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 is a simple achievement it just takes time. Just grab your favorite tractor, put a seed sower on the back and go to town on a field you own. The bigger the sower, 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.
I recommend choosing one type of seed for the entirety of this achievement chain so you only need one type of harvester for the harvesting achievement chain.
You will get this naturally while completing these.