Losing weight isn't easy, but it is simple: I ate just one normal-sized meal a day for the last six weeks, and I've lost 7kg. First two weeks were hard, but it was quite easy after that. Going somewhere unfamiliar made it easier to break old, bad eating habits. Ask me anything.
But it's going to be (2) which lets you down, because there are all kinds of psychological effects that aren't conducive to long-term success, e.g. "I've already deviated from my plan ∴ I can eat whatever I like, and start afresh tomorrow".
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My advice would be to know broadly what's healthy or not, don't get hung up on sticking to a specific plan, and try to be aware of the psychological effects which could cause you to do anything other than what's good for you right now: don't plan, and don't overanalyse the past.
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In my case, my plan was to eat a meal a day, but a couple of times I had two (for social reasons, but it would have been the same if it were just out of hunger). I didn't make plans to eat less the next day, nor did I eat less on any day because I'd eaten more the previous day...
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