How I Motivate My Incarcerated Brother, Even When It Feels Pointless

by Claire Tak of the Prison Journalism Project

As the sister of an incarcerated younger brother, I am at a loss when it comes to motivating him to feel inspired and live his best life. I can tell from previous visits and phone calls that Isaac feels lost and struggles to get in touch with his emotions. He believes his life is at a standstill because he’s locked up — and it’s hard to blame him. Prison wears on you. It’s a slow, grinding corrosion that can devour your energy and leave you lethargic and hopeless. 

Despite that, I want Isaac to embrace a growth mindset while serving his 19-year prison sentence in central California. I realize it sounds like a tall order, and it is. In the five years since Isaac was locked up, I have sent him books and had countless conversations about why I think he should consider educational programs, find a job, or walk a few laps when it’s yard time so he can see the sun. 

Isaac is rarely receptive to this encouragement. Sometimes it feels pointless to try, but I can’t stop. For the same reason I have to send him care packages, I can’t rely on the prison system to give my brother the support he needs. 

Over the years, each time I visited Isaac, I inquired about enrolling in classes. He argued that they were too inconsistent due to lockdowns, which could happen at any time for a variety of reasons, including COVID spikes, a fight in the yard or a pair of scissors that went missing from the kitchen. 

But he could still read the books I sent him, I pleaded, or go to the library. I pointed out he had plenty of time to learn and grow as a person. Reading was surely better for him than watching TV and sleeping all day. 

To counter this perspective, I offered my brother real-world examples of incarcerated people. These included Jeff Henderson, an ex-felon-turned-chef and author, and the poet Reginald Dwayne Betts, who was imprisoned for carjacking but later attended Yale University and became an attorney. 

“I can’t do much from here,” Isaac would say. “My life is on hold.” 

“Their desire to change started while locked up,” I said. 

In response, he would stare at me as if I had instructed him to sprout wings and fly out of prison. My words felt empty.

The importance of showing up

A few years back, I read “The Sun Does Shine: How I Found Freedom on Death Row” by Anthony Ray Hinton. Hinton spent 30 years on death row for a crime he didn’t commit. 

His story taught me that one person can profoundly change another’s life.

For Hinton, that person was his childhood best friend, Lester Bailey, who visited him regularly for three decades. During his darkest days, Hinton recalled how these interactions and their friendship saved his life. 

Reading Bailey’s book, I realized that even if Isaac believes “everything is pointless,” I can’t. I have to keep rooting for him. When I feel like giving up, I think about Bailey’s love and support. He showed it in a variety of ways, including through small talk about what he did that week or laughing about a childhood memory they shared. 

I knew Isaac hated my lectures, and I didn’t want to sound like a broken record. So, eventually, I decided to let him lead the conversations. He would ask about the latest movies in the theaters or if I had watched anything good recently. Even though I knew he would likely never get to see any of the TV shows and movies we talked about, it didn’t matter. All that mattered was that we were having a relaxed conversation and he felt engaged.

Getting creative with mail

Currently and formerly incarcerated people will tell you that receiving mail in prison is a big deal. It means someone on the outside cares about you. 

At some point, it dawned on me that I had stopped writing letters to Isaac because we mostly communicated through his prison tablet via text messages. (The California Department of Corrections began distributing tablets to incarcerated people in the state in 2021.)

I decided to shift course and make it a point to send him a steady stream of mail, mainly in the form of postcards and online articles I thought he would be interested in reading. I send him all kinds of things: advice on how to do stretches, breathing exercises to lessen anxiety, or transcripts of Ear Hustle episodes, a podcast about life on the inside at San Quentin State Prison. 

Over the last several months, I noticed Isaac asking about the packets if he hadn’t received anything recently. To me, it felt like a sign that he appreciates these gestures. On a visit last month, he told me he liked a PJP story of one woman’s Stage 4 cancer diagnosis and her fight to get treatment from behind bars. It was the first time he complimented something he read from my packets. 

Holding on to hope

Change is hard for anyone, and I know Isaac has to want it for himself. Until that time comes, I will be mindful of lecturing him and continue to:

• Keep showing up, even when it feels like he isn’t listening
• Let him lead the conversations
• Send postcards and printed articles

I hope these simple gestures of showing up convey that I support and care about him. 

A quick note: If you’re unfamiliar with what you’re allowed to mail, check PJP’s “Contacting People Inside By State” resource page. There are strict rules about what you can send. For example, in California, you cannot send hardback books or notebooks with spirals. Also, any sexually explicit content is not allowed. 

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Have a question or comment? I’d love to hear from you. Subscribe to my Substack, Stories About My Brother, or email me: pjp@prisonjournalismproject.org, attention Claire at Outside/In.

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This story by Claire Tak first appeared at the Prison Journalism Project, which trains incarcerated writers to be journalists and to publish their stories

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Also, check out Claire Tak’s “Outside/In,” an occasional column in which she describes it’s like to have a loved one in prison from a sister’s unique perspective. From sending commissary money to visiting prison for the first time, Claire shares tips, advice and of course, stories.