Former Prisoners Reveal The Hardest Parts Of Adjusting To Life On The Outside

October 4, 2019 | Miles Brucker

Former Prisoners Reveal The Hardest Parts Of Adjusting To Life On The Outside

When someone is incarcerated, their entire life gets overtaken by an all-encompassing system, and it can be easy for those of us who haven’t experienced it to overlook the degree to which this environment cuts its inhabitants off from the rest of the world. In fact, when people get out, they often have trouble adjusting back into normal life. Whether it’s discovering ways in which the world has changed while they were away, getting used to the independence of having no one to answer to, or just trying to cope with the reality of what they’ve been through, there is no question that the adjustment can be overwhelming for many ex-inmates.

Here are 42 examples of some of the trials and tribulations that come with returning to the outside world.

1. This One Might Fall Flat

Someone I know just had a son come out of a long prison sentence. When he'd gone in cell phones were new, so on the car ride home they were showing him an iPhone and it blew his mind. When they got home he walked up to their flat screen TV, got flat up against the wall to see it sideways, then stood in front of it to stare at it.

After a moment, he started trying to swipe it as you would a cell phone.

Prisoners Adjusting Outside factsPixabay

2. Say Hello to Our Brave New World

Five years ago I was released from prison after six years of incarceration. The list of things I missed is kind of amusing. Facebook, WoW, Wikipedia, smartphones, color screens on phones. My cell phone when I was arrested was a Nokia 3390.

Prisoners Adjusting Outside factsPixabay

3. Ask Jeeves

The dishwasher at my old job served 26 years for murder. He was 21 when he went in, came out to a completely different world. I remember him constantly asking me questions to look up on my smartphone, and I never got why. Finally, I convinced him to get one and spent hours walking him through it. Then I realized he thought my phone's sole functionality was to look up info and was taken aback at how much other stuff smartphones can do.

Nicest man in the world, still keep up with him to this day.

Prisoners Adjusting Outside factsPixabay

4. Technically Speaking

As a "community outreach" program for the bank I used to work at, we would attend these meetings that the POs and communities put together for all the ex-cons coming home. To motivate them to stay straight on the outside, there would always be one or two people who reintegrated after doing a bid. One guy who sticks out in my mind was in for 30 years.

He went in at 18 and had only been out for about a year. He said for him technology was the biggest change by far.

Prisoners Adjusting Outside factsShutterstock

5. Quit Toying With This Guy’s Heart

So many complicated toys. Oh come on, I know you know what I’m talking about. Legos were simple when I went in. Everything was simple. Something happened out here while I was inside. Now everything is Harry Potter themed, Star Wars themed, or complicated kits and sets. I mean I’m not saying it's bad I just wanna know what happened.

Prisoners Adjusting Outside factsPixabay

6. The List Goes On and On

A family member recently got out after 15 years. A few things: Couldn't find a payphone anywhere on his first day out. Amazed with his iPhone 5C, especially the auto switch from portrait to landscape when rotating it. Has trouble differentiating between texting, email, and Facebook messenger. Thinks GTA 5 is the most amazing video game ever made, and I agree.

All the cars look new. His little brother and sister have surpassed him in life in general and he's getting advice from them now. Nothing will play his cassette tapes.

Prisoners Adjusting Outside factsPixabay

7. Videos...Everywhere

I only did a few years but I remember trying to explain to someone what YouTube was. He came over and asked me, this was in 2013 and he was locked up in 1998. I explained how he can watch old live concerts people had recorded decades ago, or how he can go behind the scenes with different famous people, to the documentaries, and talked about the self-help videos for basically everything...

The more I explained it to him the more I realized just how crazy it is that it exists.

Lil Wayne factsPixabay

8. Oh, a Wise Guy!

Well I was in the pen for about three hours or so. I gotta say it was tough re-adjusting. All these car makes I'd never seen, technology I'd never heard of.

Prisoners Adjusting Outside factsShutterstock

9. Give Me the Simple Life

My old neighbor did 15 years. He went in sometime in the early 80s and came out in the mid-90s. Just think about how much has changed between maybe 1983 and 1998. From the time he got out until the time he passed away (2012), he did his best to stay "off the grid." He got SSI or something from the government, and would go to the VA hospital, but that was about it.

He worked cash-only jobs, didn't file taxes, didn't have a driver’s license or credit cards. He pretty much dropped out of society. He earned enough money from bartending in a hole in the wall place and working at a car wash. All he needed was rent, a little food, and beer money. He was happy, and lived a very simple life.

