When I first started, I literally made the same cheese every single day and progressively aged it. So the first one I ate the next day. The next one I aged for a few days. The next one for a week. The next one for a few weeks. After getting up to a few months (and getting tired of the same cheese), I did it again for a different kind of cheese.
This information is for a natural rind cheese. If you are vacuum packing or waxing, etc, things are a bit easier because you just dry it off, seal it up and age it for how ever long. But for a natural rind cheese, it's literally a living thing and it takes a while to get used to how to deal with the cheese.
You kind of get the first week for free. Typically very little happens that you can see. If you smell the cheese, you will probably notice that the smell goes from basically just lactic acid to progressively yeasty. Somewhere in the next week or so, things start to obviously grow on the cheese. It might get a bit greasy feeling from yeast setting up shop. You may get some white dusting from geotrichum. You may get some blue.
Most beginners err on the side of being too humid. If you are getting lots of blue, and especially if you are getting black or orange stuff, then you need to keep the humidity down. It's at this point where the "Make lots of cheese and age it for short periods" strategy pays off. Cheese that you eat early is always good, even if it can be a bit boring. As the cheese ages, it develops more and more flavor. However, it can also produce more and more weird mold and bacteria that you won't be sure about.
The thing about aging natural rind cheeses is that 80% of it is in making the cheese in the first place. A good structure, that isn't over pressed (and hence doesn't lock in too much whey) is important. And you need a very nice, smooth rind without cracks, crags and ledges for blue to hang on to. Learning that stuff takes practice and experimentation. So making lots of cheeses and aging it out 1-3 weeks allows you to get that practice and eat good, if boring, cheese.
You'll know when you have the cheese right and the humidity right because you will have to do almost nothing. You will get a nice white dusting of geotrichum (or equivalent) growing on your rind. Blue will be limited and easy to brush off. No black dots that stain your rind. You never wash your rind or rub salt in it or spray it with vinegar or all the other things that are suggested but actually tend to make matters worse. It just ages nicely. You flip it every day. You inspect it. You dry out the container it's aging in. You brush off anything you don't want. It just keeps aging.
Once you get that point, you will have found all the tricks that work well for you and your cave. You'll wonder why everybody things aging natural rind cheeses is so difficult. You'll struggle to explain it to people because, actually it's just a series of very small, well time tweaks that you do because you are paying very good attention to your cheeses every day.
So just make cheese as often as you can. When things are going wrong, eat the cheese. When things are going right, age the cheese a bit longer. Don't panic. Just make more cheese.