Walden, a game

You can do this achievement on the same playthrough you are using for the Hermit achievement. However, you must wait until after you have received the Hermit achievement to unlock this one as this requires you to go into Concord.

If you go to the General Store in Concord, and you go over to the household tab, you will see you have an option to pay bills. This costs $10.50. I recommend waiting until you get the Walden Millionaire achievement to do this, or you can just make a save, pay the bills, then revert back to your previous save.