Episode 12 - Civil Disobedience as a Leadership Strategy: Housing Works' Charles King on Using Every Tool at Your Disposal to Influence Change
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.
Related Episodes
– The High Line and Beyond with Robbie Hammond
– Community Leadership as a Business Developer with Sachin Shivaram
– Lead Like a Learner with Helen Tupper
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Full Transcript
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Charles: All too often we have our own ideas about what help looks like. We have our own ideas about what the solutions are. We don't necessarily listen to the people who are the beneficiaries, and frankly, in my experience, they know ever so much more what they need than I could even imagine.
Ben: Welcome to The Lift, the show about leadership, growth, and getting what we want. I'm your host, Ben Brooks. For over a decade, I've worked with CEOs, their executive teams, HR departments, and entrepreneurs to identify what drives their success and what holds them back. And now I'm excited to share those insights with you. On The Lift, we pull up to see the bigger picture from accomplished leaders who know how to get things done in a rapidly changing world. We've got all of that and a lot more coming up next on The Lift. Back in 2010, I was introduced to the group Housing Works. It's a nonprofit founded in 1990 to fight the dual crises of homelessness and HIV/AIDS right here in New York City. A friend of mine got me involved and I saw the amazing work they were doing, and one day I was in the presence of their co-founder and CEO, Charles King. Let me tell you, this guy is a force to be reckoned with, with a background in ministry, law, and activism. He spent decades connecting the dots between housing, healthcare, advocacy, and the social enterprise. He's launched thrift shops, a bookstore, cafe, even a cannabis business, all to support the mission and employ their clients. He's also stood at the front lines of protest, and he's been arrested hundreds of times for civil disobedience. And on top of all that, he's 70 years old. He still runs marathons. Charles is one of those rare leaders that has dedicated his life to the mission that he serves. He's a leader who shows us that real change requires vision, conviction, and frankly, a lot of courage. But not only that, he's clever. He knows how to navigate and use various systems and tools, using the right form of influence at the right time. He's here to teach us today about how to fight for what we believe in and make the most of the short lives that we have. Well, Charles King, welcome to The Lift.
Charles: It's good to be here.
Ben: Actually, Charles, I believe it's a great day to end the AIDS epidemic.
Charles: To end the AIDS epidemic.
Ben: Well, Charles, we're excited to have you on the show, and we're talking to a variety of leaders, and I think you're a profile of courage. Our podcast team, as they were researching you, called you a bad something or other, and bold —
Charles: Oh, me?
Ben: And fascinating. So for those of you listening, I'm actually looking at Charles in his office here, and there's a lot of stuffed animals behind you, and I'm just curious, Charles, what are these stuffed animals? What do they represent?
Charles: Well, you'll notice — I don't know if you can see, but in the corner there is a big brown bear.
Ben: Yes, I see the big brown bear.
Charles: There was a period of time under the Giuliani administration where we'd lost a lot of our funding, and part of that meant that the executive team and our advocacy staff had to move our offices into the basement of the building where we were headquartered. So we had steam pipes running overhead, rats running around the floor. Advocacy thought that the circumstances weren't so good, and they decided to do a sit-in in my office. I of course joined them, and they really felt like that wasn't the best response. So they handcuffed the bear to my chair. So I've kept the bear with the handcuffs ever since, and because this beautiful stuffed bear sat in the corner of my office, folk got the idea that I loved stuffed bears and then other stuffed animals. And so every year people started giving me stuffed animals for Christmas. And so I've allowed them to accumulate and keep me company. And it's a great backdrop for interviews like this.
Ben: It is. And when you kept that bear with the handcuffs, what's the lesson it reminds you of when you see it?
Charles: Anytime your staff feels strongly about something, enough to do civil disobedience, you need to join with them.
Ben: Yeah. They thought you were the antagonist and you might be a protagonist.
Charles: Exactly.
Ben: So Charles, you co-founded Housing Works in 1990 with your late co-founder and partner, Keith Cylar, but previously you were part of another activist organization. Tell us about the genesis of what is Housing Works.
