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Homelessness: Going Into it and Getting Back Out

Updated on August 23, 2012

Getting into and out of homelessness

I entitled this article, not just "getting out of homelessness" but also how to "go into homelessness." A lot of us who have been homeless have had some time and could see the very scary writing on the wall: Home is being foreclosed on, jobs have been lost, divorce and breakups, fleeing an abusive relationship, etc.

Despite the obvious stigma of homeless people being a bunch of drug users and lazy people that don't 'want' to work, the reality -- especially in the past 5 years -- couldn't be farther from the truth. Normal, every day Americans are either facing the nearly impossible prospect of homelessness, or are already stuck in it.

This article is about what to do when you're looking at the prospect of homelessness, or are already homeless. The fact that you're on the Internet and found this article in the first place is a good sign: You have at least some resources and you're actively looking for a way out.

A Little About My Experiences

Some time back in 1997, I had a conversation with a new girlfriend about "The American Dream" and, being a disillusioned immigrant from Poland, she thought it was a big lie. I didn't. In a 'Truth, or Dare" game, we dared each other to go to Boston with nothing but the clothes on our back and get a Beacon Street (Boston) apartment within 2 years. We did it in one.

That may seem like a slap in the face for people who are in homelessness for real, but trust me, that crazy adventure was good training for when I also became homeless for real. In the June of 2009, I suffered Delayed Onset PTSD from a war I had photographed in 1989 Beirut and suffered complete amnesia and very simply couldn't find my apartment. Overnight, I lost my apartment, my work, my possessions and even my very identity and some of my skills.

At the time, I was in Washington, DC and I promise that that is not a very easy town to be homeless in. Richmond, Virginia was even worse.

Three years later, I'm writing this article in a nice Allston, MA (Boston) apartment on my beloved (used) eMac computer, while watching Stephan King's "The Stand" on a second MacBook Pro. I'm doing this while sitting on an office chair with a nice desk, feet away from a bed and, if I get hungry, there's food in the fridge, pots and pans, a nice gas oven and... you get the picture.

You're going to get out of this situation and I'm going to help you out as much as I can.

This article isn't for everyone

Everyone that becomes homeless has their own unique story about how they got that way. Since this article is based on my own experiences, there are situations I can't possibly give advice on. For example, this is mostly about one person getting out of homelessness and not a family with kids. I've never been addicted to drugs and, if your homelessness is caused by that, then you've got to deal with the addiction first and then come back to this article.

I have a very severe mental illness called PTSD and many homeless have various mental illnesses, but this article avoids that issue: Mine is manageable and this article focuses on the homeless issue and not the mental health complications of homelessness: You need either not to have that complication, or you have it and are very high-functioning and disciplined.

You're About To Be Homeless

If you're looking at homelessness staring you in the face, you have a very tiny window of opportunity to make the situation as easy to get out of as possible and very little time to do it. There's three things you have to do immediately and these things are going to save your life and make things easier, more quickly.

  1. Accept that you're going to be homeless and stop crying about it and especially stop blaming anybody or anything for your problems. This is the card hand that you've been dealt and any time or energy you spend complaining about it and feeling sorry for yourself is time you don't have. I wasted a lot of time in DC thinking that PTSD wasn't fair and it cost me dearly.
  2. If you can, buy, beg or borrow long-term (1-2 years) storage of any possessions you have that you can't carry on your back. Even if you have a car, you may have to abandon it and anything you can't carry. When you get out of this situation, you'll be glad you did. If you get that kind of storage, store personal and memorable things there: The worst feeling is to make it out of the situation only to have lost your past: Photographs, heirlooms, contact information of people you'd like to reconnect to, financial and tax information, birth records and any other important documents, passport, ... anything you don't want to lose forever.
  3. Get organized and get it into your brain, heart and body that the only way out of this situation is to focus on basic needs, a plan to get out and the discipline to follow that plan. This is maybe the hardest thing you're going to do in your whole life. You have to decide if you're strong enough to do it, or not. If not, stop reading and good luck.

Location, Location, Location

You have to understand that every state and city has it's own way of dealing with you, "the Homeless Problem." Your main concern is going to be three things: Food, Cleanliness and Shelter/Bed in that order. That said, your very next concern is getting out and I'm sorry to say that homeless shelters are more about giving you the basic needs of food and bed, but even more, feeling powerful, attending to their own religious needs and putting a boot to your neck and demanding that you comply with whatever rule they can come up with no matter how irrational.

