A funny thing happened on my way to becoming a multi-million-dollar real estate entrepreneur. It never happened. Yup, I decided to get a little greedy and made a detour on the felony highway, thus prematurely ending my real estate career in brutal fashion. Which now that I’m writing about it, doesn’t seem that funny at all. Ugh, and so goes life.

Be that as it may, I did happen to learn a few things when I was negotiating with banks for the customers who could not pay their mortgage. In order for the lender to offer some form of leniency to the borrower, they’d require a collection of financial documents showcasing the reasons as to why they didn’t have the means to pay.

What is a Hardship Letter?

One of the key centerpieces of that financial package was something called a “hardship letter”. The point of this letter was to describe the “hardship” being experienced by the individual (borrower), thus the reasoning behind why they could not afford to pay the bank at this moment in time. All this in hopes that the lender would somehow show some act of mercy.

I dealt with many different banks, and more often than not they were extremely heartless. Almost robotic (no emotion) in their response. People were getting thrown out of homes. There were kids involved. And I pleaded with them, but it didn’t matter. The bank wanted their money.

Ultimately though, I found myself coaching many people on how and what to say, in order to gain some leverage in the matter. And what I found was these letters could be universally used for many different stressful and despairing moments in life, whether it be monetary (mortgages, credit cards, auto loans), and even legal (court costs, probation fees, restitution).

One of the things I would stress is for the person to understand you are not trying to gain sympathy or pity from this letter. That is not how business works. It is not how the courts work either, but there are similar patterns in how you talk to both where applicable.

Take heed, as this is not merely a tip I’m passing along to you, but a prescription to help remedy a tough situation you may find yourself in that is temporary. It all seems to be trending in the wrong direction as we’re facing one of the worst labor markets since the great depression.

Historically high unemployment (due in part thanks to a raging worldwide pandemic) and then you couple that with a felony (even a misdemeanor), and you could easily find yourself in a real predicament. Face it, the times we’re living in warrants (bad word) the need in understanding how to put one of these letters together, and then have them within arms reach to use at your discretion.

Now it’s not exactly rocket science, but there are certain things you should know in order to make it an easier process when creating one.




So one of the things I’d hear time and again from customers was but I’m not a writer. That they didn’t know what to say, and they couldn’t do it. Yes, you can. Everybody has a story. Everybody has a hardship. Everyone.

How do you create the perfect hardship letter?

First step would be to make things easy on yourself and stick to the point of doing all this, which by definition would be:

You are taking all the bad shit that is happening in your life, and formulating it in a clear, professional manner in order to convey that message inside someone’s head (and heart). That is what good communication is.

On that note, so many people I know are so dramatic. Well drama queen, NOW YOU PROVE IT. A few points to know when crafting these types of letters would be:

  • One page. Nevermore.

Doesn’t matter if you’re a hunchback one-legged paraplegic with an eating disorder whose child was just abducted. Yes, that does suck, but still though, keep it to a clean one pager and not a graphic novel of your shitty life.

  • Presentation

You need your letter to look visually appealing to the eye. You can have the most gut wrenching, terrible ordeal you’re facing, but nobody reading it can focus and pay attention because they’re distracted by the clutter.

My handwriting looks like a three year old wrote it with his toes. It’s truly horrific. Thank god for technology, so I’d type the thing, whether on a computer, or even a type writer. Does anybody even remember typewriter? I guess I just aged myself. The point is you want to avoid any distractions from the message you have to deliver.

As weird as it sounds, this isn’t about you. This is a letter about you for someone else to understand. And in order for that to happen, it has to be legible, with correct spelling and grammar. Then you can focus on the next step.

  • Do not ramble (as tempting as it may be). Just the facts.

Remember that show Dragnet from back in the day? You don’t, well I guess I just aged myself again by talking about it. Anyways, there was a famous line in there where they’d say, you guessed it, just the facts, maam. Why did they say this: Cause people are really emotional and things get misconstrued in the heat of the moment. We tend to give our opinion a lot.

We get tired, frustrated, and angry at everything that happens to us at that precise moment, that we tend to overstate things and exaggerate a bit. Keep to what is true and fact.

