Failure: A Talk in Five Acts

Last week I was just about to give a keynote at a conference on ending homelessness when I realized I needed to rewrite the entire thing.

I didn’t plan to give this talk.

The night before a conference last week, I was sitting at a dinner, wrestling quietly with some of what’s been weighing on me lately—job applications going nowhere, the exhaustion that comes from pushing systems that don’t want to move, the feeling that I’m supposed to know what I’m doing even when I don’t. I ended up in conversation with someone I admire—a veteran in the field with a continent spanning career and all the success you could ask for—and asked about an old economic development project he’d worked on. Without hesitation, he said, “Oh, we messed that up. Spectacular failure.”

There was no performance to it. No spin. Just honesty. And I was struck by how rare that felt. Not the failure itself—we all fail—but the willingness to name it without flinching. To say: we tried something, and it didn’t work.

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The clarity of that moment struck me. I asked him what he’d learned. And I found myself wondering—what would it look like to actually index the learning that emerges from all the times things don’t go as planned?

I went back to my hotel room and rewrote my keynote. This is what I said the next afternoon.

Act I: America Has a Problem

We live in a culture terrified of failure—afraid to admit it, learn from it, or be seen experiencing it. This fear paralyzes progress. During the time I was Director of the SPARC project—Supporting Partnerships for Anti-Racist Communities—I often said that a nation unable to confront its shame cannot move past it. America’s categorical denial of its racist past prevents us from building an anti-racist future. It's why books are banned and curriculums censored. Those restricting history know an informed person would reject racism, so they present failure as glory to children unable to question it.

But our fear of acknowledging where we have failed has grown so vast, so all encompassing, that there is almost nothing left outside of it anymore. The notion that we could successfully reinvent America, that we could rewrite its narratives and redeploy its wealth and power, feels laughable when left leaning conversations often devolve at precisely the moment that the risk of failure enters the discussion. To attempt solutions is to risk failing to solve. America’s problem, or one of them, is that no one is willing to admit that a thing they’ve tried isn’t working. Or worse, didn’t work. To fail has become personal. Permanent. You don’t fail, you become a failure. And are often treated as such by whatever field you worked in.

I think it’s time for the homelessness response sector to admit that there have been some failures. Homelessness is rising, and public support is declining. We're not winning our political or fiscal battles. That’s failure.

Yet, failure often precedes success. As Winston Churchill said, “Success is the ability to go from failure to failure without losing your enthusiasm.” True innovation requires risk, and taking those risks means accepting the potential for failure. Moreover, when we fail—if we do it right—we learn something. If we index the knowledge that is gained from every attempt we don’t have to live like Icarus. Or worse, Sisyphus. Naming failure isn't about shame, it’s about unlocking future possibilities.

Act II: What I’ve Learned from Failing Spectacularly in Very Public Settings

So let me tell you two stories about times that I really didn’t nail it—and what I learned.

The first is a story from when I founded the National Innovation Service (NIS) with a small team focused on creating true systems transformation in communities tackling complex policy issues. And while the team and I shared the goal of creating wide-reaching impact, I mistakenly equated impact with visibility. Driven by anxiety and ego, I spread our organization too thin, compromising the founding vision by staffing up too rapidly and without the appropriate attention to culture or organizational design. Decisions prioritized our visible presence over coherence and depth, causing extensive harm internally. I learned that while being seen doing important things may indeed lead to more opportunities to do the things you love, letting what is essentially a marketing decision drive everything will only create deep flaws in the final product. Reflecting on this personal failure I can now see it much more clearly in the behavior and dynamics that animate our national technical assistance ecosystem. And yet, NIS reshaped the national conversation on systems transformation and housing justice. In failure, fruit. And where there’s fruit there are seeds to be planted—knowledge gained through not getting it right.

The second story I want to tell you is about my time as the inaugural CEO at the King County Regional Homelessness Authority (KCRHA). Here I failed in two core ways. The first is that I rushed. Almost everything. Under intense pressure from regional officials to have it all put together yesterday I rushed critical systems—hiring, internal processes, and community building. Trying to do two years of work in six months created flaws in, for lack of a better term, load bearing structures that would later collapse under the weight they needed to hold. But my second failure was more severe, and farther upstream. I committed the cardinal sin of nostalgia. Like many of us who have been working in homelessness for a long time I remember when my work wasn’t on the front page. I remember when, although stressful, my work was not political. And I made the mistake of thinking that time was better—and that we could return to it. So I attempted to design a system that would insulate the agency from politics by creating a complex board structure. Overly complex many would say. But one thing I’ve never been accused of is simplicity. However, attempting to depoliticize homelessness amid a growing international politicization was unrealistic and that complex board structure meant to shield us from politics only gave politicians the cover they needed to make their interference covert, damaging our efforts without having to take accountability. Nevertheless, KCRHA achieved significant successes, developing the nation's leading emergency housing voucher program, and pioneering encampment resolution and outreach strategies that advanced the field nationally. Fruit, seeds, etc.

Act III: What We Know Because We’ve Failed

We often talk about how we know how to end homelessness— and this is certainly theoretically true (it really is just housing and supports and we know how to do those things) but is just as clearly flawed in practice. Knowing theory differs from applying it effectively, particularly under pressure. The homelessness sector suffers not from ignorance but a deep and abiding unwillingness to acknowledge where we don’t have the strategies necessary to implement our work during this time when elected leaders lack political courage. Ignoring these realities yields temporary solutions and false senses of security and accomplishment. Here's what I think we've truly learned from failure:

1. Housing Is the Solution, But Not Everyone Tells the Truth About Housing First

Housing first approaches are the right way to address homelessness. They yield significantly higher positive results than other approaches. Permanent Supportive Housing effectively supports over 80% of individuals with complex needs. Vouchers, if well-implemented, rapidly house economically disadvantaged populations. Ethical encampment resolutions that lead with housing avoid displacement and trauma. Yet, we've allowed too many programs to claim the mantle of "Housing First," with functionally no fidelity to the model, resulting in the erosion of public trust by avoiding honest critiques of poor practice. We’ve let people call themselves housing first without DOING housing first or saying they were resolving encampments when they were simply sweeping people. We’ve let people coopt our language without having to use our methods. That’s part of why public support is eroding. It’s not because Housing First failed. It’s because we failed to tell the truth about what we were seeing because we wanted to be nice.

