7 Life Lessons I Learned from 5 Years of Probation - Erin's Inside Job

7 Life Lessons I Learned from 5 Years of Probation

After serving a 9 month sentence, I was released and immediately started 5 years of supervised probation. This week marks the end of those 5 years, so in reflection I'm sharing some of the life lessons I learned from 5 years of probation.

Tuesday of this week (May 10) marked 5 years since I was released from a 9 month incarceration. I was finally able to leave the detention center where I had spent almost a year of my life and work on rebuilding everything I had lost.

No idea what I’m talking about? Check out this post.

It was also the day that started several other components to my sentence, including community service, restitution, and 5 years of supervised probation. If, during any point during those 5 years, I was found in violation of that probation, either through a subsequent arrest or failed drug test, I would have to return to court to determine whether I should serve out the remainder of my sentence — 7 years in state prison.

For those of you unfamiliar with the court system (good for you!), all but 12 months of those 7 years were suspended, so I was sentenced to 12 months in jail but served only 9 due to good behavior (pat on back).

Probation is a tough thing. Not for people who are actually committed to turning their lives around, but for those who aren’t and for the probation officers who work there. If you are actively working on improving yourself and moving on from whatever crime(s) you committed, it’s more of a nuisance. There are frequent reporting visits, supervised drug tests where there are no doors on the stalls (woooooo), fees to pay for you to be supervised (??), no unapproved travel out of the state, and DEFINITELY no travel outside of the country (unless there’s an awesome officer who works to get you out for your honeymoon).

If I had stayed in Maryland for the entirety of my term, more than likely I would have been released early, but because I moved to a second county in MD, then VA, then Chicago, I was shuffled around between states and officers. Each new state meant I had to prove myself to a new person and since MD only had basic reports letting them know I was complying, they denied my (and two officer’s) requests for early termination.

I learned A LOT in these five years, and I can definitely say that some of those things came from my time in probation. In weekly thinking out loud fashion, here are some life lessons I learned from 5 years of probation:

1. Labels are harmful

On paper, I am a thieving criminal. Something got crossed when I moved to VA and suddenly my charges classified me as a felon even though they were misdemeanors in MD (note to self: make sure you’re not classified as a felon). This meant I had to give up a DNA sample and fingerprints as well. When I was released from jail and tried to pursue employment opportunities, I struck out for three months straight because all people were able to see were those words on a piece of paper.

It’s taught me the danger of labeling other people. Whether that be through stereotypes or a person’s life on a piece of paper, it’s never fair to the other person. Every person I know is a complex character and it’s important for me to give others the benefit of the doubt or actually get to know them before labeling them and writing them off.

2. Save everything

I can’t tell you how many times paperwork got messed up when moving states or even within one office. I made sure to save EVERYTHING related to probation, from copies of money orders to receipts. On several occasions I was asked for proof that I had paid my restitution (over $3000), and the only proof I had was one copy of all the money orders that were used.

I may be a little paranoid after this ordeal, but I make sure to save everything that I may need in the future until I’m sure that enough time has gone by before I can trash it. You can catch me on a new episode of Hoarders next week.

3. You won’t always get your way

99% of my travel requests were approved because I had proven that I wasn’t a flight risk and had a record of good behavior. Shortly after moving to Chicago, however, I had to cancel a trip to India because I was in a brand new state and hadn’t even been assigned a new officer yet. In fact, the man on the phone told me that “I was a criminal who was technically still in jail but lucky enough to be living outside its walls.” Thanks dude.

I learned that some things are just out of your control and you have to be able to make the best of them. It turned out to be a blessing in disguise because we were also closing on our condo during that same time and if we had been in India we wouldn’t have been able to get them all the documents they needed.

4. It’s hard not to judge

Even with all the judging that’s been done to me, it’s still hard to stay neutral sometimes. I would find myself constantly annoyed at the people who showed up to probation and behaved disrespectfully. I overheard phone conversations where people failed to show up, made excuses, or were having new arrest warrants issued. Some of my first thoughts were that these people had no desire to change and would remain in the system for who knows how long.

The truth is that I have no idea how willing these people are to change. Just like recovery, sometimes you don’t get it on the first try. It’s so difficult, but also so important, to try and support and encourage people to do the best they can. I have to constantly work on not judging people since I have no idea what they are going through in life.

5. Even if you do everything right, people still might not like you

My last day of reporting, I was waiting in the waiting room and was sitting Indian style on a bench since my legs were too short to reach the floor. Another officer came down, glared at me, and snapped for me to “put my feet on the floor.” It was one of the most disrespectful ways I’ve been treated and I was immediately filled with shame and rage. Even with a clean probation record and the respect I showed for others every time I reported, I was talked down to like a child.

