From Homeless to Hopeful in One Year



Today, we have an inspiring guest post from Mr. FWP of Finances with a Purpose.  He is a small-town guy with an ivy-league education and professional career.  He impressively repaid $200,000 in student loans and now encourages others to improve their own finances and achieve greater purpose in life at his blog.


Could you take a homeless* (see footnote) person and move them to financial stability?


from homeless to financially stable

You get the idea…


My father’s final year, he gave a gift that keeps giving: helping a homeless person become a financially stable saver.


Growing up, we would sometimes visit my mother’s friend.  She lived in one of those houses where you don’t see the house from the road, a country highway.  Instead, you saw a long, winding driveway that wound over a bridge, through the tall oaks, and curved up the hill beyond.  Twenty years later, I remember that driveway and the home at the end of it.  I never would have guessed, as a kid, that its owner would become homeless.


Yet twenty years later, I pursued a professional career, while my mother’s friend—we’ll call her Lisa—was divorced, broke, and homeless.  Her last close friend had kicked her to the streets: she lived in her car.  She had financially deteriorated for years, but now, even her own relatives refused to help her.  She had called in every favor, used every indulgence.


My parents, however, decided to give her a chance.  But they would do so only if she worked her own way towards independence, and eventually, she changed the course of her life.


Beginning a New Story…Assessing the Problems, Making a Plan

Despite some unease, my parents allowed Lisa to stay temporarily, but they insisted Lisa pay rent.  She would have one month to work with my father and make a plan to become independent again, or she was on her own.


from homeless to financially stable

A financial albatross…


She agreed, moved in, and sat down with my father to create a budget—for the first time ever.  They went through her finances and discovered that Lisa had some unpaid consumer debts and paid too much for things like insurance.  She could squeeze together enough money from her low-wage hourly job to make her basic payments if she managed her money well, though, even though she was deeply underwater on a usurious car loan with a car that needed significant maintenance.  The car had no easy solution; she needed to pay down the remainder of the loan as quickly as possible.  (Lenders will charge 25+% interest to those with poor credit, which is like paying a 25% tax every year on what you owe!)


Dad had her plan to save up an emergency fund each month until she reached $1,000 in the bank.  She didn’t like it and didn’t see the need for it, but eventually, she assented.  They also began saving up her “down payment” money so that she could find an alternative living arrangement with a deposit and a month’s rent in advance.


They set up a system of cash envelopes, and Lisa began managing her money.


A Bumpy Start

For the first few weeks, everything went well: Lisa made her major payments, and everything seemed OK.  So another month went by.  But, by the end of month two, my parents realized something was off: Lisa was struggling hard to make some payments and continue saving, yet, she wasn’t struggling at all to go out to bars and buy some drinks most weekends, even though it wasn’t in her budget.


from homeless to financially stable

Too bad the bars weren’t this nice…


My parents confronted her, and she confessed: she had been hiding extra income from overtime.  She was actually making a good deal more than she had disclosed.  She didn’t want to tell them about that, because she wanted to continue having fun times—even though she couldn’t pay for her own place to live.


Rather than kick her out, my parents decided to give her a firm new plan: she could give up control of her finances, and agree to use all of her income to help herself become independent, or she could move out at the end of the month.


Once again, she agreed—she had no other option, and really wanted to be back on her own—even though she still didn’t see how it would happen.  At times, she would hint about staying longer, or renting for a longer period of time.


But my parents continued to make their boundaries clear: they had allowed her to stay a month, then a few months, but they decided that she had to be out in a year’s time total—that was more than enough for her to get back on her feet.  And, she would have to leave if she quit moving towards independence at any point.


