Finances & Money

My Side Job Teaching Criminals

side job, teaching criminals, side hustle
(This is a guest post by blogger Natalie who teaches on the side for some extra money. You can find her blog at

There are some things that we plan thoroughly for and expect. You do all the appropriate research and develop a plan of action to execute. Then there are things that just kind of happen. There may be no rhyme or reason for it, but it happens and its quite funny when it does.

The same can be said for jobs. Such a thing happened to me not to long ago. In addition to my day job, I teach criminals. Well, that may be putting it too dramatically. I teach people who have been legally mandated to take certain classes in order to increase better decision-making skills.

How I Got Started

I have to go to networking events for work every week to get the word out of our services. At one of these networking events, I met a man who owns a center teaching education classes for people who have gotten in trouble with the law. This includes everything from anger management, drug awareness, stress management, and more. If you are arrested and depending on your charge, the court could mandate you to take certain classes in order to complete your probation.

After a while of him explaining what he did and finding out my psychology background, we agreed for me to help him teach some of his classes. I was to start the following week.

My First Day

I was terrified my first day of class. I was sure that the students would see how my fingers trembled when I stood in front of them. Luckily, my lesson plans that I prepared were right in front of me and it helped me stay focused.

How did I start? I started off quite simply by telling a funny story to break the ice. Once that was done, we played a game for me to learn everyone’s name-which really helped. Once we all got comfortable with one another, the class really started to flow.

I realized I liked what I was doing and getting to know the students. It made teaching the material so much easier for myself and the students.

What I Do

I prepare my own material for the most part. The whole point of the classes is to teach the students how to make better decisions making skills so they don’t make the same mistakes again.

I usually focus the teaching also around a central theme that helps with the decision-making process. Examples of themes include Triumph, Triggers, Determination, and Courage. Students usually fill out worksheets or watch the occasional movie that correlates with the theme.

We also do a lot of discussion on everything from why the student got there to better alternatives to engaging in risky behavior. The discussion are my favorite part because you get to really know the student and help give them ways to improve their lives.

What I Don’t Do

When I tell me friends what I do, they have this idea that I am dealing with hardened criminals who come in with handcuffs straight from prison. This is simply not the case.

Most of these students were caught making a bad decision and are now trying to better themselves.  Most of them are just normal, everyday people seeking to fulfill a requirement. I don’t provide individual counseling as I am not a licensed counselor. I simply provide teaching services and fill out the appropriate paperwork for the courts.

What I Get Paid

I usually get anywhere from $15-25/hour for my teaching services depending on the class. This does not include the preparation of the class material or the worksheets.

This additional stream of income has been monumental in helping to pay down debt and build savings. I am thankful for this little side gig and my bank account is equally as appreciated.

This job is certainly not easy and its not for the faint of heart. I have learned to be more assertive as you have to keep a room full of people on task. You need to be able to be prepared and knowledgeable in what you are teaching as students will always expect you to know the answers.

However, it is fun to help people in making better decisions and gain control over their lives. It is rewarding work despite its drawbacks and pitfalls but the same is true with any job.

Have you ever considered teaching or taught? What was your experience? Was it something you enjoyed?

Natalie is writer, instructor, marketer and a full time debt destroyer at her PF blog. Read more about her story at!

About the author

Clever Dude

1 Comment

  • I have taught formal classes of toddlers, preschoolers, middle school drama, and a freshman programming course for engineers.

    In an individual setting, I’ve tutored kids in reading and also taught a 5-year-old kid with Down syndrome all one summer in preparation for Kindergarten and brought him from being functionally 18 months old in all subjects to reading at an end-of-Kindergarten level and able to do one-to-one counting and recognize shapes and colors and say the Pledge, as well as write a few letters. I also bowel trained him. That was exactly as fun as it sounds. I had achieved every objective on his IEP for the next year with him by halfway through the second week.

    I am a homeschooler, too. I’m just beginning to teach my 4-year-old, and my 10-year-old is reading at at least a 10th grade level and his finishing his honors geometry course this summer and his second high school level science course. 🙂 He takes two languages and plays two instruments, too!

    Kids can do a lot more than we give them credit for, in the right setting!

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