That wasn't me being bitter: It's a truth that you have to navigate with intelligence and humility and a lot of gritting your teeth when instead you want to fight back.

Moving from DC to Richmond, was the worst mistake I ever made because the CARITAS religious system for dealing with homelessness made it absolutely impossible to get out. It's impossible to get a job if you have to choose between a bed and a job, food and a job, etc. If you have to be in the shelter by 4 pm or lose your bed, how can you get a job that's 9-5?

If you're in a state or city that makes getting out difficult, you HAVE to leave that area and find a better one that is more interested in you making it than whether they are going to heaven or getting a paycheck, or playing out some power game by making themselves feel better about their miserable life by making you feel powerless.

Leave, but plan on where you're going to go, first. Whatever you do, do NOT try to fight the system or the people or the injustice and petty malice as an homeless person. Learn how to say "Yes, Sir" and "Yes, Ma'am." Say it now. Say it with an innocent smile. Practice it in a mirror. If it helps, just know that you can come back later to correct injustices when you make it. Right now, suck it up.

So, I made it in Boston. There are other places to make it. You have the Internet if you're reading this, so, do a Google Search of "Homeless Friendly Cities" without quotes. If you have to walk it because you don't have a car, then pay attention to your basic needs and how you're going to get through all that distance with food and shelter: Cities have homeless support, smaller towns, don't. Those are your stopping points.

There's also the option of doing a couple of days of labor jobs and getting a bus ticket. Do what you gotta do.

In any case, get there. That's where you're going to really start.

Making a Plan and Sticking to it

I hate writing To Do lists. My personality is that if I made a shopping list, I'd forget the shopping list and wouldn't realize it until I made it to the grocery store. I'd also think I didn't need it and would do the shopping and, I have to admit, I'd remember what I forgot to buy after I got home.

No matter how much you hate making a To Do list and actually following it, you're going to do what I did: You're going to get a pad of paper, or better, a Day Planner, and you're going to learn how to make My kind of To Do list and you're going to follow it every day. You're not going to want to hear this, but you're going to fail to follow it regularly and get stuck a few times until it sticks, but you're going to remember this advice and you'll get back to writing and following the ToDo List.

Don't feel bad about failing on this step, but definitely keep trying to get back to it until you get it right. You are otherwise going to stay stuck, or worse, you're going to start to make it, then fall back in the same place, over and over again. You have to master this.

The Five Year Plan and Values

Goals and your personal values are completely intertwined. It's easy to "say" that you value something, because you think you should, but you can't keep to a goal if you don't really believe in your deepest heart that you really follow that value. It's a rude awakening to discover that you thought you valued something and have been following that path when you actually don't.

Right now, though, you're going to write a list of what you value, then write a long-term goal that matches that value. The reason you're doing this exercise is to get rid of baggage and help you focus on daily things that will actually get you to that goal. More importantly, if you 'say' you value something, but find that you really don't, you're going to be able to get rid of goals and values that you aren't really valuing, anyway and you'll stop wasting time on things that are getting you nowhere.

The two resources you don't have is time and energy to waste and I discovered this with nearly a year of wasted time. Once you understand the connection between goals and values, you'll understand the logic behind this.

Write a list of what you think you value. When you write it, write it in this format in a single statement: "I value ______" and then for each single statement, write a descriptive statement about what that means: "X means Y."

For example, I value Honesty, integrity, financial independence, mental health, physical health, sex, a good relationship, real friends, security, etc. What 'Security' means to me is written in my planner like this: "Security means knowing where my money is coming from, tomorrow, and that I have a bed, food and a future."

When you get that list down on paper, know that you're going to be constantly editing it. What I want you to do now, though, is to prioritize it: Write "A" next to every value that is MOST important to you. Write "B" next to those that are important, and you aspire to them, but you don't always follow it. Write "C" next to values that you find valuable, but ... whatever. Nice idea, but you don't really follow them.

Then rank all your A's 1, 2, 3 based on what's most important and all the B's and all the C's.

Five Long Term Goals Based on Values

Pick five items for your A list of values and develop long-term goals based on it. A long-term goal is something you can realistically achieve in 5 years, or less, that is based on a value that you actually value. If you don't value it, you won't achieve it: You won't do the daily things to achieve it.

The relationship between goals and values is this: If you value something, you're willing to achieve a long-term goal based on what you value. If you don't value it (and fool yourself in thinking you do) you will not achieve a goal based on that value.

