Don't mistake consensual heartbreak for naïveté
Vivianne Castillo taught me that hope is a discipline. Not a feeling that arrives when circumstances warrant it, and fades when they don't. An active practice: a choice you make, repeatedly, and often against the mainstream interpretation of the evidence in front of you.
The imaginative work of hope is to see the world as it could be, unconstrained by the material realities of the present. When it's working well, people move beyond the imagining: they map the path from here to there, articulate their own piece of it, put actual effort into making it, and find ways to bring others along their own path to the same endpoint. That's what it looks like when hope is functioning. When the discipline creates something.
What we talk about less is what that discipline requires at the base. Choosing hope means looking the inevitability of despair and betrayal when choosing to work within broken systems directly in the face, and doing it anyway. Not naïvely. Not without knowing what's coming. With full knowledge of what you're signing up for, and without the protection of being able to say you didn't know.
How I learned the lesson
I've been doing some flavour of social justice-oriented work since about 2013.
The start was really in graduate school, dropped into a cohort designed to keep Black, Latine, and Indigenous students from leaving: something the programme had an aggressively mid record of achieving, though the experience itself changed the direction of my life. Conversations in that room turned experiences I had individualized into the beginning of a social consciousness and a lot of curiosity about how my identity vs. positionality issues fit into that work. A presentation a fellow student gave in the Political Science department on unconscious bias was what set it off in a real way: the specific combination of my hyperfocus and justice sensitivity clicking into place, and locking in. That fusion still animates most of how I move in the world.
Seeing structural barriers clearly is not always a comfortable gift. At Stanford, it eventually meant I could see exactly what was happening around me: a female department head whose attitude was, essentially, it was hard for me, so it'll be hard for you too, get better at sucking it up. A comparative politics professor who quietly stole a Black graduate student's research idea and handed the project to more senior (non-Black) students. A methods professor who didn't notice — or didn't care — that his White male TA had arranged, via refusal to do any work, for his Latina co-TA to carry the full workload, which nearly made her fail her own classes. And a handful of professors who told me that my research interests were outside their area, while simultaneously agreeing to supervise White men with... comparably divergent interests. So I quit.
I got a job in tech, because I needed to pay rent, the industry was there, and I had always had an interest in tech (but had gotten sick of being the only girl in the room). I was genuinely enthralled by the promise of meritocracy, and genuinely hopeful. I picked up a second shift: leading employee resource groups, running original research on bias in talent processes, doing enough of that work to eventually make it my full-time job. Atlassian scooped me up in 2015, after Mavengate, and a lot of what happened from there is already documented somewhere on the internet.
What's not on the internet is how many times my heart has been broken doing this work. The sheer despair I’ve pulled myself out of.
The specifics don't matter and I'm not going to provide them. What does matter is this: nearly every leader I have worked for — the genuinely good people and the arrogant, privileged jerks alike — has broken my heart at some point. And they've done it because they are embedded in a system designed to produce exactly that outcome. Most of them are trapped inside their own economic and political incentives, which override, at least sometimes, at least partially, what I know from direct experience are extraordinary internal moral compasses.
(Let's be honest: there are also a fair number of psychopaths in the mix. That's a different conversation.)
At some point, I reached a junction. I could quit again. Or I could accept that this feeling, this specific flavour of betrayal, was going to happen again and again, and make my peace with it.
I am both stubborn and a pragmatist. I did the arithmetic: if I do nothing, the probability that the world gets meaningfully better is zero. If I put most of my effort into it, those chances might still be very small. But they'd be better than zero.
I decided to look despair in the face and say: Alright. Give me everything you've got. And I can tell you honestly that this has helped.
Building the cushion for despair
If you know something is coming, you can plan for it. That's not defeatism: it's just operational planning and risk management.
I've had the enormous luck of having resources of many kinds to draw on, and the cushion I've built is partly possible because of that luck. The first layer is community, and I'd distinguish two kinds that serve different functions. One is people who know the struggle: people who are doing this work or adjacent to it, who can hold the specific weight of it and offer something closer to real empathy than sympathy. The second is people who have nothing to do with my work but share my values: people who ground me in who I am outside of what I do, who I can show up to as a whole person rather than a professional or a practitioner. Both are essential, and they are not interchangeable.
The second layer is somatic and psychological: therapy, and a solid routine for when this work activates my nervous system beyond what my normal routines have planned for (it’s, at minimum, supplements, massage, gravity blanket, soothing sounds, and darkness). I have an EMDR person on call. I have a significant trauma history, and this work connects to it in ways that are specific and, once I understood them, pretty manageable. The key word is routine: having something pre-built means I don't have to construct it in real time, when I'm already dysregulated. The basics are handled all of the time because the emotional load never really drops: I eat healthily, am pretty rigorous about my sleep routine, and move and lift things in ways that mean my system has a good baseline.
The third is a system for metabolising harm. Most of what I teach and write has come from something going wrong: I saw the failure, I thought through what a better approach would look like, and I wrote it down. Writing it down and sharing it as widely as I can feels like a more reparative response than the alternatives. It gives the harm somewhere to go. It converts it into something that might, in some small measure, prevent someone else from inflicting it or absorbing it.
This is also, for what it's worth, the reason I largely don't namecheck people or organisations when I write. The problems I'm writing about are structural, and pointing at a single instance of them almost always causes a lot of hand wringing about a symptom rather than getting to the source of the problem. And the internet has become a genuinely wild place: I don't want to be responsible for harm I could prevent. What I will say is this: if I know that you've done something harmful, there is probably a doc with your name on it somewhere in my writing archive for inspiration when I feel wordy. So I might write a character profile of you, but your name won’t be on it. You won’t see me go nuclear, because that distracts from the long-term aim of the work.
The fourth layer is daily practice. I spend time every day imagining the world that could exist: not strategically, just imaginatively, the way children do before they're taught to call it unrealistic. And alongside that, I do things that bring me genuine joy, which are nearly always the simplest of things. I have a particular coffee mug I bought on a trip with someone I love, and something about drinking from it in the morning is, improbably, part of the infrastructure. The little joys give me a tiny sliver of the experience of the joy that could exist if we lived in the world I’m trying to help build.
Don't call me naïve
My earliest memory of learning about the unfairness of the world is when I brought an issue I was distraught about to my dad. He looked at me and said “Aub, the world’s not fair.” And my response was “Well that is a lazy thing to say!” Since then, I’ve been called naive more times than I can count.
But it’s not naivete that drives me: it’s courage in the face of truly tough odds.
To see those odds clearly and choose to act anyway is a specific kind of bravery that doesn't get enough credit, partly because it looks, from the outside, like someone who simply hasn't understood the situation. I understand the situation. I have spent over a decade inside it, absorbing what it costs. So have the brilliant people I work alongside: we know what the incentives are, and how entrenched they are. But we also see, every day, people who are planting seeds of organisations that understand that preserving the humans inside them is a part of, not a hindrance to, their strategy to win. Who define “winning” not as the founder being a bajillionaire and having 15 houses, but everyone contributing having enough. And more and more of those seeds are flowering. The joy I imagine is accessible now in pockets and just needs a bit of nurture.
The argument for continuing is not that success is likely. It's that doing nothing guarantees failure, and doing something doesn't. That margin, as small as it is, matters. And when more people push in the same direction, in their own ways, with their own pieces of the problem, the odds start to move. Not easily or simply, but they move.
That’s the math I do every day.
