Hi, do you realize that isn't even a Jade (Crassula) but a Portulacaria afra? Same family, same needs, but more fun for bonsai! Now, this is not the time of year at all for you to be pruning anything - spring is the right time. As far as what branches to cut, or whether to trunk chop altogether would be up to you I guess, after you've looked at similar trees (Jades, P. afras or whatever) and found styles you like. In all honesty, I would not bonsai that tree, but allow it to just do what it's doing as it's gorgeous! I would maybe get it into a pot that won't be problematic in future re getting it out (the overhanging rim) and you'll have to be very careful when you move it (again, tho', in spring). Once you have it out of there into a better pot (tho' having it 'spill' over the sides of that one is cool) maybe you can get a better idea of where to go with it. Do you know that you can just pinch/snap off any leaf, stick it back in the soil and it will take root? Just think, you could have a 1,000 baby trees in one season :-)! Wiring is not often done on these trees because the branches tend to snap (also) easily unless allowed to go very dry, in which case they'll be soft, but the wire can also cut into them easily, so basically I'd use 'clip n' gro' styling vs wires. You must also be aware by now that it's best to let most of the mix get dry between waterings, though what you've done with it outdoors I don't know of course, not being in a place where I can grow these outside!

In a pot, it's much better to not use 'potting' soil, which is full of peat that hangs onto water and can rot roots - certainly makes it harder to water when you find the top dry but the rest still damp or even wet lower down. A mix of some small (1/16") soft wood bark bits as 20% of fast draining grit (natural colored small aquarium gravel works fine) will allow water to go right through without causing problems.

It's often "Elephant bush", though I have no idea why!

Chris,
your plant is awesomely out of control.

I recommend that you make a few minor cuts, just to see what you're working with.

Even if you were to make a "mistake" - which would be damn near impossible -
your plant would re-grow in a matter of minutes....okay, well, a matter of months.

Josh

Josh - you're right about the "family" (I really did not mean the formal Latin 'family', just that they were so alike) but I've never heard the 'food' part of the common name before.

Copy that! I see what you meant.

The 'food' part isn't commonly transcribed, in my experience, either.
However, when I came across the reference a time or two, it stuck in my brain.
I find it easier to remember, if I imagine an elephant munching on the bush.

Another thing to keep in mind is that Port. afras require slightly more water
than the common Jade Plant (Crassula ovata). The Crassula is more succulent;
the Portulacaria is more woody. This difference will also determine pruning
and subsequent branching. The Port. afra back-buds more readily than Crassula,
although the stubby scars do tend to last longer.

Josh

Thank you.. some of that might explain why mine is growing as it is.