Not everyone in this world is going to like you. I didn’t understand this concept until a few years ago, mainly because I was an obsessive people-pleaser who tried to find any way to make others happy. If someone didn’t like me, it meant I was doing a bad job and was a failure. It finally clicked that a) that behavior was absurd and b) with so many people in the world, you can’t get along with ALL of them. There are some personalities that I don’t mesh well with and that’s fine. Make some friends, keep them close, and go about your day.

6. Take responsibility for your behaviors

I learned this more when I was in jail, but every time I was faced with some facet of probation, it helped reinforce it. I learned that unless you take responsibility for your behaviors, you won’t be able to move past them.  For the longest time, I was a perpetual victim, pointing the finger and placing the blame on everyone else but myself. This left me feeling resentful, sorry for myself, and certainly not ready to move on from whatever or whoever I was blaming.

Every time I had to do something I didn’t like through probation, my first instinct would be to throw a tantrum and find a way to be angry at the system. After that accomplished nothing, I remembered that I was in this situation because I had betrayed trust, stolen A LOT, and put others at risk. All me. It had nothing to do with anyone else. As soon as I remembered that I was able to show up and work through each situation.

Related: Stop Playing The Victim and Learn To Succeed

7. There’s always an end

OMG — It may not seem like there will EVER be an end to a difficult situation, but time passes and so do life events. I honestly didn’t think it would be as big of a deal when I was released from probation, but it’s a wonderfully freeing feeling. No matter what you are going through, as long as you keep going forward, you’ll get out on the other side. It may be harder to trudge through and those steps may get smaller, but keep taking them and I promise there will be an end.


  • Have you gone through something that has taught you bigger lessons for life?

43 comments on “7 Life Lessons I Learned from 5 Years of Probation

    1. Hi, just came across your blog on the lessons learned from probation. I loved it! I myself was just released from probation due to good behavior and even had some of my civil rights restored by the governor. I served over 10 years in a really bad prison for bank robbery. All of which is now behind me. Your blog excited me because I am currently writing a book about the lessons I learned from my experiences in prison and on probation. Very similar to your piece on the lessons you learned. Just wanted to say that I admire your patience and efforts to pull through and take something positive from a situation that most only want to forget about. I know how difficult it is to be optimistic about experiencing unfair treatment at times, but you held it together and proved to have a great attitude and character traits! Have a nice day! Michael Guertin

  1. So happy for you! I have gone through horrific trauma, more then anyone I ever met, it changes you to the core of your being then teaches you.

  2. We’ve talked quite a bit about this in our lunch summits (we need another soon), and I know how frustrating this process has been for you. But I think of it kind of like me breaking my back: it has SUCKED and taken so many great life opportunities from us, but ultimately, we are better people, better teachers and mentors and coaches, and more thankful for the little things in life than so many others. There is a lot to be said for that.
    Susie @ SuzLyfe recently posted…Living with Anxiety Disorder: Beyond Your ControlMy Profile

    1. Totally. I don’t think I would have as much perspective and insight if it weren’t for everything that’s happened

  3. My stepdad was in jail for almost 2 years when I was in college for white collar crime stuff and I lived with my mom to make it easier on her and then I was there when he was released and on probation (he was actually released into a program that was more like the step before probation but not a halfway house or house arrest, if that makes sense. Someone came to our house each night to make sure he was home by 8 and took a breathalyzer and they worked with him to secure him a job.) So much of this resonated with me even though I was just a family member. I think most people immediately assume it’s an experience they will never have but the truth is shit happens and you just never know. The judging people is definitely tough – I went to visit him plenty times and I also went to his hearings and visits with his officer and it’s hard not to judge other people there. And the labels – they’re hard. Again, it was hard even for me as an outsider, explaining to people that my stepdad was in prison.
    Thank you for this post! It really made me remember some of the important things a tough moment in my life taught me.
    Morgan @ Morgan Manages Mommyhood recently posted…There Will Be TimesMy Profile

    1. Thanks for reading it and for sharing your own experience! I definitely never thought it would happen to me but you’re right sometimes we have no idea where life will take us!