Charles: So, there were two parts of my life that kind of came together in Housing Works, I should say. I had resigned my position as a Baptist minister, the assistant pastor of a church in New Haven, Connecticut. I was trying to figure out how I could enter into the fight to end the AIDS epidemic. And decided to go to law school. And my first year of law school, I was here in New York City at Cardozo, which is the law school for Yeshiva. Imagine an out gay Baptist minister at an Orthodox Jewish —
Ben: A New York story for sure.
Charles: Yes. A New York story for sure. In any case, I joined ACT UP New York while I was in law school, and the year before I graduated, Ginny Shubert had joined the Coalition for the Homeless as the director of the AIDS project, and she had filed litigation on behalf of homeless people living with AIDS and HIV, who at the time were in the mass congregate shelter system. She got a court order, ordering that the named plaintiff, Kenny Mixon, be moved out of the shelter and into at least a commercial SRO. The city appealed the decision, which stayed the order. And so a group of us went and did a sit-in in the Human Resources Administration commissioner's office and handcuffed ourselves to his furniture and refused to leave until the named plaintiff got housed. And he got housed. And out of that we formed the Housing Committee of ACT UP. Actually, the proper name was the Committee to Demand Housing Now for Homeless People Living with AIDS and HIV, because we really believe in short names. In any case, our second action was the day after Thanksgiving, where we did a sleep-in at the foot of the escalator that Donald Trump descended when he announced his campaign for president —
Ben: I did not know this.
Charles: And were arrested, sleeping on sheets with signs covering ourselves, demanding housing for homeless people living with AIDS and HIV. Well, the Coalition for the Homeless hired me to work as Ginny's legal assistant. There were about a dozen plaintiffs in the lawsuit, and I provided case management services for them while I was sitting for the bar exam and all the rest of that good stuff. After doing this for some time, David Dinkins had basically adopted our platform, then promptly repudiated it, you know, within 48 hours of his inauguration. We continued with the litigation, and we were deposing a white gay man who himself would later die of AIDS, who was the deputy commissioner who oversaw the HIV/AIDS Services Administration. And in his deposition he testified that homeless people were all either chronically mentally ill or chronically addicted to drugs, and consequently they were better off in the shelter where, quote, they would be less of a menace to others. And it turned out we had a housing committee meeting that evening, and I put forward that we needed to prove him wrong, and the best way to prove him wrong would be to set up an organization that could serve homeless people who were using drugs. And so that was the genesis of Housing Works. And very specifically, we came into existence and were the first supportive housing organization of our kind in the United States to house people without regard for their use of drugs and alcohol in the privacy of their own apartment.
Ben: And how did you pick the name Housing Works?
Charles: It was actually that very night. Basically, what this commissioner was testifying was housing wouldn't work for people addicted to drugs, and we wanted to send a message: no, exactly the opposite. Housing is what works for people who are using drugs, and we see that every day. You know, what I can tell you from our own research data is, when we move people into our supportive housing who are actively using drugs, within a period of a year to 18 months, about a third stop using drugs altogether or switch to something that doesn't interfere with their lives. So if you've been using opioids and you switch to smoking cannabis, it's obviously a huge difference what kind of impact that has on your life. Other folk decrease their use or regularize their use to a point where they're able to carry out all their activities of daily living. And then a third continue with very chaotic use, but they're doing it in the privacy of their apartment — not shooting up out on the street, sitting between cars on the street, not leaving syringes on the street, not engaging in the other so-called nuisance behavior that makes people shun homeless people who are living on the streets.
Ben: You know, Housing Works has a dual mission to end homelessness and HIV and AIDS. What's the connection between HIV and AIDS and homelessness?
