Staying with the Trouble

What Seven Conversations Taught Me About Trust, Systems, and Finding Your People

Dec 04, 2025

I didn’t notice the patterns until I sat down with my morning coffee to reflect on all the conversations at once.

A medieval literature scholar and a startup marketer. An intuitive coach and a branding executive. A higher education researcher and a trauma-informed yoga instructor. An executive coach. On the surface, these individuals had little in common. Underneath it, though, they all are living out - and wrestling with -variations of the same question:

What do you do when the systems meant to help are actually causing harm?

Every one of them had experienced a form of isolation. It wasn’t loneliness exactly, though, of course, sometimes that too. It was something more structural. They all experienced a moment when the systems or relationships they depended on failed to hold them up. Call it betrayal, burnout, or displacement. The phenomenon may cause different symptoms, but it is grounded in the same underlying condition.

Those who found sustainable paths forward didn’t just “find their people.” They found specific forms of alliance or practices for staying together through difficulty that our culture has largely forgotten. Such transformation requires us to hold two things at once: First, clear-eyed recognition that many systems are not broken but working as designed and designed badly. Second, a genuine belief that transformation is possible, even when the evidence is scarce.

That’s a hard tension to hold. It’s easier to tip into cynicism, to say nothing will ever change, so why bother? Or we veer into naive optimism, pretending the systems are basically fine and need tweaking around the edges. The guests I spoke with over the past few months weren’t doing either of these things.

They were doing something much harder. The scholar Donna Haraway calls it “staying with the trouble,” or the practice of remaining present to difficulty rather than fleeing toward false hope or collapsing into despair.

This is what hosting Season 2 of Trust Be Told taught me: Not just that systems fail, but that isolation is how those failures land in our bodies. And not just that we need each other, but that we’ve lost the practices that make enduring togetherness possible.

Success and Sustainability Aren’t The Same

Kevin McClure has spent years studying what happens to people who work in higher education, specifically, what happens to those who care most about students. His new book, The Caring University, highlights what he calls the “turn and burn” model: institutions that place people into high-pressure jobs, set impossibly high expectations, celebrate the few who survive, and replace everyone else with whoever is willing to step in next.

For decades, this model worked. The model works, in a narrow sense. It produces outcomes. It generates metrics. It looks like success. Survival and flourishing aren’t the same thing. The people who survive those conditions do so by hollowing something out: their health, their relationships, their capacity to sustain the care that drew them to the work in the first place.

There was always a line of people eager to work in higher education, the sort of people who believed in the mission and were willing to sacrifice for it. The COVID-19 pandemic exposed what the model actually costs. Burnout became impossible to ignore. Now, as Kevin told me, institutions are being forced to contend with a new reality: the line of people banging on their doors isn’t as long as it used to be.

Of course, there is a problem lurking here: recognizing that a system is harmful doesn’t tell you what to do about it. If American higher education routinely burns through its employees, the solution isn’t to tell individuals to be more resilient; instead, it’s to change the conditions. Changing the conditions requires power. And the people most harmed by these systems often have the least of it.

What Happens When Trust Breaks

Michelle Thielen carried a different weight. She knows something about systems that turn on you. After building Yoga Faith from nothing, Michelle survived a devastating early business failure and created something that now operates internationally. A few years ago, she faced a betrayal from within her own leadership team - people she had trusted, people she had “done life with,” who forged an alliance against her and tried to take the organization down.

It wasn’t just a business betrayal, she explained. It was a friendship betrayal, and it took her two years to work through it.

What she learned in that process became her framework, which she now teaches others. I call this framing the three F’s: Forgive, Reflect, Refrain. Forgive, not because what happened was okay, but because carrying it will destroy you. Reflect, examine what you could have done differently, with honesty and without self-destruction. Refrain, choose how you’re going to interpret the experience going forward.

Michelle’s story reminded me that staying with the trouble isn’t just about systems. It’s about what happens inside us when the systems (or the people within them) let us down. The work of rebuilding trust after devastation is slow, unglamorous, and deeply personal. There are no shortcuts.

Isolation Takes Shape

Genevieve Pitturo was a successful television executive; she was quickly climbing the corporate ladder in New York City exactly as she’d planned. One afternoon, in a quiet moment, she heard what she calls her “heart voice” ask a question: If this is the next thirty years of your life, is it enough? That question sent her spiraling. And when she finally told someone what she was experiencing, the first person told her she was crazy. Didn’t she remember she had a mortgage? Couldn’t she figure this out on a Saturday afternoon?

So she went quiet again. For months. Until she launched Beyond Bedtime.

Reem Borrows brought a different dimension to this question. As a Palestinian who immigrated to Australia at fourteen, she had to rebuild her identity from scratch. She told me about the moment her family arrived at Sydney immigration and her father, for the first time in his life, was able to proudly say: “We’re Palestinian.”

That freedom (to name who you are) became the foundation for everything else. You can’t lead from your values if you don’t know what they are. You can’t build critical mass if you don’t believe that you belong.

Critical mass, Reem told me, starts smaller than most people think. You only need 5% of the population to start something moving. Once you reach that particular threshold, others will join. The movement snowballs.

Shannon Lucas studies catalysts. Catalysts are the people in organizations who are constantly connecting the dots, creating visions for how things could be better, and taking action faster than anyone around them. Organizations desperately need these people. They’re the ones who drive transformation.

