It seems like a cop-out, but I would have to identify the remote teaching between March and May 2020 as the worst experience with technology. That was a tricky time for a whole bunch of reasons:

1) The pandemic was legitimately frightening due to the scope of the lockdowns, my perceptions of the poor national leadership, and the general concerns over my family and students dealing with the stress of the whole situation.
2) I was leaving my old school. I had literally juuuuust interviewed for the new position at a different school district the week schools are doing emergency professional development to get ready for long-haul googleclassroom instruction. I was dealing with some “feelings” about the decision, because leaving my school was certainly a big choice. I had really developed a reputation at my school as a good educator and had built close connections with fellow staff and many families in the community. The fact that I didn’t get to finish out the school year in a traditional setting felt like I was cutting them off in a cruel way considering I was not coming back.
3) The remote teaching was just no fun. I realized I am someone that definitely thrives off the energy of a classroom of students. I’ve heard stand-up comedians talk about the same thing-no shows during the lockdown or attempting zoom shows just fell flat due to no laughing audiences. My lessons were essentially independent assignments and recording PPT note lectures.

Speaking of recorded PPT lectures, I was proud of utilizing that aspect as much as I did, but I was trying to both get across material in the small amount of time we had, change up the remote workload many students were dealing with, and also providing an asyncronous way for students to engage with material because it was clear the students were all over the place in terms of their ability to sit at a laptop and do work. One of my go-to teaching practices is indeed lecturing because I typically do well keeping students engaged in a lecture. It’s really just epic storytelling if you do it right and with high energy.

There’s a rap artist named Sage Francis who I really like and one of his lyrics is “technology made it easy for us to stay in touch while keeping a distance. Until we just stayed distant and never touched, now all we do is text too much”. This sort of melancholic lines really speaks to how much of a bummer the remote teaching was for me and the millions of kids and teachers that went through it. I was indeed able to get education done via googlemeet, audio/visual recordings, and other tools. But the old brick and mortar classroom was really where I felt at home, even while teaching in my living room or the spare room of the house I lived in at the time.

Why was this my worst experience with technology? Probably because it was a long, drawn out process where technology was looked at as the savior, when in reality it seemed to stand in as my oppressor. I felt isolated even though I was able to tune into meetings with staff and students at my school. Doubly challenging was the knowledge that I was leaving my school, so I was concerned about “slipping away in the dead of night” feeling I had knowing that my time in that classroom was over.