Charles: So, at the time that we started Housing Works, it was estimated that there were some 12,000 homeless people in New York City living with AIDS and HIV. And so our original goal was to end homelessness for people living with HIV. We actually achieved that in 2016, when our then Governor Andrew Cuomo changed the state regs, with the consent of the city, to require the city to provide enhanced rental assistance or supportive housing to every single person living in New York with HIV who was eligible for public assistance. So all of a sudden, thousands of people, thousands of households, were receiving enhanced rental assistance or moving into supportive housing. In 2020, we took our first contract with the Department of Homeless Services, specifically to open a hotel, to house homeless people who were living with COVID disease. The Department of Homeless Services had issued a memo to all of their contractors — this was in late February of 2020 — telling them that they needed to check for symptoms. We didn't have wide access to COVID testing, and if a person showed symptoms of COVID, they were to be discharged, and they're not allowed back in until they had proof from a test that they did not have COVID. Of course, only hospitals had tests, and they were basically only testing people for COVID if they were looking for an admission to the hospital, which meant discharging thousands of homeless people, potentially with COVID, to the street. So we sent a pretty damning letter to the mayor and to the then commissioner of Human Resources. And he called me a few days later, said, because of your letter, we've gotten permission to lease as many hotels as we need to house homeless people who have symptoms of COVID or who have COVID, but we are not going to have operators. So of course, I stepped forward, said we would run one, and we opened a hotel with 170 beds for people with COVID disease. And that actually took us into the path of saying, okay, we've ended homelessness for people with HIV — could we end homelessness in New York City altogether? So that has now become a part of our core mission.
Ben: And, you know, when we think about leaders having impact, you think about being a clergyman, being able to leverage faith and ritual and belonging and belief. Think about going to law school and knowing how to file impact litigation or individual cases or work through the mechanisms of the law and government. You think about being at the bottom of an escalator with sheets on and protesting, or chaining yourself to a commissioner's chair in their office. Very different forms of advocacy and activism. You sort of know how to wield all of them, including the COVID hotels as an example, where you were seeking to be part of the solution, not just cast blame. I mean, one, how do you develop so many different forms of influence, and how do you know which one to use in which moment?
Charles: I like to say it's all advocacy. It's just in front of different judges.
Ben: Oh, well said.
Charles: So I truly believe that. In fact, if you ever go to an action where I'm anticipating doing civil disobedience, I will always be wearing my clergy collar. That's very deliberate, to say that what I'm doing is an act of faith. I feel like founding Housing Works was an act of faith. And actually, it's kind of interesting, because I came out as a gay man and left the ministry because, the church I was at, the minister of music was dying of AIDS. And he told me that praying for him, literally on his deathbed, wouldn't do any good, because God was punishing him because he was a homosexual. And so — that really tugged at me. I came out to him, and after we'd prayed together and I'd held him in my arms, I went straight to the church, walked into the pastor's office, said, I'm tendering my resignation. I'm coming out as a gay man, and I'm gonna do something about AIDS. And so for a long time I was angry at God, I was angry at the church, I was angry at AIDS for having taken away my ministry. And it wasn't until two or three years into running Housing Works that I was like, oh, this is what God wanted me to do. I didn't realize that everything I'd done up until that point had simply been preparatory for my true calling, which is what I've been engaged in for the last 35 years.
Ben: You know, I've been involved in Housing Works for some time now, and I remember going to one of your facilities and seeing the names of clients, you know, that had wanted their remains left there. And it's my understanding, you know, you are often the clergy that provides services.
Charles: Part of having a clergy hat is that I can actually officiate at those affairs. Which, you know, frankly is a meaningful way to connect with the community. We're all gonna die. The fact that we are not just this health center or this case management or housing organization, but a holistic community that honors people for who they are, even in death, I think is very important for folk.
Ben: And Charles, you know, I believe Housing Works is 1,200 or 1,300 employees and approaching $200 million annual revenue, and the largest stock of private HIV supportive housing in the country. So you're the chief executive officer. You have a big job. Why don't you just hire a chaplain to do some of these things? You personally choose to do this. Why do you continue to do this?
