Solo Travel - Getting Stuck
First, check your connection times. If you live in an area where you usually have to book connecting flights through major cities, watch your connecting times very closely. In the last year, it's become more and more common for online booking sites to "recommend" flights that have very tight connections - 45 minutes or less in a lot of cases, I've found. Check your connections before you book that great fare, especially if you are connecting through cities where notoriously bad weather can strike at any moment, like Chicago, Denver, or major east coast airports north of the Mason-Dixon line. Generally, during the winter, I always try to have at least 90 minutes between planes, in the event that a connection is delayed.
Second, choose your connections wisely. If you have a choice between going through a famously-snow-bound airport or through something in a sunnier region to get to your destination, choose sunny over snowy. The odds of weather interfering with your travel plans lessen.
Third, flying on Mondays, Fridays and Sundays will nearly guarantee that you'll be entering an environment that is packed with people. Flying Tuesday through Thursday and sometimes on Saturdays (holiday season excluded) can lessen airport crowds and stress.
Fourth, if you're flying to a winter travel area and you have to get a rental car, make sure that you're prepared for driving in icy, winter driving conditions. If you're not accustomed to driving on winter roads, take cabs or get a ride. If those options aren't available, please remember that "four wheel drive" does not equal "four wheel stop." Winter driving hazards are greatly exacerbated by people driving too fast, following too closely, and assuming they have enough room to stop.
Fifth and last - be prepared for the long haul. During the winter, I always prepare for trips with the thought in mind that I may very well get stuck overnight somewhere that I didn't plan. Choose your travel attitude. Try not to book meetings the following morning if you have a late flight home the night before, to reduce the stress of having to get home right away. The last place you want to be is on a plane in the air that can't land. Take a book, find your travel zen, graciously accept the hotel voucher from the airline, take a deep breath, and smile at the people who help you get home safely. It's worth it.
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