Backpackers do it in tents...
But the real challenge is getting the tent back in the bag...
Start by laying the tent out flat on top of the ground sheet. Fling all the guy lines into the middle of the tent--don't leave them hanging around outside.
The next step is easier with two people, but I do it on my own all the time--fold the two sides of the tent in towards the middle, so that they meet in the middle. Now you have a tent that is half as wide, but still full length.
Fold the right half of the tent over so that it just covers the left half of the tent. Now you have a tent that is 1/4 as wide, and still full length--it should be about the same width as your tents poles, once they are taken apart. If it's not, adjust the width of the tent now with a little more accurate folding.
Take one end of the tent and fold it about 2/3 of the way up towards the other and of the tent. and place the tent poles about six inches in from this fold. They should be just about the same width as the tent is now.
Slowly roll the tent up around the tent poles. If you need to, fold in the edges as you roll to make sure that the finished roll isn't much wider than the tent poles. By leaving the far end without any folds, you allow all the air to escape the tent, and it will roll up nice and compactly.
Follow the same technique with the rain fly, if you have one. fold in the sides towards the middle, and repeat until it is the same width at the poles, Fold one end up towards the other end, at least halfway. 2/3 of the way it better.
Place the tent roll on the folded end of the rain fly and start rolling it up .
Once it is rolled up, slip it into the bag. It will fit. It helps to have a second person hold the tent bag, but again, I've done this lots of times on my own. Stuff the tent into your pack.
Oops. Forgot the tent stakes. Put them into their own little bag and shove them down into the tent bag. If you can't reach that, then just shove them down into your pack. Either way, hope they don't poke a hole in something important.
When you are done, your hands are filthy, but don't wash them, because you have to fold up the ground sheet next.
Next--packing the bear can for fun and profit.