The relationship between a long-term goal that you're motivated to achieve and getting out of homelessness is that it takes a lot of time and energy and discipline. If you're not ready or committed to the daily drudgery, frustration and humiliations you have to endure, then you're wasting your time and you're going to find yourself stuck, re-stuck, making it only to lose everything again, banned, beaten up, dead, etc.

Five, realistic, long-term goals that you can attach to something you value. I need that in writing. If you don't do it, it's a dream and you're just talking and it never leads anywhere. If you write it, it's a Bible that leads you out of the desert, or if you prefer, a road map out of the same desert.

The last steps in writing down long-term goals is that you have to put a deadline -- a date -- on this goal. When you do the next step, you may find it necessary to adjust the deadline to make it more realistic, but understand that without putting a deadline to each long-term goal, you will never achieve it. Write a short description about what achieving that goal will actually mean.

For example:

Value: Financial Security: Earning $100,000 per year and have a solid retirement and investment plan set up.

Working Backward from a long-term goal to develop a plan

You're homeless, or about to be. You listed things that you value and you listed long-term goals that are attached to some of those values. The next step is creating a set of tasks that achieve those long-term goals.

The problem with long-term goals, initially, is that they are simply too, big to chew. You have to break them up into smaller, achievable goals. Essentially, these are milestones that each lead you closer to your long-term goal until you've finally achieved it.

For example, I had a long-term goal of getting my business back up off the ground which I attached to my own value of financial security:

Value: Financial Security: I pull in enough revenue to provide for my lifestyle and secure my retirement.

Goal: My business is successful: My business pulls in $100,000 Net and I have employees that help me finish projects. Deadline: 6/12/14

Milestone 1: Get a temporary job to cover daily expenses and pay for an apartment. 6/14/10

Milestone 2: Save enough for First, Last and Security on a room in an apartment ($1500). 7/14/10

Milestone 3: Redesign my Portfolio Site when I'm not working and get a moonlight design contract. 7/21/10

Milestone 4: Save $20,000 in a separate bank account from contract jobs. 6/14/11

Milestone 5: Etc.

You get the idea.

Daily Tasks

Now, after that is done, you're ready to start writing a daily task list religiously, every day. The second you become homeless, you have immediate survival tasks to deal with. You have absolutely no time to waste and you have to get it into your head that time is constantly working against you. Your priorities are Food, Hygiene, Shelter, Getting out. The priorities are in that exact order with Hygiene coming before shelter.

You need to be meticulous about staying clean for several reasons: Self respect is hard to remember when you're homeless for any extent of time. Meticulous hygiene will actually get your spirits up in the morning. Secondly, being homeless opens you up to crowded situations where disease can become an issue. Lastly, when you respect yourself, you'll find other people such as future employers respecting you and seeing you as human.

You can get and keep a job even if you sleep under an overpass, but you can't get a job if you stink or look homeless.

So in your daily list of things that you'll be writing every night for the next day, add each hygiene task, as well as finding food tasks and shelter tasks.

Finding Food.

Pretty much every major city has a soup kitchen. It may feel humiliating to stand in line for food, but if you're hungry enough, you'll do it. Any cop can tell you where it is, or since you're on the Internet reading this, you can look it up that way. Find out what time the meals are and what time you have to start lining up.

The problem with soup kitchens is a question of time. What you'll find is that very few of them have convenient times that are work-friendly. The very first jobs you get until you get on your feet may have to be service jobs, restaurants, cafes, convenience stores, etc. The hours of those jobs may very well conflict with those of the soup kitchens (and even the shelters), you may find yourself with the terrible and unfair choice of eating, or working.

At first, there's nothing to be done for it, but as soon as you can, apply for your state's Food Stamp Program. In Massachusetts, it's called EBT and it gives you the flexibility you need to work without starving yourself. Once you get it, there is a temptation to buy your food at a convenience store especially if a grocery store is a far walk. Don't.

Use it only to replace those meals that you're missing because of work. Most states require that you report a change in income, so eventually (and hopefully) the benefits will stop and you're going to need what's left to stock the refrigerator of your new apartment. For all other meals, stick to the free ones.


Homeless shelters suck. They smell. They are crowded with some very strange and usually sick people. They are staffed very rarely by intelligent and kind people, though there are exceptions. Nobody cares that you used to be a lawyer, plant manager, truck driver, housewife, programmer. Nobody cares about you and your personal needs.

The very first time you walk in can feel humiliating and neither the staff nor its residents are people you could ever imagine even 'seeing' on the sidewalk as you walked by, let alone sleep in the same room with them.

