Jacko is in the same situation any professional is faced with whether a footy player, an elite sports person, even brain surgeon in your work/life cycle.
Slowly, gradually, eventually, after maintaining your elite performance for several years, you come off your peak and start to regress. The younger competitors start catching you up and you struggle to keep up to your previous standards.
No matter the loyalty and value you once provided, and the hard yards you've put in, it must be faced that new players, and employees, are waiting for their turn to shine and replace you.
It's no disgrace, and transitioning to retirement and new horizons should be as natural as the anticipation of first starting your career.
Jacko's first grade career is approaching that time and all due respect to him with that eventuality.