The Prison Survival Guide for People-Pleasers
“What are you in for?” — “Writing shite articles…”

Prison is the last place humans want to end up.
Well there, or a Mexican restaurant with Donald Trump. We definitely won’t be asked back, and Donald never tips.
But yeah, prison would still be pretty bad. Murderers and bank robbers know what they’re getting themselves in for though. They fit in with the crowd. People-pleasers … not so much.
You know the type. Think Michael Scott in “The Office”. If you’re always like:
“Let’s try and please everybody and have a positive outlook on life”.
Prison probably isn’t for you.
Nice people can end up in prison for a range of reasons:
- Maybe you were arrested for shouting abuse at an old lady taking too long paying for milk at the supermarket?
- Maybe you finally punched that kid who was making too much noise on the plane when all you wanted was some shut-eye.
- Maybe you offed that annoying nun at church…but they really had it coming.
Either way you’re now slammed up with “Razor Roy” as a cell-mate and potential love interest.
What should you do?
Fear Factor

That’s right guys — fear is everything in prison. Are you quite timid and shy around people? Well never fear, some of these tips should help.
- Dress up as a scary witch (see my Tinder match above) and hide in the corner of the yard to give your fellow inmates a jolly good fright.
- Assert dominance by not saying “thank you” when offered a contraband cigarette.
- In the gym, do your squats right in front of the mirror so everyone knows not to mess with you and your Kim K butt.
Make Friends

It can get lonely in the slammer. Especially with only Razor Roy for company. That’s why it is so, so, important to make friends.
It could be the nice man in the gym beating someone to death with a weight, the dinner lady with three teeth, or even the warden who only told you to “f*ck off” twice yesterday.
Some of these friendships will last a lifetime. Which is probably quite useful if you’re serving a life sentence. You can kill those lonely hours and flourish in a prison environment with a new jail bestie.
Here are some things you could try with a prison pal:
- Make friendship bracelets for each other.
- Play hide and seek together — until one of you is so good at hiding that the guards raise the alarm.
- Play spin the bottle and stay up late talking about your crushes.
Also, don’t look your potential new brother from another mother directly in the eye.
They’ll probably murder you.
Host a cell party

It’s Saturday night and that means only one thing — it’s party time! Yeah I know you’re locked up right now, but that doesn’t mean you can’t have fun!
Round up all your friends — Razor Roy has cards, one of the wardens said they can smuggle you a bottle of White Zinfandel, and you have your charming social skills. If that’s not a party, then I don’t know what is.
Do you still need some prison party tips? Don’t you worry, Mr. Inmate. I’ve got you covered! Why don’t you:
- Catch up with old cell-mates you haven’t seen in a while. Even “Crazy Carl” who tried to strangle you in your sleep last week.
- Play “Shag, Marry or Kill” until someone gets shagged, married, or killed.
- Discuss the social and economic ramifications of COVID-19 and how global markets can recover from the pandemic.
- Make sure everyone has enough dip.
Your sentence is up!

So what’s the verdict? Does prison sound awful? Or is it made out to be a lot worse than it actually is? Will your nice, kind personality flourish around Razor Roy and Crazy Carl?
It’s a tough one to call.
But what have we learnt? Well…
- Make friends with the guards so they can smuggle you fine wines.
- In the prison gym, squat like your life depends on it.
- Take good care of your friendship bracelet.
Thanks for reading guys and make sure to tell your cell-mates about my Medium articles. I need the money.
Seriously. Tell them.
I’m broke.
