The Questions That Wouldn’t Let Me Go

Me, in my office, mid–deep dive into research, startup overwhelm, and asking way too many questions at once. The Flip4Good origin era.

It wasn’t a decision. It was a disruption—quiet but undeniable.

The idea was already there. And then came the questions. They looped constantly. They filled pages. They kept me up.

It wasn’t anger at any one place or person. It was deeper than that—this pressing, unresolved thing I couldn’t let go of.

Why do we think it’s okay for people to live in spaces like this?

Do we assume they should just be grateful to have a roof?

Where’s the dignity in that?

What about care? What about choice?

I started questioning everything. The structure of transitional housing, how it’s funded, what makes it feel temporary, who gets access, and why the bar is so low for physical space. None of it looked like it had been designed to support healing or stability.

I didn’t know anything about housing or homelessness. But I knew how to learn. So I did what I always do when I’m in unfamiliar territory: I buried myself in it. I had just discovered ChatGPT and used it obsessively, alongside every article, research paper, database, and white paper I could get my hands on.

I dumped every question I had—every search, every finding—into a single Google Doc. It maxed out at 254 pages. #RIP

And one of the first things I learned? People living in transitional housing are still considered homeless. The government calls it “sheltered homelessness.”

That stopped me in my tracks.

Like a lot of people, when I heard the word “homeless,” I thought of tents. Encampments. People living on the street.

Not families in apartments trying to rebuild. Not places with locked doors and working kitchens.

But even with a roof, it’s still considered homelessness—because it’s still temporary. That shift changed everything.

And the deeper I went, the more obvious the gap became: design was missing. Transitional housing was being discussed in terms of logistics, services, compliance. Not how the space made people feel.

Some of the questions I found myself circling back to:

What does it take to get into transitional housing?

What role does environment play in someone’s ability to stabilize? How does it affect children?

What’s the emotional impact of receiving secondhand items when you’re trying to rebuild?

What messages does a space send—intentionally or not?

How many transitional housing facilities even exist in California? Nationwide?

How many people live in these spaces every day?

Why are most units decorated so poorly?

Where do facilities get their furnishings?

What would it actually take to raise the bar?

I went down every rabbit hole I could find—funding, policy, public health, childhood development, architecture, behavioral psychology. And all of this happened before I had ever even heard the phrase “trauma-informed design.”

And when I finally did, it felt less like a discovery and more like a remembering.

Maybe that’s because I had already lived something that made it make sense—even if I didn’t have the words for it yet.

Around age seven, my mom lost everything. We became homeless—but I didn’t know that’s what it was.

What I knew was that we were moving into my grandpa’s house. He had a pool. My grandma stocked the pantry with good junk food, and my mom was a pseudo health nut, so that felt like a win.

That was my understanding. Not housing loss. Not instability. Just: new house. Pop-Tarts. Pool.

But looking back, I also remember something else.

Once a month, my mom would take me and my older sister down to Skid Row. We’d pass out brown bag lunches with a sandwich, a piece of fruit, and a drink. She never framed it as charity. It was just something we did.

At the time, I didn’t put it all together.

That we were technically homeless. That the people we were handing lunches to were homeless.

That there were different ways homelessness could look—and feel.

I didn’t have the language for any of it. But I think that’s part of why this stuck.

These weren’t abstract, academic questions. They felt personal. Urgent.

I was frustrated when I couldn’t find the data I needed. Angry at the conditions I kept reading about.

But more than anything, I was energized. I knew the work mattered. I felt it in my body.

Even when I was overwhelmed, I never doubted the idea. I was clear. I was ten toes down.

But clarity didn’t mean ease. It came with pressure.

I’ve never wanted to run a company. I’ve never wanted to lead. I’m a builder-operator.

I thrive behind the scenes—making the thing happen, solving the puzzle, holding it all together.

Not being the public face. Not pitching. Not having to explain why it matters.

And yet here I was—building the thing and defending it.

I couldn’t just make the magic. I had to represent it. Translate it. Fight for it.

Still, through all that research, all that writing, all that planning, the most important question hadn’t even occurred to me yet. That wouldn’t come for nearly two years:

What if design was the intervention?

That shift in framing didn’t arrive until a January 2025 call with McKinsey + Company—after we’d already launched, fundraised, flipped a unit, and built a model from scratch.

But in this early chapter, I wasn’t trying to prove a thesis. I was just chasing the questions.

I wanted to understand why housing didn’t feel healing—and how to change that.

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