For a long time, I've been inspired by those who do more with less, live with high style on tight budgets, and are thoughtful and mindful about the items they bring to their lives (like the people in this article from the NYT archives).

It's an ages-old concept that living with less will make you happier, and that you don't need a lot of resources to live (or dress) well. It's amazing what you can do with a little creativity and a few dollars at Goodwill.

While that all sounds nice, it's easy to underestimate how attached you can become to things. A systematic approach to deciding what to keep versus what to toss helps. 

Pretending to be organized is one of my secret professional talents. At work, my inbox never has more than 25 emails, I use my Tasks folder religiously, and I rely on OneNote to take over where my brain leaves off. My coworkers think my favorite hobby is giving them unsolicited advice about optimizing Outlook when they complain about out-of-control email. (But they are wrong: giving unsolicited advice in general is my favorite hobby.)

But when I get home from work (and am back in my natural habitat), my shoes and blazer get tossed onto an armchair where they'll stay for days. My needs-to-be-dry-cleaned bag is overflowing in the trunk of my car. I have piles of receipts stashed away in strange places, boxes of high heels, and more iPhone chargers than outlets in the house. The attic is stuffed with things I love but don't have room for. My Gmail is my worst nightmare, like an out-of-control monster that just keeps growing, burying into oblivion the stuff I really need to read.

In my professional life, I once went through a training (it's also a book) called 'Getting Things Done' that changed everything about how I worked, and I am ashamed to admit that it's taken me this long to commit to applying it to my personal life.  The core principle is to create a system, make rules and stick to them, and ask yourself two questions every time you open an email:

1. Can I delete this? If yes, delete! If no, move to step 2.

2. Can I take action immediately? If yes, do it. If no, file it in your Tasks folder for future action labeled with the first step you need to take (e.g. call Cathy)

This is a system that works for eliminating other unwanted items from your life (junk snail mail, receipts, clothing, you name it):

1. Can I toss or donate this? If yes, add to the pile! If no, move to step 2.

2. Can I use this in the next month? If yes, set aside. If no, pack up for storage.

I've been applying it drawer-by-drawer, room-by-room and am amazed at what I can toss. (And also amazed at how I can fulfill my fashion dreams at Goodwill.)

What has helped you to simplify your life?