An Epilogue…and A Foreword: Living & Scaling Teacher Leadership

As I prepare to say goodbye to my 8th graders and close one professional chapter in order to plan for a new role next school year, I reflect on the benefits of teacherpreneurism and share my hopes for scaling teacher leadership in my school district. This post is written with deep gratitude for my CTQ Family: thank you for helping me spread my teacher leader wings, and for working tirelessly to reframe public education, so that teachers are viewed as the solution and lead experts to a more just and equitable system that serves all students.

Epilogue — Reflections on Teacherpreneurism

In less than a week I will complete my third (and final) year as a CTQ Teacherpreneur. I will finish one professional chapter and prepare to transition into a new role.

Here’s what I’ll miss most:

  • Leading Without Leaving: The best part about working in a hybrid role is the opportunity to teach and lead simultaneously. Looping with the same group of students for three years helped me blur the lines between classroom teaching, advocacy and policy work, family partnerships, professional learning and instructional coaching. Beginning each day with students grounded me in the purpose of public education and fed by teacher soul. Opening my classroom doors helped me improve my practice, bolstered my credibility, and allowed me to lead from the inside out.
  • Virtual Connections & Partnerships: While I plan on continuing to nurture and grow my professional learning network, serving as a teacherpreneur provided time and space to connect with colleagues across the nation and Twitterverse. Collaborating with passionate educators through social media and digital environments provided a safe place to reflect, refine, and problem solve. It also allowed for connections with other education stakeholders, organizations, and advocacy groups on a regular basis, which expanded my perspective of what it means to be a teacher leader.
  • Having a Homebase: At the same time, I had the security of having a “homebase.” Being a part of a school culture and community helped me feel connected in ways that virtual collaboration cannot (yet) match. I will miss the quiet in classroom 214 early in the morning before the first bus arrives. I will miss the hustle and bustle, the hugs and hilarious one-liners, of boisterous adolescents in the hallways during passing period. Most of all, I will miss the staff, families, and students of Vista PEAK Exploratory.


The growth mindset girl deep within me feels that the time is right. I’m sending my 8th graders to high school. I’ve balanced two roles in two spaces and have grown increasingly more comfortable and confident in my teacher leader skin. I’ve made tough decisions about what to take on and what to let go.


Foreword (& Onward!)—Scaling Teacher Leadership

And now it’s time to let go. To send my students on to high school and to say goodbye to life as a teacherpreneur. It’s time to settle in and focus, to continue developing as a teacher leader, but more importantly, to support the development of other teacher leaders. To build capacity. To tell other teacher leaders who want to teach and lead that they can. And that they need not do this work alone.

Next year I am working full time as a “Teacher Leadership TOSA” (Teacher on Special Assignment) in my school district.

Here’s what I’m jazzed about:

  • Paying it Forward: I’m excited to facilitate the development of teacher leaders in my district. My goal is to recruit, retain, and support passionate teacher leaders and help them build their own learning lab classrooms. I want to “pay it forward” by mentoring National Board candidates and advocating for a career lattice of options for teacher leaders — so that they can teach and lead.
  • Focusing: Juggling classroom teaching and teacher leadership initiatives is tricky work that requires a split schedule. I’m looking forward to focusing on growing a cadre of emerging and established teacher leaders and scaling the concept of teacher leadership. I’m relieved to bring 100% of my energy to this goal, instead of guiltily dividing my time between classroom teaching and teacher leader development.
  • Figuring It Out: Mostly, I’m looking forward to providing agentive opportunities for teacher leaders to figure it out for themselves — from designing and evaluating their own professional learning structures, to crafting a teacher leadership plan, pathway, and possible destination. I can’t wait to champion reflection and push and nudge teachers outside of their comfort zone, knowing firsthand that each risk they take will pay dividends in student learning.

This quarter my students read Harper Lee’s To Kill a Mockingbird, and I read it alongside them for perhaps the sixth (and certainly not the last) time. It was bittersweet to turn the final page in the text and to reach the end of this professional chapter in my life.

My blog is called In a Teacher’s Shoes and I’ve been wondering about how I will stay grounded in these shoes as I transition into a support role and pack up my classroom.

I can’t help but hear the words Harper Lee penned for Atticus Finch play over and over in my mind: “You never really understand a person until you consider things from his point of view…until you climb into his skin and walk around in it.”

Teachers — this is my promise to you — to consider work from your point of view and to walk alongside you in your leadership journey.

Will you join me?

  • Jessica

    Eloquent! It was wonderful

    Eloquent! It was wonderful being your teammate. You are an excellent teacher not only because you're brilliant but because you love the kids. The students always come first and I know that will never change which is why I know you always help support teachers. Congratulations on your new role but know you will be greatly missed. 

