From Awkward to Authentic: Creating Spaces of Real Belonging
If you’re an educator or school leader who wants to host gatherings that build real community, not just fill a schedule, you’ll find real value in The School Community Events Guidelines at www.charlesvogl.com/downloads.
This free guide distills years of lessons from community leadership into clear, actionable practices you can apply to create spaces where people feel welcome, connected, and seen.
In this conversation with Madeleine Hewitt, Executive Director of the Near East South Asia Council of Overseas Schools (NESA), we explore how intentional design transforms discomfort into comfort and how that shift helps people truly belong.
When Comfort Isn’t Helpful
Madelein observes, many “comfortable” events accomplish little.
Schools hold polished ceremonies at the start and end of the year, events where no one risks connection.
Everything appears perfect, yet no real bonds form.
This kind of comfort is deceptive.
It shelters us from awkwardness but also from authenticity.
Real comfort, the kind that fosters belonging, requires courage, vulnerability, and design.
The Art of Designing Comfort
Madeleine approaches every gathering as both craft and art.
Her role, she says, is to “shepherd comfort.”
When convening heads of school online or students in a classroom, she begins by imagining where participants are coming from emotionally.
She asks herself:
What might they have experienced today?
What energy will they bring into the room?
How can I meet them where they are?
By anticipating these answers, she creates spaces that feel genuinely safe.
Designing comfort isn’t about focusing on the right music or offering polite smiles. She focuses on empathy and intentional flow.
Guiding the Arc from Discomfort to Belonging
Every gathering follows an invisible arc:
anticipation → awkwardness → connection
If we ignore that rhythm, participants remain stuck at the surface.
She encourages us to guide them through it. If we do so, community emerges.
Madelein uses simple tools to ease that passage:
Humor disarms anxiety.
Vulnerability from a leader gives permission for honesty.
Prompts like “What surprised you this week?” invite safe and directed sharing.
These helpful elements help guide strangers into allies on a journey toward fellowship.
Rediscovering Old Wisdom
For generations, of course, communities relied on shared stories, laughter, and ritual to bond people.
Modern institutions can reclaim these tools.
Schools, especially, are microcosms of society, rich with diversity yet prone to isolation.
Intentional gatherings can heal that divide.
Madeleine reminds us that even small design choices, for example, a circle of chairs instead of rows, or a moment of gratitude before closing, signal recognition that our guests belong.
When Comfort Becomes Complacency
Comfort without curiosity leads to stagnation.
Leaders often equate peace with progress, yet silence can mask disengagement.
True comfort encourages participation, not passivity.
The convener’s role is to hold space for honest expression, to make the unfamiliar feel safe without dulling its power to change us.
Five Design Principles for Effective Comfort
Begin with Empathy – Understand what participants carry into the space.
Model Authenticity – Lead with sincerity; it breeds trust.
Invite Participation Early – Shared voices build shared comfort.
Use Ritual Wisely – These create memory and meaning.
Close with Gratitude – Affirm what is built together.
These practices can lead a meeting into a transformative moment.
From Event to Experience
Madelein calls herself a “convener.”
She sees each gathering as a sacred opportunity to connect human beings, not just deliver information.
When leaders take that role seriously, the outcome is more than a successful agenda, she supports a living community.
Comfort is not a finish line.
It’s the fruit of moving through discomfort together.
When we design for that journey, connection naturally follows.
For inspiration on how to make your school events better for connecting, download The School Community Events Guidelines at www.charlesvogl.com/downloads.
You’ll find time-tested ways to move from formality to connection and cultivate true comfort in your school community.
Get free resources on building the community you long for at www.charlesvogl.com
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