Half-Life 2

After having to run out of Dr. Kleiner’s lab on the chapter “A Red Letter Day” Barney will drop you down your trusty crowbar. Pick it up, and the achievement will pop up. I also made a video guide going over all of the achievements in the game here.

On the chapter “Point Insertion'' when you’re in an apartment, and it gets raided by the combine, you’ll have to start running. Once you run across the roof for a block or two you’ll go into a window and the achievement will pop up. I also made a video going over all of the achievements in the game here.

This is also achievable upon the return to Kleiners lab during the chapter "Entanglement"
The flower pot is no longer present (at least it wasn't in my playthrough) but any item can be used instead - book, junk etc.
Just keep using the teleporter until the achievement pops.