Changing Hearts to Change Finances

My parents did nothing for her that Lisa could do herself (such as make meals) and encouraged her to transition towards living independently.  They admitted that the biggest challenge wasn’t finances, it was Lisa’s attitudes about life.  She believed she could never have much money, manage money, take care of things herself, or that she was worth it as a person.  (Money is like a mirror: it reveals emotional problems, spiritual problems, and ignorance—sometimes all of them at once.)  My parents gently reminded Lisa that she was worth it, and that anyone could manage money.  All it requires is some self-discipline and planning.

from homeless to financially stable


Month after month, Lisa brought her cashed checks home to my father, who would sit down with her, go over her budget, make sure she paid her bills, and refill her envelopes.  She didn’t seem to believe them, but she didn’t want to be on the streets, either, so she complied.


Confronting Challenging Attitudes About Money

One day, Lisa became ill as a chronic health problem flared up.  She knew she needed medication, but she refused to go to the doctor: she owed him $75, so he would refuse to see her until she paid him, and she didn’t see any need to pay a debt that couldn’t be collected.


Her solution was simple: feign a crisis, call 911, and hop aboard an ambulance.  The county would pony up thousands of dollars for a chauffeured emergency room visit at no cost to her.  Plus, she had no credit and no assets, so the county could never recover any money from her.  She was right about the financial math.  The government would pay for it, she reasoned, so why should she?


My mother, however, who worked for a government, pulled her aside and told her she absolutely could not do that, not while living with them, at least: my parents wouldn’t incur thousands of dollars’ expense for county taxpayers because their tenant refused to pay a $100 bill.


My parents told Lisa that her doctor, like her, deserved to be paid for his time.  She couldn’t refuse to pay him any more than her own employer could refuse to pay her.  Nor could she force others to pay piles of money for her.  At their insistence, she dug into her budget, even into the emergency fund, and paid the $100.


(There’s a lesson here about how all the government plans and free money in the world cannot fix human problems when it comes to health care or finances, which politicians should learn, but we’ll leave that for another day…)


Changing Attitudes…From Homeless to Hopeful

Even after the doctor visit, Lisa began to accrue some modest savings in her emergency fund.  She also began accruing money towards a new place to live.  At three months, she could see that she was slowly saving money.


But then, a month or two later, she came home sobbing (yes, sobbing): her car had broken down.  My father took her to his mechanic, and they told her it would be $500 to keep her car on the road.  Her maintenance fund had less than $100.


She had no idea how she would ever pay for it, or where the money would come from.  Lisa felt defeated and thought her plans were done.  (She knew my parents wouldn’t lend her $500.)


“But Lisa, that sounds like an emergency,” my father said.  “This is why you have an emergency fund.”  Her face changed, and she agreed.  They gathered the money and paid for the repair.


Afterwards, she began sobbing more intensely: “I’ve never had the money to pay for a car repair.”  She told my parents that she would borrow money, beg friends to help her, or obtain personal loans to pay for repairs.  She said it was the first time in decades that she had money for a repair.  She literally couldn’t believe that she had money.


After that, she gained intensity, and by six months, she was fully invested: she would sit down with my father and actually work more to add to her savings.  She would even offer her own limited fun money for her down payment fund instead.  She became eager to find a place to live.


At the same time, her relationships with friends and family improved: Lisa no longer came to them asking or begging for things, and she continued working through some of the attitudes and issues that were causing her both financial problems and relationship problems.  She began having more spring in her step and looking forward to her future.


A Home for the Homeless

Lisa and my father made a plan, and well before the year was up, they began shopping: she would buy a trailer and move into a trailer park.  It may not be fancy, but when you have no roof of your own, it’s a cheap and effective option.


from homeless to financial stability

There’s no place like home.


My father joined her and helped her pick a suitable and affordable one that she preferred.  (He didn’t want her to buy something with a leaky roof or poor construction: that wouldn’t help anyone.)  My parents decided to chip in all the rent money she had paid that year, even though she had enough to buy a trailer on her own.  She wisely used that money to buy a nicer trailer and save more for her down payment/rent.


