Benjie Colberg, M.Ed.
Founder & lead consultant. Husband to Ali. Dad to Walker. Lacrosse Program Director at The Covenant School.

I grew up in Charlottesville and learned lacrosse at The Covenant School. I went on to play four years at Denison University, where I captained the Men’s Varsity team my senior year and graduated in 2015 with degrees in Economics and Communication.
I then spent nine years at Christ School, an all-boys boarding and day school near Asheville, North Carolina. In that decade I worked in admissions, taught classes, coached soccer and lacrosse, lived in the dorms with teenage boys, served as Dean of Campus Life, led the strategic planning process, ran campus-wide reform task forces, and sat on the senior leadership team. I earned my Master’s in Independent School Leadership from the Peabody School of Education at Vanderbilt University in 2021.
Somewhere in the middle of that, I took a year to complete the Trinity Fellows Program, a vocational discernment fellowship in Pittsburgh. The Fellows program used three lenses for self-knowledge — the Enneagram, Myers-Briggs, and the Highlands Ability Battery. Of the three, only one produced what I’d call objective data: the Highlands. That year planted the seed for the business I run today.
Why Timshel
Timshel is the Hebrew word at the center of Steinbeck’s East of Eden. It means “thou mayest.” Not thou shalt, not thou wilt — a choice. Steinbeck called it the most important word in the language. I believe that, too. The whole purpose of this practice is to put the right information in front of someone facing a real choice.
Credentials
- M.Ed., Independent School Leadership — Vanderbilt Peabody
- Certified Highlands Ability Battery Consultant
- Trinity Fellows alum (vocational discernment)
- Former Dean of Campus Life, Christ School (Asheville, NC)
- Lacrosse Program Director, The Covenant School (Charlottesville, VA)
- Captain, Denison University Men's Lacrosse (D3, NCAC)
Where I work
My family and I split our time between Charlottesville, Virginia and Asheville, North Carolina. I see clients in person in both cities and run group engagements at schools across Virginia and North Carolina. The Highlands assessment itself is completed online; the debrief and coaching can be done in person, over video, or some combination.
Writing
I write for The Washington Institute on culture, vocation, and the formation of young men. You can find that work — and a monthly newsletter I send to clients and friends of the practice — in the Journal.
