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Begin by filling the jar only to the first row of holes.
Continue filling, one row at a time. The easiest way to insert the plants is usually to push them through the holes from the inside out. It is easier to wiggle the leaves through the hole from the inside than it is to cram the root ball through the hole from the outside. Just handle the stems gingerly to avoid breaking.
Save the largest herbs such as rosemary, basil, and dill for the top. Your regular harvests will keep all the plants pinched to a manageable size. Don't let them get too big or the pot will dry out quickly.Keep a pinch of fresh herbs for delicious meals just a few steps from the kitchen and all in one place--a strawberry jar. Originally designed as a novel way to grow clean strawberries, the pockets in a good-sized jar are big enough to hold an herb plant. Mix it up by planting one of each of your favorite herbs in each pocket. Good choices include sage, thyme, parsley, mint, oregano, and rosemary.
Here is a hint for planting. The natural inclination is to fill the jar to the top with potting soil and try to plant the pockets from the outside, but this ends up being very awkward. Instead, plant the jar in stages, a tier at a time, pushing the tops of plants through the pockets from the inside out. Fill as you plant and the plant that will grow largest, such as rosemary, at the very top.
Water with a gentle stream, making sure to water at the top and each pocket along the sides of the jar to settle the soil. After the first good watering, you should be able to water just from the top.