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

Dr Jessica Cabeen

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

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Austin, Minnesota

Dr Jessica Cabeen
Biography

Dr. Jessica Cabeen is a nationally recognized leader, author, speaker, and advocate for sustainable leadership. Known for her humor, honesty, and practical wisdom, Jessica helps leaders reject hustle culture and build lives and organizations rooted in clarity, purpose, and well-being.

Her sessions blend real leadership experience, relatable storytelling, and actionable strategies audiences can use right away. Jessica speaks to the realities of modern leadership: the full calendars, constant demands, complex relationships, and deep desire to make meaningful impact without losing yourself along the way.

Whether she is speaking to educators, executives, teams, or emerging leaders, Jessica’s message is both inspiring and practical: lead with purpose, protect what matters, and take the next small step that creates lasting change.

 

Dr Jessica Cabeen
Featured Videos

Current: Jessica Cabeen - Elevate Keynote Clips

Time 08:34

More Videos From Dr Jessica Cabeen

Jessica Cabeen - Elevate Keynote Clips
Time 08:34
Hacking Early Learning
Time 00:49
Kid Principal
Time 04:39
Meet Jessica Cabeen at the Happiest Place in Southeastern Minnesota!
Time 04:57

Dr Jessica Cabeen
Featured Keynote Programs

The Drip Effect
Small, Sustainable Actions That Create Lasting Leadership Impact

Keynote | Breakout | Workshop

Big change rarely begins with a dramatic overhaul. More often, lasting transformation happens through small, intentional actions repeated over time.

In this powerful and practical keynote, Jessica introduces audiences to The Drip Effect: the idea that sustainable leadership is built through consistent, values-aligned choices that compound into meaningful impact. Instead of chasing hustle, perfection, or constant reinvention, leaders learn how to identify the daily actions that shape culture, protect energy, strengthen relationships, and move important work forward.

This session helps leaders slow down long enough to lead with clarity, focus on what matters most, and build rhythms that support both high impact and personal well-being.

Participants will walk away with:

A clear understanding of how small actions compound into long-term leadership impact

Practical strategies for leading with clarity instead of urgency

Tools to protect time, energy, purpose, and relationships

A simple framework for identifying the next right “drip” in their leadership

Renewed confidence that sustainable leadership is possible

Best fit for: leadership conferences, executive teams, women’s leadership events, education conferences, nonprofit leaders, emerging leaders, and organizations seeking a healthier path to high impact.

DREAM BIG
Live Colorfully, Lead Boldly, and Build a Life You Don’t Need to Escape From

Keynote | Breakout

DREAM BIG is an inspiring and energizing keynote for people who want to live and lead with greater purpose, courage, and joy.

Many leaders spend their days serving others, solving problems, and carrying responsibility. Over time, it becomes easy to lose sight of personal dreams, passions, and priorities. DREAM BIG invites audiences to pause, reflect, and reconnect with the kind of life and leadership they are actually trying to build.

Through personal stories, practical strategies, and Jessica’s signature warmth and humor, this session helps participants explore what it means to lead boldly while living fully. Audiences will reflect on their roles, relationships, goals, and values while identifying small, meaningful steps they can take to move toward a more colorful and intentional life.

This keynote is not about doing more. It is about living and leading with greater alignment.

Participants will walk away with:

A renewed sense of purpose and possibility

Reflection tools for clarifying personal and professional priorities

Practical strategies for managing stress and protecting what matters

Encouragement to pursue meaningful goals without sacrificing well-being

A clear next step toward living and leading more intentionally

Best fit for: opening or closing keynotes, women’s leadership events, educator conferences, staff development days, leadership retreats, and audiences needing inspiration with practical application.

The Grace Gap
How Strong Leaders Communicate with Clarity, Courage, and Care

Keynote | Breakout | Workshop

Leadership is not only measured by what we accomplish. It is also revealed in how we communicate, especially when conversations are hard.

The Grace Gap explores the space between our intentions and our impact. In this session, Jessica helps leaders examine how authenticity, empathy, boundaries, vulnerability, and clear communication shape the trust and culture of any organization.