Charles: So, when we started Housing Works, it was very clear to us that we were entering what was going to become a booming industry. And so there were two things that we thought were important to distinguish ourselves. One was that we remain committed to advocacy, including direct action that we practiced as a part of ACT UP. And I still — if I go six months without getting arrested, I feel like I've done something wrong. With Trump in the White House, I haven't had to worry about that. Had plenty of opportunities to get arrested. But the other way was to ensure that we were staying in constant touch with the community. And part of that was that we put in place a job training program. So right now some 20, 25% of our staff are people who walked in the door as homeless people. And to me, that's very important. I love the idea that when you walk into our offices, the person at the reception desk is someone who maybe just a few months ago came in just like you, looking for assistance. But the other is personally staying connected. And so since 1996, I've actually lived in one of our residential facilities, so that I'm actually living with the people we serve. To me, that's just an amazing experience. It keeps me humble. It also brings reality to everything that we're doing. I have an open door policy. I want to spend my time with the people we serve, and so there's probably not a setting much more intimate, particularly for a group, than a memorial service or a funeral. That's when life gets very real, if you will, and the inevitability of our own demise. And I want people to know that when they pass on, assuming I'm still alive, I'm gonna be there to usher them through that process.
Ben: A lot of people probably haven't thought about what is a funeral for someone that was formerly homeless. It might look different than the funeral for the average middle or upper middle class person in our country. What does that look like?
Charles: So generally, who attends is the people who've been an important part of that person's more recent journey. And so that would be other consumers here at Housing Works, staff who've worked with that individual. At memorial services, it's a fairly unstructured process, where everyone is invited to share in whatever way they feel comfortable — whether it's a song, a poem, a prayer, or expressing a memory, a reflection. Can be quite humorous at times. It can also be very tearful at times. And then usually, once everybody's had their say, I offer a scripture, a eulogy, a poem, and a closing prayer to tie it all together, 'cause we do hybrid in-person and Zoom for these services. And what people may not realize is that often, as folk are speaking, I'm going into my eulogy and doing some edits to incorporate elements that somebody brought up that I might not have realized or had left out of that person's story.
Ben: So not only do you know law, do you know ministry — you're quite a contemporaneous, you know, speaker, right? To bring those moments in and to be very present.
Charles: You know, I grew up in the South in an evangelical church, and you never brought a scrap of paper into the pulpit with you when you were preaching. The whole idea was that you knew it. You were supposed to be an open vessel, and the Holy Spirit would just flow through you, and all those words would come out in exactly the right way. In truth, I would spend days carefully crafting a sermon in my mind, walking and speaking, figuring out all the important turning points in the sermon, et cetera, so that I could get up there and look like I was just being filled with the spirit, completely spontaneous. So that kind of extemporaneous editing comes a bit natural to the experience of my youth, if you will.
Ben: I wasn't expecting to ask this, Charles, but if we were to sort of have an x-ray on a sermon, what makes a good sermon?
Charles: Well, what they will tell you in homiletics is three points. A minimum of three points, no more than three points. That's the fundamental rule. But beyond that, it's really about telling stories. And what's really key is that the stories that you tell are resonating with the lives of the people who are sitting there listening to you. We tend to think of death as this horrible thing. Well, is it really? The fact is that if we're human, it's inevitable to our experience. We're all going to make that journey. And for some of us, that journey can actually be a relief. For others, it can be a painful passage. But we shouldn't just assume that death is the worst thing that can happen to us.
Ben: Yeah. The resistance to the inevitable, I think, creates a lot of torture in advance. I had a dinner with someone recently and I was talking about death, and he wanted to change the subject 'cause it was morbid. And I said, honestly, I said, for me, talking about death makes me feel alive.
Charles: Exactly. Exactly. Accepting that there are certain parts of our existence that are inevitable, and being prepared for that inevitability, is important to being able to live your life whole. You know, I seroconverted and —
Ben: And for folks, what is seroconversion?
Charles: So I became HIV positive, and I noticed very quickly the symptoms, went in, got tested, and in a matter of a week, the doctor called me in to tell me I was HIV positive. And I was like, I do not want this virus in my body. Fortunately, there was a clinical trial that was testing hitting newly HIV positive people early and hard with antiretroviral drugs. And I got in that clinical trial, and you would take the drugs for six months, and they would take you off and see what happened. I rebounded, did another six months, rebounded again, and they threw me out of the trial. But my doctor went to the insurance company, said, look, this guy's been virally suppressed on antiretrovirals for a year now. We shouldn't take him off those. And fortunately, the insurance company agreed. And so I've been virally suppressed for 25 plus years. I am very unlikely to die of anything related to HIV. Meanwhile, I could step out into the street and get hit by a car or a bus, whatever, in an instant. And all the beautiful plans I have for whatever's happening next week are just going to be gone. And that's the reality of all of our lives. And we ought to build that into how we plan and how we live our lives.
