<===Trick #1: Curb-hoppable bikes like this Fargo help tremendously with being "tricky" on your commutes.
After I did the "A Paved Battlefield"series (Part I, Part II, and Part III), I got to thinking about all the little things I learned over the years on my commute. Things I do that make my life a little easier with reference to being around cars, and with regards to making my route a safer, funner one.
I call them "tricks", like one might refer to "tricks of the trade'. These are my specific tricks for commuting on my specific route. They may not work for you, but maybe they will give you some ideas. The key is there are no rules to being a commuter, per se'. You need to be creative, and you'll need to be able to be a problem solver. If you can manage those two things reasonably well, you will be certain to come up with specific "tricks" of your own for your specific route and its conditions.
Commuting Trick #1: The Bike: I don't like to be limited on my commutes. You might be different. That's cool, but I like options. Options to find very alternative routes. Fat tires open up a bigger "playing field" for me, so I use 'em. Look around your route choices. "What if" you had fat tires, and you were not limited to streets. What could you do? It makes your commute more interesting, fun, and safer, (if you get off roads with traffic and the "alt route" isn't heinous), so keep an open eye and think what bike would suit these options best. For me, a fat tire works. It might be different for you.
Fat tires allow for bad roads, pot holes, dirt, mud, sand, gravel, and any surface you're likely to find on an inner city commute.
Commuting Trick #2: The Clothes: Bike specific stuff is okay, obviously, but don't limit yourself to that. Open up your options. Double front Dickies jeans make great cold weather riding pants with a Velcro strap around each ankle to keep the flapping at bay. Don't have any Velcro straps? Bandannas work great too. Use your imagination. Layer when it is cold, wear loose fitting, cool clothes when it is hot. Experiment. The only cycling specific things you really should consider are a helmet and some protective eyewear. everything else is fair game. The easier and more fun you make this, the more apt you are to do it.
I mix-n-match civies and cycling gear to taste. Dickies are a staple of my commuting clothing. Cotton t-shirts in the summertime. Just don't limit yourself. Lots of types of clothing could work. Just as long as you keep things out of the rotating parts, that is!
Commuting Trick #3: The Route: First of all- Do Not Go The Way You Would Drive There!! Nine times out of ten, the way you would drive to work is the worst way to bicycle to work. It makes better sense to take a few exploratory trips, either by car, or preferably by bicycle, to scout out your route ahead of time. This can be a fun adventure, and is a great way to learn your city. Trick #1 comes into play here as well. some of your route may not even be on streets or roads! Parking lots, alleys, grassy fields, parks, road right of ways, and more may become part of your daily commute. City maps are readily available, Google Street View, and other route finding options can help get things narrowed down. However; don't rely on this technology, or even paper maps. The only sure-fire way you'll know if the route works, if it even exists, or how it "feels", is to actually scout it out ahead of time.
Scouting out and confirming your route is the first step. then after you have something figured out, you need a "dress rehearsal". Ride the route as if you were going to work, in the clothes you would be wearing, and time yourself, so you have an idea of how long it takes. Don't Race It!! Take it at a leisurely pace, so you get a "real" time for the trip. Remember that wind and weather may extend your commute times, so don't forget to factor that in.