Nate, try using a soft wood like white pine or poplar and see if you can get the technique down. I've bought both at Home Depot and Lowe's near where the red oak in. Precut "craft" lumber. On hardwood shoot shafts I hold the shoot in one hand and the plane in the other and sorta "free hand" the operation.
One of those pencil sharpener type dowel makers works well too. You get them mail order for $20 to $30.