Ben: And Charles, just for our audience, do you mind sharing how old you are?
Charles: Sure. I'm 70 years old. As a matter of fact, I can proudly report I turned 70 in February, and two weeks ago I celebrated my fourth run of the New York City Marathon as a sort of a victory run for having achieved this ripe old age.
Ben: And earlier, Charles, you mentioned getting arrested every six months or so. Do you have a rough sense of how many times you've been arrested for civil disobedience?
Charles: You know, I stopped counting at a hundred, and it's probably at least triple that at this point. So —
Ben: And in arrested, I mean, that's like in handcuffs arrested?
Charles: Yeah, in handcuffs, arrested. That's the way they do it.
Ben: So it is quite an act of courage. It's one thing to write a letter to the commissioner and make an argument, or to file a lawsuit, or maybe even to protest, or now people, you know, put up a social media post. If people were to have a body cam and they were observing someone practicing civil disobedience even today, what does that look like, and what's the experience like for you practicing it?
Charles: I'll actually tell you about my first act of civil disobedience. A little bit humiliating and a bit of a funny story. So, I was a counselor when I was in divinity school at Yale to a group of Yale undergrads, and they came together and they wanted to protest the then new mandatory registration for the draft. We had stopped registration for the draft after Vietnam, and Ronald Reagan put it back in place. They wanted to do a protest. So this was in New Haven, Connecticut. We needed a federal building. Well, of course, the post office. So a group of us — seven students and myself — we chained ourselves together, walked over to the post office, wrapped the chains through the main entrance to the post office and put on the padlock and locked it. And, you know, there we were. We hadn't thought about the possibility that there were other means of egress into the post office. The mayor ordered the police not to arrest us. So the day came and when the post office closed, and we were still standing there chained to the front. Disobedience done. Exactly. We had to dig around until somebody finally found the key to the padlock, to the front door, and, very humiliated, walked ourselves back across the New Haven Green to the Yale campus, still all chained together, because we'd left the keys to the locks chaining us together in Dwight Hall. Civil disobedience can be different depending on what venue you do it in. If you get arrested inside the United States Capitol Complex, it's usually a fairly routine procedure. I got arrested two weeks ago sitting in Susan Collins' office, protesting her lack of action to get the director of the Office of Management and Budget to spend $4 billion. You know, you get arrested by the Capitol Police. You would either get given a summons, which means you have to put in a court appearance, or more often than not, you get what's called post and forfeit. So you have to put up a $50 fine, which you forfeit, and the charges go away. In other jurisdictions, you might spend a night in jail. So if I got arrested by the police in the District of Columbia, they would undoubtedly put me through the system. So it's sleeping in a cell all night, spending most of the rest of the day in this big holding pen behind the courthouse, appearing before a judge, doing a urine analysis, and then being freed, for whatever process they put you through. A couple of us had disrupted a reception that then Mayor David Dinkins was holding in Gracie Mansion, and he wasn't pleased. And so we ended up sitting handcuffed in jail for 48 hours before we were released. But that's actually the longest I've spent in jail. I have one misdemeanor out of all of those arrests, and that was for a sit-in that I did in George W. Bush's reelection headquarters. I actually handcuffed myself to a chair that happened to be a chair with wheels on it, so the police literally rolled me out of the office.
Ben: And at Housing Works, I know part of the culture for your staff is to volunteer or have the option to participate in advocacy. One form of it is the civil disobedience. It can be other different things.
Charles: It's actually written into our union contract.
Ben: Oh, I didn't know about that part. Okay.
Charles: Yes.
Ben: What's written in there, since you're a lawyer? What's in the contract?
