Here is the full list of all 10 Sickness achievements. It takes around 0-1 hour to unlock all of the achievements on Windows.
Fail your first paid kill
Turn down the opportunity of a lifetime
Attend counseling
Kill Mr Roth while he's indisposed
Turn the tables while being seduced
When things get messy, neglect your duties
See this season's biggest blockbuster
Cohabitate with Misa
Give up everything to stop history from repeating itself
Spend eternity with Sara