Before long, they found the one, a trailer that had barely been used; I visited it with them.  They negotiated for it, bought it, delivered it to my parents’ house, and she began moving in her things.  They found a place that was both safe and close to her workplace, and she arranged for a start date.


As Lisa’s year ended, my father gave Lisa her envelopes, including her emergency fund, and we all bid her well on her new adventure.  My father, unfortunately, became increasingly unwell (he had chronic problems).  At the hospital, he smiled on his deathbed as he learned that Lisa had moved into her trailer.


The Importance of Boundaries

I can’t recommend that you take in a homeless person, especially a stranger, but the one thing that made it all work was boundaries.  My parents placed boundaries with Lisa, knew their limits, and would kindly but firmly continue enforcing those boundaries.


Rather than enable Lisa, they confronted her about her overspending.  They insisted she do something about it, or move on.  Rather than feed her for free, they allowed her to take care of her own meals and remain independent.  Rather than give her money, they helped her use her own money effectively.  That, in turn, encouraged her to go and make more eventually.  They insisted that she live peaceably with others (no ambulances!) and encouraged her to take care of herself.


Giving her money would have simply enabled her to continue making poor decisions.  Instead, she learned that she really could do this herself, without any help from anyone.  (There’s a lesson here for how we should approach giving to others in need.)

from homeless to financial stability

We also learned from her: being homeless often means being spiritually poor, emotionally poor, and relationally poor as well.  More so than we knew.  So my parents had to have great boundaries to avoid being swept into poverty themselves.


Boundaries are important in all areas of life, and nowhere more than when you’re helping someone who struggles with them.  (If you want more on boundaries, there’s an excellent book on the subject: Boundaries.)


How did things fare after Lisa left and was on her own, though?  That’s the best part.


A Life-Changing Success

Not every story ends happily: we had no contact from Lisa again for more than a year.  We wondered whether she had jumped back into those old, well-worn habits and buried herself in debt again.


But eventually, my mother ran into her – it’s a small town – and Lisa ran up and hugged her.  She told my mother how much she appreciated my father.  “I would have never made it if it wasn’t for David.”


She still has an emergency fund, still saves, and still uses my father’s lessons on finances.  Lisa shared eagerly with my mom how she was doing.  She lives in the same trailer and has money saved to do the things she wants to do now.  She said that her time with my parents had transformed her entire perspective on money.  Now, she hates spending because it depletes her savings, and her savings allows her to be independent.


from homeless to financial stability

Think more Hyundai than Infinity, but you get the idea…


We ran into Lisa again more recently, now several years since her stay.  She showed us pictures of an almost-new car which she recently purchased (mostly with cash!).  She is already saving up for her next place to live, but this time, she has a plan…


Have you helped someone in dire financial need?  How did it work out?  Or, do you have a personal rags-to-riches story?


*Although appropriate here, homeless, the word, is a misnomer.  Researchers refer to the problem we call homelessness as “chronic vagrancy.”  Research reveals that a high percentage of “homeless” people actually have reliable places to sleep.  Many have apartments.  But we see “street people” or beggars and think of them as homeless.  The term “homeless” became politically popular and has stuck ever since.  Chronic vagrants may appear unkempt or beg for money (and some do actually lack a reliable “home”), but what sets them apart as a group is that many eschew societal norms regarding public spaces: they will sleep in public, beg for money (often before taking a job), urinate in public, and so on.  Thus, researchers refer to the group we think of as “homeless” instead as chronic vagrants; they are characterized by a chronic refusal to obey societal norms.  Truly homeless people are a much smaller group.

Mustard Seed Money

Welcome to the website. A mustard seed is a very small seed but astonishingly grows very large over time. My hope is that through your financial journey that your small investment in time, money and faith will grow beyond anything that you could ever imagine.


  1. Rob, thanks for sharing this post from Mr. FWP. Truly inspiring stuff. Mr. FWP, clearly your father was an amazing man. Now, you’re imparting his wisdom to the other “Lisas” of the world. Talk about sowing a seed. A very moving story. God bless.