Disappointed in their children factsShutterstock

10. Family Ties

Both my brother-in-law and my cousin said that technology was absolutely incredible. (BIL was in for seven years, cousin was 15). They were excited not to wear white ever again. Getting their affairs in order was difficult. My cousin had 0 credit so he was able to just go out and buy a truck and work for my dad doing plumbing.

Prisoners Adjusting Outside factsShutterstock

11. Adjustment Period

For me, it lasted about a month until I was used to being on the outside again. I caught up on all the TV shows that were mentioned in magazines, ate at new restaurants I read about in the newspaper. I spent time with my family, got the chance to take a dump with no cellmate present (sometimes it occurs if your cellie is doing work/school programs) but I also did programs so I always had someone in my cell when I had to poop.

I could walk around barefoot coming out of the shower...crowds in prisons normally point to either someone getting into trouble, or just walking to chow. Prison, for the most part, is quiet, not too many people scream or make scenes because if you draw attention to your group you get dealt with by the shot caller in your group.

Prisoners Adjusting Outside factsPixabay

12. Is Freedom a Step Down For Some?

I don't care what most people think, but jail's freaking awesome. Most of the guys are alright except for this one jerk Cyrus who thinks he's God's gift to the world even though he never even finished grade 10. But aside from that, I love jail. We get to play hockey all day and the dope's actually not that bad believe it or not.

So anyone who knocks on jail can just screw right off cause if it wasn't for jail I wouldn't have a place to spend the holidays.

Prisoners Adjusting Outside factsShutterstock

13. This One Really Drives the Point Home

I remember reading a newspaper piece about someone who had been in prison in India for about 20 years and then came back to the UK. One difference he mentioned was "all the cars look the same now."

Prisoners Adjusting Outside factsShutterstock

14. Turning Over a New Leaf

My husband did three years in prison for a petty drug offense, nothing violent, nothing sexual. I got pregnant five months before he started his sentence so it wasn't the best timing in the world, but we managed. I'd visit him three times a month, he'd call me daily, and we also wrote letters to each other daily. Even though three years is a pretty short amount of time, a LOT changed while he was gone.

All phones became tiny little touch screen computers in your pockets which is what he had the hardest time with. He also couldn't believe how expensive everything got while he was gone. Gas prices, grocery prices, etc. He's been out for four years now and you wouldn't even be able to tell he went to prison by looking at or speaking to him.

He's got a college degree and owns his own business and people cannot believe that he's a felon. Thanks, Ohio for your awesome drug laws!!!

Prisoners Adjusting Outside factsPixabay

15. The Information Revolution

My dad is currently 12 weeks away from finishing his sentence. He went in nine days before 9/11. Since then, he's been in maximum security but been moved to a satellite camp that allows him to work and actually get out (driving to pick up inmates, supervised). One day he had to sit in the park waiting on someone and he said he looked around and couldn't help but notice that no one talked to each other.

He saw three people walking in a line and all had their heads down typing away on their phones. He thought it was sad but mostly funny. Also, he said my mom told him I shared something on Facebook one day and he had literally no idea what she was talking about. My mom is almost 60, so I wish I could've heard what that conversation sounded like.

He has no idea what world awaits him. Last fact I swear: Jay and Silent Bob Strike Back was still in theaters when he went to prison.

Prisoners Adjusting Outside factsShutterstock

16. Old Habits Die Hard

My brother was in and out of jail/prison for all of his adult life. The longest time he was in prison was five years for attempting to steal a truck. The person saw him trying to steal his truck, so it also became aggravated assault because he tried to jump into the truck and my brother dragged him a bit. My brother was on heroin, and yep, it wasn't good.

He got really depressed in prison, and he seemed out of touch each time he got out. I tried to get him to get his GED, and maybe not go back to our hometown where all his "friends" were. He would try to be good for a few months, but then he always went back to the same. He ended up being murdered a couple years ago. If he wasn't murdered, he was almost certainly going to get arrested again by the FBI as part of a RICO investigation, and probably would have been in prison for 20+ years.

Prisoners Adjusting Outside factsPixabay

17. At Least He Gained a Good Habit

My brother did six months last year, maybe not super long term, but it didn't change him much. His diet took a huge turn for the better, he can't eat junk food anymore without getting sick. That's a positive change, but the only one. He was in prison for multiple DUIs, possession of and dealing weed and a couple other things.

He lost his license obviously, and after getting out, he stole my dad's car while he was away on business. He could have gotten that car impounded or something. He still smokes weed and his stupid vaporizer, still drinks like a fish, barely holds any jobs he finds, and makes idiotic decisions every chance he gets. Still hangs out with the scumbags that got him into that lifestyle in the first place. He's 21.

