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That Feeling as a Leader When You Have to Disappoint People

Barrie's cat Oscar - entirely satisfied with the "Stay Home, Stay Healthy" order

Barrie Hillman, WSA Head of School, and Oscar the cat's favorite person in the whole world As a leader and Head of School, I try to say “yes” as much as possible. Even if it is really a no, I work hard to find a mutually beneficial solution that feels like and really is a sort-of yes. However, lately, I have been a disappointing leader. I disappointed some people when I didn’t close my school fast enough at the start of the coronavirus spread. I disappointed students when I sent them home to remote learning and then again when I said they had to stay home for the rest of the year. And most heart-wrenchingly, I have seriously disappointed the graduating Class of 2020, of which my first child is a student, when I said that I have to conduct graduation virtually after initially thinking we could at least do a drive-in version.

Barrie's dog Hana, wanting to go outside It seems the only living thing that appears delighted with my actions every day is my cat, who thinks that working from home is the best thing ever, and he is never more than three feet from my physical presence (even when I am in the shower). You would think the dog would be equally delighted, but apparently, I am constantly disappointing her by allowing her to continually end up on the wrong side of the door every five minutes.

And so…these disappointments really can’t be helped. Everyone does understand, and some even go so far as to send thank-yous to my disappointing messages – a true measure of their goodness. And those for whom the disappointments are adding up at least keep it to themselves for which I am grateful. However, I have a deep dark feeling that my role as Head of Disappointment is going to continue for another year or two and that I need to come to terms with that. I need to be okay with it because I am not alone.

Barrie's dog Hana, wanting to come inside We are all messengers of disappointment these days. Parents, kids, bosses, employees, colleagues, friends…we are all having to let each other down in some way every day. No, you can’t go to your friend’s house, I hope this furlough is just temporary, I have to delay my mother’s funeral, I forgot to clean the litter box three days in a row, I can’t make burgers because there wasn’t any ground beef, or worse, we don’t have enough money. Together we are living with and dispensing disappointment daily, but in that space, aren’t we really just shining a light on all that is good?

In a crisis, we see the best of people. We see their true nature. We appreciate the small things more. We value what went well in each day. That walnut of guilt that resides in our hearts because of how we have to disappoint people will still be there, but it can also be a reminder to forgive ourselves and those around us for the disappointments. I accept that we all are just doing the best we can, including me.

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