Charles: We just renegotiated the contract, so I don't know if any of this has changed in the renegotiated version of the contract, but in the one that preceded, it was three in-person events a year and at least two electronic advocacy communications a year. We don't require anyone to engage in civil disobedience. That's completely voluntary. But we do require that everyone participate in advocacy. For us, it's a core part of who we are as an organization, and just like seeing ourselves as a healing community, it's one of the things that distinguishes us from your average healthcare or social service organization.
Ben: I remember over a decade ago, when we were up at the Tarrytown house and, you know, codifying the community values of Housing Works. And one of them was all in, and it was the idea of bringing your full self to the fight. And fight against HIV and AIDS and homelessness — and spending 48 hours in jail is about as all in as you can get. And you know, for folks that join your organization, whether they're in the union and collective bargaining or they're just, you know, at-will staff, if they wanna do civil disobedience, how do you prepare them for that experience?
Charles: So we routinely offer trainings in civil disobedience, which covers pretty much all of the nuts and bolts of what's involved in it, including how to dress for jail. Okay? One of the things that's important to let people know is they're likely to take your belt away. So wear pants that are tight enough where they'll stay up on their own, so you're not walking around the whole time you're there holding your pants up. They're likely to take the laces outta your shoes. So if you have loafers that don't have laces, that's probably a more comfortable way. Even in the summer, bring a light jacket, because if you end up spending the night, undoubtedly they're gonna have the AC on, so you're gonna get really cold. And even if you don't get cold, it's nice to have something you can use for a pillow. We talk with people about what it's like to be handcuffed — you know, the difference between plastic handcuffs and metal handcuffs. We talk about how to talk with the police, how to negotiate with the police, how to engage others with the police if the officer who's arresting you isn't listening, and how to bring shame and embarrassment. We talk about how to go limp, if that's something that the group decides that they want to do as part of their act of civil disobedience. We talk about what type of documentation to bring with you. So if you've got a driver's license that's got your correct address on it, that's what you need. Otherwise, bring some other type of official ID and bring an official letter. It can be a letter from Verizon. It can be a letter from Con Edison. Bring a letter that's got your proper address on it. So we go through all of the experience of it, and then we role play so that people get a sense of what it feels like. So we do those trainings pretty much on a quarterly basis, and then also a training before every action. And then we bring people together who are going to participate in an action and plan it together. So it's not me as the CEO saying, this is what we're gonna do. It's people talking about what they're comfortable with and what that action should look like. Now, interestingly enough, you'll find that the police, depending on where you're at, can respond in very different ways to your actions. So, one of the things that we learned earlier this year is the DC Metro Police, whether it's their lack of love for Donald Trump or whatever, have basically made the decision that they are not going to arrest people engaging in civil disobedience unless they destroy property. So that has really changed our thinking about what we can get away with to send out our message, and knowing that there are options that don't necessarily inevitably lead to an arrest.
Ben: One more question. 'Cause, you know, you think about the civil disobedience as a form of power to get, you know, attention or awareness or to drive something. But I also think about — you know, that you talked about Housing Works could have a cannabis cafe. And you said this 10 years ago, and I was around some of your staff when this was said, and other donors, and people thought, oh, another crazy Charles idea. But you wound up getting the first license in the state of New York for a cannabis facility, and even impacting some of the way that legalization was rolled out. I would assume that was not achieved through civil disobedience. Is that correct?
Charles: That is absolutely correct. Back in 2015, 2016, when the governor's office was first negotiating a cannabis legalization — initially it was just a decrim and then became a legalization bill — the health legal staffer who was working on the legislation had rightly proposed that they prioritized people who had been incarcerated for cannabis-related offenses in New York State. And I came to him with this suggestion that we also allow the same early licensure for organizations that serve people who'd experienced incarceration for cannabis-related offenses. And he agreed. And that's how we ended up being in the first batch of seven entities that were licensed to begin the operations. The funny story there is, the staff had approved our license, but our application still had to go before the board. And the Saturday before Thanksgiving, I had dinner with the chief of staff and his wife, and over dinner he said, Charles, I need a favor of you. He said, Governor Hochul held a press conference in August where she promised that there would be two dozen licensed stores up and running by the end of the year, and we still don't have any. Is there any way you could open your store by the end of December? And I immediately texted our president and our chief financial officer and said, hey guys, we gotta get our store open. And within two weeks we had a lease. We did a very quick build out, bought our product, hired up our staff, and sure enough, on the 30th of December, 2023, we opened the first cannabis store in New York State.
