Controls are the hardest part of this achievement. You need to pick up supplies, ladders work well for this one. On the second level to the right I found a couple ladders(I'm not sure if spawns are random or not). Once you have a couple ladders, find a couple ledges and save the game. Use X to select the ladder and then A to drop the ladder. Load your game and repeat.
BTW, B to Jump. A with the shovel to swing.