About Stephanie Hogan

I was raised in New Hampshire and Vermont, where I attended Stowe public schools and the Mount Mansfield Ski Academy. I matriculated to Guilford College, in North Carolina, where I majored in Art, Education, and Psychology. After traveling around the world, I taught at a therapeutic day school in Massachusetts, owned and operated a dog walking and pet sitting company in Portland, Maine, and moved to Connecticut to teach, coach and dorm parent at the Rumsey Hall School. In 2015, I moved abroad, with my husband and two boys, to work at Cayman International School and as a private homeschool educator and curriculum manager for elementary school aged boys.  I also worked with Dorm and Day, an educational consulting company, to provide SSAT and SAT tutoring for families on island. 

Today, I am an Academic Support Tutor at Waynflete School, and an Executive Functioning Coach, Positive Discipline Classroom Educator, and Owner of Be Brave Seek Joy Consulting.  I am committed to supporting the whole child through one on one and small group instruction, alongside the use of encouragement tools: solution based thinking, self awareness, and mindfulness.



I began as an Ed Tech at the Gifford School in Weston, Massachusetts,  where I supported students with significant learning and behavioral challenges. Later, I worked as a member of the English faculty at the Rumsey Hall School in Washington, Connecticut. This was followed by teaching 480 students, across four schools, pre-k to high school, as the Director of Aquatics at the Cayman International School. Before moving back to Portland, ME, I served as curriculum coordinator and lead teacher for a family who homeschooled their two boys on Grand Cayman, in the Cayman Islands. 

StandarDized Test

For the last ten years I have specialized in preparing students to sit the SSAT and SAT. I spent last year researching the best practices for the revised verbal SAT, working closely with the Kaplan and Princeton Review texts. I have assisted countless students over the years, beginning with boarding and day students at the Rumsey Hall School in Connecticut, and most recently, at the Cayman International School, and private schools across Grand Cayman. Presently, I work with students in Portland, South Portland, Falmouth, Yarmouth, Cape Elizabeth, and Freeport. 

Home School

Starting in 2016, I worked for one year managing a full international homeschool curriculum for two elementary school students, with a focus on social emotional growth, dyslexia, and high ability learning. I managed a certified homeschool curriculum, designed and implemented Project Based Learning and Curiosity Curriculums, while overseeing course materials for Language Arts, Geography, History, and Social Studies. I also incorporated the positive discipline platform into the classroom to help facilitate independence, respect, honesty and kindness.

Positive Discipline
Classroom Educator

I am a certified Positive Discipline Classroom Educator; supporting teachers, students, and parents through social emotional guidance and effective, positive discipline strategies and tools.

Learning Styles

I utilize teaching methodology from Susan Barton, Orton Gillingham, and Sarah Ward to address student’s learning differences associated with ADD, ADHD, dyslexia, auditory processing, executive functioning, and non-verbal learning disorder. 


I am the mother of two amazing boys. I am the Waynflete Girls Varsity Field Hockey Coach and a former ski racer. I owned and operated a successful dog walking and pet sitting company in Portland, Maine a decade ago. I am the Waterfront Director at a boys summer camp in Maine, American Red Cross Lifeguard Instructor, and a Swim Instructor Faculty for Starfish Aquatics Institute. I own Be Brave Seek Joy Consulting, which feeds my entraprenurial spirit, and supports families from a positive discipline approach to raising children to thrive and be resilient.