Today we’d like to introduce you to Jacklyn Westbrook
Hi Jacklyn, so excited to have you with us today. What can you tell us about your story?
I come from a family of theater people—so much so that I was named after my grandfather, Jack, who happened to be Cloris Leachman’s first on-stage kiss. Growing up around music and entertainment gave me insights that many don’t often recognize.
In the world of theater, music, and production, there’s a behind-the-scenes wisdom that’s often overlooked. One of the most crucial aspects is timing—the ability to synchronize a team’s efforts into a seamless production. Creative people thrive in a space where they’re free to express themselves, yet structure and coordination are just as important. Striking that balance—honoring both the artistry and the discipline—is something I’ve learned to navigate well.
This same dynamic manifests in unexpected places, like a busy restaurant kitchen during a rush, with hundreds of customers streaming in and out. A small, tightly-knit team becomes a creative machine, moving as one, pulling off miracles that only those involved can truly appreciate.
That’s the hook. It’s not just about being part of a magical production; it’s about being in the trenches, making sure the magic happens. Whether in a kitchen, on a stage, or within a software team, there are always moments where we have to look out for one another. Over time, I’ve realized that I’m particularly good at this—stepping in, lending support, and helping the team flow like water, performing at its best.
My mom used to call me “Wendy,” a nod to Peter Pan. These days, I often hear myself referred to as “the team mom.” But being a “mom” in a leadership role isn’t always what people assume.
Some think of a mother as someone who carries a suffocating burden, sacrificing her own ability to create. But real leadership isn’t about self-sacrifice—it’s about guiding people toward healthier, more productive behaviors that serve both the individual and the team.
This understanding has shaped my role in stakeholder relations within a company that helps people build intentional communities. It’s work that allows me to align my experience to empower others, helping them realize they already have what they need to succeed.
But just as I help others grow, I also need a high-quality team—people who know how to hold their ground and navigate challenges without getting caught up in unnecessary friction. Teams aren’t perfect from day one; they learn how to work together, and that’s a process.
Anyone who’s been in a band, a production, or a fast-paced kitchen knows that sometimes you have to have hard conversations. They don’t have to be difficult, but they do require maturity. And when a team successfully navigates challenges, they emerge stronger than before.
I’m also an Intermediate Actor Combatant with the Society of American Fight Directors (SAFD), trained in unarmed combat, longsword, knife, small sword, single sword, rapier, dagger, and sword & shield. Fight choreography isn’t just about executing movements—it’s about collaboration, precision, and storytelling. Every scene requires trust between performers, just as every successful team requires coordination, discipline, and a shared vision.
Whether it’s managing high-stakes sales negotiations, analyzing intelligence data, or choreographing a fight sequence, the thread of continuity in all my work is the same: understanding people, anticipating movement (whether literal or figurative), and ensuring that every step serves a larger purpose.
Which brings me back to “Wendy.” Sometimes my role is to draw the lost boys forward, helping them step into stewardship of their own shadows. I can’t do that for them—but when they take responsibility for their own growth, they transform into something greater.
And in many ways, this process—the initiation and evolution of a team—isn’t all that different from my role as the mother of three boys.
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
One of the biggest challenges I’ve encountered is realizing just how many people underestimate the importance of what I call “the squishy stuff.”
They focus entirely on the bottom line, stepping all over the human dynamics that actually make a project succeed. Logically, they know that neglecting morale leads to burnout, attrition, and eventual failure, but many don’t care—because they don’t have to. Their positional authority allows them to frame the endeavor as a success, move on before the cracks show, and leave the consequences for someone else to clean up.
This is exactly why I work with stakeholders—to ensure that everyone, even the bottom-line thinkers, has real skin in the game. When people feel invested, they act more like stewards than managers, and that shift changes everything.
The people in the trenches—the ones actually doing the work—already understand the importance of morale, support, and culture. The bigger challenge is dealing with those who talk the loudest, listen the least, and dismiss the “mommy stuff” as unimportant.
Rather than go head-to-head with this mindset, I’ve found a better way. I don’t subscribe to the toxic version of “leaning in”—a phrase that too often feels like a disingenuous invitation at best. Instead, I invite stakeholders into stewardship. If they can’t recognize or respect that invitation, they’ll either adjust or remove themselves. Culture is either oil or water—and as a steward of community values and culture, my role is to ensure alignment, not force it.
