This could very well be a technique issue, but something else to consider for pre shave prep: after a hot shower (or hot towels, your choice) lather up BEFORE stropping, and let the lather soak in while you strop, brush your teeth, comb your hair etc. Relather, and by then your whiskers should be plenty soft no matter how many day's growth you have.
Trust me, no matter how bad it may seem it's not worth going back to an electric....