Pretty straightforward achievement. Just travel to each of the nine major cities (Riften, Windhelm, Winterhold, Whiterun, Falkreath, Markarth, Solitude, Morthal, Dawnstar) and kill a random person where someone else can see you. This will give you a bounty 1040 (40 for assault, 1000 for murder). Escape the guards if necessary and repeat in the other cities. You'll probably want to save before you do this so you don't have to eventually pay the fine/go to jail or accidentally kill someone important.