Words Of Encouragement For Someone In Jail

Words Of Encouragement For Someone In Jail

encouragement jail
Inmates buy supplies at Najayo jail’s store in San Cristobal, west of Santo Domingo, May 30, 2007. Latin America prisons overflowed with men, women and minors who have not been sentenced. In the Dominican Republic, around 15,000 prisoners, almost two-thirds of the jails’ population, have not been convicted. (AP Photo/Ramon Espinosa)

Coming up with encouraging words for someone in jail can be challenging, especially if you’re not sure where to begin or it’s your first time sending a letter to an inmate.

Keep in mind that just by you sending a letter means a lot because just hearing your name at mail call will definitely put a smile on your inmate.

Even if you just send a quick note like saying, “Hi how have you been?” would mean so much to someone you know incarcerated.

It’s a good reminder for them to know that they still have people that care about them and that they can talk to during the hard times.

Either way, you would want to send the right words to let your loved one know you’re there for them as well as words that will help keep their spirits high which can help keep a positive attitude while doing time.

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What to write in a letter to a prisoner?

  1. Funny stories
    In your letters, it’s always a good idea to mention funny stories about you to someone in jail that you think will put a smile or bring a positive attitude as it’s really important while doing time to help them stay out of trouble. 
  2. Encouragement Quotes
    – “Fall seven times, stand up eight.”– Japanese Proverb

    – “It doesn’t matter who you are, where you come from. The ability to triumph begins with you. Always.” –Oprah Winfrey

    -“The only person you are destined to become is the person you decide to be.” –Ralph Waldo Emerson

    -“Embrace uncertainty. Some of the most beautiful chapters in our lives won’t have a title until much later.” –Bob Goff

    – “Life doesn’t let you go back and change things. All you can do is learn from the past, and prepare for what the future may bring.” –Unknown

  3. Inspirational quotes for inmates
    Sending inspirational quotes to inmates is also a good way to keep their spirits up.
    It helps them stay motivated and focused to finish any program they are attending to help them have the best success once they’re released. 
  4. Mention you’re not judging your inmate
    Writing about how you don’t judge your inmate can be a relief to them as they might now know what you’re thinking about them and can cause for your loved one to not be as open to you as you may like or your relationship be as tight as you want it to be.
  5. Play games in your letters
    Playing games with an inmate in your letters can help keep the conversation fun and let them know you’re still interested in staying in touch. Below are a few ideas that you can start with:

Listen to GHOGH with Jamarlin Martin | Episode 53: Frederick Hutson

Part 1: Jamarlin talks to justice-tech pioneer Frederick Hutson, who founded Pigeonly to create communications products for inmates and their families that reduce the destructive impact of incarceration.

Choosing how to send your letters to jail

When you write a prisoner, online is usually one of the best methods for sending off a letter. It can save you time and can have your letters sent off from anywhere you may be without having to buy stamps or taking a trip to the post office to mail your letter to an inmate.

It also helps you get the right format on the envelope when you address a letter to an inmate as the company will do all that for you and make sure the size of the envelope is the correct one.

Most facilities will deny any kind of envelope if it’s not the right size or a plain white envelope.

We understand that loved ones tend to move around a lot so if you’re unsure of your loved ones address or where he might be located then we suggest using our free inmate locator tool to find where your loved one is located and make sure your letter arrives at the right address.


At times you can feel like you’ve run out of things to tell your loved one and you want the conversation to stay interesting. We understand.

But, as long as you keep trying out different things you think would work to keep your conversations from not dying out you should be OK.

And as long your letters are sent the correct way you should have no problems having it being delivered to your loved one.

We love hearing from our readers. Let us know if you have anything to add!

This blog was originally published on Pigeonly.com. a tech solution to improve communities by building products that reduce the destructive impact of incarceration. In addition to low-cost jail calls, Pigeonly customers share photos, letters and more, taking the hassle out and providing an affordable, easy way to keep in touch with your inmate. This blog is reposted here with permission from Pigeonly Founder and justice-tech pioneer Frederick Hutson. Read the original.

Listen to GHOGH with Jamarlin Martin | Episode 54: Frederick Hutson

Part 2: Jamarlin talks to justice-tech pioneer Frederick Hutson, who founded Pigeonly to create communications products for inmates and their families. They discuss how he raised capital, the importance of focus, and spending too much time perfecting the product before launch. They also discuss Jay-Z’s blueprint for parting ways with team members via his break-up with Damon Dash.