Your friends are your good friends—by all means buddy-up, and listen to your body and your buddies. Communicate about clothing options, likely weather conditions, and your meeting time. Pick a rendezvous point that offers a place for people to get out of the weather, or make it a no-waiting-for-latecomers appointment.
Get motivated, sure, but don’t put yourself into cold weather exercise situations if you’re not fed, dressed, well-equipped, and mentally ready to go. If you’re hurt, hungry, too cold, or losing concentration, bail. You’re not doing any favor to the group if you suffer in silence and only announce you need help after you’re already in serious trouble. If you wait too long, instead of being able to say an orderly “good-bye-and-see-you-next-time,” you won’t be able to talk for your teeth chattering, and everyone else will be like, “Omigod, Jeff’s lips are blue, are any of you guys physicians?”
Ridiculously expensive sports clothing is sometimes much, much better quality than the cheap stuff. Is a cycling jacket that costs more than my Barneys business suit really worth it? (Okay, basement-warehouse-sale Barneys, but Barneys, nonetheless.) In a word, yes. If you’re still hitting the road looking like Stallone in the first Rocky, give some thought to investing in key items that mean the difference between enjoying fitness and suffering for no reason. All that stuff—about wicking base layers, insulating and adjustable middle layers, proper outer shells, and protecting your extremities—is true. Do some research, and set a budget, but do make an investment in quality gear. It doesn’t have to match, doesn’t have to be new, and doesn’t have to look cool—as nice as all of that is. Really good sports clothing can often make the difference between a good workout and packing it in all too soon, spending the rest of the afternoon watching DVDs, drinking hot chocolate, and trying to get the tingles out of your toes.
Eat, drink, and don’t tarry. Your mom was right, breakfast is key. For cold weather workouts, be well-fed. Your body is going to plow through calories keeping warm. Eat something substantial, and include some good carbs and protein. You just took great care of your outside by putting on proper clothing—now take care of your insides with thoughtful nutrition. Pack snacks, stay hydrated, and don’t sit around once you’re primed to work out.
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