This is not a session about being nice or avoiding conflict. It is about becoming the kind of leader who can enter hard moments with courage and care. Jessica shares practical tools and real examples from both successful and imperfect leadership moments to help audiences strengthen communication, repair disconnection, and lead with humanity.

Participants will walk away with:

A deeper understanding of how communication shapes trust

Tools for navigating difficult conversations with clarity and care

Strategies for aligning intentions with impact

Practical ways to strengthen empathy, authenticity, and accountability

A renewed commitment to leading people, not just managing tasks

Best fit for: leadership teams, school and district leaders, executive teams, team development, women’s leadership events, and organizations navigating change, conflict, or culture-building work.

Present and Accounted For
How Belonging Drives Engagement, Culture, and Achievement

Education Keynote | Breakout | Workshop

Being present is physical. Being accounted for is relational.

In today’s schools, showing up is not enough. Students need to be known, seen, valued, and connected to a place where they believe they matter. Present and Accounted For explores how identity, relationships, and belonging serve as the foundation for meaningful engagement.

In this inspiring and practical session, Jessica helps educators and school leaders examine the conditions that allow students and adults to feel connected, invested, and ready to learn. Through stories, reflection, and actionable strategies, participants will consider what it truly means to create classrooms and schools where every person is not only present, but accounted for.

Participants will walk away with:

A stronger understanding of the relationship between belonging and engagement

Practical strategies for helping students feel seen, heard, and valued

Tools for strengthening adult connection and school culture

A renewed lens for attendance, engagement, and relationship-centered leadership

Clear next steps for building classrooms and schools rooted in purpose, presence, and belonging

Best fit for: K–12 conferences, school districts, principals, teachers, student support teams, attendance initiatives, culture and climate work, and professional development days.

Dr Jessica Cabeen
Featured Books

Principal in Balance: Leading at Work and Living a Lifeby Dr Jessica Cabeen

Principal in Balance: Leading at Work and Living a Life

by Dr Jessica Cabeen

A must-have guide to succeeding at school leadership without sacrificing personal balance

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 manager 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.

Nationally Distinguished Principal and four-time author Jessica Cabeen shows you how to navigate leading at work and having a fulfilling life. Throughout the book, you gain actionable points to help you set achievable goals, find time in the day to accomplish them, and have time to enjoy rest at home. You’ll learn to better meet the needs of your administration, staff, parents, and students using intentional and creative actions without sacrificing yourself.

  • Learn to balance work and life to create higher productivity
  • Gain proven tips for successful goal setting, staff retention, and student learning
  • Discover lead-to-win strategies that can help you improve your leadership in all areas
  • Make intentional space in your daily life for self-care and permission to rest

Principal in Balance offers a practical, timely approach by a school leader for school leaders to cultivate work/life balance. This book is an essential companion for K–12 school leaders and administrators, aspiring school leaders, and teacher trainers.

Unconventional Leadership: Bridging the Connected World with Meaningful Relationshipsby Dr Jessica Cabeen

Unconventional Leadership: Bridging the Connected World with Meaningful Relationships

by Dr Jessica Cabeen

Today’s educational leaders are working with more resources, more research, and more stakeholders – all within the same, limited time in a day as we had a decade ago. Author Jessica M. Cabeen takes readers through an intentional journey of current trends and buzzwords, helping leaders understand how social media is a tool for connection, collaboration, and learning. This exciting book explores the importance of care and collaboration with all members of the educational community – students, teachers, staff, families, and community partners. Each chapter highlights examples of leaders that have made positive change in their schools, and provides key actionable strategies that can be implemented at a pace that is sustainable and tailored to fit your needs. You will discover a deeper understanding of the critical importance of your role in:

Elevating the student’s experience

Building a strong school culture

Creating small ways to make big impacts with families

Advocating a clear message with community partners and legislative leaders

Creating time for self-care

Filled with practical examples, tools, and strategies, Unconventional Leadership is a resource school leaders can pick up today and implement tomorrow.

Lead with Grace: Leaning into the Soft Skills of Leadership (Lead Forward)by Dr Jessica Cabeen

Lead with Grace: Leaning into the Soft Skills of Leadership (Lead Forward)

by Dr Jessica Cabeen

Why do even great leadership books leave out the soft skills?

