Boundary Riders

Horizontal people living in a vertical world.

As a design strategist gone MBA, gone startup founder, gone UX Researcher, I’ve worn many different hats over the years. Following my curiosity, connecting diverse experiences, and discovering possibilities has been the defining pattern of my path — but it’s a pattern that began long before I joined the work world, and it’s by no means unique to me alone.

When I was 12 years old, my family moved from a small town in Massachusetts to Quito, Ecuador, where I enrolled in a local school, became fluent in Spanish, and assimilated to the culture. I returned “home” to the U.S. three years later, only to be blindsided by reverse culture shock. I no longer knew how to fit into my own culture or, for that matter, how to navigate an American high school. An outsider yet again, I felt simultaneously exposed and unseen. It was only through lots of exploration, a good deal of confusion, and more time abroad that I came to understand I didn’t have to pick between cultures. Aspects of each made me who I was.

Years later I stumbled upon sociologist Ruth Van Reken’s book Third Culture Kids, which shed light on my experience — and gave it a name. In her research on expats in the 1950s, she discovered that people who moved to a different culture had actually formed a third culture — one that was distinct from their home and host cultures. She calls children who grew up this way “third culture kids” and explains that “through friendships that cross boundaries, they’ve learned the very different ways people can see life.” I’ll never forget the day I spent reading Van Reken’s book cover to cover, and how everything suddenly made sense. This explained why I navigated life and work the way that I did, and that there were others out there like me. I wasn’t alone.

Living between worlds and across conventions extends beyond third culture kids, the culturally blended, the culturally mobile, bicultural children, multiracial children, children of immigrants, and international adoptees. It’s also a way of thinking and being for people whose life experiences have made it necessary for them to develop multilayered identities and become highly adaptable and creative in uncertain circumstances. A few examples include moving frequently and starting over at lots of different workplaces or schools, receiving an alternative or hybrid education, and pursuing creative or entrepreneurial endeavors.

While these folks may sound like outliers, in many ways they represent an amplified version of most people’s experience these days, particularly at work. A growing pool of people are taking on multiple jobs at once, switching jobs frequently, collaborating across organizational boundaries or as free agents in the gig economy, and continually collecting and developing new skills. And companies are facing ever-greater pressure to transcend silos, grow in new ways, keep up with the pace and scale of innovation, and compete for multitalented employees.

Yet, despite the growing demand for more fluid, multidisciplinary ways of working, it seems most employers still operate on a foundation built for the industrial era, one that’s designed to optimize efficiency, control, and specialization. It was not built to traverse the edges of what’s possible or to maximize discovery and creativity. Jobs are still largely defined by function. Few roles and organizational structures are set up to leverage polymaths or integrate cross-functional teams. In a vertical work world, horizontal people — those who embrace multitudes — often struggle.

For instance, searching for jobs based on industry and function essentially requires them to tell a partial story of who they are, and only a fraction of the value they bring is formally recognized. For me, this felt like I was being asked to embody a subset of tasks, instead of showing up as a whole human being. Despite my efforts to find where I belonged, I never did land on a clear-cut solution. My journey led me right back to a lesson that I learned as a third culture kid: vilifying boundaries is not the answer. Instead, you have to learn who you are as a person and then figure out how to skirt the edges, operating across and around the boundaries that often shape our lives.

To better understand what that requires, I did what I often do in exploratory research: I found a variety of people wrestling with similar questions and brought them together. This began with the Boundary Riders Salon, an event I hosted in San Francisco last spring. During this salon, I facilitated an in-depth, open-ended conversation with six participants. We traded stories and ideas about navigating the work world and, more broadly, what it means to be human. Building on that session, I continued to explore these issues in a collaborative research project. This has included an event at One Salon in San Francisco, with about 50 attendees, as well as ongoing one-on-one conversations and secondary research. From this work, five key themes have emerged:

1. Create safe spaces to explore and experiment.

A fear of making mistakes and not immediately having the right answer can easily permeate a company’s culture and get in the way of learning. But those who feel compelled to explore the unknown can be innovators, change makers, and culture builders, even if they don’t formally have that role or title. Often, the people I’ve spoken with have found, senior leadership actually wants what they have to offer but doesn’t always know how to relinquish control or enable that behavior within a vertical structure. So, the question becomes: Which environments allow this behavior to blossom, and how can you protect those environments?

Several salon participants (myself included) set out to address that question when we started Culture Labx, a community focused on advancing the conversation on company culture and experimenting with the future of work. We wanted to create a neutral convener, so we’ve structured Culture Labx to allow people to start local chapters, do projects, and share insights back into the larger community. One way we do this is through a Culture Design Workshop Series that we host with partners from different companies who facilitate activities and share content.