Prisoners Adjusting Outside factsShutterstock

18. Things Change So Rapidly

One time I was in detention for a solid hour and a half, when I came out my friends had invented a new game called Shin-Ball. Took some adjustment getting my head around it I can tell ya…

Memorable Overheard Comments FactsShutterstock

19. Quit Slacking Out There

I only have one question since getting out: How is Half-Life 3 not out yet??

Prisoners Adjusting Outside factsShutterstock

20. Looking the Part

I used to catch the bus about a block from a halfway house. You could always spot the people who just got out, because they walked with their chests out and their arms up, like they had big imaginary muscles. They reminded me of mating birds, actually.

Memorable Strangers factsShutterstock

21. The Other Side of the Coin

Not everything is crazy sometimes, remember we have TVs, MP3s, CDs, magazines, etc on the inside. Heck, at HDSP (High Desert State Prison) during visits we could use our family members’ cell phones to take pics, surf the web, etc...

Prisoners Adjusting Outside factsPixabay

22. Makes Sense

What cell phones are capable of today…by far the biggest surprise.

Prisoners Adjusting Outside factsPixabay

23. Some Things Should Never Change

What happened to Legos? Legos used to be simple. Now they’re so complicated.

Prisoners Adjusting Outside factsPixabay

24. Is This Really a New Development?

That people suck even more than I once thought.

Prisoners Adjusting Outside factsShutterstock

25. We’re All Wondering the Same Thing

What the heck is "the dab"??

Timur FactsShutterstock

26. Show Me the Money

My dad was a guard and he told me about a guy who went in in the 70s and got out in the early 90s and they had to show him what ATMs were and stuff.

Prisoners Adjusting Outside factsPixabay

27. Is This Really Your Number One Concern?

I still can't believe that people who got out haven't figured out why kids love Cinnamon Toast Crunch™ so much!

Prisoners Adjusting Outside factsWikimedia Commons

28. Things Are Seldom as They Seem

These self-driving cars I’ve been hearing so much about just keep swerving off to crash.

Prisoners Adjusting Outside factsFlickr, smoothgroover22

29. Back to a Different Set of Laws

Returning to society is the greatest feeling in the world! You can eat what you want and do whatever you feel like. There is a moment where you feel like "Damn, I can use the phone when I want, I can do what I want." The thing that changes is the fact that life moves on while you’re locked up and you hope to pick up where you left off but it's not like that.

You also come to see that big crowds suck, there are no "prison" rules on the outside.

Prisoners Adjusting Outside factsPixabay

30. They Grow Up So Fast

I know some guys who really struggled when they got out after 15, 18, or 20 years. A lot of these guys never lived as grown-ups. They moved from a home life (that was messed up) to a gang life (that was messed up), and in both they had their lives run for them, and then they got locked up. So now they're supposed to be released and make their own decisions, build up their own lives?

When you get out of prison in that kind of situation, it's like moving out of the house when you're 17. You've got no work history, no references, no bank account, no place to live, no credit, no skills. But you're not 17, you're 40. Or 50. And you don't want to have to tell your family you got lucky and got a job at Pizza Hut, and you're living in a rented room and riding the bus.

Delivery Experiences FactsShutterstock

31. Some People Really Have it Rough

My dad just got out of prison after eight and a half years. He says the biggest adjustment is trying to learn technology such as phones and texting. He also has trouble remembering that no one is trying to kill him on a daily basis. He gets very fidgety in groups even if it's with people he knew before he was arrested. Also, he was just diagnosed with large gland leukemia so he was essentially given a death sentence right out of prison.

Overall, he seems to be doing ok. I just worry that he will go back to his old lifestyle since it's all he knows and with being ill it's hard for him to do manual labor which is his only other marketable skill.

Randoms Acts of Kindness factsPixabay

32. Adjusting Back to the Real World

As soon as my dad got out, he had to battle depression and addiction. He did eight years. He seemed fine the first few years after release, with a few exceptions. He always had to sit back to a wall, with the entrance/exit in view. He was very wary of automatic urinals and sinks. Absolutely terrified of using a computer himself (he got over it and sent me his first email).

He almost had a heart attack when he saw gas prices. He also swore never to eat beans ever again. He still worked as a carpenter. Only profession he knew. People knew his work ethic and connections. Always had a good reputation (despite the convictions). He had a shattered shoulder and hip though, so he was a little restricted, but he still worked hard.