Probably because soft skills are not flashy. But soft skills are critical to graceful leadership, and you will find the stories and strategies to hone them and to empower people around you, inside this book. National Distinguished Principal and leadership advisor Jessica Cabeen understands the soft skills better than most.

In Lead with Grace Cabeen shows you how to seamlessly integrate authenticity, empathy, integrity, and the power of vulnerability into your daily work, turning you into someone who is leading young minds with grace and someone who will empower people around you.

Using frameworks and insightful leadership advice, Cabeen provides insightful leadership advice in an informative leadership memoir style. She helps you nurture relationships, enhance communication, manage boundaries, and provide the grace you need to effectively lean into your work, at school, home, or the office.

Leaning into the soft skills of leadership will help you:

  • Find ways to confront negative workplace behaviors.
  • Leverage opportunities that help people interact in healthier ways.
  • Create a workplace culture that supports risk-taking, while amplifying individual voices.
  • Enhance social media interactions to empower all stakeholders.
  • Implement habits that make grace an intentional practice in your personal and work life.

Great leaders, teachers, parents, and are typically good at the hard skills: organization, guidelines, and management. Very few, though, are great at the soft skills. And even fewer really understand how to lead with grace. Now, you can be a great and graceful leader, who understands and leads with soft skills.

Grab Lead with Grace today, and integrate authenticity, vulnerability, empathy, and integrity into your work immediately. Under your graceful leadership, staff, students, and co-workers will perform like never before.

Balance Like a Pirate: Going beyond Work-Life Balance to Ignite Passion and Thrive as an Educator (A Lead Like a PIRATE Guide)by Dr Jessica Cabeen

Balance Like a Pirate: Going beyond Work-Life Balance to Ignite Passion and Thrive as an Educator (A Lead Like a PIRATE Guide)

by Dr Jessica Cabeen

“I just can’t get it all done.”

“I’m crazy busy.”

“I never have time to enjoy life.”

If you relate to those sentiments, you know that in today’s 24/7, always-on culture, life feels busier than ever before. That hectic pace combined with the constant demands that come with being an educator create the perfect conditions for burnout. But life doesn’t have to be that way.

Balance Like a Pirate, a Lead Like a PIRATE Guide, was written by educators for educators with a focus on helping you create a lifestyle that allows you to break free from “shoulds” and “have tos.” Educational leaders Jessica Cabeen, Jessica Johnson, and Sarah Johnson equip you with practical strategies and tools to thrive in every area of life.

Balance is a myth, but living with purpose, passion, and priorities is within your reach.

Hacking Early Learning: 10 Building Blocks to Success in Pre-K-3 That All Teachers and School Leaders Should Know (Hack Learning Series)by Dr Jessica Cabeen

Hacking Early Learning: 10 Building Blocks to Success in Pre-K-3 That All Teachers and School Leaders Should Know (Hack Learning Series)

by Dr Jessica Cabeen

What if we raise the bar on early learning?

School readiness, closing achievement gaps, partnering with families, and innovative learning are just a few of the reasons the early learning years are the most critical years in a child’s life. In what ways have schools lost the critical components of early learning -- teaching preschool through third grade -- and how can we intentionally bring those ideas and instructional strategies back?

In Hacking Early Learning, Kindergarten school leader, early childhood education specialist, and Minnesota State Principal of the Year Jessica Cabeen provides strategies for teachers, principals, and district administrators in best practices for preschool teachers and leaders, kindergarten teachers, teaching first grade, teaching second grade, and teaching third grade, including connecting these strategies to all grade levels.

It's What You Can Do Tomorrow

Using the popular Hack Learning Series problem-solving formula, Cabeen brings educators a simple guide for making the early years more meaningful, engaging, and full of intentional learning experiences. Cabeen shows all stakeholders how to:

  • Create learning environments that are conducive to play, technology integration, and movement
  • Provide a clear understanding for ALL staff members of what we want students to learn
  • Give parents detailed, timely information about what their children are learning and how they can support teachers and learners at home
  • Bridge the gap between early learning and K-12
  • Create innovative professional growth for pre-K-3 educators
  • Grant access to research-based practices and give teachers time to reflect on their teaching with others, in order to learn the best strategies for ALL children -- Pre-K-3 and beyond -- to succeed

Experts gush over Jessica Cabeen and Hacking Early Learning

"Hacking Early Learning gets to both the heart and mind of our youngest learners. The practical strategies allow the reader to set up an environment that works for everyone in the learning community. If you work with kids, or adults who work with kids, Hacking Early Learning is an essential component to your leadership toolbox.”

