Sunday, February 1, 2009

“Free Sleeping” -- A Life Without Strings

Camping illegally on the beach in St. John, Virgin Islands, May 2008. I probably won't do this again but will camp in a less obvious (illegal) location inland.

Welcome to my new blog on the virtues of homelessness.

Only I prefer not to use that word. The politically correct term is "Free Sleeping."

You like it? I just made it up a few hours ago. "Homelessness" has the connotations that you're unkempt, drunk, mentally ill and stink to High Heaven. I don't think I'm any of those things, or at least not the first two. I belong to a health club, so I shower almost every day, and hardly a lick of liquor ever passes my lips. As far as I know, I don't smell too bad, but my ability to smell myself is probably impaired by familiarity, so I can't say for sure. As for the mentally ill part, you'll have to judge for yourself.

I prefer "Free Sleeping" because it boils the problem down to the essential element: Where are you going to sleep tonight? That is the most critical function of what we call a "home." Sleep seems to be a required thing, and to do it successfully, you need to be protected from predators, cold, precipitation, mosquitoes and your fellow man. The inexplicable unconsciousness of sleep makes one vulnerable, and in response to this weakness people have built ever-more-elaborate protective edifices—i.e. "homes."

I say that much of what is now associated with the home is unnecessary, imprisoning and wasteful. Experiencing homelessness, or at least thinking about it, might actually clear out some of the dead wood in your life. What do you really need, and what is just vanity? This is an opportunity to find out.

I say that if you can take care of the sleeping problem, then everything else associated with a "home" is negotiable. Storage? There are alternatives, such as rented storage units. Cooking? Do you really need to cook in a land where so much food is precooked anyway?

Due to the wireless revolution, you no longer need a home for communication or all the various data-processing functions the home used to serve (paying bills, collecting photos, etc.). Thanks to advances in mobile technology, this ought to be the Golden Age of Homelessness—and thanks to the recent crash of the world economy, it probably will be!

"Free Sleeping" has the double connotation of sleeping that doesn't cost you anything and sleeping that leaves you the liberty to change your life at will. Imagine how rich and free you would feel if you made the same money you normally do but didn't have to pay rent or a mortgage. Think also of the many other burdens associated with renting and home ownership and how much easier your life would be without them. How much of your life is spent actually doing what you want to do, and how much is absorbed just maintaining all the ponderous Stuff you have surrounded yourself with?

If you could get over the sleeping problem and renegotiate all those other things associated with the home, you just might end up with a life that's easier and more pleasurable than the one you are living now. That's the theory, anyway. It has worked for me, but I'm a strange duck, and I'm not saying it's right for you. All I'm saying is that it's worth thinking about.

I've dabbled privately in homelessness for some time now, but I have just now decided to go public. The catalyst was my serendipitous arrival in a new city, San Diego, and my discovery that this is a virtual paradise for Free Sleeping. Why didn't I come here before? San Diego is new to me. I had passed through before but never stayed. I don't know anyone here and have no significant connections to the place, so it makes an ideal case study. How do I create a new life here with almost no money?

In the interests of adequate disclosure, I should reveal that there are at least two things that set me apart from the typical homeless wraith (apart from those four things previously mentioned). One is that I have a little bit of income coming in from various small business ventures so I'm not dead broke. However, I certainly don't have enough to afford rent in San Diego. My financial life has been precarious for years, and even buying a dollar burger causes me great bouts of soul-searching, but I'm not exactly starving.

The other thing that makes me different is that I can fly anywhere in the country for free. I used to work for an airline and was recently laid off due to service cutbacks. The good news is that I get to keep my flight benefits until the airline decides to rehire me. To me, this is like winning the lottery: I get both free flight AND the time to use it.

The only downside is that I have very little money to travel with, even less than the starvation wage the airline once paid me. There's not much point in flying free if I can't afford to leave the airport at the other end. If I can make this Free Sleeping thing work, then I can make better use of my flight benefits.

My free flight pass also gives me an opportunity to try the concepts of homelessness in a variety of environments: tropics, desert, woods. If find myself in an environment I can't handle, I can always hightail it for the airport and try somewhere else. I am not committed yet to staying in one place.

Eventually, though, I will be committed. My flight windfall will not go on forever. On a certain future date, if I am not rehired by the airline, my coach will turn into a pumpkin and I will become simple Cinderella again. At that point, the homeless life might not seem so free, but we'll see.

In the meantime, let's conduct some experiments and collect some data. We'll work with this virgin location for a while and see what we can make of it. I'll talk about what I have learned so far in the field of "urban camping," and we'll delve into all the myriad practical and philosophical aspects of being "not of fixed location." I think you'll find the whole topic of homelessness (excuse me, Free Sleeping) can be very deep and not at all what you think of when you trip over a bum in the street.

We're going to try to do it with intelligence, grace and style, okay?


  1. New observer aboard, eyes open and with the typical or harsher view of the homeless. I look forward to the virtual and educational ride...thanks...Mike

  2. I just found your blog and other interesting sites and looking forward to some vicarious explorations and education. Thanks for sharing a life that is less dull than most!

  3. I was so excited to find your blog today. I'm not far from your starting off point (for your blog) of San Diego.

    I'm a 40 year old woman and I've been free sleeping for almost 4 months, mostly by choice. I sleep in my van and I house sit. I really want to get a tent and live in the wood though. If you aren't completely sick of the topic of free sleeping by now, please check out my blog at

  4. I've been 'free sleeping' for a while now, even with the possibility of giving up my apartment because Im never home to use it. ive recently explored key west and oahu. will a little income and a cellphone(android), as long as one can shower, i dont see the need for possessions like apartments.