An achievement that simply must be done over time. Remember to take it slow, as each bobby pin has a 'health' bar such that if you guess wrong you can stop before it breaks. Should you fail often, you might want to invest in the Infiltrator (Perception 7, Lockpick 70) perk which lets you repick a broken lock one more time. This achievement can easily be done with "Hack the Mojave," as many locked doors have a terminal next to them that can unlock the door. If you do them simultaneously, access the terminal first, hack it, but then unlock the door manually instead of through the computer.