Problem: You'll sweat on the way to work.
Solution: Bring a spare shirt. Keep deodorant and, depending on the level of formality expected at your office, a couple of blazers at the office. Or even drive in on Monday morning with the week's wardrobe and drive home with it again on Friday afternoon. If you use hair gel, keep that at the office too and use it when you get there after you take off your helmet.
Problem: You haven't ridden a bike since you were thirteen.
Solution: Practice. Take the bike out early on a Sunday morning when there's not much traffic and, if it would bother you, not too many spectators. Go to an empty playground or a park, and...
- Practice riding in a nice straight line.
- Keep your thumbs hooked over the handle bars, and one finger on each brake, and your elbows nice and loose so you don't feel like your fillings are going to fall out every time you hit a crack in the road.
- Look over one shoulder, then the other, to see what's coming, still while riding in a straight line.
- Practice signaling left and right, by sticking one hand and then the other wayyy out to the side so nobody can possibly miss it. And make sure you're still riding in a straight line.
- Come to a complete stop, still in that nice straight line, and then start up again without letting the handle bars sway left or right. Much.
- Try braking and accelerating while signaling.
- Practice turning with one hand, and then the other, off the handlebars.
- Find some parked cars, or a parked car by a building, and practice riding between them. Get to know how much clearance you need.
- If you can, find a dirt road or a trail and ride around to see how it feels. If you hit a patch of sand or gravel, you'll notice that you can stay up if you can keep the bike in a straight line (there's that again) and keep the wheels turning.
Solution: Check the weather forecast the night before, and again in the morning. Buy rain gear according to your budget, and carry it with you depending on the chance of rain and the temperature and how uncomfortable you'll get if you get caught out. If you can, get a waterproof/breathable jacket, but even then, see item one.
Today, there was a 30 percent chance of rain in the morning, plus cooling temperatures throughout the day. I biked to the train station in a T shirt, with blazer and rain jacket in my bag; I wore the blazer for the ride from train station to office, and on the way home, wore both blazer and jacket -- for warmth. I didn't get rained on during any of the legs. Layers are helpful year-round, because you'll warm up after 10 or 15 minutes of riding, and temperatures can change quite a bit between 8 a.m. and 5 or 6 or 7 p.m., depending on when you head home.
If you do get caught -- or decide to ride -- in the rain, slow down. Braking takes longer, sewer hole covers and train tracks are treacherously slippery, and you never know what's under that puddle. Also drivers will be less likely to see you, because of crud on the windshield plus because they won't expect bikers out there -- so take extra cautions.
Problem: It's dark.
Solution: Lights and brights. Your rain jacket can be any color, as long as it's neon; you might also want a reflective vest and ankle reflectors. Put red blinking lights on the back of the bike, on your helmet, on your backpack if you carry one, and a white light on the front of the bike.