  2. Great story Mr. FWP. I think that your parent did a great thing by taking in Lisa and helping her. I love the concept of setting boundaries and the insistence that Lisa must make to choice to live within her means or be gone.

    Your father’s teaching method is like this famous proverb that I subscribe to: “give a person a fish, you feed that person for a day. Teach that person how to fish, you feed that person for life.”
    Leo T. Ly @ recently posted…Basic Investment ConceptsMy Profile

  3. Thanks for the moving story Mr. FWP. I really admire your Dad for help out someone like that.

    “Giving her money would have simply enabled her to continue making poor decisions. ”

    Yep, it’s like giving crack to a crack-addict. Not a good idea. I have a relative who is not homeless but she hasn’t saved any money for retirement even though she has a high-paying job. I have a feeling she will arrive at our doorstep when she can no longer work and I will be forced to take over her finances and try to teach her like your Dad did. I just hope I can be as patient as your Dad.
    Mr. Freaky Frugal recently posted…To budget or not to budget?My Profile

    • Thank you, Mr. Freaky Frugal. I’m sorry about that situation with your relative; I really pray it goes well. This story talks about the good that happened, but as you know, it’s tough actually doing it. At the time, you have no idea it’ll turn out well. It could be a disaster, or get more complicated. We’ve been fortunate: I’ve been happily impressed with how well Lisa continues to do, years after any input from anyone about finances. It’s like a gift that keeps on giving. So at least there’s that hope: if it works out well, it can work out *really* well! I hope you’re able to work through that situation effectively!
      Mr. FWP recently posted…From Homeless to Hopeful in One YearMy Profile

    • Thank you, Mrs. Picky Pincher! Yes, you have a great point there: this only happened because my parents already knew her and had a relationship with her (spanning decades, in fact). They also had a mutual friend who was aware of the current situation and who they spoke to before they did it, too. They *weren’t* concerned she would steal from them, for instance. It would be a very different situation if the person were a stranger. And indeed, attitudes are absolutely key.
      Mr. FWP recently posted…From Homeless to Hopeful in One YearMy Profile

  4. I love this story. It is one thing to throw money at a problem or a non-profit and say that you are helping. It is a completely different thing to take someone in like your parents, educate them, and work with them each month to make them a better person. This is a story that we could all learn from and hope that one day I can make this kind of an impact on someone.

    Thanks for the read.

    Dividend Diplomats recently posted…Dividend Investing to Take Back ControlMy Profile

    • Thank you, Bert. And me too! I was honored simply to observe it. You’re dead on, that it took a lot of effort and patience over a long period of time. And it’s easy to forget, but we all had no idea how it would go from the beginning. It’s a great story now, but when it started, we didn’t know whether Lisa would continue on or whether my parents would have to have more hard conversations with her, or eventually just send her on her way. Thankfully, she responded well, took responsibility, and is now doing even better than before.

      You are just dead on about that. People don’t just have financial problems: they have spiritual, emotional, and other issues; they are whole people. Those other problems often need to be considered and addressed just as much or more as the one problem we see (in this case, a financial one). You wouldn’t just hand an alcoholic some liver pills and tell him he’ll be fine, for instance; it may take some hard conversations and more serious intervention. And doing that work is difficult and complicated – but very rewarding…
      Mr. FWP recently posted…From Homeless to Hopeful in One YearMy Profile

  5. WOW. Your parents are truly incredible and selfless people. From personal experience, VERY few people would stick out their neck for someone else to that degree, even a family friend – especially if they aren’t accountable in their behavior, and haven’t shown that they’re willing to drastically change.

    I’ve struggled myself (and still do) with the whole ‘creating boundaries’ issue when helping others, so this is very helpful. It’s far too easy to confuse ‘helping’ with ‘enabling’.
    Ava recently posted…Hell Yeah We Keep Our Money Separate When Married!My Profile

    • Thank you, Ava! That is incredibly kind of you. I didn’t know whether they would take it on, and they thought about hard before they did.

