I think of cooking as having three different components; these aren't increasing advancement or anything:
1) what one of my co-workers referred to as "guy cooking," i.e., throwing together something from guidelines/idea more than a recipe
2) cooking from a recipe
3) recognizing idioms. E.g., recognizing when the recipe is really telling you to make a white sauce and knowing what to do from there. Alton Brown is probably your best friend here, although Jeff Potter's Cooking for Geeks is pretty good.
Experience, incidentally, is the only solution to feeling overwhelmed. Thrown down, fail, and learn! Humanity's been cooking for thousands of years, long before there were TV chefs to make us feel inadequate.
Here's what I planned for the grocery trip I did yesterday morning:
0) chicken quesadillas: not planned but I wound up buying a BIG thing of chicken and it sounded good for lunch. Cut up chicken, pan-fry fairly dry on high heat, throw in between tortillas with cheese and green chile, fry medium-high heat with substantial oil.
1) hot dogs--yeah, I wanted comfort food, and 3-4 times a year I just crave hot dogs. (typo'd that as gods to start!) Threw together a potato salad to go with: boiled cubed potatoes, radishes, onions cooked in white vinegar, hard boiled eggs, sauce of about 1/4c miracle whip, 2-3T yogurt, 2T dijon mustard, sprinkle of garlic powder, onion powder, paprika, pepper, salt.
2) fajitas: chop up onions and peppers (this is one of those experience things--you have to make the onion slices thicker than you think to have them cook as slow as the peppers), fry (either high heat and fast, keeping crunch, or caramelize long and slow), fry chicken, again fairly dry on medium-high heat, throw in a fajita seasoning of chili powder plus cumin plus cornstarch to soak up the fat/liquid, wrap in tortilla, cheese optional
3) chicken kiev: this is more of a real recipe, they're all over the place. Drat, just realized I forgot to pick up scallions for it, but at least I have red onion
4) curried chickpeas: recipe from my sister, will dig it up. Goes nicely on basmati rice. Thank goodness for pressure cookers....
5) fish: I bought some flash-frozen salmon, we have teriyaki sauce, we have two pineapples from the CSA--that's all going to go together somehow.
6) an ethiopian lentil bowl: this is a nice red lentil recipe, from Simply in Season (that and More With Less are great cookbooks)
7) some sort of pasta alfredo with chicken and broccoli: again a throw-together (alfredo sauce: white sauce + garlic + parmesean), probably lightly steam the broccoli and again cook the chicken in the skillet, fairly dry, high heat
8) open a can of tuna and throw it in the leftover potato salad
Wow, that's a meaty week. Stupid four pound things of chicken....
I gave up on planning vegetables in advance or matching to the main course; often we'll just have a salad. I have a theory that there are four kinds of vegetables: appetizer vegetables (e.g., salad); side vegetables (e.g., asparagus on the side with your salmon); intrinsic vegetables (peppers in the fajitas); sneaky vegetables (adding spinach in a lasagne, or throw frozen mixed veg in with macaroni). Get two kinds per meal and you're good.
Our CSA dump a box of lovely produce on my doorstep every week so there's always something healthy to eat.