Heather Whelan was born and raised in Illinois. After high school she moved to Stevens Point where she got her degree in Psychology with a minor in German. After graduation she worked in a residential group home setting for adolescent girls. It was a challenging and rewarding job. There she solidified her decision to go into counseling. Heather went to Oshkosh for her graduate degree. During practicum hours in an elementary school, she fell in love with working with children in that capacity and became a School Counselor. She was hired at Hartland Lakeside right after graduation and is beginning her 25th year with the district.
When not at work she enjoys working out, relaxing by the pool, reading current novels, and spending time with family. They have lived in Hartland since 2005 and love this community.
About Heather Whelan
Q: Please tell us a little bit about your family.
My husband and I were married 4 years ago and we have a blended family. We have four children that we love spending time with as often as possible. Maiya is 26 and works in design and marketing and lives in Chicago. She recently got engaged and we are excited to be planning a wedding that will take place next August. Kaiyli is 23 and graduated with her masters degree in Communication Sciences and Disorders. She works as a Speech-Language Pathologist and lives in Chicago as well. Kaiden is 19 and attends the University of Iowa where he is a sophomore studying business finance. Keely is 19 and will be heading to the University of Minnesota this fall as a freshman to study Kinesiology.
Q: Please tell us about your life and what you do (whether working in our community, a business owner, volunteer, etc.). How did you choose that path?
After serving as the School Counselor for several years, I decided I wanted to further my education to pursue degrees in a different capacity and began working toward a degree in Administration and Curriculum and Instruction. I was offered the opportunity to take on the role as a principal in our early elementary building, which is the role I’ve been in for the last three years.
One of my biggest passions is being a foster parent. We have been fostering children, specifically babies for 11 years. Being a foster parent is a deeply rewarding experience, filled with many moments of joy and connection. The moment a baby is placed in our home they are part of our family. Our kids have always embraced each child and willingly helped with the daily responsibilities. It’s an opportunity to provide a stable, loving environment for children who may have never known such security. The bond that forms as you watch a child grow, heal, and thrive under your care is unparalleled.
The experience teaches patience, resilience, and unconditional love, often creating a lasting positive impact that goes beyond the foster care period. The knowledge that you are making a difference in a young life, offering hope and a sense of belonging, is one of the greatest joys of all. We are truly blessed to be able to love each and every baby placed with us!
Q: What do you love most about what you do?
I love working with our students, staff, and families. The kids are at the center of everything we do and every decision we make. Supporting our exceptional staff so they can come to work each day and pursue what they are incredibly passionate about is one of my top priorities. I am also committed to ensuring our families feel connected to Hartland North. As the first school experience for many, we lay the foundation for learning, and building trust and relationships with parents is a key priority.
Being an elementary principal is a role I love because it allows me to be at the heart of a child’s early learning and development. Every day brings the chance to inspire young minds, foster a love of learning, and create a positive, nurturing environment where students can thrive. I find great satisfaction in supporting teachers, guiding them in their professional growth, and working together to make a lasting impact on our students’ lives. The relationships I build with students, staff, and families are incredibly meaningful, and I cherish the opportunity to be a leader who shapes the future of our community. Seeing the excitement and curiosity in children’s eyes as they explore new concepts and develop their skills is a daily reminder of why I chose this path.
Q: What is the most rewarding part?
The most rewarding part of my job is watching our students make connections and grow each year, both academically and emotionally. Seeing them grasp new concepts, build on their knowledge, and develop resilience is truly fulfilling. It’s inspiring to witness their progress, not just in their core subjects, but also in how they interact with others, manage challenges, and build confidence. Every step they take forward is a reminder of the impact of our collective efforts, and it’s what makes this work so meaningful.
Q: What are some of your future goals? Do you have anything exciting coming up that you would like to share?
My goals for this year are to continue making learning exciting for our students by bringing innovative, developmentally appropriate ideas into our school. I am thrilled to open a state-of-the-art library, where students can explore endless worlds through books. We will also enhance our gym, where physical activity meets fun, and expand our musical garden, where creativity blossoms through sound and nature. The woods will become a place of exploration and hands-on learning, while our new book vending machine will spark a love of reading with surprise selections. Additionally, our phonology program will empower students with the foundational skills they need to become confident communicators. With these new and exciting spaces, I aim to make every day at school a thrilling journey that students look forward to with enthusiasm and joy.
Q: What advice would you give to someone interested in doing something similar to what you have done/are doing?