      Yes, that’s very true. It’s often hard to know where/when that line is, too. In our personal life, we draw upon the wisdom and counsel of others to help us see better where that line is, and it’s still hard sometimes.
      Mr. FWP recently posted…From Homeless to Hopeful in One YearMy Profile

  6. That’s a great story. Thanks for sharing. We have a big homeless problem here in Portland. It’s a tough situation to be in. Seems like a downward spiral that’s really hard to get out of. You need the kind of help your parents gave.

    • Thank you, Joe! You know, I recently heard about that through friends who moved away in part because of the problem. It is a really difficult situation that requires significant intervention. Sadly, many homeless folks also suffer from mental or substance abuse problems. (Lisa wasn’t in either group, thankfully.) There are a few non-profits in certain places that are able to help homeless people transition somewhat effectively, but not many, I think; it’s difficult work.
      Mr. FWP recently posted…From Homeless to Hopeful in One YearMy Profile

  7. I’m not surprised at the huge list of comments here. What a sweet story of tough love changing a life. I think your dad would be proud of your helping others through this post as he helped that lady. It takes courage to offer your hand to someone in need, once they grab it you really don’t know where that might lead. So many of us are afraid of becoming entangled in a messy situation but your dad did it with grace and firmness. I hope some of us are inspired to step outside our comfortable lives and help others like that.

    • Thank you, Steveark! That’s a profound compliment. I very much agree, and the longer I go on in life, the more I realize how great of a father he was and what I gift I had. That has been the story of his entire life, from helping raise another man’s kids, being an excellent father to me, all the way through to this story.
      Mr. FWP recently posted…From Homeless to Hopeful in One YearMy Profile

  8. That was a great story. I feel best when I am trying to help other people. It is amazing what can happen when you give someone the resources to succeed. Many of the homeless who live near me seem to suffer from severe mental illness. It is heartwarming to read about finding someone who was able to do for themselves once they were taught how to.

  9. You equate Lisa’s problems to addiction: “You wouldn’t just hand an alcoholic some liver pills and tell him he’ll be fine, for instance; it may take some hard conversations and more serious intervention.” One of the other comments likened it to crack addiction. I agree that people who spend more than they make are usually coping with some issue very much like an alcoholic copes with his/her problems by drinking.
    I’m not an expert but I have had some experience in these areas. Most addicts relapse. The fact that Lisa didn’t/hasn’t is unusual.
    Trying to treat an addict on a one-on-one basis like your father did usually doesn’t end well. Interacting with addicts is the fastest way to lose your faith in humanity. It worked out for your father but frankly I think you are doing a disservice by posting this story. You are posting the exception not the rule. At least you caution anyone from trying this but that seems lost on the readers who have commented. If you haven’t been deceived/taken advantage of by an addict, you can’t really relate.
    Speaking for myself, I would never have taken in Lisa. She was a liar and she had no compunction of not paying her debts which is a form of sociopathy. As I mentioned, the odds of success were small. To put yourself in a vulnerable state for an addict is more foolish than brave…regardless of the outcome

    • Dan, thanks for your comment. I actually agree with you: I made a mistake analogizing to an addict. I have, sadly, personal experience with both situations before, and addiction is a different beast. You’re exactly right; I could have picked a better analogy. And you’re dead on about addiction and the problems; I’ve had the unpleasant experience of walking hand-in-hand with very close friends who lived with/had close relatives who were addicts. It’s horrible. This situation wasn’t an addiction.

      Totally understand that you wouldn’t have taken her in. It’s hard after dealing with an addict, and if there were one in the family, I don’t know that my parents would have taken her in either afterwards; we’ve seen firsthand the devastation that that involves.

