Set your weight goal at one pound a week and avoid bounce-back gain. By doing that I can search secondhand stores at each dress size reduction, taking my time to find things I will love and feel happy wearing, instead of having to buy new clothes every two months and breaking the bank.
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Don't waste money on charities that waste money or don't do what they say they are doing, Many "charities" are really scams that give themselves names that sound similar to the real charities that do good work.
Check out watchdog groups that rate non-profits such as: www.charitynavigator.org and www.bbb.org/charity
"Your time is limited, so don't waste it living someone else's life. Don't be trapped by dogma -- which is living with the results of other people's thinking. Don't let the noise of others' opinions drown out your own inner voice. And, most important, have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary."
Also don't waste this opportunity - you will be touching all your stuff anyway, don't keep anything that does not bring you joy, that you don't consider beautiful, that you haven't used in the last 6 months (or seasonally, in the last year), or that you have duplicates of.
1st purge is easy; when it gets down to "the good stuff", use your feelings of uncertainty/confusion/torn as a signal to donate. Call Salvation Army, they pick up good stuff.
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