I used to do this. I need to start again. Thing is I can’t stand running indoors and it’s like 0 out (I live in Chicago and its December) so I think I’ll have to hold this one for spring 05.
get a hat
Running in the cold sucks at zero farenheit, but it can’t be that cold in Chicago (can it?). If it’s above 25F you should be able to run—it’s like cross country skiing.
Man – you need to drink a can of Harden The Fuck Up.
Damon Clinkscales is in awe
You can do it
Having the appropriate attire is important. You will definitely warm up when you get moving. Instead of a hat as Daniel suggests, you might try just an ear wrap thing. This allows the top of your head to still breathe while keeping your ears warm. Also, avoid cotton like the plague. You want Coolmax or Dri Fit type material to wick away moisture.
If you just can’t make it out into the cold or its icy or whatever, there’s always the treadmill.
Ironically enough, I think the benefit you would get from exercising would actually give you more time during the day because you would have more energy and be in better shape to deal with the issues you are facing. There was a recent article in Runner’s World about CEO’s running regimens and that issue referenced this concept.