When reflecting on one’s life, there’s very few people who carry the weight, power, and overall authority to make one’s life truly miserable. In no specific order, that would be:

  • Spouses – what you come home to.
  • Bosses – what you go to work to, to pay for the home you go to.
  • Probation Officers – what you deal with in order to go home.

* With an honorable mention going to Mothers.

Regardless, this exclusive group has the ability to make life pure hell. Obviously, you always want to be in the good graces of the aforementioned parties, however, and for purposes related to this article, we are here to focus on you, the Probationer, and the relationship with your fellow Probation Officer.

More specifically, how does one go about strengthening that relationship, and what you can do to set yourself apart from the other bozos, in order to be in the good graces of this person. First and foremost, let’s answer the question.

Can you really make a probation officer like you?

Yes, it is very much possible, but this is heavily dependent on the probationer. For this relationship to succeed, one must be polite, respectful, and above all else, keep clear of trouble. Take that, and couple it with the ability to create the least number of headaches and overall work for your assigned officer, and one will find themselves gaining significant favor and building rapport.

The Probation Officer is the court-appointed eyes and ears, there to supervise your compliance with the terms and conditions of your program. They are NOT your friend and are there to do a job.

In a nutshell, this person (P.O.) holds your freedom in their hands. One bad write-up or word from them can mess you up good. Obviously, with that kind of power, one could easily let that go to their head.

Now before we go any further, are there going to be some who habitually abuse that authority and get off on it? Of course, but hey, that is life, and it is rather common everywhere you look.

Fact: There are going to be people in life who only feel better about themselves at the expense of others vulnerability. Sad, but true. That could also be said about the others in the aforementioned group we discussed earlier (spouses, bosses, mothers) – sad, but true.

No one can make you feel inferior without your consent.

Eleanor Roosevelt

Moving on, the relationship of a Probation Officer who has been placed in your life beyond any measure of your control, is one of sweet and sour.

Sweet, in a sense that you are not locked up and are able to partake in many of life’s great pleasures and treasures. Sour, in a sense that you now have another person monitoring your whereabouts, not trusting you, and having to explain yourself over and over again.

One has to come to grips with this new reality and adapt rather fast. The sooner this is done, the smoother things may be for you in this hopefully short-term relationship.

*Also, you may want to read the article titled Can You Switch Your Probation Officer?

For now, it is party of two. Someone you have to check in with and plan your coming and goings. Someone looking over your shoulder and monitoring you ALL THE TIME. Nor are you able to break up with this person.

But fret not my legally troubled friend. Much like an eagerly anticipated divorce, this relationship is poised for a celebrated breakup at date certain. And when it does, this maybe you:

What is the role of a Probation Officer?

I once read that a probation officer is considered a tattletale for the court. One would have to agree with that statement, as a Probation Officer is assigned to be the court’s eyes and ears, and there to report all findings on you. They are also there to assist with the transition and adjustment process one goes through in their obligations to the court, but the main focal point is actually on the well-being of the public at large. Meaning, the importance is to protect everyone else from you.

Okay, so now you know what the common focus is on. Now you pair that with the many different personalities, nuances, world views, et cetera, and what you truly get is a mixed bag of interactions. Hence, many different experiences reported by individuals.

Some good, some bad, and some just meh. However, the common denominator in this equation is the fact that they are people just like you and me, although it may not always seem that way.

You’re not special cupcake. We all squat down to take a shit

Mike Cernovich from Danger & Play.

In respect to that statement, they are human beings dealing with real world issues, and are prisoner to their emotions like most people. That said, they have bosses and worry about their job like most people.

  • They have credit card debt like most people.
  • Their stomach gurgles every time they get hungry like most people.
  • And like most people, they definitely do not like to deal with drama.

The crucial mistake many individuals make is to buy into a belief that the officer is out to get them, and it is some sort of big conspiracy, not realizing that they are used to the bullshit and are conditioned to tune it all out.

Day in and out, Probation Officers have countless individuals who lie to them, despise them, draw weapons on them, attack them, unleash their dogs on them, et cetera, et cetera.

Now some a-hole (hopefully not you) waltzes into their office and tells them that… you’re not gonna have any problems with me officer. I won’t get into any trouble, don’t worry. Trust me. Oh by the way, only reason I was late getting here today was cuz of ……..

