Join Date: Dec 2005
Location: O'Fallon, MO
Bikes: 1973 Raleigh Professional, 1993 Raleigh Technium Olympian, 2006 Cervelo Dual, 2008 Cannondale Caad8, 2010 Kona Unit, 2013 Trek Superfly 100 AL Pro, 2014 Trek Crockett 9, 2017 All City Nature Boy 853
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You didn't give a real clear picture of your current conditioning. But, hey, that's never stopped anyone on this board from making recommendations, so here goes...
1. I would suggest a pair of tri shorts. Wear them for the whole event. They'll have plenty of support and you won't even notice the pad on the run. If you don't want to spend the money on one race, I'd suggest run clothing over bike shorts, and just wear them the whole race. A 14 mile bike won't kill you w/o a pad. I'd skip the supporter, though. It will get uncomortable on the bike. Do you have a pair of compression shorts you could wear for the entire race?
2. How long do you think this race will take you? It's a pretty short race and you're not going to bonk during an event this short. You'll get tired, but not bonk. Food isn't going to keep you from getting tired. For me... I'd go with water only. If it makes you feel better, maybe take one gel shortly before the end of the bike, but I don't think it's necessary. You can also drink a little sports drink if it agrees with you, but, again, probably not a necessity.
3. You have plenty of time to prepare for racing these distances in April. Since you seem to be most concerned about running, that's where I'd put my greatest effort. Be careful with increasing run volume and intensity at the same time. That's a recipe for disaster. I'd slowly build up the volume until ~3wks out from your event, then cut it back a little and increase the intensity. Definitely do some bricks. Ride ~1/2hr at race pace, run just long enough that you get in a rythm (usually takes me ~1 mile), repeat. It's a short race. I'd take the day before off and possibly go short (but high intensity) the day before that. But, that's about it for taper.