The very first thing you have to get into your head and your attitude is that you're not better than them except if you get out and they're still stuck. At the moment, though, you are all on the same level. If you can't get it through your head and accept this fact, I promise that the attitude is going to come through subconsciously and the staff and fellow residents will sense that you feel this way... and they will make your life a living hell just out of spite and to knock you down (maybe literally) a few pegs.

For the first few days that you're there, don't ask for favors, always be respectful and polite to everybody, don't even try to ask for an exception to any rule. Eventually, you'll get a sense of what staff members can work with you when you obviously seem serious about getting a job and getting out. If nobody there is reasonable (a very likely possibility), then just keep your head low and make yourself as invisible as possible.

The most important thing in the shelters is to override any natural tendencies you have to talk instead of listen. Listening is important and talking will always get you into trouble with a group of often irrational people.

If the shelter makes it impossible to get a job, then you need to find other arrangements or another city. A few days of labor jobs will get you a bus ticket.

Pretty much, go in when you have to go in, take your shower and go through your hygiene list, spend some time going over your ToDo list for tomorrow, carrying everything that wasn't accomplished today to tomorrows list, then go to bed. The next morning, get up, wash up, eat and get out.

Some safety and common sense tips:

  • If you carry more than one bag with you, tie the two together and tie the straps securely to the head (not the foot) of your bed. If you're in bunks, use the bags as pillows.
  • Put your shoes under your mattress especially if they are nice shoes.
  • Never give cigs away to people in the shelter: Sell them at the going rate, usually $0.50. Firstly, it helps you buy the next pack and you can actually make your cost of cigs zero by selling half and smoking half. Better, buy cigs and tubes in bulk with a plastic rolling machine and sell THOSE at the full $0.50 and keep the good stuff for yourself.
  • I know you may feel lonely and after a while, you may hunger even for the friendship of your shelter-mates as you get to know them. It's fine to chat and hang out, but do not ever make the mistake of thinking they are your friends. Don't trust them. Don't feel safe around them. I guarantee you that any one of them that is smiling and joking with you one moment may try to steal your bags if they feel particularly desperate: Everyone is looking out for themselves and there are a LOT of very desperate people in a shelter.
  • If you have a computer, you may have a particularly hard time keeping it. Definitely sleep with it under your pillow. One thing I did was spread a rumor that my computer had a lo-jack and acted completely unconcerned about it being stolen: If someone stole it, I'd find them in about 5 minutes and they'd wish I called the police. It worked, but I sweated and it would have been a disaster if it had been stolen.

Getting Work

You have a plan, you have the food figured out, you have a bed. Getting work is the next step. No matter what your former occupation might have been and no matter how many college degrees you have, getting back to where you were, or where your long term goals are leading you, requires that you start small. If it helps, think of it as a 'job-job' instead of a job, think of it as just getting some money until you get something better. Better, don't think about it to much: If offered, put on your green apron and learn everything you can about coffee.

You need your own bed and a room, right now. Achieving this is going to be a huge help to your self-esteem. Getting money into a bank is your first step. No matter how you make your money, put it in a bank and not your pocket.

So, labor jobs are the best places to get a bit of quick cash for a day's work. It's completely menial, but I always thought of it as a way to work out, work hard and take a lot of anger and bitterness out on pure, physical labor. It also helps you fall into a deep sleep despite five people snoring like chain saws in the room with you.

Craig's List at can also help you find labor jobs as well as other short-term contract jobs. Asking around can also give you tips on jobs that don't find their way even to Craig's List.

With cash at hand, though, you need to get a steady job. Starbucks is actually a good place to start over and I know two people that have made it from homelessness and one is a District Manager with a nice salary and future. Whatever you decide, one of your ToDo list items is just to apply for and get a job at anything you can do. Earning $6.00 is better than earning nothing. Getting $0.50 is better than nothing.

The work you're getting has nothing to do with your profession or your vocation. It's about getting paid for time so you can get a room in an apartment. Humble yourself: Anybody that thinks work is beneath them, doesn't understand the work and doesn't understand life: Humble yourself and put a smile on your face.

Keep to your long-term goals

It's just a task list. You may have ended up homeless, but the fact is, you're getting out and less than 99% of homeless get out and stay out. Frankly, you'll be able to brag about it, one day: I went through a very bad thing, but I got out the other end. I had a goal and I believed in it and believed in myself and crawled out.

You can put the damn thing on your resume.

The thing is, you have to do things daily and step by step and make your long-term goals your religion and your faith and the thing you keep telling yourself about why you are doing this: You're making it from nothing. How many people can say that?


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