  4. My eating disorder taught me a lot, but the biggest lesson was probably not to judge other people because you have no idea what they’re going through. I became a totally different person when I was sick, and did so many things that were out of character, but it was what the ED did to my brain and not really me. I became a lot more understanding when I got out of it, and I’d say a better person in general.
    Amanda @ .running with spoons. recently posted…unicorn snot, too close for comfort, and obsessions galore (ToL#182)My Profile

    1. Absolutely. I was also a totally different person when I was using and I try to remember that when dealing with other people day to day

  5. So happy for you! These are great lessons. I can relate so much to #5 & #6 – because I always tend to blame others for my own issues – even the most trivial things. It’s difficult for me to accept my (many) shortcomings and easy to play victim. Oddly, my (unexpected) pregnancy taught me a lot about life – mostly how the best things in my life tend to happen when I’m planning the opposite. I became pregnant right after (what I now know was) a lengthy period of depression and it helped heal my mind in many ways.
    Catherine @ foodiecology recently posted…Would You Change Your Personality If You Could?My Profile

    1. It’s definitely easier to shift the blame and I also did it for a long time. No bueno:)

  6. I love this. I literally have been thinking of a post called, ‘Why I Don’t Like Labels’, and I really agree that labels are so harmful. For me, I think there is NO one that the love of Jesus can not reach, including me, and that means everybody is all the same in God’s mind. I just want to share that love with everybody, and I’m not going to put them in boxes or even try to judge them, because that’s not loving. I am incredibly happy and thankful to follow your journey and your honesty Erin. We love you friend!
    Emily recently posted…Best Nut Butters (II) & A GiveawayMy Profile

  7. Oh Erin, I love love love EVERYTHING about this post. I think your lessons can be applied to so many of our life situations, from avoiding labels, so womaning up and taking responsibility for our actions. I wish we had had more time to chat and connect and BlogFest…..sounds like I definitely need to get to ChiTown to pay you, Susie and Ms Beth a visit <3
    Ange // Cowgirl Runs recently posted…Why (and how) I Stopped ComplainingMy Profile

    1. Oh thank you!! Yeah I tried to make it more universal to hints that everyone can take away and not just people who have gone through probation. You should DEFINITELY come and visit!

    1. Totally. I tried to make it about more universal lessons and not just for those who have gone through probation.

  8. Wow Erin this was beautiful! Thank you for always being real. I think you are incredibly strong and I admire you for that. Going through recovery from an eating disorder has taught me a lot about myself and about life in general. I think people that go through addictions of any sort have a level of maturity about them that their peers do not. Something about hitting rock bottom changes a person. Congratulations by the way!
    Sarah recently posted…Dear Sweet Baby GirlMy Profile

  9. Congrats on both ending your probation and also on finding peace in your situation! I feel like I am still daily on these types of journeys (minus the criminal actions) 😉

    1. Thank you! Don’t worry, it’s a day to day thing that I think we never fully get down 🙂

  10. I am a Crown Attorney in Canada and struggle every day not to judge those I am prosecuting. I know everyone has a story: their own unique challenges. The criminal justice system does not always provide for or result in rehabilitation… but you are proof that both are possible and lengthy periods of incarceration are not always necessary. People can change. I’m so inspired by you, Erin!

    1. Thank you so much! I love hearing from your perspective. I can’t even imagine how difficult your job is!

  11. I just stumbled across this site. This is my second time on probation(for different unrelated items-wrong place at wrong time with the wrong people) in my life and I can definitely relate to this post. I too transferred states and my misd went to a felony-without being told in advance. I’m supposed to find a job, but that will be impossible with those words. I feel like I have aged 10 years going through all of this mentally/emotionally/physically. I constantly feel depressed/shocked/like my life is on hold. The amount of money for supervision/classes is insane.

    1. Hi Alexis –

      I’ sorry to hear you’re going through this. It’s definitely stress-inducing and there were times when I felt really beat down about it. I hope you’re not on probation for too much longer, but it does end and as long as you keep showing up you’ll get through it!

  12. First off congratulations for completing 5 years of probation. I’m an officer and I came across your article. If you feel comfortable would you share what parts of probation were helpful? Especially as it relates to how you were treated by Officers. I train new probation officers and I instruct on Motivational Interviewing. I’m trying to gather examples/ stories of former probationers and what things were done that was positive. In that vain would it be okay to share this article with my trainees?Thanks.

  13. I did this random Google search, and found your blog. I have a Felony Criminal Conviction that is for Theft. I found your blog inspiring. I needed to read/hear your words. I was lucky enough to get probation bc the restitution amount was paid. I just want to start over and lead an honest life. It is hard, and I feel super judged. Thank you so much for the perspective!

  14. Indeed, congratulations!! I just learned how in my state (PA) if you are on probation for sentence about pornography (not a megans law case) any link that comes up of a state-assumed pornographic nature can land you back into court (what you say about even jaywalking).

    I cannot believe this is so bad. I’m 74 and we thought we were going to get better about this all. It is so bad. I’m committed to work for a JUST system… this is not just. More power to you and your road ahead!

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