      With all of that said, yes, Lisa struggled with honesty issues, although I have yet to meet a single human being on earth who doesn’t…to me, the question is one of degree. I won’t understate how difficult the problem was – it was a challenge – though at the same time, I at least wouldn’t go so far as to call it sociopathy. Entitlement, jealousy, some deception, though: yes, there was all of that. It wasn’t an easy situation, and they went into it only after getting input on it.

      In the end, I agree with you about a lot: taking someone in is something to be careful about – it’s your home and family, after all – that requires a lot of wisdom and discretion before considering. My hope is that nobody came away with the idea that this should be generalized, rather than approached with wisdom and discretion. Personally, I wouldn’t go so far as to say that all overspenders are like addicts (God knows I’ve worked with lots of overspenders – including myself, at a prior time!); I think of it more like overeating, which happens on a sliding scale. People can become addicted to food, but having an a donut you shouldn’t may be overeating rather than all-out addiction; discernment is required (and sometimes it’s fuzzy, and sometimes folks disagree).

      You also raised a valid point about Lisa being less common as far as homelessness goes. I and other commenters noted that many homeless suffer from mental health issues and substance abuse problems. My understanding is that up to 70-80% of what folks call “homeless” people suffer from one or the other or both. In other words, the data backs you up – and I’m right with you that that point needs to be emphasized. I hope that’s made clear, especially now! Thank you for the valuable feedback!
      Mr. FWP recently posted…From Homeless to Hopeful in One YearMy Profile

      • You noted that Lisa was living in her car and no family would help her. That says a lot of her previous behavior. Her family would prefer her to live in her car than help her. On a sliding scale of addiction, that is near the bottom. When an addict exhausts all the goodwill of family & friends, they are close to rock bottom. She was able to hold a job (even work overtime) but that used to be called a functional addict.
        Her behavior with the overtime pay is also telling. Addicts are always pushing boundaries so they can know what they can get away with. What did she think would happen when she went out every weekend with it being budgeted for? No one would notice? Either she thought your father was stupid (unlikely IMO) or she was hoping he would let is slide.
        Lisa (based on your description) seemed closer to be an addict than a run-of-the-mill consumer debtor.

        • I suppose it would help to be clearer (but am careful about sharing personal details): suffice it to say she didn’t have much/hardly any family at all around. Your point is well taken about letting things slide. Though I think we may disagree on the end re: addiction, even though I agree it’s behavior to be careful about. If a substance had been involved, it would be a different situation. You’re right on to point out to people how dangerous that is.
          Mr. FWP recently posted…From Homeless to Hopeful in One YearMy Profile

  10. Your parents are definitely saints! I don’t think I would have done 12% of what your parents did. I would have throw in the towel and given up on Lisa – I did give up on my friend because she was impossible to get right. But my friend was long distance, very hard to control for that because I probably would have never known she’s hiding extra money or anything.
    Lily @ The Frugal Gene recently posted…3 Profound Things I Wish I Knew Before AdulthoodMy Profile

  11. Thanks, Lily! Yeah. It’s tough to do something like that at a distance. In fact, my parents weren’t aware either for a bit. And I don’t think Lisa thought of it as hiding things, but you and I and others would. It’s just giving up that last little bit of control over something can be hard, especially when we struggle with it, but to her credit, she did it.
    Mr. FWP recently posted…From Homeless to Hopeful in One YearMy Profile

  12. Mr. FWP,
    That was an inspiring story. I cannot think of a better way for your family to have handled the situation. No wonder your father smiled on his deathbed! I think he knew she was on the right path. I believe knowing that you’ve made positive impacts on others is reward enough. Thank you for sharing!

    You couldn’t have asked for a better guest post than that. That was a grand slam!

  13. Very interesting story though I vehemently disagree with what I perceive to be your conception of health and welfare entitlement programs. Glad that things ended well.

  14. Wow this is such a great story! I applaud your parents for working so hard with her but she is forever grateful to them. Thank you for sharing this feel good story, it was a nice read for me to start the day 🙂

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