My background in creative and alternative subcultures has given me valuable insights into how this works. Skateboarders and BMX riders, for example, have a built-in culture of stewardship—one that is deeply meritocratic and self-regulating. The same holds true in music, theater, and film—spaces where collaboration, respect, and shared passion drive the process forward.
I’ve taken these lessons and applied them to my current work with intentional communities. Whether it’s designing a thriving team, fostering a sustainable living environment, or guiding a group toward collective success, the methods remain the same:
Give people ownership. Give them space to create. Set clear expectations. Protect the integrity of the culture. Those who belong will rise to the occasion, and those who don’t will make that clear soon enough.
Appreciate you sharing that. What should we know about Bene Esse Inc?
Bene Esse Inc is a cooperative created to demonstrate the viability of adopting a DIY model for creating cooperatives for those who would like to live in an intentional community.
In effect, Bene Esse is both a living laboratory and an active business that guides other communities into licensing the Bene Esse model for their own usage.
Indeed the Bene Esse model has been chosen by a company called Terra Global Development, which provides high-volume low-cost 3D printed homes. Terra Global Development will use the Bene Esse model to provide self-governance and job creation so people are offered a solution they are able to afford, rather than emphasize “affordable.”
At the heart of the Bene Esse model is a commitment to aligned values that foster collaboration between landowners and community members:
Shared Vision: Landowners work alongside community members to co-create spaces that balance Community, Culture, and Commerce (the Bene Esse “C3” framework), ensuring that the development meets everyone’s needs.
Governance and Stewardship: Utilizing Bene Esse’s governance tools, landowners and residents maintain a collaborative dialogue, ensuring mutual accountability and alignment on long-term goals.
Legacy Building: Bene Esse communities offer landowners the opportunity to create a sustainable legacy by transforming their property into a thriving, values-driven ecosystem that contributes to the well-being of the entire region.
This values-driven approach not only secures buy-in from residents but also ensures long-term harmony and shared prosperity within the community.
I am on the board of Bene Esse, responsible for stakeholder collaborations, ensuring their voices are heard but more importantly guiding them to adopt methods where they can effectively make themselves heard.
Do you have any advice for those looking to network or find a mentor?
My approach to finding a mentor comes from two places: growing up in a family of performers and my years immersed in skateboarding and BMX culture.
The best way to learn how to drop in is by dropping in.
I’ve always sought out the most capable performers—the ones already ahead of me—and positioned myself in the same arena to challenge and be challenged. Growth doesn’t happen in a vacuum; it happens in collaboration with people who push you to be better.
This is the same methodology I apply as an actor combatant: my colleagues and cohort are made up of those who, at first, were substantially better than me. That’s by design.
A healthy meritocracy ensures that a rising tide lifts all boats.
This kind of mentorship isn’t always comfortable, but it’s not supposed to be. Muscle is built through resistance, and the same is true in interpersonal and professional growth. I seek out mentors who challenge me to evolve, but I’m also looking for people willing to learn—because I plan to challenge them back.
This isn’t about contention; it’s about mutual sharpening. Harmony is important, but not in the passive sense—true professionalism means balancing respect with rigor.
As the saying goes:
“Be polite, be professional, and have a plan to kill everyone you meet.”
Figuratively speaking, of course. But within my cohort of actor combatants, this is the norm. We scan each other constantly for strengths and weaknesses, not as a means of tearing each other down, but because that level of attentiveness is an expression of love.
This is exactly how it works within Bene Esse. My executive cohort operates the same way—we challenge and encourage one another in a relentless pursuit of excellence, though in a more internally facing way.
Many people seek mentors hoping to leverage connections—to manipulate a Rolodex for their own benefit. I strongly advise against this.
If you’re planning to jump into the ocean during a storm, don’t waste your time kissing up to the person with the life vests—learn how to swim.
Because when the waves hit, it’s your own strength, adaptability, and willingness to grow that will keep you afloat.
Contact Info:
- Website: https://www.futurestorylab.com/bene-esse/team
- Instagram: https://www.instagram.com/iamthethirstykitty/
- LinkedIn: https://www.linkedin.com/in/jacklyn-houghton/
Image Credits
Rain Chavez and Kent Dahlgren
