Jessica Cabeen | Nationally Distinguished Principal - Dream Big, Live Colorfully, Lead Boldly

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Jessica Cabeen

Nationally Distinguished Principal - Dream Big, Live Colorfully, Lead Boldly

Jessica Cabeen

Jessica is the Principal of Alternative Educations Programs in Austin, Minnesota. Previously, she was the principal of Ellis Middle School in Austin, Minnesota, and the principal of the “Happiest Place in Southeastern Minnesota,” the Woodson Kindergarten Center. She has been an assistant middle school principal, a special education assistant director, and special education teacher. 

Jessica was named the 2021 ED Dive National Principal of the year, 2017 Minnesota National Distinguished Principal of the Year, and was awarded the NAESP/VINCI Digital Leader of Early Learning Award in 2016. She is a NAESP Middle Level Fellow and a Future Ready Principal. Jessica is the author of Hacking Early Learning and co-author of Balance Like a Pirate, Unconventional Leadership, Lead with Grace: Leaning into the Soft Skills of Leadership and  Principal in Balance: Leading at Work and Living a Life. (releasing in March of 2023).   

She is a sought-after speaker and trainer and enjoys getting to learn and lead with other educators across the nation. Jessica enjoys connecting and growing her Professional Learning Network (PLN) on the socials. She can be found on Instagram, Facebook, and Twitter @JessicaCabeen. 

But by far her favorite space is the one that involves being with her husband Rob, sons Kenny and Isaiah, and, of course, the family dog, Herman.


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Dream Big, Live Colorfully, Lead Boldly
Developing Your Best Self at School and Home

Today’s educators have pressures that can become barriers to maintaining

wellness in all aspects of life. In this session we will explore ways in work and life to set your own goals and priorities in the different quadrants of balance (positional, personal, professional, and passion). We will learn ways to manage processes more effectively so you can be present at the moment, diffuse difficult situations with families, staff and parents so you can leave school, and rekindle your own passions so your students and staff can see the real you.

In order to lead at work and live a life we need to find ways to thrive, not just survive in the busy pace of leading, learning, and living life. As a principal, wife, mom, daughter, student, and teacher, Jessica has a passion to learn and share ideas that will provide educators with strategies to lead at home and at school. Come prepared to make a commitment to change, and find ways to make it happen.

Session Objectives:

  • Understanding the importance of developing resilience in our work and lives.

  • Strategies for successful goal setting.

  • Developing ways to set boundaries between work and life.

  • Ideas for enhancing and developing deep and meaningful relationships with students. 

Principal in Balance
Leading at Work and Having a Life

Reports of burnout, stress, and compassion fatigue are on the rise. These issues push many out of the profession, leading to high turnover and sub-optimal student outcomes. How can school leaders combat these problems? Leaders can manage their own wellness and priorities. Healthy leaders who learn balance can create motivation, confidence, quality collaboration, and enthusiasm among staff and other stakeholders. 

Principal in Balance offers principals strategies and tools to take more ownership of their lives at work and home, so everyone in the K–12 educational community can thrive. Participants will walk away with a plan that they can put into action during the summer that is sustainable throughout the school year.

Session Outcomes:

  • Understanding the importance of balance and the role stress has in our lives.

  • Developing a sense of bandwidth for the work, and boundaries to set to thrive.

  • Creating a self-care playlist that is sustainable.

  • Learning how to create goals that are relevant, achievable and exciting. 

Lead with Grace
Leaning into the Necessary Soft Skills for Success

Do you love what you do, but at times struggle with the necessary interactions and communication skills that could elevate interactions in all aspects of your life? Jessica shares practical examples from her successes and epic failures of utilizing skills to build authenticity, vulnerability, and empathy in your day to day interactions. Participants will walk away with practical tips and ways to apply these skills in their communications, relationships, and when navigating the world of social media.

Session Outcomes:

  • Understanding the key components of Leading with Grace.

  • Incorporating tenants of vulnerability and authenticity in your leadership style. 

  • Learn how to work with social media, not meltdown. 

Expect the Best! Creating a High Performing Culture.

What does it take to learn and lead in schools today? Through research and her own practical examples of leading at every level of the K-12 educational system, Jessica will share key ways to thrive in today’s classrooms and schools. Come ready to be motivated and inspired to connect to the calling of this work.

Session Outcomes: 

  • Concrete ways to build culture and capacity from classrooms to schools. 

  • How can we continue to seek the good through a season of weeds?

  • Understanding the Importance of Meaningful Relationships

Jessica Cabeen
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