Bike if you want to
In the effort to get people out of their cars, and encourage everyone to walk and bike more, I reject the stick method in favor of the carrot.
For the past two decades, I, and others in my line of work, have been engaged in the battle for the hearts and minds of those 60% the population who are "interested but concerned" when it comes to urban cycling. And I've come to the conclusion that you can't win that battle with shock and awe. Chances are you will not entice a new cyclist by painting visions sweat drenched commutes, racing the bus through clouds of exhaust, or debates on the pros and cons of actually stopping at stop signs. You will not smooth the way for him or her by describing the joys of your 40-mile daily commute. Certainly there are individuals who find this appealing and even fun. But if the point is to create more cyclists, then this is not a winning strategy.
The truth is that few people are warriors, and even fewer are warriors every day. Most of us have things in our lives that sometimes get in the way of our intentions: habits, children, distance, weather, aches and pains, fear, sometimes age, sometimes youth, winter colds, whims, moods, barometric pressure, stress. And frankly, while the heroic feats of others may sometimes inspire us, they probably won't motivate us on a daily basis. If the bar is set too high, we won't even make an attempt to reach it.
Don't see yourself becoming a bike commuter? That's OK. You do not have to become anything if you just want to try riding your bike. We have some octogenerian relatives who have been known to ride their bikes to the grocery store. I don't think they ever stopped to figure out if they are "bike commuters".
The best tip I have for riding a bike -- and possibly increasing the frequency of your biking trips -- is to do it when you want to. Here are some other tips for incorporating biking into your routine this season:
Bring your bike to your neighborhood mechanic for a tune-up or safety-check, to make sure it's ready and in sound condition when you choose to ride. Have them show you how to air up your tires, so you can do it confidently.
Keep your bike where it's easily accessible, with all your gear near at hand (helmet and lock at a minimum). This will reduce the frustration of trying to find a key item when you're in a hurry to get out the door.
Carry a backpack. It will turn any bike trip into a potentially productive one without a major investment.
Don't bite off more that you can chew. Rather than trying to build your whole day around the bike, start by planning short trips: post office, library, coffee shop, small shopping errand.
If you were planning a major shopping expedition, see if instead there are a few things you can pick up locally, and put off the big trip until you have to be out with the car for another reason.
If you are traffic-averse, ride your bike to places you can reach using small neighborhoods streets. Sometimes it's worth it to go 3-4 blocks out of your way to avoid major traffic spots. (Update: Here are some mellow Chicago routes east of Cicero. Look for west of Cicero in early fall.)
Team up with a more experienced friend, but one that will respect your comfort level.
If needed, push yourself a little once in a while.
So give yourself a break, and make it fun. Bike when the weather is nice. Bike when you feel like it. Here's the thing: just because you drove your car or got on the bus today doesn't mean you can't ride your bike tomorrow. Conversely, if you ride your bike today, It doesn't mean you have to cycle everywhere for the rest of your life. It only means that you will use your bike sometimes, when it makes sense to you.
Better to rejoice in riding a couple miles, than to feel guilty about not biking at all.