The Underdog Story

Welcome to Underdog! My name is Lynsey Fleck, Owner and CEO of Underdog Educational Support Services. I have been working in the education industry for 20 years. I have served in many roles, including Community-based Support Specialist for students with disabilities, Classroom Teacher, Special Education Teacher, Reading Interventionist, Instructional Coach, and Youth and Family Advocate for students facing mental health challenges. And in this time, I have learned one thing for sure…

The educational system is desperate for an Underdog.

Throughout my many roles and positions, I’ve kept repeating the same cycle. It is a cycle I’ve shared with students who seem to struggle in school the most. These students and I–we take on new roles and school years with unlimited optimism and a deeply-held belief that with education, all things are possible. We begin great work, grow a lot, and love school and learning. Our passion and commitment helps us see problems and challenges in ways others do not, and we speak out for the change we know needs to happen.

Then, at first slowly and then with increasing regularity and intensity, we find ourselves being pushed to the outskirts. The shoves are at first subtle, and with time become more aggressive and pronounced. We become disillusioned and stressed, sapped for joy and forgetting why we ever thought school was a good place to be. And much of the time, we find ourselves wondering if we are ignoring some sign from the universe telling us that we don’t belong, that we have no place here. But inside of us, something keeps whispering that we need to move forward.

I realized that it is OK to stand alone for a while. It is the only way that change will happen.

For me, moving forward meant leaving the public education system. And when I did, it broke my heart. Public schools were the places I had been brought up, the places I’d built my career. Public schools were supposed to be the great equalizer–the place where it didn’t matter who you were or where you came from, because your own commitment and work ethic determined your success. For better or for worse, public schools were inextricably part of WHO I WAS. It felt as though I’d lost a part of myself.

I moved into a position at a local agency, working as an advocate and specialist for students facing many academic and behavioral challenges.  All of my clients had diagnoses of anxiety, depression, and/or ADHD.  As I did my best to support students and families, I leaned into every discomfort. In opening up myself and becoming more vulnerable to those with whom I worked, I found myself identifying far more authentically with the students, families, and colleagues I worked with than I ever had with my teaching colleagues. We were moving forward together, we were focused on finding what worked and not on which expert told us to do it, we were growing and changing and doing things that others had dismissed as impossible. But we were limited by the barrage of rules and checklists that come with so many public program-based services.

One day, as I was on my way to see a client, I happened to look up and see a sign. It was a quote from the Book of Timothy in the Bible: “Never be afraid to stand up for what is right, even if you are standing alone.”

It stopped me, as they say, in my tracks. I had gotten so used to standing alone, and SO used to seeing this position as a negative thing, a sign of my many deficits and shortcomings. Wherever I went in my career, it seemed that it was just a matter of time before I became the resident misfit. While I didn’t like the way it felt to be different, belonging to something I didn’t believe in was something I liked even less. As I left the session with my client that day, and in the days and weeks after, I realized that it is OK to stand alone for a while. Underdogs always do. And it is the only way that change will happen.

And while I loved the students and families with whom I was working, I felt a nagging pull to take another look at how I might better affect positive change in schools on a larger scale. I knew too many students who were in late elementary and middle school and barely reading, and too many educators who promised to provide access and opportunities, but felt helpless to truly “move the needle” on student achievement. 

So here I am, writing this. And even though I am scared, and even though I still feel alone, I will keep speaking up for what I believe in. I will keep challenging the parts of the system that are broken. I will keep putting what students need before what people with power want education to look like. I will continue to believe that with education, all things are possible. And like all true Underdogs, I will find a way to break through. Won’t you join me? add another page.