I haven't tried Whole30 before, but it looks really similar to Paleo. I can't offer much help re: transitioning between Whole30 and Paleo, but I can offer some tips on how to sustain a Paleo-type diet.
For the last 6 months, I've followed something that is vaguely similar to Paleo and have lost roughly 18kg. I couple this with exercise, fluctuating between doing Yoga every day, and every second day, and going for the occasional 30 minute walk. The most important and effective omissions I have made, that I find have dramatically improved my health and helped me to lower my weight, is the removal of sugar, wheat and potatoes.
At first this felt like a huge adjustment, but now I can see how empty the calories are of nutrition, and how eating them spikes my blood sugar and results in me never ever feeling full. I've come to the conclusion that those foods are actually, to my body, like drugs, as I don't ever feel satisfied by them / can't get enough, so if I eat them I just end up on a perpetual food binge. (This said, on a few occasions I've been out and about and I haven't denied myself the odd burger with company, but I don't make it a daily or even weekly thing, and I need to be very firm with myself that that's all I'm going to be eating grain-wise. Following it up with a green smoothie or a salad quells any carb cravings afterwards. What you do most of the time is what makes the biggest difference.)
I guess what I've been eating is more or less the same as the 'Perfect Health Diet' - http://perfecthealthdiet.com/the-diet/
- which is similar to Paleo, but not as restrictive. I for one cannot do without dairy - I just enjoy it too much to consider removing it entirely. Also, on the very odd occasion over the last 6 months I have had a few squares of dark chocolate, a small amount of rice with a meal when out, a glass or two of wine recently, etc., and it hasn't resulted in a jump in weight gain or anything. Again, what you do most of the time is what makes the biggest difference.
On a daily basis I opt for 3 meals:
- Breakfast smoothie (generally apple, banana, kale, soaked chia seed, tumeric powder, greek yogurt, honey, cold green tea). Coffee with milk.
- Green salad and a protein for lunch
- Protein and salad or cooked veges for dinner. If a curry, I'll have a small cup of quinoa with it.
-- If I have a snack before or after dinner, it's usually either a glass of milk, some cheese, a handful of nuts and/or some medjool dates.
I have been working my way through Adriene's yoga videos on Youtube, and find the 30 day challenges to be really motivating. I have skipped days on occasion, but it still works well for me as I have something to work through and I find the meditation and reflections lower my stress levels (which is helpful for me, as I've had trouble managing anxiety since my teens, and this has played a big role in weight gain & health problems I've experienced).
Anyway, I hope some of this is helpful! I don't really see any of it as a 'diet' per se - more a new way of living and looking after myself. I also found it really helpful to watch the Science show here in Australia - 'Catalyst' - as a while back it did studies into the microbiome in our guts, and how important it is to feed your gut foods that stimulate the growth of healthy bacteria. I used to suffer from awful IBS type symptoms and have found that has started to settle down a lot by managing my diet and exercise in this way. I also find that my body craves the healthy foods now. For instance, this weekend we went for a mini-stay at a farm and the breakfast was delicious, but it was all grain-based -- pancakes, breads, muesli, etc. I ate it because it was provided, but my skin immediately started to dry out and itch, and my stomach felt very bloated. When I got home my husband made us our regular breakfast smoothie, my stomach felt instantly better and my energy lifted. In the past, I would have come home and craved more grainy carbs, but nowadays I crave my veges to feel 'normal'. You will, too, in time, and it won't feel like a 'challenge' anymore -- it'll just be the norm.
Here's an overview of the Perfect Health diet. Again, I don't really follow this to a tee, but it's pretty close to what I've eaten over the past 6 months.