Prisoners Adjusting Outside factsPixabay

33. The Field Is Changing

ATMs, internet shopping, and credit/debit cards must have affected bank robbers big time. Some of them probably don’t know what to do with themselves. Welcome to the no-cash society.

Prisoners Adjusting Outside factsPixabay

34. This is Definitely a Pressing Concern For Everyone...

The change in pubic hair trends...This was about 10+ years ago when I heard this, but a coworker once mentioned that he went away for 15 years. When he got out, the first thing he noticed and freaked out about was the lack of pubic hair on women. He felt really uncomfortable having sex with them because he felt like he was having sex with prepubescent girls.

Prisoners Adjusting Outside factsPixabay

35. Three of a Kind

Three of my brother’s friends got arrested for theft and spent a little over two years in jail. When they got out every one of them puked on the way home. My brother says they eat really weird things and they mix it all together (because everything tastes amazing to them now). They also have major paranoia and can't be in crowds or they panic.

They deserved to be locked up but the punishment lasts much longer than the sentence.

Prisoners Adjusting Outside factsShutterstock

36. The Grass is Greener

My stepfather said that standing on grass messed with him for a while so he avoided it. He spent 10 or so years in federal prison and didn't realize that he was walking on concrete or hard-packed gravel or asphalt the whole time. So afterward he tried to walk from one sidewalk to another by cutting through grass and he described it as feeling like quicksand.

Prisoners Adjusting Outside factsPixabay

37. Subscription World

When you buy a video game you have to buy it multiple times. And people are happy about this!

Acts of Kindness FactsGetty Images

38. What Happened To Just a Burger and Fries?

Not me personally but I know a guy that said after he got out he just wanted McDonald's. When he got there he spent 20 minutes staring at the menu trying to decide what to order because he wasn't used to having choices.

Prisoners Adjusting Outside factsWikimedia Commons, Michael Rivera

39. Where Did Everybody Go?

Got out last month, was in for 17 years. Drugs. Whenever I type a question about professional wrestling (trying to catch up) into Google I seem to be directed to this website and I saw this question. People had cellphones in prison so the technology isn't a huge change, but I think how accessible everything is because of tech is something I will never get used to.

Two nights ago I bought a prepaid debit card just to order a pizza online from a Dominos two blocks away. I thought that was pretty cool. I want to try Uber next, no reason why. I think I hate talking on the phone. Either I'm just really happy to be out, or everyone else seems some sort of shade of miserable now. Maybe because it's winter or something, I don't know, but everyone looks unhappier than they did when I went in.

I stopped by this basketball court/park I used to play at every single day almost from the time I could walk until I was 18 and it's just empty now. I don't live in a big town or anything, but there used to ALWAYS be people walking on our "main street" downtown with all of the stores and stuff...and now there are like no stores and nobody walking around. That was a bit sad.

Prisoners Adjusting Outside factsPixabay

40. A Tragic End

Friend of mine growing up did a long sentence. He was the same age as me, same birthday (just 12 hours apart). We were in school together, cub scouts, all that. But around middle school we drifted apart and I never saw him in high school (though he said he remembered me then). Anyways, I was working at the library when he came in. He was just out of a long prison term—a local one at that, so you'd think it wouldn't be that isolating.

Except apparently he'd burnt a lot of bridges by the time it got to that point so he didn't get a lot of visitors, the local prison doesn't exactly have current books and magazines, and apparently the TV choices are crap. What can I say, we live in the deep South. Anyway, he was amazed primarily by the changes in technology. He knew about computers and cell phones, but his practical experience with them was pretty much nil.

He had a seriously hard time adjusting and managing things. He'd been in an out of jail and prison since pretty much high school—so, for the past say 20 years he'd only had minimal contact and chances for acclimation. He couldn't really cope. He wound up taking an old pick-up truck, drinking himself "courageous," and slamming it into the courthouse in the middle of the night, killing himself and starting a small fire.

A year later, you can't even see a smudge on the courthouse wall, and he's nothing but a memory.

Prisoners Adjusting Outside factsPixabay

41. The Real Change is Within

Notice it's mostly all about technology on here. But that's just the stuff other people can easily relate to. The one that troubles me most is trust. In prison you DO NOT trust anyone easily. Not the support staff, not the guards, not the medical staff and sure as hell not the inmates. Those people you do trust must earn it and constantly show their trustworthiness from then on. I can no longer take trustworthiness on faith.

Within a month of each other I stopped talking to my dream woman and my best friend (those two were sisters). For separate reasons I found that I couldn't trust them implicitly. If I couldn't trust them, I couldn't risk having anything to do with them. My dream woman lied to me, to protect my ego, during a conversation about the importance of trust to me.