Ben: Congratulations. I believe the management team was mostly folks that were formerly incarcerated based on cannabis and drug laws. Is that correct?
Charles: Yes. Yes.
Ben: So, you know, and again, I think that that agility to move quickly, the relationships to lobby and suggest some of these things, are very much about being savvy and clever and knowing to work within the system. And certainly, you know, being chained to a chair is a very different method. And the last question I have is just, how do you pick which method of power or influence?
Charles: You know, it's interesting — even with your "friends," and I guess your audience can't see the air quotes that I put around that. Oftentimes an act of civil disobedience is a very public gesture. So even with a friend who wants to do the right thing but is feeling constrained, doing the public gesture offers the excuse. So it's not just something that — a tool that you pull out when you think you're not going to be heard. It's a strategic tool. But often, civil disobedience is a tool that you use when you want to make sure that your message is getting heard. Otherwise, I'm a nice guy, basically. And so, you know, I spend a lot of time in Washington and Albany, at City Hall, developing those relationships, those friendships, knowing who is going to be our ally, who's going to be our champion. Being able to have those relationships and have people carry your agenda forward on your behalf is obviously a more successful way than having to arrest your way into getting people to do what you want them to do.
Ben: You're the antithesis of a one-trick pony. So —
Charles: Nimble, nimble.
Ben: For future leaders, in the spirit of paying it forward, what's your advice to the next generation of leaders and activists that wanna drive change?
Charles: Just do it. Just do it. It really is that simple. I think all too often we excuse ourselves saying, I don't have the skills, I don't have the temperament, I don't have this, I don't have that. None of us comes into the world of change making with all of the answers, all of the strategies, or even half of what we need or need to know to do it. The important thing is being open and having the willingness to learn as you go, and that includes knowing that you're gonna make mistakes, and being able to make those mistakes, learn from them, and keep plowing forward. If you see something in the world that isn't going well, do something about it. One of the things that I make a point of doing is ensuring that every day when I walk outta the house, I have single bills on me. I'm not gonna pass a homeless person and not give that person a couple of dollars. So even with that — I don't save the world by giving somebody a couple of dollars. But maybe I've bought them a cup of coffee or their next meal. What's most important is I've communicated to them that there's someone walking past them who cares about what's happening in their lives. So even the smallest gestures become important. But then, when you think about what you can pull off with the small gesture, just think about what you can accomplish by doing something larger. I think the corollary to that is, don't ever be afraid of failure. A lot of the things that I've tried to do didn't come off so well, but I learned something out of that experience, and more often than not, the message got through, even if it didn't look as pretty as I wanted it to. The last thing I would say is, listen to the people who you say you're trying to help. All too often we have our own ideas about what help looks like. We have our own ideas about what the solutions are, and we don't necessarily listen to the people who are ostensibly the beneficiaries. And frankly, in my experience, they know ever so much more what they need than I could even imagine.
Ben: Well, listeners — Charles King, CEO and co-founder of Housing Works, clergyman, activist, lawyer, and all-around badass. Thanks, Charles, for joining.
Charles: Thank you. It's good to be with you.
Ben: Thanks for joining me this week on The Lift. For more info on what you heard in today's episode, visit our show notes. You can find bonus resources at pilot.coach/thelift. If listening to The Lift today was a good use of your time, please share it with a colleague, a friend — I don't know, your ex, your mother, anyone. Don't let good advice die with you. And for those of you who like to earn a little bit of extra credit, leave a comment on Spotify. We'd love to hear from you. The Lift is produced and edited by the team at editaudio. This episode was produced and edited by Ali, with additional production support from Victoria Marin. Our production manager is Kathleen Speckert. Our executive producer is Steph Colbourn. A special thanks to Korey Rich and Beth Gatsik. There's only one way to go — upward.