Imagine that scenario if you would. What do you think goes through the mind of an officer when this all happens?

Now imagine what goes through an officer’s mind when an individual shows up on time (even early), dressed smart, with all paperwork filled out, and are mindful and respectful of other people’s times, schedules, and perceptions.

Maybe this person even chooses their words a little more carefully in how they address someone. In other words, they have it all together.

How do you make your Probation Officer like you?

So contrary to the name of this article, Probation Officers are not going to like you. At least they are not supposed to, as they cannot get close to you. This is part of the job, and they are trained for this mentality. The purpose then, is to make a paradigm shift and make your probation officer like you as much as possible, when they really cannot like you.

The Exception to the Rule

The best approach to handle this type of situation is doing the opposite of what everyone else does. Everyone tries to combat and oppose the officer. People get defensive and push back. They get hostile when forced into a situation as such, as this whole experience is not voluntary.

You must adapt to the situation though. You do the opposite of running away from the fire and run into the fire. By going the opposite direction as everyone does, you separate yourself from the pack, and in a good way. You also establish yourself as “The Exception to the Rule”.

The Exception to the Rule is not the norm. They are somebody different. They are rare and special creatures who rise above the rest and are recognized as such. They are not like others, and as a result, do not get treated the same.

That said, you (The Exception) are now to move forward in your relationship with said Probation Officer (The Rule) in a business capacity. Consider yourselves business partners in a purposeful business transaction. More specifically, what they call an arm’s length business transaction.


In business, an arm’s length transaction is a deal between two unrelated, informed parties looking out for their own self-interest, yet working together for a favorable outcome.

This is not a friend. This is not family. This is business. With that in mind, be a good business partner and do good business.

When you do not do right by business partners, by not following through on what you said you were going to do, you sabotage your business, and yourself. Case in point, the unraveling of a business relationship in the movie Scarface was due to bad business…

I told you a long time ago, not to f*** me…. Alejandro Sosa disciplines Tony Scarface Montana, due to his bad business behavior and decisions.

Okay, so how do we do good business? Ready for it? It could be summed up in very few words…MINIMIZE THE AMOUNT OF BULLSHIT PROBATION OFFICERS HAVE TO DEAL WITH BECAUSE OF YOU.

Now I know what you want to say. Thanks for the breakthrough a-hole. Really great stuff you write. But one must also get into the head, and understand the fact that officers have multiple cases on an already overloaded work schedule, with you my friend being only but one of them.

Don not be high maintenance. You want to strive for and be the easy one. The one that does not require a lot of aggravation or a source of stress for the officer.

Make it so unbelievably easy for them to locate and communicate with you at all times. It will blow their mind and instill tremendous trust.


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  • Do the opposite of what most people do (be The Exception).
  • Do not f*** them over (Bad Business).
  • Do not create more work for them (Bullshit).

Again, like most people in this world, they have a boss and someone who supervises them. Do not put them in a compromising position or make them look bad with their superior. That is not good for them – nor for you.

As well, do not force their hand. Do not oversell them on whatever you are selling. They have heard it all. Remember, they already think you are lying due to being a criminal. Be real… Be raw… Be honest… Be sincere.

Tell them that you are scared, and you are worried about the future and how things are playing out for you, all without going into too much detail about issues and problems.

Build trust. Don’t just tell them about your good behavior, demonstrate it to them. They’re always observing this. Unfortunately, it is not something that occurs immediately, but built over time (good business). Consistency is key.

Give them reasons to put trust and faith that you will follow through on your word. Don’t poop on yourself, (and them) by sabotaging the relationship.

You ideally want the ability to gain favor and good will with someone to help you in a situation you probably had a hand in creating.

You may also want to check out this post right here talking about screwing up and what happens after that

Do not follow the pack. Just because every a-hole is late for their appointment, most would go on to say well, I can be late too. Wrong, you do not want to do that. Be different by being punctual. Believe me, it’s noticed, and you should pretend that your life depends on it. Which, in reality it actually kind of does.

Do not be like the majority of idiots who stroll into their office. Be you (The Exception to the Rule). At the end of the day, it will work in your favor… for you.



Okay, so this is where it all starts, and probably is the most difficult to fix. It basically makes or breaks you. So much could be said about the power of positive thinking and the correct mindset, but this will definitely factor into your whole experience with not only probation, but life as you know it.