For anyone aspiring to become an elementary principal, my advice is to embrace the journey with passion, patience, and a commitment to lifelong learning. Start by gaining diverse classroom experience. This will give you invaluable insights into the challenges and joys teachers face, which is essential for effective leadership. Building strong relationships with students, staff, and families is key, so focus on developing your communication and interpersonal skills. Be prepared to wear many hats—whether it’s being a mentor, problem solver, or advocate—while maintaining a clear vision for your school’s growth and success. Flexibility and resilience are crucial, as each day will bring new challenges and opportunities. Finally, lead with empathy and integrity, always keeping the well-being and development of your students at the forefront of every decision you make.
Heather Whelan & Our Community
Q: What is your favorite thing about our community, favorite thing to do, or something unique about our community that you love? (Feel free to share as much as you’d like!)
I love the sense of unity and support that defines our community. It’s a place where people genuinely care for one another, coming together to celebrate successes and provide help during challenging times. The collaboration between families, educators, and local organizations is inspiring, creating a strong foundation for our children’s growth and well-being.
Q: Do you have a favorite coffee shop, cocktail shop, or restaurant?
There are so many places I love in our area that it’s difficult to narrow it down. Some of our top go to places are Palmers, Beer Snobs, and Artisan 179.
Q: What 3 words would you use to describe our community?
Inviting, supportive, family oriented.
For Fun
Q: What is something interesting that most people don’t know about you?
We have season tickets to both the Brewers and the Bucks, and we attend as many games as we can during the seasons. We also proudly support the Badgers, Packers, Hawkeyes, Golden Eagles, and Golden Gophers. My closet is stocked with sports gear for every team, ensuring I’m always ready to cheer them on at any game we attend , including gear for teams not mentioned above.
Q: What is your favorite book, TV show, movie, poem, or song? Why?
I wouldn’t say I have a favorite book, TV show, or movie. I enjoy a variety of each. When I’m able to pick up a book or turn on the TV, it’s a chance to sit back, unwind, and immerse myself in a different world for a little while. It’s my way of recharging and enjoying some much-needed downtime.
Q: Who inspires you to be better?
There are a few people who inspire me to be a better person. My husband is at the top of the list. He is the most caring, generous, and servant-hearted person I know. When I’m struggling with making a decision or figuring out how to handle a situation, he is always there to listen and bring me back to what’s important. His unwavering support and wisdom guide me through challenges. His kindness and compassion remind me daily of the person I strive to be.
Q: If you were a drink (can be a coffee drink, alcoholic, non-alcoholic, etc.), what would you be?
If I were a drink, I’d be a margarita because I bring a perfect balance of zest and warmth to any situation. A margarita combines the tangy freshness of lime with the smoothness of tequila. I blend enthusiasm and energy with a laid-back, approachable vibe. Margaritas are versatile, enjoyed in both lively celebrations and relaxed gatherings. Much like how I can adapt to different environments while keeping things vibrant and fun. The touch of salt on the rim adds a bit of edge, reflecting my ability to handle challenges with grace and a hint of boldness.
Q: What is something on your bucket list?
I have a few things on my bucket list. The top two things would be to take a European cruise down the Rhine River and the other one is to go to Australia.
Q: What makes you the happiest?
I’m at my happiest when all of our kids are home for a family dinner. There’s nothing quite like the joy of seeing them gather around the table, knowing that they love being here as much as I do. The conversations, the laughter, and the shared memories make those moments truly special. I also find immense happiness in snuggling and loving a baby, even during those quiet, middle-of-the-night moments. There’s something so pure and comforting in holding a little one close, feeling that deep connection and the love that fills the room.
Q: Any general life advice you would like to share?
Always strive to be better than you were yesterday. Don’t take yourself too seriously—find humor and levity whenever you can. Always be kind and give people grace; you never know what they might be dealing with personally. Remember, life is a journey, and each day offers a new opportunity to grow, learn, and make a positive impact on those around you. Embrace challenges with a positive attitude, and approach each situation with empathy and understanding.

Nice To Meet You:
I believe in positively impacting my clients and the community I live in, which is why I jumped at the chance to be an ambassador with “The Faces of Lake Country”. It’s a perfect blend of why I enjoy being a Realtor with Shorewest, Realtors, and everything I love about living in Lake Country.
I truly enjoy being a part of this community and helping others along the way. Prior to real estate, I was an Office Supervisor for the City of Waukesha Park & Recreation Department. During this time, I had the opportunity to work with many business owners and serve the general public. It was there that I realized that it really does take a village to make a community great and each and every one of us plays an important role.
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