That she lied to me I could likely live with. That it was during that particular conversation, was just too much. My best friend drunkenly accused me of calling her husband’s parole officer. That the possibility of my being that shady even entered her mind was just too much. Alcohol is a disinhibitor. It doesn't put ideas into your head, it just lets you run with them. I still love them both, they are amazing people. But I can’t trust them.

So, what has changed on the outside? Mostly technology and social mores. But the real difference is within me. I am changed vastly for the worse, and I am one of the most socially adjusted parolees I know of.

Prisoners Adjusting Outside factsShutterstock

42. Mapping Out the Future

I used to work with parolees in a halfway house. We only took guys who did BAD things (so no white-collar fraud or even bank robbers, think more murders, forcible confinement of women, etc.). I took a particular liking to one guy. I don't tell them anything about myself more than my first name, for safety reasons. But I do my best to help 'em out.

When this guy came out, he had an old cell phone that wouldn't accept a SIM or do anything. Just a very basic brick. He asked if he could still activate it somewhere. Mind you, 9/10 of these guys have never accessed the internet. I had to tell him phones changed quite a bit and they were all smartphones now, etc. In the time he was there, I helped him set up his new cell phone (I think it was a very basic Android but could access the internet).

Whenever he'd get temp labor, he'd come and ask me for directions so I'd print off the bus directions from Google Maps and he'd take the paper with him. When he got some more money he got a better Android, like a Galaxy or something similar. My last day, I didn't make a huge deal of saying goodbye to all the guys, but I talked to him and wished him luck with finding his daughter (many of these guys have kids they've never met, and since they're in their 50s they really want to find them).

I told him since I wouldn't be around to print any maps, I walked him through accessing Google Maps and how to enter an address and get walking directions or bus directions on his screen. He was blown away. I kind of miss those guys, as weird as it may sound.

Prisoners Adjusting Outside factsPixabay

Sources: , , , ,

More from Factinate

Featured Article

My mom never told me how her best friend died. Years later, I was using her phone when I made an utterly chilling discovery.

Dark Family Secrets

Dark Family Secrets Exposed

Nothing stays hidden forever—and these dark family secrets are proof that when the truth comes out, it can range from devastating to utterly chilling.
April 8, 2020 Samantha Henman

Featured Article

Madame de Pompadour was the alluring chief mistress of King Louis XV, but few people know her dark history—or the chilling secret shared by her and Louis.

Madame de Pompadour Facts

Entrancing Facts About Madame de Pompadour, France's Most Powerful Mistress

Madame de Pompadour was the alluring chief mistress of King Louis XV, but few people know her dark history—or the chilling secret shared by her and Louis.
December 7, 2018 Kyle Climans

More from Factinate

Featured Article

I tried to get my ex-wife served with divorce papers. I knew that she was going to take it badly, but I had no idea about the insane lengths she would go to just to get revenge and mess with my life.

These People Got Genius Revenges

When someone really pushes our buttons, we'd like to think that we'd hold our head high and turn the other cheek, but revenge is so, so sweet.
April 22, 2020 Scott Mazza

Featured Article

Catherine of Aragon is now infamous as King Henry VIII’s rejected queen—but few people know her even darker history.

Catherine of Aragon Facts

Tragic Facts About Catherine of Aragon, Henry VIII’s First Wife

Catherine of Aragon is now infamous as King Henry VIII’s rejected queen—but very few people know her even darker history.
June 7, 2018 Christine Tran

Dear reader,

Want to tell us to write facts on a topic? We’re always looking for your input! Please reach out to us to let us know what you’re interested in reading. Your suggestions can be as general or specific as you like, from “Life” to “Compact Cars and Trucks” to “A Subspecies of Capybara Called Hydrochoerus Isthmius.” We’ll get our writers on it because we want to create articles on the topics you’re interested in. Please submit feedback to Thanks for your time!

Do you question the accuracy of a fact you just read? At Factinate, we’re dedicated to getting things right. Our credibility is the turbo-charged engine of our success. We want our readers to trust us. Our editors are instructed to fact check thoroughly, including finding at least three references for each fact. However, despite our best efforts, we sometimes miss the mark. When we do, we depend on our loyal, helpful readers to point out how we can do better. Please let us know if a fact we’ve published is inaccurate (or even if you just suspect it’s inaccurate) by reaching out to us at Thanks for your help!

Warmest regards,

The Factinate team

Want to learn something new every day?

Join thousands of others and start your morning with our Fact Of The Day newsletter.

Thank you!

Error, please try again.