Even as a newbie a few years ago, every transplant I did survived. First, don't worry so much about doing it; it's SUPER EASY! Just make sure that your plant has aquired enough root base into the soil. I use bigger pots than a cup (1 quart). I let the plants get nice and stable. Then, take an empty pot (or cup) that is the exact same size as your current grow is in, and use that to create the hole in your other pot.
Now, take the pot or cup into your hand and gently role your hands around the edge to loosen up the outside so the plant will easily come out with your soil when you tip it upside down. Split your four main fingers into 2, allowing a gap between your middle and next finger, placing the stem gently against the bottom of those 2 fingers. Now, tip the plant over and move the pot slowly upward, giving a slight jiggle to release the plant from the old pot.
If you waited long enough, you should see roots holding the soil together and the plant should fall right out for an easy transition.