The mind is its own place, and in itself, can make a Heaven of Hell, and a Hell of Heaven.

John Milton

Does it suck to be at the mercy of someone and have them hold this power over you – sure, but the quicker you get over yourself, readjust and play the game, the faster you can move on with your life.

Focus your energy and attention on what the Probation Officer needs from you in order to achieve the desired outcome you want. Please note: This is not kissing ass, nor is it being deceitful. This is playing the game. Playing the game to your advantage, for your best interest.

You should also understand how to differentiate between being deceitful and selfish versus being smart and committed to a positive conclusion by way of working well with others. What’s the saying, first you go along, then you get along. Adjust your attitude and play the game. Anything less is foolish.


Numerous directions to go on this, but for the sake of brevity, we’ll touch on the golden rule. Please dress appropriately to be taken seriously.

A lot of the way that you come across is by way of how you dress. It’s indicative of what’s in store for the officer, and the opinion they’re forming of you. If you’re lazy and don’t give a crap, how do you think your file is going to be handled?

In addition, this situation is very transferable in terms of what one goes through in the job screening process. Gentlemen should not dress sloppy, or as if you just rolled out of bed. Pull up your pants. Ladies too, don’t dress sloppy, or as if you just rolled out of bed. Again, pull up your pants.

You’re going to a business meeting. Act accordingly, and dress as such. Part of the acceptance to being taken seriously is to look and act professional. On that note, do not make advances or come onto your officer. Inappropriate and may get you violated. Besides, they may not be so flattered as you’re not their type.


Now this goes without saying, but be where you say you’ll be, when you say you’ll be there. Keep your word. Keep appointments. Keep time.

What is this you say? Punctuality is not your strong suit, and that you’re a free spirit that likes to go with the flow. Well time to get it together snowflake.

Don’t be the one with the drama and stories. You know them. Always an excuse, armed with a powerful victim mentality. Hopefully that is not you. Do not be late. You could lose your job, or worse your freedom.

Just as bad as going M.I.A. and not showing up, is the need for some individuals to be a constant pain in the ass by calling and trying to change appointments. Even worse, psycho dialing them. Not smart. There is a fine line between someone who is a pest with their erratic lifestyle and tendencies, and the next thing on our list.


This is a good self-serving life skill that’s in your best interest to exercise at all times with the other party (Probation Officer). In the age we live in, there’s absolutely no excuse to not have good communication, as it’s all out there.

There are so many ways to contact and connect with others. Please also be mindful and ultra-careful of your social media postings, rants, and presence. It can work against you in life, and once again in your dealings with said Probation Officers.


Last but not least, research your problems. Study laws. Know your rights. This is your situation were talking about and no one is going to do this for you, unless you have an attorney on retainer.

Even then, most including myself, did not have the means to afford this great luxury every time your ass gets into trouble. Either way, really get to understand the legal system and how it operates for you and against you. Not for ulterior motives, but to empower you in your situation, so you do not feel completely helpless.

Find answers to questions you may have. Use the internet for something other than the usual garbage. If you’re reading this, then you have access to all the answers in the world my friend.

Keep accurate records and accounting of not only whereabouts, but phone calls. Keep your receipts. Have witnesses. Just get into the habit of being meticulous, in order to cover all bases.

Do not bury your head in the sand and assume all will be well, because that is when you screw it up. This is now the part where I break away and address someone’s question of….

But all this seems like a lot of work. I’ve never kept receipts. Do I really have to do all these things?

…. of course not. It is free will. If freedom is that important to you my friend, you will find the way. If not, f*** it. But by not giving a f***, it’ll probably f*** you.

At the end of the day, as much as some do not want to admit to the notion, you want need this person (Probation Officer) placed in your life to be on your side and cooperating with you.

Ideally, you would like the person sitting across from you to view you as a person, trying to understand the circumstances that contributed to making the choices you made, thus putting you in the position you currently find yourself in. Sadly, this does not always occur. Be that as it may, your Probation Officer is not your enemy.

They are not your friend either.

They are there to do a job (their business).

You are there to do a job (your business).

Do some good business together (arm’s length).

Make this happen by you (the Probationer) being the Exception to the Rule.

The Educated Felon