Note: It doesn't matter if you do it yourself or hire a worker for this to count. However, it must be done on a field you own, hired jobs do not count for this.
This achivement chain requires more work than the other 3, because you will have to haul the harvested crop away. Different crops require a different types of harvesters so make sure you have the correct type of harvester for the crop you have before you begin. You will also need a hopper and something to pull it with so you can unload the harvester when it gets full. The bigger the harvester, the faster you can get this done. It is faster to rotate through the cultivating, sowing, fertilizing and harvesting on the same field so you are working on the achievements for all 4 instead of doing one group at a time.
Hire a worker to run your harvester, while you sit in your haul vehicle. The harvester will start flashing beacons when it gets close to full (80% full I think), and it will stop and wait for you once it reaches 100% full. To empty the harvester drive your haul vehicle up to the left hand side of the harvester and when the hopper is in place it will automatically start to fill up. You can either wait until the harvester is completly full, or drive alongside it very slowly when it gets close to full so it doesn't have to stop. Once your hopper is full you can either sell the crop somewhere, put it in your storage area, or dump it somewhere. It doesn't matter what you do with it for the purposes of this achievement.
You get these naturally while completing this one.