Walden, a game

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

Sometime during Early Fall, Emerson will send you a letter mentioning surveying jobs. Once you get this, you can go into Concord and into the Post Office and on the wall will be some papers. One of them will be a surveying job. Pick it up and you will now see the job icon appear on your map. There are 8 surveying jobs that need to be completed. Each time you complete one, you will see the money icon appear on the bottom left of your screen, and you will need to go to the Post Office and grab a new one. As you progress, the surveying jobs will get more difficult, requiring you to survey more than once, etc. The last one requires you to survey the different coves of Walden Pond. Once you are done the achievement is yours.