Bloomtown: A Different Story

First off, this is a cumulative achievement that tracks every dollar you earn / find / win until you have reached $50. You don’t need to hold an exact amount of $50 in your wallet / purse to get this.

As such, you’ll absolutely get this naturally whilst playing the game, but if you want to speed this up, your earliest opportunity to ‘grind’ this out is by working at Mr Lovely’s grocery shop once you are introduced to him early in the game.