Will I need to transplant?

The size of the pot is about a foot deep, and I'm letting nature do the flowering process.

Will I need to transplant it into a bigger planter pot or anything? It's about 2 months in vegetation.

Smaller pic. Edited.

Once you see the roots poking out of the bottom of the pot then it's definitely time to transplant. You want to try to transplant as few times as possible through out your grow so not more than 2-3 times. You especially want to not transplant after you start flowering because of the stress factor and it must stay low in flowering. If you are going to grow using a pot through out the whole grow I would advice transplanting into a 3 or 5 gallon bucket next time you transplant. Good luck with your grow. Here are our babies at 14 days flowering, Butch the one on the left our main lady outgrew 2 pots really quickly so we swtiched to 5 gallon buckets quickly. Enjoy

Oh, well the pot it is in is pretty much bigger than a 5 gallon bucket.