This achievement will take about 20-25 minutes to obtain if you set up a game of LIFE with 2 controllers. I want to point out a few things that may be helpful in ensuring that you win. With your profile, make sure to take the career path and not the college path so that you don't owe any money at the end of the game. You'll then get to choose cards to see what career you get. Make sure that you get all of them so that you have more choices to choose from. You'll then want to choose the highest paying job and continue to move on down the board. At some point, you'll get married and have to play a mini game similar to TWISTER. Make sure to try and do good at this cause it will benefit you in the end. Lastly, make sure to invest in a decent house so you get a better resale value as well. At the end of the game, you'll want to retire at Millionaire Estates. If you do this with your profile and basically the complete opposite with your 2 controller, you are guaranteed the achievement. Hope this helps!