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The time of the year does not matter much since you will be keeping the plant indoors. What does matter, however, is the soil. Water the plant thoroughly, then wait 1 hour; this will dampen the soil and make it easier to remove the root ball. If you are transplanting a seedling, wait until it forms a pair of true leaves. True leaves are hardier than the delicate leaves you see at first. It's better to gradually increase the size of your plant's pot as it grows rather than putting it into a giant pot from the start. Get a pot that is 1 size bigger than the one that the plant is already in. Cover the drainage hole in the new pot with a piece of mesh or a coffee filter.  You want to cover the drainage hole so that the soil doesn't fall out. The water will still be able to come out. If the new pot doesn't have a drainage hole, fill the pot with 1 to 2 inches (2.5 to 5.1 cm) of gravel. Use enough potting soil so that if you were to set the root ball into the pot, the top of the root ball would sit 1 inch (2.5 cm) below the pot's rim. Do not use gardening soil.  Gardening soil often contains insects, diseases, and fungi. Your plant is not used to these, and it can get sick or die as a result. For the healthiest, happiest plant, look for soil that contains equal parts of rich loam, sand/perlite, and organic matter.  If you are transplanting a seedling, fill the pot to within 1 inch (2.5 cm) of the rim. Dampen the soil with warm water and wait 1 hour. Cover the top of the pot with your hand so that the plant sticks out between your fingers. Turn the pot upside down, then gently tap the pot's against the edge of a table. This should loosen the root ball and cause it to slide out of the soil and into your hand.  Do not grab the plant by the stem and pull it out. Break the pot instead as a last resort. If you are transplanting a seedling, use a spoon to carefully dig the seedling out. Hold it by a leaf, never by the stem. Most root balls clump together, which is normal. If the plant was in the small pot for a long time, however, the root ball may retain the shape of the pot. In this case, gently squeeze the root ball with your fingers to loosen it.  If you can't loosen the root ball, use a sharp, clean knife to slice into the sides of the root ball; make the slices 1⁄8 to 1⁄8 inch (0.32 to 0.32 cm) deep. Be sure to cut away any dead or rotten roots with sharp, clean scissors. Cover the top of the root ball with a thin layer of soil. Leave 3⁄4 to 1 inch (1.9 to 2.5 cm) of space between the soil and the rim of the pot. If you are working with a seedling, poke a hole into the soil, then tuck the seedling inside. Pat the soil around the seedling. It would be even better if you added some water-soluble fertilizer into the water, but make sure that it's the right kind for your plant. This will help the plant recover faster. Once you are done watering the plant, do not water it again until the top layer of soil is dry. If you are working with seedlings, keep the soil damp, but not soggy. If the pot has a drainage hole, keep watering until water comes out of the hole. If the plant does not have a drainage hole, use your best judgement. Do not put the plant in full sunlight right away or you will shock it. Instead, gradually move it into brighter and brighter areas over the next 2 to 3 days. Keep the plant warm, but avoid heat. If the plants start to wilt, mist them with water, then cover them with plastic wrap. Keep them in a cool area, away from direct sunlight for 1 to 2 days. How soon you do this depends on how fast the plant grows; some plants grow faster than others. A slow growing plant typically needs to be transferred to a new pot once every 2 to 3 years. A fast growing plant will need to be transferred to a new pot once per year. If you notice the roots poking out of the drainage hole, it's time for a new pot!
Water the plant a few hours before you transplant it. Choose a pot that's 1 size larger than the old pot. Fill the new pot with a few inches/centimeters of potting soil. Turn the pot upside down and gently tap the rim against a table. Slide the root ball out and loosen it if the roots are tangled. Set the root ball into the new pot, then fill it with more soil. Water the plant thoroughly. Bring the plant into sunlight over the next couple of days. Move the plant into a larger pot as it grows bigger.