Everyone is attached to their possessions in some way. Your things represent your personality, your style, memories, financial outlays, security, and a sense of wealth. At some point you decided to acquire everything in your home and now you will have to decide what will stay and what will go.
There are a multitude of questions you can ask yourself about your things to make the decisions easier. If it is an item in your wardrobe ask yourself: Does it still fit? Do I wear it? Is it still in style? Does it make you feel great when you wear it? Is it in good condition? If you answered no to any of these questions, it is likely you should donate, toss, or sell the item.
For kitchen items, you could ask yourself: Do I use it? Do you need more than one, when one is enough? Do you have all the parts? Is it worth the space, when another item could do the same job? Again, if you answered no, you could sell, donate, or toss the item.
For food and pantry items: Is it still good (not expired?) Will I ever eat it or cook it? Does anyone in the house like it? If you answered no, toss it or donate it to a food bank (if unopened and still within the expiration dates.)
For bathroom and vanity items: Is it still good (not expired – especially medication?) Do I use it? Do I need this many of the same item (eg. six bottles of shampoo?) If you answered no, toss or donate (if still good and unopened.)
Memorabilia, knickknacks, and furniture may require more difficult questions: Does it still reflect who I am? Is it being honoured in its present condition? Do I use it or could someone else use it more than me (eg. paring your books down?) Do I have space for it, especially in the case of downsizing to another home? If you answered no, donate, toss, sell or honour (eg. memorabilia) the items.
When you are working with a Professional Organizer you will still be the one making these decisions. The Professional Organizer may prompt you with some of these questions and may offer some guidance but you will be the one ultimately deciding what stays and what goes.