I can relate to that. Please know that any resource that prescribes a schedule to water your plant is not worth taking seriously because it's impossible to predict how often a plant will need water. A Dracaena marginata can be a tiny thing that is just a few inches tall, or a much older entity that is taller than a person. The bigger plant will use a lot more water. Throughout the year, the usage could vary. Plants don't take a drink periodically like humans, the roots are constantly at work to obtain moisture and deliver it to foliage, so some moisture must be present at all times.

Factors like temperature, humidity, air movement, amount of light, size of plant, size of root mass, size of pot, type of soil, type of pot, and vigorousness of a particular plants' metabolism all play a role in the speed at which the plant is using moisture, and the speed at which the soil is drying.

"Overwatering" is under a hyped-up emphasis lately. This occurs when moist soil has insufficient oxygen in it. Roots need moisture and oxygen at the same time to function, and to not suffocate and rot. There are ways to ameliorate the risk to virtually none.

Because I have so many pots, I can't give specialized care to each one or check them before adding more water. I just water all often enough so that there is never a moment when the soil has no moisture. I haven't had a plant die of rotting roots ("overwatering") since I quit using potting soil with peat in it, and many plants have been moved from plastic pots to clay pots. Clay pots allow oxygen to penetrate the entire surface of the soil, not just the top, so plants can enjoy consistently moist soil without having the roots rot.

At this time of year, all of my pots are outside, where it's 95°, so they need water about every-other day. If I waited 2 weeks, most of the plants would be dead. But when they are inside over winter in cooler temps and a lot less sun, some plants only need more water after about a month.

In addition, when repotting, don't pack the soil and water gently the first few times until the particles lock in place so the soil doesn't compact. The little air spaces will further eliminate the risk of rotting roots.