In the four times I have been homeless, it has never once occurred overnight. There had always been a buffer between the deciding event and the actual homelessness. That brief window is crucial to ensure that you start your adventure off on the right foot.
First thing you need to worry about is clutter. You are going to have to trim your house-full of possessions down to what you absolutely need to survive. It's a daunting task I'm certain, but once you consider your basic needs of food, warmth, and shelter, you'll find that most of what you own will be of little use on the road. Any small multitasker is going to be a necessity (folding knife, thermos, backpack, water bottle), as will several sets of clothes (I tend to keep a week's worth of summer wear in my trunk, along with a day's worth of long-sleeve stuff, during mild weather and vice versa) and non-perishable ready-to-eat foods (if you can spare the space and money for some kind of camp stove it will drastically increase what you can haul/eat). I can't say anything for the female side of hygiene, but I know that men really only need soap, shaver, comb, and toothbrush (anything more is entirely up to you, but I cannot stress enough the need for packing light). A few entertainment items can be brought along so one has something to do in their downtime.
So what do you do with what's left over? You can either sell it via yard sale, consignment, Craigslist, etc. or you can stick it some form of storage if you're lucky enough to have it available to you. Personally, I would sell as much of it as I could save for items of great sentimental value (if any), then donate what I didn't sell to Goodwill. Any money you can have stashed before becoming mobile will make things a bit easier for awhile.
There's no real way to mentally prepare yourself for homelessness, or at least not one that I've found. Each person handles it differently, and there's no way to know what you'll experience until you get out there. But later I'll talk about ways to handle the stress and sadness that comes with the territory.
It's also important to network with others as much as possible before you become homeless. The more people you know, the more potential resources you have available to you in an emergency. NOTE: This is NOT me telling you to take advantage of your friends and family. Just know that close kith and kin will generally be willing to help you in some fashion when asked, though each individual is different in how, what, or how much they can offer in assistance. And don't be put out if you are turned down; times are hard for everyone. An extended network can provide rumors about potential jobs, food, shelter, and other services that may not make the public eye. I'll discuss that more in a future post.
Lastly, make sure you have a viable and stable method of communication with the outside world. A cell phone is ideal, but you may not have the funds to continue paying for minutes. I personally rely on email, as I have a laptop and can check it several times a day. I also communicate using virtually every internet-based service out there. (Also, if your funds allow, take out a P.O. Box. Government services such as food stamps require a mailing address, and they will turn you away if you don't have one.)
Every situation is different, but hopefully I've provided enough information here to get you ready to face your upcoming challenges.
-Adam
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