Will the non compete clause in my contract hold up after employment?

Restrictive employment covenants are not favored in the law, but they will be enforced if they are reasonable in scope and are supported by consideration. A recent court case decided in June in Cook County has changed the landscape in this area. Even pre-employment covenants are now treated the same as post-employment covenants, requiring up to two years continued employment to be enforceable. If you have been at it for more than two years, they still must be reasonable in scope. You stated the geographical scope is 100 miles, the time scope is one year and the subject scope is the same curriculum. That may be reasonable. If you leave and teach at a school that uses a different curriculum, the covenant does not apply. They cannot enforce it if it does not apply. As long as the curriculum is different, then you should have no problems. If the curriculum is the same, then you will need to consider the reasonableness of the scope, and that may be a crap shoot. Frankly, I think one year is reasonable, but 100 miles is not reasonable, but I am not the person who would need to be convinced. If the school were to sue you, a judge would decide.