Start a new game and skip the opening cutscenes. Once you have control of Jane (you character) follow the prompts to learn the movement controls and pick up the pickaxe. Now turn 180° and click on the blue arrow to move towards the next scene. Click on the next blue arrow to exit the cave and as you do so there will be a cave in. Follow the prompts to clear the rocks using the pickaxe and click on the final blue arrow to move outside.
Once outside use the back arrow to return to the cave and then the blue arrow to exit again. Repeat until the achievement unlocks.