What Shannon has discovered through her work at Catalyst Constellations is that most organizations are designed for homeostasis: they plan for stability rather than change. In practice, this means the people the organization needs are constantly swimming against the current. Catalysts often feel alone, often burning out.

The isolation here isn’t social. It’s structural: it’s the experience of seeing something clearly that the people around you can’t or won’t see. This type of social isolation is exhausting in a way that “finding your tribe” doesn’t automatically fix.

Slowing Down to Show Up

Sonia Baschez brought a communications lens to this issue. Her entire career has been about translating. Through her business, Yapping as a Service (YaaS), she takes what experts and leaders say and makes it compelling for people who don’t already care.

She pointed out something I’ve been thinking about ever since I started this project: Trust, in the context of brands and communication, is relational. Trust is built through consistency, through showing up the way you said you would. We build trust not just by saying the right things, but by offering something real underneath.

Leadership is influence. That’s all it is. Every single one of us has that influence, whether it’s at the grocery store, in our emails, or in how we treat the person next to us. The question isn’t whether we’re leaders. The question is whether we’re being the leaders we want to see.

Deep Attention as Trust Practice

Shannon Gayk is a medieval literature scholar. At first blush, her work might seem like an odd fit for a podcast about trust, but her latest book, Apocalyptic Ecologies, bridges centuries in ways I didn’t expect. She studies how people in the Middle Ages made sense of catastrophe. Plagues. Climate disruption. Social discontent. Political violence. Sound familiar?

Those living in the Middle Ages didn’t just survive these catastrophes; instead, they developed embedded practices for making meaning together in the midst of them. They built collective rituals that held communities together when everything else was falling apart.

One of the things we’ve lost, Shannon told me, is that capacity for deep, sustained attention. The kind that takes time. The kind that can’t be rushed. The kind that requires us to stay with something long enough for it to reveal itself. Her practice recommendation was almost embarrassingly simple:

Leave your phone at home. Take a walk in the woods. Be present.

She also explained why it matters. This practice reconnects us to the fact that we are part of something larger. We are all part of something extraordinary and extraordinarily vulnerable. Deep attention works against the grain of a media ecology designed to fragment our attention and keep us scrolling. In a world that profits from our distraction, sustained attention becomes a form of resistance.

Shannon introduced me to the scholar Donna Haraway, who writes about “staying with the trouble,” or the practice of remaining present to difficulty rather than fleeing toward false hope or collapsing into despair. Haraway also writes about finding “oddkin,” the act of making unexpected alliances, building relationships across difference with those who share your commitment to a more livable world.

Here’s what Shannon’s medieval lens adds: oddkin isn’t just about finding the right people. It’s about developing shared practices that can hold through difficulty. Medieval communities didn’t survive the plague because they happened to like each other. They survived because they had rituals, rhythms, and forms of attention that bound them together when individual will wasn’t enough.

You can’t stay with trouble if you can’t stay attuned with anything. You can’t find oddkin if you’re moving too fast to recognize them. Attention isn’t just a personal virtue. It’s the precondition for the kind of togetherness that actually sustains.

From Oddkin to Building Trust

So, here’s where I’ve landed after these conversations.

We all live inside systems that often work against the people they’re supposed to serve. That’s true of higher education, of anti-poverty programs, of organizations that say they want innovation but won’t tolerate innovators. Recognizing this clearly matters. We can’t change what we won’t name.

We’re not only shaped by those systems. We also shape them. I don’t think we need to do this heroically. Building trust is not done through grand gestures that change everything overnight. Trust is cultivated in the small, sustained, relational action. When we show up, we build trust. When we ask for help, we build trust. When we find our people - our oddkin - and connect with them, we build trust.

The work of transformation requires us to resist both cynicism and naive optimism. We must be able hold the difficulty without fleeing. We owe it to ourselves to believe that change is possible while remaining honest about how hard it is.

The question isn’t whether to find your people. Of course, you need your people. The question is: What kinds of alliances can actually hold through difficulty? What practices bind you together when individual will isn’t enough?

Medieval communities understood this. They built shared rituals of attention, of presence, and of collective meaning-making that didn’t depend on everyone feeling inspired at the exact moment. The practices held when the feelings didn’t.

We’ve inherited a culture that treats transformation as heroic individual work. We are told to pull ourselves up, find our passion, and build our personal brand. Isolation shows up in every story of burnout and betrayal I heard this season. The guests who sustained their work didn’t just find allies. They found, or built, practices of togetherness that could hold through the hard parts.

Shannon Gayk put it beautifully. She described sitting with dying loved ones in the final year of writing her book: her colleague, her beloved cat, Tabby, and her mother. What she found in those moments was that little else mattered other than presence, attention, and care.

I’m not promising that this will be a formula for fixing all the systems around us. But, it just might be a formula for staying human while we try.

Trust for Thought

We can’t transform alone, and our culture keeps insisting we try. The systems that burn us out are designed for individual heroism. The betrayals that wound us often come from people we tried to do it all with, without the practices to hold us together.

Here are the questions I’m sitting with as this season of Trust Be Told closes:

Where in your life are you trying to transform something alone, not because you want to, but because that’s what the system assumes? What would it look like to name that isolation clearly?
Who are your oddkin, the people who share your commitments even if they come from entirely different places? And what practices, not just relationships, bind you together?
What form of attention have you lost that you might need to recover? What would it mean to stay with something (a walk, a person, a problem) long enough for it to reveal itself?

Trust Be Told

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