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When you reach 2020, you get a prompt telling you "Congratulations... It's time to retire." You're then given two options, "Exit Game" and "This is my Job! I'll decide when to retire." If you choose the later one, you can continue playing for as long as you want. You will get this message every time you load a save game that is past the selected map's end date.
If you mean promptly ends in any other manner, such as crashing, please feel free to email me the log file.
Please email me the log file then after it crashes. http://wiki.gearcity.info/doku.php?id=troubleshooting:steam_logfile
Are you sure you didn't click "Exit Game" or close the prompt with the red X?