Keep It Simple
It seems that one of the hardest parts of learning to eat Paleo (or even just eat more real food), is that people get overwhelmed so easily wondering what exactly they are going to eat, will the get enough protein, and how can they possibly live without bread?!?
The key in these situations is to keep it simple. Don't overthink it.
The best way to get started is with some very basic menu ideas for a couple of weeks. Master those, then add some different veggies, proteins, fats, etc. You don't have to come right out of the gate with gourmet, Pinterest-worthy meals because that will actually make you crazy. If you slowly familiarize yourself with different Paleo/real food options, you confidence and you palate will expand. Soon you'll be whipping up all kinds of things you never thought you could make and you'll be telling all your friends how easy it is!
A good place to start is with basic proteins like baked chicken, grilled salmon, and seared flank steak. Your veggies could include steamed or roasted broccoli, mixed greens with some berries (if they are in season) or apple and avocado. Put a little lemon juice and olive oil on it and you've got yourself a Paleo feast! These options could get you through an entire week and then from there you just vary your components.
In the long term, you want to have more variety, but the most important thing is optimizing your plan for success. You will not suffer any ill consequences if you eat chicken and salmon with broccoli for a couple of weeks until you figure out how this all works. I think that setting simple goals and mastering those skills and habits before moving on to more challenging goals is essential to long-term success.
If you have not spent a lot of time in the kitchen and are not comfortable cooking, do not set the expectation that you will be Paleo-ifying Julia Child's recipes from the start. Start with something simple like baked chicken breast and sauteed spinach.
Start each meal with veggies as the base (#morevegetablesthanavegetarian is the goal), add some good quality proteins, some healthy fats, and a little fruit on the side and you've got yourself a meal! Repeat for every meal by simply varying the individual components!
Enjoy your Paleo/real food and reap all the benefits of eating what humans are meant to be eating! Also, remember that being a Paleo perfectionist is not cool and won't make you healthier!