    • JessicaCuthbertson

      Thank you for your unwavering support!

      It was a pleasure being YOUR teammate 🙂 and watching you grow into a new leadership role as Dean this year — while I greatly missed sharing a classroom wall with you ;), it was reassuring to have ALL of our students in your care with an emphasis on restorative practices and counseling and coaching students to make supportive choices (vs. a punitive/punishment model).

      Thank you for your unwavering support of both me as a teacher leader and of our students — your advocacy voice inspired and empowered me to constantly consider all of our systemic decisions from a young adolescent’s perspective and to keep our middle schoolers at the forefront. 

  • Robert DeLair

    Becoming a teacher of teachers…

    I wish you more than the best for your new role. We teachers are a hard bunch. We don't like intrusion into our little worlds, we feel we are the best at what we do. When someone comes out and says, "Here, try this, it might work for you!" we tend to "poo poo" any new suggestions. A teacher is the hardest student you will ever have. Every once in a while, though, you will find that teacher that says, "Ok, I will give that a go and see what happens." Lo and behold, it works,(as you knew it would) and all of the sudden, what you say now (as it has been all along) is true! Remember from whence you came, but keep looking at where you are going. You have taken on the hardest role of all, a teacher of teachers! I, as I am sure Kevin does, believes in you and how you are going to touch so many more lives!

    • JessicaCuthbertson

      Teacher of Teachers

      Thank you Robert, for reading and commenting and for your kind words and powerful reminders — I do believe our system needs and deserves to be led by teachers — and that teachers teaching teachers is the most powerful form of “professional development” and learning that can transform our practice, from the individual classroom to the systems (schoolwide/districtwide) level. When I think back on the most powerful professional learning experiences in my career to date — they all involve teacher leadership and learning from vulnerable teachers. From local/national writing project work which is founded on the premise of teachers teaching teachers, to organic work with colleagues (locally or virtually), to peer observations and feedback — I learn more from colleagues and these lessons “stick” in ways that one-off conferences and workshops do not. I think it’s critical for teachers to keep their “street cred” however by interacting with students, guest teaching, modeling and co-teaching whenever possible — and so I hope that I can do this work in collaboration with interested teachers next year.

      I agree that we can be a challenging, complex, skeptical group of professionals — but our collective power is great if we remember to be the lifelong learners we aim to create in our students. 

  • BarnettBerry

    reflections on 3 amazing years…and more to come

    Jessica. As a CTQ teacherpreneur you have been the quintessential boundary spanner (a concept often used in both organizational development (and political science) to depict special change agents who communicate across different, and often competing groups, and establish links among them). I have learned a great deal from you — and will continue to do so as we work with you in the years ahead as a TOSA in Aurora.

    Once again you have offered us the most compelling reflections on your work as a teacher and a leader in this poignant piece. At the end you point out how you soon will not be able to call yourself a teacher since you will no longer be in a classroom and be responsible for the complexity of directly teaching with young people on a daily basis. I find it fascinating that so many former teachers, now in a leadership position (and often working the policy circuit in Washington DC), want to continue to call themselves teacher leaders even though they have not taught in a decade. You are still teaching and are questioning whether you will be able to adequately stay grounded in the classroom as you transition to a TOSA. I would love to explore this more with you – and hope you will maintain a way to continue to reflect on and write about this very important issue as we all in the CTQ family continue to advance a bold brand of teacher leadership for those who lead without leaving the classroom.



    • JessicaCuthbertson

      On Boundary Spanning…


      Thank you for your kind words and for your leadership and dedication to the teacher leadership cause. I particularly appreciate you naming the power of boundary spanning. Indeed, I believe it is a key disposition of teacher leadership, and a skill that I was able to develop only with the support and implicit trust of you and the CTQ family. I will continue to dream about, advocate for, and work toward a system that truly represents distributive leadership and teachers taking charge of their own profession for the benefit of student learning. 


  • JenniferHenderson

    I definitely know the feeling

    I definitely know the feeling of starting that new chapter!  I hope your students know how blessed they are, to have you guide them and support them for three years (and more years to come, I am sure!).  I know how blessed I have been to be able to work with you and learn from you – you are the guiding force in my attempts to lead from the classroom.  I am also thrilled because I know I get to be a part of this next chapter in your career – teamwork makes the dream work!  

    • JessicaCuthbertson

      Yes to Teamwork!

      Thank you so much for your support, encouragement, and laser focus on teacher leadership in all areas of our system. I can’t wait to see what you and your students accomplish at AWCPA next year! It is exciting to see schools emerge as leadership models with passion for deprivatizing and sharing best practices. 

