My boys are 10 and 12 and as I was carving pumpkins with them, we got into a lively chat about Halloween. They were thrilled to dress up as monsters - each picking a costume that would let them act in ways they couldn’t on any other day. One of them was excited to roar and stomp without any “be quiet” or “you’re too loud” reminders, while the other imagined casting “monster spells” all around the house. It was a day where they felt they could bring out sides of themselves that usually stayed hidden, fully embraced for the little wild characters they are.
Watching them, it struck me: there’s something valuable here for me, maybe for others, so let me share what came up:
Halloween creates this unique space where we can safely experiment with who we are, step outside our usual roles, and reveal hidden parts of ourselves without fear of judgment. And if we’re talking about creating a Deliberately Developmental Organization (DDO)—a place where people feel safe to grow, learn, and be truly themselves—this Halloween spirit of openness has a lot to teach us. What if every day could be a little bit like Halloween?
For leaders, this means fostering a workplace culture where people can reveal those “hidden secrets”—like doubts, fears, or areas of struggle—that usually stay masked. Just a bit more “roaring” and “stomping” than usual! Maybe it’s the pressure to appear constantly competent, the stress of being seen as “not enough,” or the fear of speaking up with new ideas that might flop. When leaders model this kind of everyday vulnerability, they create a ripple effect, allowing team members to open up as well. This authenticity strengthens trust, allowing everyone to collaborate more effectively, try new things without fear, and grow individually and as a team. Vulnerability doesn’t just strengthen the person—it strengthens the entire culture around them.
At the heart of it, we connect more deeply to our humanity. It sounds simple, yet in a world where external validation has become the norm, we’ve made it difficult. What if we allowed ourselves to be more human—to fail, learn, grow, and even try out a little roaring and stomping now and then?
And the benefits? Leaders get to work with a team that feels genuinely connected, motivated, and supported. Teams can innovate more freely, feeling safe enough to think outside the box and even make mistakes along the way. By bringing down the masks we wear, we start seeing each other not as “roles” but as whole people, full of potential.
So, let’s not be afraid to let the “little monsters” out once in a while—they just might help us scare up some true growth! And remember, being a vulnerable leader doesn’t mean showing up in a vampire cape…unless you really want to drive home the “blood, sweat, and tears” approach! 👻
Happy Halloween!
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