High Aspirations School
Elite Education for Everyone
We believe that education is the best tool for unlocking human potential. We are building an online community that connects highly motivated students all over the world with elite teachers to help them turn their dreams into realities.
Our Background

Dylan Farrell
Co-founder and Chief Executive Officer
Dylan received his BA from Harvard University in 2018 with a Joint Concentration in Statistics and Mathematics and a secondary in Economics. After graduation he worked as a strategy consultant, data analyst, and machine learning engineer at Curinos, a financial technology company specializing in retail and commercial banking solutions and advice.

Stephen Farrell
Co-Founder and Chief Educational Officer
Stephen recently retired from Choate Rosemary Hall after teaching English there for 43 years. Over that span he held just about every administrative position at the school, including Assistant Headmaster, Dean of Faculty, Dean of Students, Dean of Academic Affairs, and Head of the English Department. Since 2016, Stephen has also been teaching online History, Literature, and Writing classes to Chinese students who are interested in attending US schools. Stephen has a B.A in English from Wesleyan University, an M.A in English from Middlebury College, and a M.A.L.S from Wesleyan University. He has received multiple honors and awards for his teaching.

Caitlin Farrell
Co-Founder and Chief Operations Officer
Caitlin received her BA from Georgetown University in 2019 with a major in Government and a minor in Spanish. She went on to play professional soccer in the NWSL for the Orlando Pride. Following her professional soccer career, she worked as an operations coordinator for the summer programs office at Choate Rosemary Hall. She then worked as a senior paralegal for Murphy & Riley in Boston before joining High Aspirations School.
Our Inspiration

The inspiration for our school's name and ethos comes from a 1973 painting by Black American artist Ernie Barnes entitled High Aspirations. Stephen purchased a framed copy of this painting in 1980, and ever since it has hung in his home. As a basketball player and coach, he was immediately drawn to the work, and he especially loved how the details of the painting captured the title. Dylan and Caitlin grew up looking at this work of art every day, and when it came time to choose the name of our school, Dylan quickly said let's use the title of the Ernie Barnes painting we all love. Thus, we chose this work of art because both the artist and his painting embody the character traits that we believe are essential for success in learning and in one's career.
The painting depicts an elongated young Black male about to dunk a basketball into a homemade wooden basketball hoop. He is playing alone amidst a barren rural landscape with only a large wooden house depicted in the background. The focus of the painting is the young male, seemingly of high school age, his dreams of the future, and his willingness to extend himself (literally) in the pursuit of them. Like Jay Gatsby in Fitzgerald's famous novel, he is not going to let his impoverished origins, social isolation, or uninspiring landscape limit his dreams. In fact, they will be the inspiration to make his dreams larger than life.Read more