-Joe Sanfelippo, Superintendent, Fall Creek Schools, Co-author of Hacking Leadership

“Jessica Cabeen is not afraid to say she’s learned from her mistakes and misconceptions. But it is those mistakes and misconceptions that qualify her to write this book, with its wonderfully user-friendly format. For each problem specified, there is a hack and actionable advice presented as “What You Can Do Tomorrow” and “A Blueprint for Full Implementation.” Jessica’s leadership is informed by both head and heart and, because of that, her wisdom will be of value to those who wish to teach and lead in the early childhood field.”

-Rae Pica, Early Childhood Education Keynote Speaker and author of What If Everybody Understood Child Development?

"Jessica’s amazing successes as a school leader give credibility and weight to her shared knowledge so that the readers feel empowered and confident in turn-keying these strategies into a plan of action to be successful at their schools. You’re going to love reading this book and want to share it with others!”

-Andy Jacks, Award-winning principal and Co-founder of #DadsAsPrincipals

Start Today

Dr Jessica Cabeen
Featured Reviews

Dr Jessica Cabeen
Featured Articles & Resources

Teacher for the Day. Reflections from a Principal turned Kindergarten Teacher. #HackingEarlyLearning

The 2006-2007 school year was the last time I was listed as the teacher of record for any classroom.  In November a veteran teacher met with me and asked me to sub in a...
Read More

The Greatest .No.

This weekend we went to the movie The Greatest Showman. While I wasn’t looking for a life changing lesson in that 2 hours, it came anyway. During the movie the lyrics of the...
Read More

Leadership In The Digital Age: Considering The 3C's

Earlier this year, the TEC Center asked early childhood educators, libraries, museums, home-daycare providers, parents, and children’s media developers to connect how the...
Read More

Frequently Asked Questions

Quick answers to some of the most common questions about booking Dr Jessica Cabeen for your event.

How do I book Dr Jessica Cabeen for my event?

Booking Dr Jessica Cabeen with Premiere Speakers Bureau is a streamlined 4-step process:
  • Availability Check: Contact us with your event date and budget to verify if your desired speaker is available.
  • Hold Date: We place a temporary "hold" on the speaker's calendar while you finalize internal approval.
  • Contracting: We issue a contract outlining the fee, cancellation policy, and event expectations.
  • Logistics: Once signed, our event management team handles all travel booking, itinerary, and AV requirements.

Why should I partner with Premiere Speakers Bureau rather than contacting speakers directly?

Partnering with Premiere Speakers Bureau provides a comprehensive safety net for your event that direct booking cannot match. You get the same speaker for the same price, but with a dedicated team with over 30 years of event experience handling contracts, logistics, and are prepared for any emergency. We know what it takes to run an excellent event.

What makes Premiere Speakers Bureau unique compared to other agencies?

Premiere Speakers Bureau distinguishes itself by having over 30 years of experience while partnering with more than 35,000 events. PSB has also built a streamlined, fully online process that makes booking a speaker, handling travel and payments extremely easy for anyone looking to plan a speaker led event.

How does Premiere Speakers Bureau's 'Zero Cost Service' model work?

Premiere Speakers Bureau operates on a 'Zero Cost Service' model for event planners. Our services—including research, booking, and logistics—are always free to the client. The speaker covers our commission from their standard honorarium as payment for our role in marketing and managing their engagements.

How are speaker fees structured, and what is typically included?

A speaker's fee typically covers the keynote presentation, a pre-event planning call, and standard customization. Travel expenses are usually billed separately.

What are the standard policies for speaker travel and expenses?

Travel expenses are negotiated during contracting. We generally recommend a flat travel fee for simplicity, though we also offer line-by-line invoicing when preferred. PSB ensures these expenses adhere to professional standards, and our Event Portal allows for easy tracking and invoicing.
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