Welcome to Thoughtful Homeschooling


About Us


I'm Holly Ramsey and for two decades, I have home educated my five kids ages 10-24. From colic to the Common App, I've been there, done that and have the wrinkles to prove it. 

I offer Planning High School workshops for home educators, a Common App class for rising seniors working on college applications, as well as one-on-one consulting services and essay coaching.

My three college-age sons received combined merit in the amount of $442,000 to their first choice schools. Sixty-four thousand dollars of that total came because I learned the right way to ask the right questions at the right time. I'm happy to share what I've learned with others.

Within the homeschooling community, I have taught or organized creative writing classes, literature clubs, public speaking clubs and contests, Science Olympiad teams, parent support groups, competitive math clubs, and field trips too numerous to list. My articles have been featured in Practical Homeschooling and Home School Enrichment. I also coach online writing classes for Brave Writer.

Prior to home educating, I taught social studies in the public schools, and in a Coalition of Essential Schools program. I received a MA in Teaching from the University of North Carolina at Chapel Hill and graduated with High Honors from Binghamton University with a BA in History and Philosophy. I am an associate member of the Independent Educational Consultants Association.


Join us on the Thoughtful Homeschooling Facebook page for conversation contemplating all things home education. 

Follow us on Instagram @Thoughtful_Homeschooling

On Twitter @ThoughtfulHSing


Email ThoughtfulHomeschooling@gmail.com for details about consultant services: 

how to start homeschooling, individualized curriculum selection, high school planning, transcript packages, college application workshops and essay review. 

Fees for 2020

Free, no-obligation, 30-minute phone call for any parent new to or considering homeschooling. 

Group planning high school workshops: $75 per individual, spouses attend free.

Individual planning high school consults:

$100 for 60-minute consultation.

Two rounds of feedback for the personal statement and activities list:


Supplemental Essay Review with 2 rounds of feedback for up to 5 supplemental essays:


If you host a planning high school workshop or college application workshop with four or more participants within a 20-mile radius of Naperville, your own attendance will be free. Details upon request.