When dealing with my student loans, I like to save up a lot of cash ($5,000 - $7,000), then send in a massive check to the student loan company. It feels so good. I don't like to set it and forget it with monthly payments. This also has the added benefit of giving me a temporary saving account/ emergency. Before I send the check, I ask myself, is everything good at work, life, do I feel secure? Of course there is the off chance that something bad happens, but my husband and I both work, so we are okay with the risk.
A little over a year ago, we were $60,000 in debt. Now, we are $30,000 and I remember each time that we made a big payment. Very motivating.