Simplify Your Life-- How to Start
The challenge of simplifying one's life is essentially a mental/spiritual task. Its not so much a matter of getting rid of stuff as of getting rid of fears and irrational cravings. Once these INTERNAL complexities are dealt with, one's outward life automatically becomes easier and simpler.
My first recommendation is to get rid of your TV. TV is the greatest source of distraction and conditioning in most of our lives. Through it we are fed a steady diet of craving and insecurity. Advertisements pound away at us... its always the same message-- "this product will make you happy". We withdraw from our very real lives and begin to live in the virtual reality of television. We focus our energies on the 'News" instead of what is happening directly to us. We tune out and avoid the hard questions. We distract ourselves from the gnawing sense of boredom, depression, and loneliness which shadows every quiet moment. We fail to ask, "Just why is it so hard for me to sit quietly alone? Why must I always be distracted by the TV, the radio, the newspaper?"
Facing these questions is the most vital step one can make towards freedom. When I went off to college my TV could not pick up any reception. I decided not to pay for cable. I've now been 14 years without television. I would not have achieved the level of freedom I now enjoy if I had not made this crucial step.
So my advice is to destroy the TV... or at least cut off cable and cut off the antennae (leaving yourself the option of renting movies.... which are generally a notch above TV shows and do not have commercials). Start living your "free time" instead of wasting it in passive lethargy. Join clubs, go to the gym, take classes, read spiritual/philosophical books, walk in the woods, meditate, draw, write poetry, go to museums, people watch in cafes, visit friends, host dinner parties, do yoga, play disc golf, write letters, start a website of your own,... live! Or in Hakim Bey's words: "Dance before you calcify"!
"And I am sure that I never read any memorable news in a newspaper. If we read of one man robbed, or murdered, or killed by accident, or one house burned, or one vessel wrecked, or one steamboat blown up, or one cow run over on the Western Railroad, or one mad dog killed, or one lot of grasshoppers in the winter,--- we never need read of another. One is enough. If you are acquainted with the principle, what do you care for a myriad instances and applications? To a philosopher all NEWS, as it is called, is gossip, and they who edit and read it are old women over their tea."-- Henry David Thoreau