You might find it beneficial to study some planking tutorials. It pays to either add some temporary harpins to help maintain the shape of the hull and prevent twisting. From that point it is up to you. After I mark out the hull so I know how much taper is needed on the breadth of the planks I start with the wales. I then go down to the garboard strake and work upwards, alternating port/starboard every strake or two. Once you have a few strakes and the wales you can remove the harpins and continue the planking. I highly recommend the four part planking video - Part one can be seen here
There are other articles and books on planking that have helped members as well as posts here at SoS. Keep in mind that planking is not a hit or miss endeavor.
Allan
Allan