For this achievement the player has to deliver 5 cargos from the Russian city of Kaliningrad (found to the left of Lithuania) to any other city in Russia.
The other cities are: Pskov, Luga, Sosnovy Bor, Vyborg and Saint Petersburg.
If choosing quick jobs, select Kaliningrad and check if any of the routes available are going to a Russian city. If not, travel to another garage or sleep to skip some ingame time one such job is available. The quickest route is to Pskov, but I often didn't found cargo destined for that city, and had to drive a few hundred kilometers further to Vyborg.
So there are a few things to keep in mind, the starting city needs to be Kaliningrad, and it needs to be delivered to another Russian city (not Kaliningrad itself), thus requiring the player to drive through the Baltic states for every one of the rides.
Upon successful delivery of the fifth cargo, the achievement should unlock.