It's based on several factors. I don't know all of them, but here's what the User Guide says:
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Simulate a realistic career length: Select this option to automatically retire the Commander after a random number of patrols (based on the number of days spent at sea and the minimum and maximum number of patrols completed by real commanders). If you select this option, please be aware that the randomisation occurs every time you launch a career using SH3 Commander, but not when your career is mid-patrol. So, if you like to tinker between patrols without actually starting a patrol be aware of this and uncheck this option prior to launching Silent Hunter III.
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