      YOU inspire me as a champion for social justice and culturally responsive teaching — looking forward to learning from you at Thursday night’s webinar and to working more closely with you in all things teacher leadership next year! 🙂 

  • LaurenHill

    Thank you!

    So often during these last years have you articulated for me what my heart could not.  Thank you again for clarifying what matters and setting such a strong example.  I am honored to work on these challenges with you.  

    • JessicaCuthbertson


      The honor is mutual, Lauren, and I wish you the best of luck on your next endeavor! I know your school will miss you greatly but your AP legacy will live on in all of the successful graduates you supported! 

  • TriciaEbner

    Amazing . . .

    You are simply amazing.

    The mere fact that you are concerned about staying grounded in the teaching world, keeping the teaching viewpoint in mind, tells me you are going to do just that. Robert is right: being a teacher of teachers is just as much teaching as is teaching 8th graders. Maybe moreso–he’s right, we’re a tough crowd. 

    I have no doubt you’ll be amazing in this new role. If you ever find yourself wondering, remember that you have made such a positive, powerful impact on teachers thousands away. You have a wonderful talent for seeing in others what they don’t yet see in themselves. How much more will you impact those around you? 

    Thank you for being such a supporter and encourager of my own teacher leadership steps. 

    Excited to cheer you on as you take these next steps!

    • JessicaCuthbertson

      Fellow #CoreAdvocates


      One of the many blessings of this past year was getting to work with you virtually through the TLI CCSS strand and getting to meet you in person at Teaching & Learning in March :). The #CoreAdvocates and #CTQCollab tribes are strong and mighty groups of teacher leaders and I’m proud, honored and humbled to be a part of both with you!

      Thank you for all of your virtual support and for being there bright and early on our T & L presentation day with a smile on your face, verbal encouragement AND caffeine! You’re the best and I can’t wait until our leadership paths cross again. Until then — I know where to find you! Have a great summer and take some time for R and R – you earned it! 🙂

  • MarciaPowell

    Leading without Leaving


    I often think about the definition of leading without leaving as a teacherpreneur, and I find myself looking for Teacherpreneur 2.0   You have traveled an amazing journey as the Teacherpreneur as conceived in the first order of business.  We need teachers who learn and lead and live their life and their passion, give ideas and voice to the profession.  We need teachers who try new ideas, voice their successes and failures and who dynamically lead their students.  As we empower more and more teacher voices as a teacherpreneur, and empower them to be a force for the future, we will need to rethink the role of Teacher Leader again and again.  The next generation of Teacherpreneurs will need to be more than just the dynamite instructional coaches out there, as we carve out district roles for advocacy, community building, parent involvement and healthy living.  Changing to a focus on personal skill sets, rather than personal titles, is a need that will come next. With these changing roles, definitions, and quirks in our system, your growth mindset and student-centered background role will allow you to provide voice for that change.  A teacher-of-teachers extends the role of teaching, in my mind, allowing for partnerships to be build beyond district boundaries; I am grateful to know that you are one of the extraordinary people able to invest in that work, Jessica

    • JessicaCuthbertson

      Teacherpreneur 2.0, 3.0 & Beyond

      Thank you, Marcia for the powerful reminder that learning and leading is iterative work. One of the most impactful professional learning opportuntities I’ve engaged in during the last few years has been design thinking workshops which are framed around rapid prototyping and constant revision/iterations for “test users.” I agree that we need 2.0 (and 3.0 and beyond) teacherpreneurs and that the roles of teacher leaders will continue to evolve as our system progresses and distributive leadership in public schools is actualized. Exciting stuff! Thanks for being one of my virtual colleagues in the teacher leadership journey forward! 

  • akrafel

    Call Yourself a Teacher

    Sounds like you will be leading and teaching teachers.  That you will be one step back from the kids, does not mean that you a less of a teacher.  You will be a teacher’s teacher, a powerful teacher just the same.  Your reflections will be from new shoes, but oh such interesting and stylish shoes.  Teaching is teaching in my book.  I am a teacher leader and sometimes I do feel like an outsider, but I have to journey to inside the classroom through other people whose practice I am influencing.  May you touch young teachers who need to know that teachers can and do lead and operate schools.  Who better to know what needs doing?  You are a pioneer. Journey well.

    • JessicaCuthbertson

      Thanks for the encouragement!

      Thank you for your kind words and encouragement — indeed teaching can take many forms and I dream of a system where all classified and licensed staff at every level — including teachers, teacher leaders and administrators work in closer collaboration to benefit students. And where teacher leaders are not outsiders (or insiders) but just one of many roles serving students and supporting adults. Perhaps one step in getting closer to this system is for us all to walk in each other’s shoes a bit more to understand the different roles and responsibilities involved in school leadership? 🙂

  • JustinMinkel

    Go, Jess, go!

