When I took out my mortgage at the end of 2005, I started by owing $92,800 (at 5.875%). I refinanced in 2012 for a lower rate and changed the term from a 30 year to a 20 year. And whenever possible, I've paid some extra principal in, usually down to the next "round" number.

At the beginning of the year, I started by owing $60,700. Now that the March payment is made, I'm down to $59,900--I threw an extra $65 in this month to get down to a multiple of $100. Feels good having broken the $60K barrier. I'm 57.5, so it feels doable to have the mortgage paid off by the time I am 65.

I am not planning to retire at that age at this point, but having the freedom to be able to afford to would be nice. Once the mortgage and other debt are gone, I'll be accelerating my savings into a brokerage account, building a bucket of "safe" money I can live off of during any market downturns in my early retirement years.