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Leadership Lessons from Halloween



Halloween is a big holiday in my town. For weeks leading up to October 31, you start seeing the decor, the costumes, and the parties. One glorious day per year, you get to choose whoever you want to be without any limitations of ability, money, or opportunity.


Do you remember being a child?


What did you dress up as?


One sad truth is children dream much more than adults. Before the harsh realities of adulthood set in, we were all superheroes, celebrities, athletes, and other aspirational characters. As a parent, I attempt to teach my son through this holiday. When he asks for a specific costume, I ask him what about that character appeals to him. He’ll say something to the effect that this character is “powerful“ or "cool“ or a hero. Those are qualities that I do not want him to abandon in adulthood. Our culture tends to begin the process of domesticating boys about his age. I desire to preserve his sense of wonder, masculinity, and adventure as he grows in responsibility and maturity.


As I have this annual conversation with my son, I can’t help but ask myself which of my childhood costumes appealed to me. Whether a soldier, a Jedi, or even an animal, each character signals elements of empowerment, strength, or service - all good qualities.


Do I resemble any of those qualities today?


If you want someone to tell you to "grow up," say something aspirational.

So many times, adulthood is associated with settling down and settling for less. This article does not endorse a selfish mid-life crisis or shirking of responsibilities. As adulthood provides new dreams and challenges, however, it is not wrong to balance aspirations with responsibility.


What would happen if November 1 functioned like another New Years Day?


Ask yourself:


1. What unfinished business do you have with your younger self?


Within reason, did you let go of some good dreams? Did you buy into the myth that physical fitness ends in high school? Are the credits for your unfinished degree languishing on your transcript? Do you have relationships that need closure or healing? Seize this moment to make this right.


2. What circumstances or obstacles prevent you from an aspirational life?


It is important not to rely on blaming people, events, and circumstances to answer this question. Perhaps the step you need to take this year is to get counseling, a personal trainer, or career mentoring. Those preliminary steps alone can be a huge step in heading you in the right direction. Most importantly, coming to peace with your past, owning self-destructive habits, and eliminating excuses are essential steps to move you forward in this journey.


3. What aspirational qualities of your childhood could fit into your life now?


What adventures await in your life? How can you look forward with optimism and excitement? What are some physical and professional goals that you can achieve? Are you a person your children, look up to? Don’t look forward with dread; see life as a quest with challenges and purpose. Remember to bring your loved ones along with you and let them share in your quest. Seize this moment to make goals and action plans. More than likely, these goals will take time and effort, but next Halloween, you might get to go as an improved version of yourself.

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