supportive housing. In 2016, what had seemed unimaginable at their founding came to fruition when state regulations changed to require enhanced rental assistance or supportive housing for every HIV-positive New Yorker eligible for public assistance, effectively ending chronic homelessness for people living with HIV in New York City. In a country where an estimated 653,000 people are experiencing homelessness on any given night (a number that saw an 18% increase from 2023 to 2024), this is a staggering achievement.

What does it take to sustain activist leadership for 35 years without burning out?

Since 1996, Charles has lived in one of Housing Works' own residential facilities, even as Housing Works has grown into a $200 million enterprise. He maintains an open-door policy. He continues to attend memorial services for clients who pass away, often serving as the officiant.

Staff at Housing Works are contractually required to participate in advocacy via at least three in-person events and two electronic communications per year. Civil disobedience training is offered quarterly (though civil disobedience itself is not required). About a quarter of Housing Works' current staff are people who walked in the door as clients seeking services.

Charles believes that the moment you stop being in proximity to the people you serve, you start solving the wrong problems.

"All too often we have our own ideas about what help looks like. And frankly, in my experience, [the people you're trying to help] know ever so much more what they need than I could even imagine." – Charles King

This operational philosophy has kept Housing Works from drifting into the kind of well-intentioned paternalism that hollows out so many nonprofits from the inside; it’s founded in a humility that has demonstrably affected real, positive change across decades.

“Whether it’s wealth or career success, none of us comes into the world of change-making with all of the answers. The important thing is being open and having the willingness to learn as you go.”

What to do this week:

Pick one decision you're currently making on behalf of people you serve:

a product change
a policy
a program design

Then ask yourself: when did you last actually talk to those people about it? Not through a survey, not through aggregated feedback, but in a real conversation. If you can't remember, go do that now – find out what they actually need before you ship the solution you've already designed.

Have fun changing the world.