For this achievement, you will have to travel to
Riften . You will be soon approached by
Brynjolfand he will offer to let you in on a job which he's working. Accept and do his quest. Then he will direct you to the
The Ratway, an underground tunnel system underneath Riften, there is a tavern there called
The Ragged Flagon, and when you get there you can join his organization. If you fail to plant the ring, you will still be asked to go to the
Ragged Flagon and join the Guild.
Go there and he will then give you a quest
Taking Care of Business. Keerava has a soft spot for family, Bersi has a priceless - and fragile - urn, and Haelga has her devotion to Dibella, goddess of beauty.
The debts may be collected in any order you choose, but keep in mind that after you have two debtors in line, the last - whomever that may be - will cave immediately, having heard how you dealt with the others.
Return to him and this will end
Taking Care of Business rewarding you the achievement.
Have in mind that if you have not traveled to Riften yet you can use
Bjorlam's carriage outside of
Whiterun Stables to travel there for a small fee.
Good luck and enjoy Skyrim on the One
.