2. Criminalization Tempts but Doesn't Solve

Arrests and sweeps worsen homelessness—leading to prolonged instability, poorer health outcomes, and compounded legal challenges. But our opposition is one note. We are against things without acknowledging the obvious: encampments are bad. No one should have to live outside so the counter strategy to criminalization cannot be nothing or indefinite waiting. Our opposition to things that don’t work must be rooted in proactive, scalable solutions as alternatives.

3. Shelter Alone Solves Nothing

Shelter availability crises—like the ones we see in California or Connecticut—highlight system inefficiencies, not just bed shortages. The failure lies in neglecting exit pathways: affordable housing, skilled navigation, and proactive resource alignment. We mistakenly believed the homelessness response system alone could solve broader housing market issues and have been too slow to bring housing justice paradigms into our broader work and to build the coalitions that will sustain it.

4. Temporary Funding Isn’t Real Funding

We’ve built entire interventions on short-term funding. We can’t afford the illusion that temporary grants are durable solutions. The public sees the gaps. The people in those programs live them. And every time we stand up a program we can’t sustain, we make it harder to get people to trust the next one. These temporary solutions set us up to fail. Rejecting unsustainable funds, even when difficult, preserves program integrity and public trust. Perhaps it is because of the fierce urgency of our work or because so many of us come from housing instability and poverty ourselves that we’re always ready to turn a nickel into a dime. But we have to say enough is enough. If it will take three years to do something and we are offered one year of funding then we weren’t offered the funding necessary to accomplish the goal.

5. Politics IS the System

Homelessness work is inherently political not due to visibility but because it is intimately connected to racism, the tax code, land use, and poverty. These are political constructs in America. Ignoring politics doesn’t remove its influence—it empowers covert sabotage. We must embrace political engagement as essential to systemic change.

Act IV: All Power to the People

I’ve spent a lot of time working (and failing) to build broad coalitions within the homelessness sector focused on equity and justice. In some instances those coalitions have flourished and become powerful enough to shape discussion about resources and strategy. Others have died or withered away. In those failures I have drawn one critical lesson about our work: we almost always work alone. And building alone means losing alone.

We've allowed homelessness work to become isolated from broader movements. Our lack of diverse, enduring coalitions leaves us vulnerable. Our nation’s working families, immigration, labor, disability justice, racial justice, and gender justice movements offer strategic alliances we must engage deeply, not superficially. Without strong coalitions, even our best efforts are undermined. We must build these coalitions not just at the national level but at the state and local levels as well. Ending homelessness is the product of a more equitable and more just America. One that centers racial and housing justice. We cannot get to that America alone.

Act V: The Responsibility of Survival

I want to end by building on that note of not going alone, because we cannot survive alone. Ultimately leadership is not about having never failed. Leadership is about being willing to get back up again after you get knocked down. But where Churchill didn’t have the whole picture is that while we might get knocked down alone, we get back up together. And we have to get back up. To move through the failure, through the harm, through the exhaustion—and still choose each other. Still choose the work.

I know this moment is hard. I know you are tired. I am too. But if you're still here, then you already know how to survive a moment that was not meant to be survivable.

I want to end by briefly touching on my own lived experience. I’ve couch surfed, I’ve been hospitalized for mental health issues twice, and I continue to navigate those issues today. And what I know is that, at this point in my life, I have more evidence that I will survive what’s thrown at me than I have to the contrary. I have more evidence that we will get back up than evidence that I won’t. I have more evidence that we can learn from our failures, be sharper, more thoughtful, more inclusive, more deliberate the next time then I do that we will just be Sisyphus, pushing that same boulder, day after day, year after year.

I have this evidence because, in my low times, in the times like the time we’re having now, I’ve never been truly alone. I’ve always had community. Sometimes just one person, sometimes 600 people like we have today. But my failures have taught me that as long as I’m not alone I can get back up. We can tend to our wounds of ego and pride, we can tend to our very real hurt as we see those we love hurting because we weren’t able to accomplish something important. And then we can steady ourselves and begin again. Audre Lorde wrote: “Caring for myself is not self-indulgence, it is self-preservation, and that is an act of political warfare.” I think about that often—how survival is its own strategy, how tending to each other is rebellion, how staying in the work can be the most important form of refusal we have in the face of powers that would seek to destroy us.

If you’ve heard me speak before you’ve heard the story of how when I was being discharged from the psych unit one time a nurse pulled me aside and said, “What happened to you isn’t your fault. But what comes next is your responsibility. And it’s not fair. But it’s true.” I tell that story every time I speak because I’ve never ever stopped thinking about it. I did not make this country. None of us did. I was born into it by chance and I didn’t choose to shape it this way, and nor did any of you. But I am responsible for it. I am responsible for what it will become next.

James Baldwin told us: “The world is before you and you need not take it or leave it as it was when you came in.” We are not what we have inherited. We are what we decide to do with it. We are what we refuse to accept. We are what we are still trying to build. Through failure and success.

So let this be our work: not to pretend we have never failed, but to insist that even when we fail we are still worthy of the fight. To take those failures and make new more fantastic futures. To lift each other up and begin again. Now. Especially now.