    “The greatest adventure is to give up all that we are to become all that we can become.”

    Contrast or integrate that with D.T. Suzuki: “After 15 years of practicing Zen, mountains were no longer mountains and rivers were no longer rivers. After 30 years of practicing Zen, mountains are again mountains, and rivers are again rivers.”

    All that to say, in one sense you’re being courageous and losing sight of shore to seek new lands. In another sense, you are absolutely true to who you have always been, and your gifts as a teacher will make you a wonderful teacher of teachrs, of policymakers, of legislators, of curriculum developers….or whoever else might cross your path. 

    Thanks for bringing us along on your journey! 

    • JessicaCuthbertson

      Always #Inspiring

      Thanks for the vote of confidence, Justin, and for the inspiring quotes to guide all of us teacher leaders on our respective journeys! :)At the risk of getting English teacher geeky by borrowing from the oh-so-quotable Robert Frost, I’ve always been a bit of a “road less traveled” kind of gal and thus far it is has in fact made all the difference :). I expect this journey will be another adventure…I’m really excited to gently nudge others to take these roads and risks in their own practice and respective school cultures and to explore teacher leadership through different context across the district. And all the while of course I’ll be directing teacher leaders to edu-bloggers like you for inspiration, tenacity, and the ongoing reflection that keeps us passionate and positive about this work. 

  • SusanGraham

    Loving Your New Shoes!

    Oh Jessica, you got new shoes! And, of course you’ll still be walking In a Teacher’s Shoes because one of the coolest things about being a teacher is that we get a closet full of shoes! 

    • Baby shoes that support us as we take our first steps as novices.
    • Track shoes for running as fast as we can
    • New high heels for our teacher leader debut (don’t forget your boa!) 
    • Flip flops when we have to get over ourselves and to admit we were wrong 
    • Rubber boots because sometime we’re knee deep in you-know-what trying to find the pony that’s in there somewhere 
    • Fuzzy house shoes to match our fuzzy brains because we’re still at our desk at 2 am. 
    • Magic slippers for magic moments when we find that teacher dreams really can come true

    It doesn’t  matter which shoes you’re wearing, Twinkle Toes, ’cause you’ll always have Teacher Feet! So, as Pete the Cat says, “…keep walking along and singing your song, because it’s All Good!”

     I’m putting on my pumps and doing the Happy Dance for you! 




    • JessicaCuthbertson

      And about that Children’s Book?

      Oh Susan — your comment made me smile widely and giggle with glee! In fact, reading your words of wisdom was almost as much fun as actually going shoe shopping! 🙂

      I love your reminders of all of the “shoes” we teachers wear depending on the day or the situation :). I’m going to click my heels together three times and repeat my own “There’s no place like home,” mantra (maybe – “There’s nothing like virtual mentors?”) to conjure your image on the tough days. 

      To #FeatherBoas and #Friendship — think of all of the teachers you have supported and inspired through the years…so many footprints walking the teacher leadership journey because of you! You have several pairs of magic slippers in your closet I’d say — so thanks for sharing your wisdom and metaphorical wardrobe with the rest of us! 🙂 

  • KelleyCusmano

    Thank you

    I read your post and was completely inspired. I am new to the teacher leadership movement and was completely disillusioned on Friday when our district unceremoniously laid off 50 teachers. I think your quote from TKAM was exactly what I needed to hear: that in order for people to truly understand this profession, they need to walk in teachers’ shoes. I am reading different books, trying out the collab for real (this is the first post I have ever responded to) and hopefully putting together a teacher leadership summit for Michigan. 

    Thank you again and I wish you best of luck on your new journey! 

    • JessicaCuthbertson

      Welcome, Kelley!


      Thank YOU for reading and responding and for shaking off the hard day(s) in the name of teacher leadership. Bloggers sometimes write for themselves (to think out loud and process) which is what this post was for me and we often wonder — is this actually helpful or inspiring or movitvating or interesting? Does anyone feel the same way? So, it is very humbling and a huge honor that you read and responded to this blog as your first written interaction with the Collaboratory — so…thanks again and WELCOME!

      Many of my favorite edu-bloggers, virtual coaches/mentors, muses and rockstar educators write, read and respond here in the Collaboratory. As you work through the planning process for your teacher leadership summit in Michigan know that there are many here who can cheer you on, push/challenge your thinking and/or lend a virtual hand in the planning and implementation process. At its heart, the Collaboratory is about virtual community and offering solutions for the complex teaching, learning and leadership challenges we all grapple with in different ways. So…don’t be shy about starting a thread and reaching out with anything you need! Best of luck and…Onward!