In order to obtain this achievement, you have to enter MyCAREER, obviously. Then, go to ‘The Neighborhood’.
Once loaded up, you should spawn in front of your house/MyCOURT. Go to the left, and you should see a long street called, “2K Beach Parkway”. Walk or run down that street and you should get to the end of the street.
Now, turn to the right and you should see a building called, “Jeff’s 2K Arcade”.
Enter the building and the achievement will unlock.