My cousin went to the emergency room last night and I had to accompany her because I was the only family member available to drive her there – is much better than….


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The topper to my shitty day was I had to drive my cusin to the E. R because that side of family is worthless an didn’t want to help.

Notice the misspellings and hastily put together sentence. Not to mention, you come off looking bad and overly emotional. Don’t portray the victim, even if you are one. There’s always a line to tote. Remember the primary goal for this letter to accomplish is leniency, because they understand the situation you’re going through NOW due to providing them a letter. For them to understand you clearly, you must not be overly dramatic.

Disclaimer: What I’m about to share is an example of a hardship letter from someone who’s been through the ringer and back. It seems they’d found themselves in a predicament with the courts and needed some help to ease the financial burden they were facing.


To whom it may concern,

I’m writing this letter in respect to the difficult situation I currently find myself in, all while trying to meet my financial obligations in payments.

Due to ___________, my place of employment closed, thus losing my job. As a result, I’ve been applying and interviewing for something new, however, that’s a monumental task when contending with a felony that rears it’s ugly head on a background check.

I know things are difficult for many, but that aside I’ve also been taking care of my elderly parents, as my father had a stroke recently, so I’ve now also become their primary caretaker.

My credit is horrific, no one will lend me anything, and I live in a constant state of stress and worry. Despite all these challenges, I still make consistent, albeit small payments with anything I have in order to make the concerted effort to sincerely make good on my part. I say all this mind you, not to garner sympathy or in gaining favor, but to just convey to whomever it is that I’m genuinely doing the best I can with the little that I have at the moment.

I’ve never violated, or have had any issues during my time on community control, and/or probation. I’ve maintained employment during all these years, and have always communicated when I needed help. This being one of those times. I understand I’m not the victim in this situation, nor trying to portray one. I’m truly blessed and grateful for all I have, and am determined in resolving my situation in order to make right, God willing and through the assistance of the court.

Thank you so much in consideration, and God bless.

Your Name

Believe it or not this is my life and based on a true story. Or at least just a little excerpt from it that is. And for the people who’ve always said their life sucks and is terrible, bitching and complaining to others that you think you got it bad, my life is way worse – well it’s your time to shine cupcake. You’re up to bat.

And finally this key point:

  • Read it out loud after written.

Things get distorted and mis-communicated when read out loud. You will find yourself editing words and taking some out due to it not sounding right and flowing together. You want this to be a powerful statement about the person you are and what you’re experiencing. Not to be garbled up due to things getting lost in translation.

It is time to bare your soul, however you are not to come off as whiny, so this needs to be practiced. You’re asking for help – not sympathy. Not pity. Just some assistance. A lifeline to be thrown your way. And in order to do that with the powers that be, you have to scale back the words and make them digestible (simplified) in order to get your point across. Read it out loud after written, so it sounds good.

In closing things out, you want to make someone understand your pain. Why it is what it is. Why you find yourself in this situation, yet you want to remain upbeat and positive regardless. Getting back to my point of earlier in my real estate scenarios, I’d find myself telling people this was all for temporary.

I’d ask them what it was they wanted to happen from all of this. What was the outcome they were seeking. I mean, the lender was not going to go away. They wanted their money. Ultimately, you’d have to pay them. If you couldn’t give it to them at that moment in time, fret not. But you were going to need a long-term solution after getting through this tough period, and you’re trying to explain why. That’s what will give your letter direction, along with maybe your life.

Just to stress my golden rule of thumb in life.

Above all else, the worst possible thing you can do is nothing. Nothing requires no effort. Nothing is easy. Nothing gets you nothing. You have to open your mouth and ask for things in life, and that includes help. Please note, this is not begging.

There are some out there who will not allow their pride to write this letter. Don’t be foolish. Ask.

Will this letter single handedly change your life and rescue you – probably not. But it will do a pretty damn good job of giving you a helping hand in aiding to pull you out of the rathole you may be trying to climb out of. It is something to be valued and used with creditors, the government, the IRS, and others.

Armed with this baby, you can be superman and do a whole lot of ass-saving in this world. It’ll be the gift that keeps giving. So, practice getting good at it. And educate yourself on your situation, because nobody will do it for you. Stay well and out of trouble.

-The Educated Felon