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I think the biggest challenge of loosing weight is that you want to do it for yourself - there is no else you want to show off to. There is no bigger challenge than surprising yourself.
But the toughest thing is also to stay motivated when there are no apparent reason to do so (no major occassion, no family event, no girls to impress, no health problems). It is hard to punish yourself day in and day out to get to the ideal weight just so that you and YOU alone will be the most happy at the end of the day.
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