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I’m a Chicago Principal Overwhelmed by ‘What Ifs.’ Here’s How I Got Unstuck.

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I’m a Chicago principal overwhelmed by ‘what ifs.’ Here’s how I got unstuck.  was originally published by Chalkbeat, a nonprofit news organization covering public education. Sign up for their newsletters here.

I’ve reached out to my network, created a self-care jar, and helped teachers reframe their narratives about the coming school year.

When Chicago Public Schools announced that school would open fully remotely in the fall, I called a meeting with my staff. That first meeting was to gauge their feelings, reactions, and levels of anxiety.

As principal of a pre-K-8 school in Chicago, I took note of their questions and concerns, most of which I had, too. What ifs prevailed: What if a student isn’t engaged? What if they won’t turn on their camera? How will we know they are learning? What if the internet goes down? What if a student misbehaves? What if our meeting platform is hacked? What if students don’t have needed supplies?


I had very few answers, and I felt ill prepared to guide them through the year ahead. When the meeting ended, I cried. Alone. Inside the three-story brick building that houses my school. School was going to start in three weeks for my staff. I was overwhelmed and stuck in my own cycle of “what ifs.”

But then I did what all educators do after being knocked down. I stood back up. I brushed the emotional dust off my brain. I got to work.

Wendy Oleksy (Courtesy of Wendy Oleksy)

First, I called an educator friend and asked her to help me. I could not lead the school through this moment with a negative and defeated mindset. I needed to adjust my attitude. She reminded me that I wasn’t alone. I had lots of support. I was being stubborn thinking I had to have all the answers. She and I discussed how taking care of myself could help me feel less overwhelmed. I created a self-care jar filled with suggestions for doing something nice for myself, such as “have a glass of wine on the deck,” or “buy yourself some flowers.” I also started to journal each day before I left school, getting out my feelings and frustrations.

Next I reached out to principal colleagues I respect and said, essentially, “Help!” They surrounded me with support, positive energy, and shared resources. One shared a presentation deck with me so I didn’t have to create my own. Another reminded me how awesome she thought I am, which is always good to hear. Why didn’t I reach out earlier? I honestly think my brain got stuck. I am human. The virus and its massive fallout were never far from my thoughts. The police killings of George Floyd and Breonna Taylor and the resulting racial justice protests taking place, in addition to COVID-19, hit me hard. I had worried since March about the well being of my students.

These rough couple of days after Chicago’s Aug. 5 announcement that school would begin fully remote led me to realize how much support my team might need. Was I ready to provide it?

The staff always meets during the first few days of school for professional development. As we did the work to prepare for remote learning, I kept hearing them say, “This is challenging!” “This is difficult!” “This is frustrating!” They were overwhelmed. They were stuck. Like I was. During a break I felt my defeatist attitude return. How was I going to soothe my worried, anxious staff? I wasn’t a counselor. I wasn’t trained for this. But then I thought to myself, “What did you need? What helped you?”

There was a quote by Albert Einstein in the presentation I was giving to the staff: “Out of clutter, find simplicity. From discord, find harmony. In the middle of difficulty lies opportunity.”

I stopped the presentation on this slide. I asked the staff to change their mindset. We couldn’t go into our virtual classrooms feeling defeated. Students would pick up on that. I asked them to change their vocabulary, especially when talking with each other. Instead of “challenging,” call it an “opportunity.” Instead of “tricky” or “hard,” they could remind themselves of the “need to be creative.” Instead of “frustrating,” say “I need to persevere.” Changing our language doesn’t make underlying and systemic issues go away. But it can help us reframe the challenges ahead so that we are in a mindset to address them as best we can.

I encouraged them to find a win each virtual school day. Our students may surprise us with their technological know-how. We might learn how to simplify small group lessons. Maybe our collaboration will be taken to the next level. For the rest of the teachers’ professional development, whenever one of us heard a negative word, someone would chime in with the alternate word or phrase. As we approached the first day of school, I sent out daily informational emails in which I reminded staff to “look for the opportunities to learn, be grateful, and laugh.”

“You got this!” I told them. “We got this!”

Not taking my own advice, I suffered from horrible insomnia the weekend before school started. I couldn’t stop working. Checking in with teachers. Speaking with the engineer about the Care Room, a space where students who have signs of illness, especially COVID-19, will go until a parent can pick them up. Making sure I knew how to assist parents with setting up accounts. Gathering all the Google Meet links to be able to join the staff. Reading all I could about best practices for remote learning.

As I work to change my own mindset, let me say: This is challenging. When everyone feels like a first-year teacher, when technology glitches, when 100 parents are calling to say, “Help!” it is challenging.

During the first day of school, I popped into each Google Meet classroom. What I saw was nothing short of amazing. Every single one of my teachers was online, smiling, going over this new way to learn. They were conveying a sense of adventure! They were making students feel proud of themselves because they knew some skills the teacher didn’t.

There were some opportunities that presented themselves. The first grade teacher couldn’t log back in after lunch. She panic texted me. I joined her class and got to have a few minutes of fun with 6-year-olds as she traded computers and hopped back on.

The third grade teacher’s students persevered as they kept getting logged out of Google Meet. They would jump right back on and use the chat feature to exclaim, “I’m back!”

There were heartwarming stories of older siblings helping younger ones navigate links and websites. The middle school science teacher shared how wonderful it was to see how enthusiastic students were. The students had missed school and were happy to be back in any form of class there was. Day 2 continued apace.

Seeing all the students lifted my spirits. They are why I do this job. They are why I have been in education, with Chicago Public Schools, for over 27 years. Seeing their faces for the first time since June was a stream of happiness I hadn’t felt in a long time. I have to say, when students are excited to see me, the principal, when they exclaim, “It’s Ms. Oleksy!” and wave ecstatically at me, I kind of feel like a rock star. I hadn’t felt like a rock star since the winter.

Wendy Oleksy has been the principal of Chicago’s Columbus Elementary for eight years. She was raised in Chicago and is a product of Chicago Public Schools. Throughout her career with the district, she was previously a classroom teacher, literacy coach, Network Instructional Support Leader, and an assistant principal. 


Chalkbeat is a nonprofit news site covering educational change in public schools.

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