I started by looking up logos of other organizations' 50th anniversaries.
After some research looking into the symbology of the number 50, I decided that there was a great power in the number and its associations, and I wanted to reflect that power elegantly. Fifty years is a long time and that age mark comes with connotations of experience, strength, and endurance.
In order to better understand how I could reflect those traits in two numerals, I played around with different styles of typefaces:

After looking at the variation I generated, I suddenly knew that I wanted to go with a classic choice.
I took oldstyle numerals from Caslon and Jenson and combined their forms for the 5, making something both sturdy and energetic. The 0 is simply Caslon.
To further activate the form, I added the trademark Governor's School flame to the 0. Like I've mentioned before, I really feel like this flame is a unique representation for GS as an organization, through both perceived concept and form. It also tends to spring into action along with the 5, complementing it nicely.
I experimented with this relationship below.

I then took my favorite combinations and paired them with NCGS text, set in Minion. This may not be part of the final logo- I just tried to understand how to place the text with the image of the 50.

Further refinement.

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