How important is it to train in the conditions you'll race in? Very! Let's take a look at a few important situations.
Running Hills
It's hard to race on hills without actually training on them. Your body position strengthens different muscles (glutes and calves) more than on the flats. And you need to learn how to drive off of your back leg much more than running on the flats. There can be a tendency to shuffle up hills--which is slow.
Descending steep hills also takes practice. Being too controlled on a descent is hard on the knees and the quads--not to mention slow! The key is to learn a controlled fall--leaning forward and bringing each leg out in front of you just long enough so that you don't fall on your face.
Cycling Hills
Riding hills demands a different position on the bike--shifting your weight back to use your quads more, and maybe getting out of aero position. If the climb is steep enough, knowing when to get out of the saddle. While many argue that time trialing should involve a consistent effort, there are huge time gains to be made on hills. Knowing for how long and how hard you push on a short climb without blowing up can really affect your bike split.
Like running, descending hills takes practice, especially if they're steep and windy. If you're speed is over 30, you're probably better off just going into a tuck and not pedaling at all. The extra 1 or 2 mph you'd gain probably is better used in resting. But the amount of time you can gain through excellent descents is generally a lot less than the time you can gain by excellent climbing skills.
Open Water Swimming
Swimming in open water is so different than swimming in a pool it should almost be considered a different sport. I think the difference is like running trails in the mountains versus running on a treadmill. I'm not a fast swimmer at all; but in open water swims I beat a lot of people who smoke me in the pool. Here's why:
Swimming Straight. There's no black line on the bottom of the lake or ocean to follow. The straighter you can swim, less frequently you have to sight to stay on course. And no matter how well you sight, each time you do it slows you down.
Sighting. Learn to sight with minimal interruption to your stroke. Beginners--and even a lot of intermediates--will come nearly to complete stop, pull their head out of the water, and go vertical in the water. Obviously it's slow, it also results in a lot of collisions.
Drafting. If you're near the front of the pack, you probably already know about drafting and its benefits. At the middle of the pack and back, it's a tougher concept to implement. People aren't swimming straight, or they're slowing when they sight. You probably won't draft off the same person for the whole race. But anytime you can find someone to get behind--even for 5 or 10 strokes--is energy saved and speed gained.
Using a Wetsuit. Swimming in a wetsuit takes some getting used to. Getting a good fit can even be tricky. Getting out of one efficiently takes practice. But you benefit by getting great floatation, and can use your legs a lot less--saving them for the bike and the run.
The Creep Out Factor. People who only swim in pools can have phobias about swimming with anything alive. Sharks and alligators, of course. But also jellyfish, kelp, and marsh grasses. Or gross mud at the entry/exit. If these things distract you on race day, you'll go slower.
Currents, Surf, Swell and Chop. Swimming in the ocean you'll likely need to deal with currents and swell, and possibly surf when you enter and exit. Chop (small, frequent, wind-driven waves that seem to always be right where you want to breathe) can happen on lakes or the ocean.
Swimming in a Pack. During an open water swim, you will get kicked, hit, and collided with. Women-only heats are more cooperative--I understand there's much less physical contact. Men, however, will swim overtop anyone in their way. Get used to this, lest you have a panic attack in the water.
Running Surfaces
In general, you should train on the surfaces you'll race on--dirt trails, asphalt roads, or sand. During a recent race we encountered a 1/2 mile stretch of "unadvertised" semi-soft sand. I watched people ahead of me wilt, as they weren't prepared for it and started despairing over the time they would lose from their projected pace. I do a fair amount of beach running, so threw my projected times out the window and just concentrated on passing people. It worked great. Curiously, though, just before this stretch I had passed a woman wearing a U.S. Marine Corps jersey. Within a minute of being on the sand, she had passed me back. I asked as she went by, "You do a lot of beach running, don't you?" and she responded, "Every day." Interestingly, within a minute of hitting the asphalt again, I had repassed her.
One exception to this rule is concrete. Don't run on concrete. Ever. It's so amazingly hard on your joints. If you insist on racing a course that's on concrete, don't train on it.
Weather
While you don't want to do most of your training in extreme weather conditions, you need to be physically and mentally prepared for adverse conditions during the race.
Cold Water. Learn what happens when you jump into cold water and immediately start swimming (many of us hyperventilate). Learn how much time you need to acclimate. Learn when you need a wetsuit. And a neoprene hood. And booties...
Cold Air. Learn experiment with how few clothes you can wear and still be comfortable on the bike. It takes time in T1 to put them on, and you'll likely need to shed them during the run. Learn what it feels like to run on numb feet for a couple of miles (or invest in neoprene toe covers for your bike shoes).
Rain. Be comfortable on your bike in the rain--both cornering and descending. Be prepared to have cold hands and feet.
Heat. Heat seems to affect running much more than any of the other sports. If it may be hot during your race, schedule some of your training runs--especially those in the weeks preceding the race--during the heat of the day. Become accustomed to that feeling of discomfort, and learn how much more water you'll need. Many of us run mostly in the cool of the morning or evening due to work schedules. But not understanding how your body reacts to the heat can be disastrous on race day.
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