While only nine percent of workers say their employers expect them to check voicemail or email on vacation, others may feel the pressure to do so anyway. There are a host of reasons why employees feel compelled to forgo a vacation or obsessively check in. Some may fear if they are gone and things go smoothly, it will send a message that they aren't needed. However, the opposite can actually be true. If you prepare in advance and anticipate issues, it can positively reflect on your management and organization skills.