It’s currently dumping snow in Boulder while I’m writing this, so it’s an opportune time to start daydreaming about next season. Even if it’s not snowing in your neck of the woods, you are probably getting antsy sitting on your hands waiting for next season to come around.

Ideally, this might be a time to start giving some thoughts to what races you want on your calendar, but with the popularity of Ironman races, your key races of the season might have already been decided. Nevertheless, whenever you decide on adding a (key) race to your calendar, you should use the following suggestions to narrow your choices down.

Does it motivate you? This, in my opinion, trumps everything else. I can talk about some of the objective components to choosing your race (and I will in a second), but if you are not excited about racing, you certainly won’t be excited to do the training. I would advise an athlete to race an event that did not quite suite them as well as another if the less-than-ideal event had them motivated to get the work done.
Time of year. This has more to do with what time of year you will be doing your training as opposed to the actual time of year of the race. If you have a real winter, placing a race early in the year is going to create training difficulties. If you live in hot, humid climates with long summers, then I would stay away from races in the later half of summer. The most ideal time of year to train will most likely result in your best races.
Terrain. Do you thrive in wetsuit swims or non-wetsuit swims? Do you race well in cold or hot? Do you race well in the hills or the flat? Do you prefer technical bike courses or ones that rarely deviate from straight? Ideally, you will be able to simulate the conditions and terrain of your key races on your home training grounds. If you train in Florida, you might not excel in a race in the Alps.
Competitiveness of the event. This has a connection to my first point, but it applies directly to your motivation_while_racing as opposed to training. Some athletes find themselves more motivated if they can place well in their AG at a smaller, low key event. Others, particularly those at the tippy point of their age groups, might find that they get the most out of themselves at highly competitive races.