How to Leave it All Behind

Posted: April 11, 2015 in Sidewalk Spirituality

In today’s society there are a number of good reasons for someone to leave everything behind and take up a wandering nomadic life. It might be to satisfy a sense of wanderlust, or to save a bit of money, or because you’ve seen the truth. Any which way you slice it, if your journey calls you to be homeless, then you’re going to want to be smart about it.

This article is written from one particular perspective – that of an intelligent, single, white, heterosexual male who still had a few bucks in the bank and chose to live on the street. If you are coming at homelessness from another angle then this article may be missing things that are important to you. Just be sure to think about all of the aspects of what you are doing and fill in the blanks for yourself.  I chose to be homeless because I found enlightenment and would rather spend my time helping others than acquiring more money and things.  Your circumstances may be more pressing than mine were – there are other sites that may be more useful than mine if homelessness is being thrust upon you instead of chosen as an option.

#1. Pick your area. This is about setting your intentionality around the kind of homeless life you want to live and where you want to be. Research the area and see what kinds of services are available. Identify those services that you are most likely to use and call them to learn about their services, the ins and outs of how those services are delivered, and anything else you might need to know. There are three basic things to keep in mind: Access to bathrooms and showers, access to food and water, places to sleep at night. You may also want to rent a small storage space within walking distance.

#2. Get to know people. You should spend some time among the homeless in the area you intend to take up residence in. My advice is to be loving and kind to the homeless. You should be doing this anyway, but by making a point of it, you’ll gain their respect and their trust before you are reliant on them. If you just show up one day with a backpack asking where to sleep you may be in for a rude awakening. But if you’ve sat with them, listened to their stories, gotten to know them, and become a friend, they will take you under their wings and help you make it through the tough days.

Quick Point: You should be kind to the homeless no matter what – and you should not be looking at this as a way to worm your way in through lies, tricks, and deceit. Every single one of us has a duty and a responsibility to take care of others. Don’t be kind because you are expecting something in return – be kind because it’s the right thing to do. It’s honest, genuine loving-kindness that people will notice. If you’re just hoping for a reward of some sort, or something in return, you’ve missed the point.

#3. Plan your budget. Once you take this journey you’re going to find yourself appreciating everything that you have because you will be surrounded by those who have so very little. Be smart with your money. Only buy simple portable foods, stick to the cheapest versions of basic necessities, etc. Don’t waste your money on nonsense like expensive coffees. Be sure to figure in the cost of sharing what you have. Be careful in terms of how you share, or else you can quickly go broke, but also make sure that you aren’t the rich homeless asshole who hoards everything. This balance is one of the hardest things to achieve – something I’m still working on myself.

#4. Sell your things. Money is an unfortunate reality of our world – at least for the time being. If you want to eat then you will need money. Look at your possessions and identify those things that may have value. Put together an inventory and start using services like Craig’s List and E-Bay to liquidate your assets. You may be surprised to find out how much you can actually generate this way. Be sure to hold onto things that you can make use of on the street, and donate things like extra clothes and camping gear to other homeless people.

#5. Set up the basics. For me there are three things I recommend you make sure you set up and continue to pay for; a cell phone, a storage unit, and a gym membership. Make sure these are all within walking distance of the place you intend to spend most of your time. The phone will make sure that concerned friends and family members can stay in touch and it gives you internet access to stay on top of things happening in the world. The storage unit is for clothes, food, and a few other odds and ends that you may not want to carry with you all the time. The gym is for staying physical and taking showers.

#6. Get the right gear. At a minimum you need a large enough pack to accommodate your gear, a sleeping pad of some sort to keep you off of the ground, a sleeping bag rated for temperatures appropriate to your area, appropriate layers of clothing for warmth, a rain jacket and umbrella if you live in a rainy area, and a water bottle. Basic hygiene is important, so bring a toothbrush and toothpaste, etc. It may take some time for you to sort out what’s really necessary and what is not – and you’ll likely find that the weight of your pack and the distances you are walking will be the ultimate limiting factor that helps you sort out the difference between needs and wants.

#7. Make sure you’re really ready. This is the most important step – and if you’ve gotten this far then chances are you are ready. What you are about to do is going to be very hard – harder than you think. But it’s also not going to be as bad as you imagine. The first week will require you to examine your choice deeply. Stick with it. In fact, give yourself about two weeks to acclimate to being on the streets before you start to think about going back again. You may adjust your gear, your location, the people you hang out with, etc. Just roll with it and let things unfold as they will. Be open to learning, be open to change, and things will turn out just fine – as long as you are smart and loving!

#8. Ignore the fearmongers. Yes, something terrible could happen to you three seconds into your journey of homelessness. But something terrible could happen to you while sitting on your couch at home. Just because other people think it’s a terrible idea doesn’t mean you’re making a mistake. In fact, you are making a leap of faith that goes beyond their comprehension. They are the ones who are trapped, not you. Our society is desperately broken and so many people are so lost within it that they have given up their power, lost their freedom, and have no real clue how insidious it all really is. Listen for real advice that may be helpful, but lovingly dismiss people trying to discourage you. Honor your own journey, not the nonsense that society tries to fill your head with.

#9. Find something to do. Now that you are homeless you are going to want to find something useful to do with your time. In this regard its best to follow you passions. What is the one thing that you always wanted to do but never could because you were always so worried about money? Was it art? Music? Gardening? Writing? Whatever it was, find a way to do it as part of your new homeless life. You should also look at ways to contribute to your local community. Don’t be the homeless bum that everyone expects you to be. Be a beacon of light shining in the darkness and do something meaningful with your time – even if it’s just spending time with others and being a true friend.

#10. Continue to grow. Your journey of homelessness came to you for a reason. It’s intended to teach you something about yourself. Use it as the lesson it’s meant to teach. This one can be a bit tough though because living the street life means that you will be surrounded by alcohol, drugs, and mental illness. There’s also tons of drama, terrible hygiene habits, and numerous other challenges to the senses. Love and trust yourself enough to honor your own journey and don’t let yourself get caught up in these things. You don’t need to do them in order to be accepted – in fact, you can help others step out of these places if you are walking with love and in balance with all things. Stay positive, push back the darkness and shine your light.

If you have additional questions about how to pursue some of these things feel free to post them below and I’ll try to provide answers. I’m sure I’ll also be writing more articles on this particular subject over time. Until then – be love… amen.


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