I became paleo in April 2010 after a friend suggested I check out Marksdailyapple.com. That same year I decided to become a paleo chef. My digestion was reasonably under control (still figuring out the nuances), I weighed less than I had in high school. I wasn't running everyday and I got lots of sun! I follow a Primal/Paleo diet which includes meat, fish, eggs, very few nuts and seeds, all vegetables,very little fruit, and some tubers. My indulgences within Paleo are dark chocolate, occasional wine, and coffee. I will also enjoy some corn from time to time (1-2x a month) in the form of mexican food. And rice maybe 3-4x a year for sushi. If I'm being strict I omit alcohol and all natural sugars. (dates, honey, coconut sugar, and most fruits).
Over time I've found myself putting on weight again. I think my fat intake has been much higher than when I started paleo. Also, since I'm a chef, I'm around food all day. So even if I'm paleo-compliant... I'm probably over-feeding myself in a caloric sense.
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Social situations. Going hungry or saying no to foods offered at other's houses or at a "questionable" restaurant.
Don't rely too heavy on nuts or nut-based products. Also coconut and coconut based products. It's too easy to try and replace neolithic foods with paleo alternatives... but at the end of the day the meals should always be very similar. Meats, veggies, and fat.