Leadership Lessons From Halloween

Amy Stapleton · October 23, 2018

I was six the first time I remember eagerly waiting for Halloween. Practically hopping from one foot to the next as my mom got the most epic of costumes ready: a purple unicorn. And not just any unicorn — a unicorn with a golden horn and a rainbow mane and tail! I was going to be the best dressed of Ms. Miogan’s first grade classroom.

The holiday arrived and I happily set off to school to show off my magically costumed self — only to find that my bestest buddy was Catwoman, along with three of the most popular girls in the first grade! The class photo shows them front and center with their arms wrapped around each other — and a grumpy purple unicorn in the second row.

Reflecting on this small memory from more than 20 years ago, I find that this day and that experience has taught me so much about being a leader and teaching leadership.

Identity Matters
On Halloween, we can be anyone. And the masks we put on allow us to blend in with a crowd that maybe we never truly belonged to in the first place – such as a group of Catwomen. Leaders need to own who they are, in all aspects of their lives. It is only when all of ourselves — in person, in the classroom, online, at home, at work — match that we are honest with both ourselves and the people around us, but especially those looking to us.

What masks do you wear? How do we show our authentic selves?

Engagement Matters
One of the very best things about Halloween is how engaged people are. You can dress up a little or a lot. You can hand out candy or go trick or treating. You can attend a party or watch scary movies in the dark at home. But everyone participates!

Leaders have the unique opportunity at their schools to be engaged and to engage others. We can engage people in a multitude of ways from simply inviting another person along to help set up an event or asking for whole system feedback to improve yourself or an activity. Or to simply look for the grumpy purple unicorns and invite them in.

Who are our isolated people, just waiting for an invite? What discourages participation? And if we don’t engage, but expect others to, what does that say about us?


Creativity Matters 
For Halloween, I’ve seen everything from people shopping their closets for DIY costumes to creating elaborate designs from duct tape and cardboard. Halloween spurs creativity. As does leadership. When we encourage our students to use their gifts and allow them the freedom to do so, they shine.

Unfortunately, in the age of testing, in the fear of being left out, we’re discouraging the purple unicorns of our leaders due to a variety of reasons.

In what ways are we killing creativity at our school? How can we encourage creative thinking, processes or problem solving? What traditions might need to be re-examined?

Fun Matters 
Halloween is all about fun! The holiday continues to be so popular among children and adults because it is simply that -- FUN. In the first grade, it was an excuse to get out of our uniforms and do things that were special and different. Now, working in a high school, looking at students and all their stress and pressure to succeed at school, work, extracurricular activities, to fit in…maybe what we all need a little bit more fun.

What is fun about your school? Where do we need more opportunities to play? What opportunities can we create for play?


Amy Stapleton

About the Author: Amy Stapleton is a leadership teacher, Spanish teacher and ASB adviser at Yelm High School and constantly challenges her students (and herself) to serve their school, to find light in dark situations and to light the way for others. In addition to working on Mt Olympus camp staff for AWSL, she is also a CharacterStrong advocate and strives to make education about building relationships and teaching the whole child.