Here is the full list of all 27 Orwell: Keeping an Eye On You achievements. It takes around 8-10 hours to unlock all of the achievements on Windows.
End a career.
Find out who is there.
Administer justice.
Avert catastrophe.
Make Thought crimes.
Reunite a couple.
Don't bother the law.
Win the war.
Repay the debt.
Set Thought free.
Complete Episode Five.
Choose the simple answer.
Uncover the truth.
Complete Episode Four.
Pick up what was left behind.
Make an unlawful arrest.
Complete Episode Three.
Forgive a crime.
Keep quiet about the intention.
Complete Episode Two.
Don't read minds.
Allow catastrophe.
Know all favorites.
Show the peaceful side.
See no crime in buying a bottle.
Complete Episode One.
Show the rebellious side.