How about Howard Wilkinson ?
I think he went into teaching after playing, and then was quite advanced in taking coaching badges which was then in an academic environment..
Thereafter successful manager (including England caretaker), technical director, representative of peers (LMA), football club chairman, etc.
AND another name on the roll of honour of those who we have to thank for still having a football club. No sentiment in football? I am sure Sgt Wilko combined good business and sentiment when we were due in the High Court all those years ago.