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It had snowed the day before I was scheduled to attend orientation, so I gave myself ample time to make the drive up to Redmond. This is a drive I did on a daily basis just over ten years ago when I was a developer at an outdoor gear website that was headquartered nearby.

That was one of my mulligan jobs I’ve had over the years – and perhaps that added to my insecurities for the day. But I was still excited to be there at that nondescript office building near the airport on the crisp Thursday morning in December.

I backed the truck into a parking spot, and watched as members of my orientation cohort filtered into the building. I was certain each of them had more experience then I, and were much more qualified to be in the room that day. This is an internal dialog I’ve come to know well over the years – it’s the things I tell myself when the imposter syndrome shows up.

But I gathered up my paperwork, along with my courage, and headed inside… signed into the class list, grabbed my folder filled with orientation materials and took a seat in the back row of the room.

While lowering my mask to sip my coffee, I eyed the room and counted thirty total people in attendance for Substitute Teacher Orientation. There was a wide range of ages present, those older ones in the crowd I was certain were life-long educators like Becky. And there I was, a business school graduate who has worked more closely with computers and code then little kiddos over the years.

I also was quick to note there were only two other males in attendance. That made me feel even better for showing up that day, as one thing I always disliked at my old jobs was the gender inequity of tech – it was cool to be in the minority for once in that regard.

The materials covered that day were more targeted around basic duties of a substitute teacher, and how to use the administrative systems to do things like find jobs and track time. There was of course no instruction on how to even be a sub… I suppose fake it till I make it sorta thing.

Many words of caution were shared. Lot’s of things to watch out for and warnings of things not to do. But I suppose my background as a parent helper in various classes over the years, and my stint teaching Art Masters to kindergarteners years ago will be the foundation I start to build upon in my new journey as an educator.

While I was beyond nervous that day to attend training, I’m over the moon excited to start this new chapter in my life. If I’ve learned one thing over my career, it is that the times I’ve experienced the most growth and happiness is when I have stepped way outside of my comfort zone. The times where I have felt the challenge of imposter syndrome trying to hold me back.

And of course I have an amazing mentor to help me out at home, and some test subjects to bounce ideas off of in my kiddos. So I think I can make it happen as Mr. Timmy – or Mr. Crawford… not sure about that yet. But I am sure that I’m stoked for my first day back in class.


I’m still waiting for my “profile” to be established in the substitute teaching system ( AESOP ), and I’m experiencing just how slow the State of Oregon is at processing teaching licenses. But I’m hoping that by the end of this week that I’ll be ready to help the community with the great need that exists for substitute teachers right now. And I’m certain I will have many stories to share here once I get started.


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