So, here's a little recap of my fun midnight "commute."
And while I don't recommend these cycling shoes for your daily commute, I found the pumps with the Crank Brothers cleats to be really easy to get in and out of. Depending on which foot you put which cleat on, you can determine the ease with which you clip out.
Another thing that makes your commute easier is a good light. I prefer Light and Motion for a number of reasons. Most all of their lights are compatible with most all their chargers, so the charger you have from 6 years ago will still work with a new light if you get one (the plugs don't change from year to year), and the lights and connectors are really robust.
Another part of my commute equipment is the repair kit. You never know when you're going to get a flat tire, and you should be prepared to make the repairs.
As it happened, my friend Alison got a flat about 2 miles out. She had a slow leak from a thorn puncture. While we could have patched the tube and re-inflated the tire, in the interest of time, we chose to replace the tube with a spare and use CO2 to inflate the tire.
Hopefully the start of your commute won't look like this...
And finally, when I can pull it off, I bring along my mechanic, dressed up as Cookie Monster. There are few things that will make you feel secure like a good mechanic riding with you, and few things to cheer you up on a cloudy day like Cookie Monster.
Armed with this knowledge of the gear and equipment you need, you are ready to tackle the midnight commute!