My daughter was told to try the Whole30 for health issues in October. My husband is away on a long term work assignment, so since I'm the only other one home with her (and I do the cooking), I did it too. As the program says - don't stress. It's not forever. It's just 30 days, so don't look at it in the long range, just take it a day at a time. Treat it like a real learning experience.
First, I purged the kitchen and pantry. Items that would be ok in storage (unopened pastas, bags of sugar and flour, oats, unopened crackers, unopened jars of peanut butter, honey, etc) went into a Rubbermaid bin. Perfectly edible but opened items (that would either spoil before the 30 days were up or that would be too tempting) like practically new cereal, bags of tortilla chips, cheese, butter etc, were donated to two neighbors - they're young teachers sharing an apartment and they're on a super tight new teacher's budget. They were so happy to "shop" in my pantry. I encourage you to find a college student or someone on a budget who won't mind taking your not-quite-brand-new-but-edible food items.
We didn't buy a lot of new and unexplored items at first. We bought chicken, eggs, uncured bacon with no nitrates, tuna, and fruits and vegetables that were allowed and that we already liked. We started out simple, with bacon and eggs, a nice salad, chicken with roasted potatoes, things like that for our meals. I made nice salads with tuna, Kalamata olives, hard-boiled eggs, greens and tomatoes. I also made simple but flavorful marinara sauces, added cooked ground beef or turkey, and served it over baked potatoes or roasted sweet potato slices or spaghetti squash.
We found ghee at a Whole Foods store and bought that. My daughter was skeptical, but then she realized it wasn't that different from butter. I used coconut oil and avocado oil and I already was in the habit of using good quality olive oil.
We also found Boulder Canyon brand potato chips that are fried only in avocado oil (Randall's Supermarket carries them) so my daughter could have a few potato chips. I switched from a glass of wine in the evening to a glass of sparkling water (Topo Chico) with orange wedges in it.
What I liked about the program: It helped me to realize what I could do without. And I learned how to make some easy switches. For example, my daughter wanted sloppy Joes, and those are traditionally made using brown sugar or another sweetener. So I caramelized onions (cooking them very low and slow for nearly an hour in good olive oil and ghee) until they were deep golden and sweet, and used those to add that familiar slightly sweet taste to the sloppy Joes. My daughter learned how good roasted sweet potatoes are. And I appreciated that the program specifically tells you not to try to make things like cookies, pancakes, and puddings using "cheat" ingredients (no making something that looks like pancakes using seeds and coconut flakes). The point is that your food should look like its original form. It should be recognizable. That was great. And even though I love to cook and consider myself a good cook, the program encouraged me to try some new things and to consider options.
What I didn't like: breakfast was hard. Some people just say to eat a dinner for breakfast, but I didn't like having salad or tuna for breakfast. Eggs and roasted potatoes got kind of boring, but it was ok. We got through it.
I happen to be in the "against stevia and agave nectar" camp (they're not natural, not nectars, and are highly processed), so it wasn't hard to use dates for sweetening. Even before Whole30 we only used pure maple syrup and raw local honey for sweetening.
There's a good facebook page (a couple, actually) dedicated to recipe ideas and support. Just type Whole30 into the bar where you would search for a friend's name. I really liked that resource. There are some creative people on there!
You can still eat out: Chipotle has some possibilities and steakhouses do too. There are ideas for eating out online and on Facebook.
The end result: we did the program faithfully for 40 days. I lost a few pounds, as did my daughter. She was really addicted to sugars and carbs and the program helped her make some great substitutions and break some very bad habits.
I learned quite a lot of enlightening things about what we rely on, and what we can and should change. Unfortunately my daughter did not notice any health changes in her medical conditions (autoimmune disease plus a couple others). She has gastroparesis among other things, so eating all the vegetables and meats were ultimately too difficult for her. Right now we are trying to figure out some kind of blend of the best parts of Whole30, a gastroparesis-friendly diet that includes soft foods and a low-residue diet. So there's my challenge!!
Good luck with the program. You can do this!