First of all, you’ve got to make sure that your bike is in decent working condition. If it’s been quite a while since you last rode anywhere, you might want to go get a full tune up before trying to go very far. Check on all the basic things like noticing if your tires are full of air or totally flat, and if your gears still work. If you find that you have to fill up your tires quite a bit, it is a good idea to check the next day to make sure they haven’t gone completely flat again.
Next, find all your bicycling stuff. Locate your helmet, blinky lights, water bottle, fancy biking gloves or clothing. Check to see that the batteries in your blinky lights are still charged, and that your clothing still fits. You might want to do a quick smell check of all your gear before you put it on again.
On the weekend before you are planning to start commuting, go for a bike ride of a similar length to the commute you are planning. If you’ve never traveled by bike to your job, you should probably try out the actual route to make sure you are not in for any surprises. Many roads that seem fast and convenient for commuting in a car are terrible on a bicycle. Check a map of local bike routes to see if there are any particularly dangerous hazard points or better streets to bike on. In Portland, many bike great bike routes parallel busy traffic heavy streets.
You might even discover that there is one route that is better to ride on the way to work and a different route that is better for the ride home. For instance, I found that on my trip to work I have one very steep downhill that is fun for speeding to work in the mornings, but that I dreaded biking back up after a long day at work. Through a little research I planned a different, less direct, but much less steep route for the way home. On the other hand, if you live really close to where you work, you might want to find an adventurous workout route that includes challenging hills for your ride home.
So if those are the necessary steps to get ready for a bike commute, the following is my personal selection of (completely optional) first day commuting tricks that just might make that first ride to work one that you actually want to repeat. I always find that if you have a great time doing something the first time you try it, you’re much more likely to stick with it through those inevitable not-as-good days.
1. Select your work outfit ahead of time, and bring it into work a day before you try your first commute. This way you can be light as a feather on your first ride of the year.
2. Bring a kit of things like deodorant, a hairbrush, and makeup (if you wear it) that you can leave somewhere at work.
3. Plan a nutritious breakfast ahead of time, especially if you need coffee to think straight!
4. Pick a day that has no chance of rain but that is also not too hot. You don’t want to make yourself miserable on your very first trip.
5. If you bring your own lunches, pack your lunch the night before and make sure it is leak proof. It’s better to put some old plastic bags and rubber bands around any containers that look iffy, rather than get to work and find that you have chili all over everything in your backpack.
6. Try your first commute on a Friday. That way if you are exhausted by commuting you’ll have the whole weekend to recover.
7. Since you picked a nice day, and it’s also a Friday, you might want to locate a restaurant with a nice outside patio halfway home. This will break up your ride in a relaxing way so that it will seem like hardly a commute at all. In fact if you can convince some friends to attempt a bike commute on the same day, you could make a bike commuting celebration of it!