One of the most surprising and interesting things that’s come out of these events has been the variety of people that show up, ranging from learning and development professionals to product designers in corporate environments, to university administrators, to employees of Burning Man. Because they are engaging with one another outside their offices, they feel freer to discuss topics like contradictions between organizational values and behaviors, the lack of diversity in tech, and a campus drinking culture that’s landing more students than ever in the ER. The neutral environment allows them to discuss these sensitive yet real challenges without fear of impact on their jobs. It also allows them to generate and share creative, diverse ideas — and road-test them a bit before raising them with bosses or coworkers.

2. Practice humble learning to bring others along.

Many salon participants also say that having open conversations and allowing space for self-critique isn’t always welcome where they work. Yet, they feel that these activities are essential to continual growth — and that empathy and humility are key to both individual and collective learning.

For Roxann, a social innovation strategist at Second Muse, humble learning is crucial to the work she has done with the internet freedom community — developers, designers, NGOs, funders, policy makers, and activists devoted to empowering people to communicate without fear of surveillance or censorship. For instance, when developers want to design tools that support the free exchange of information and ideas, this intent is often hampered by a lack of understanding about the people they want to serve. Roxann and her colleagues bridge that knowledge and empathy gap with workshops and coaching teams. They also draw on design-thinking techniques like ethnography to learn more about the community members themselves, posing questions and creating environments where they feel comfortable talking openly about their experiences.

3. Connect with like-minded people to build partnerships.

Finding others who also think and work across boundaries can be a major challenge, especially in hierarchal environments. Hadar, a strategist working in process innovation for a media company, described it as isolating. “For me,” she said, “it’s been really lonely.” In order to feel more connected, she started getting coffee with like-minded people outside of work.

Talking to them provided some of the support and validation she craved. It motivated her to informally reach out to others within her organization — people in different roles and at various levels who struck her as curious, creative, integrative thinkers. She found them simply by asking about their interests. Once they started interacting more regularly, they developed partnerships of sorts. With senior folks, this meant learning more about their work, pulling in their point of view, and engaging them as advisers and influencers. With folks she needed to collaborate and build consensus with, it meant understanding their needs and sharing mutually beneficial resources, like research from different territories.

4. Create slack for reflection and wellness.

Continually translating and engaging with a range of different people across different contexts requires significant attention and energy, and salon participants described it as a challenge to keep this up, especially when most people are overworked. Creating slack for these purposes is crucial but can fly in the face of external expectations, productivity biases, and norms around linear value creation.

For Emily, this tension became increasingly apparent when, after 10 years in the social sector, she hit her point of burnout. While she loved the work, she realized that she didn’t fully know how to be compassionate or how to fully take care of herself. Part of the issue, she realized, was that reflection and wellness go hand in hand, and her work wasn’t designed to allow for wellness. To be healthy, happy, and productive, she knew she needed more sleep, better nutrition, more time with loved ones, and so on, and the hours simply didn’t add up to a single day.

Emily got past those hurdles by leaving her corporate change management job. She allowed herself six months of what she called “protected play.” During this time she began to explore meditation, which for her is less about sitting quietly and more about choosing how she responds to things. It’s about deciding “I’m going to let this in” or “I’m going to let this go, and I’m not going to beat myself up over it.” She also decided to be part of the solution, by cofounding Culture Labx and joining The Energy Project, where she now consults with other organizations on wellness.

5. Scale storytelling and communication.

Many salon participants explained that when you’re used to constantly having to tell your story to explain yourself to people, you understand the importance of telling other people’s stories and letting their stories be told. Connecting with others on an individual basis tends to come fairly easily to this group, but connecting at a larger scale becomes more difficult, especially when environments are permeated by fear.

To tell the story of Boundary Riders I had to find the place where stories can live across conventions and contain multitudes. Medium enables people to pose questions, engage in collaborative dialogue and build off of each other’s ideas. Boundary Riders began by bringing people together to share their experiences and support each other in navigating complex and ambiguous journeys. Scaling communication in this case has meant having conversations with communities of Boundary Riders, folding in layers of insight and evolving the work by sharing it out in iterations. My hope is that building a collective narrative in this manner will continue to make it easier for others to share their experiences as well.

As human beings, we’re all faced with this choice of learning how to exist fully in who we truly are. In a world where standard job descriptions rarely capture what we do and what we have the potential to become, living and working across boundaries applies to more and more people. After all, when we look for meaningful work that “fits” our many facets and engages our whole selves, we are all, in a sense, seeking home.