Craft of the College Essay

Learn to nail your anecdote,
show up boldly,
and gain admission to college.
Services
In-Person Workshops
In-person workshop teaching the Craft of the College Essay framework.
1:1 Essay Consulting
Individual consulting sessions on your college essay.
Online Course
Learn the Craft of the College Essay framework at home and at your own pace, launching June 2025.
Hi, I’m Ann
After a decade as a trial attorney, I decided to pursue a career in education, believing I couldn’t lobby for schools without firsthand classroom experience. What started as a three-year plan turned into a 22-year passion for teaching.
I’ve had the joy of teaching AP Language and AP Literature to hundreds of students and coaching the nationally ranked Pinecrest Speech and Debate Team. Along the way, I was honored to receive the Golden Apple Award, be named Moore County Teacher of the Year, and serve as a semifinalist for North Carolina State Teacher of the Year. Helping students find their voices—especially in their college essays—has always been a passion. To that end, I’ve studied with Nancie Atwell in Maine and Mary Ehrenworth with Harvard University to deepen that work.
Beyond the classroom, I’ve been committed to my community, serving as Chairman of the Friend to Friend Board, President of the Friends of the Southern Pines Library, and a volunteer for the Boys and Girls Club and Habitat for Humanity. Today, I’m proud to serve on the Southern Pines Town Council.
I have two grown daughters, Katie and Jennie Cunningham, who “trained” me well in guiding students. I spend my spare time wrangling two unruly, spoiled golden retrievers—and baking a mean gluten-free oatmeal chocolate chip cookie.
Nail your anecdote
·
Show up boldly
·
Gain admission to college
·
Nail your anecdote · Show up boldly · Gain admission to college ·

Upcoming Events
Craft of the College Essay: May Session
Learn the Craft Framework in 90 minutes, hosted in Southern Pines, North Carolina
May 20, 2025
6:00-7:30pm
The Pilot
145 W Pennsylvania Ave
Southern Pines, NC 28387
$40 registration
For more information and to register, please contact craftofthecollegeessay@gmail.com
Craft of the College Essay: July Session
Learn the Craft Framework in 90 minutes, hosted in Southern Pines, North Carolina
July 23, 2025
6:00-7:30pm
The Pilot
145 W Pennsylvania Ave
Southern Pines, NC 28387
$40 registration
For more information and to register, please contact craftofthecollegeessay@gmail.com

1:1 Essay Consulting
I work with students individually, both in person and virtually, on their college essay at $75/hr.
To book time on my calendar, please reach out to craftofthecollegeessay@gmail.com.
Recommended Resources
Conquering the College Admissions Essay in 10 Steps
by Alan Gelb
Fiske Guide to Colleges
by Edward B. Fiske
Online Course
Get Notified:
The Craft of the College Essay online course is launching June of 2025, just in time for the college application season.
Please join the waitlist to be notified when the course has launched.