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Extraordinary Destiny

In a newly published book, a motivational speaker who works with female prisoners reflects on the life lessons she’s learned behind bars.

· 9 min read
Extraordinary Destiny
Photo by RODNAE Productions from Pexels.

After entering the Vanier Centre for Women in Milton, Ontario, visitors undergo a full body scan for contraband. The scanner, a high-tech miracle, detects swallowed or inserted items. That’s right: it shoots clear through the body and peeks right inside your vagina.

During my training, the instructor advised us to “go dark.” That means leaving all personal belongings in the car (no purse, no phone) when we entered the prison. Upon clearance, our keys and coats would be placed in a locker, and the locker key was to be kept well-hidden. Keys can be used as weapons.

I had arrived to deliver my first anger-management presentation to an audience of women. Penny McLean, who co-ordinates volunteer services at Vanier, would be assembling about 100 inmates for the event.

I was nervous at first, but the experience ended up feeling wonderful. After I’d thanked the audience for allowing me into their home, the group of orange-suited women stood, smiled, and applauded. These were women desperate for hope. During the discussion period, one woman asked, “Why didn’t anyone tell me this stuff when I was growin’ up? I sure coulda used someone like you to tell me I had them choices.”

One of the audience members was Destiny, affectionately known as “Trucker”—apparently a reference to her experience turning tricks at truck stops. A 37-year-old natural beauty, Destiny had blond wavy hair that flowed down her back to slightly above her butt. She was gorgeous.

Destiny had been a part-time prostitute, and a part-time drug dealer. She would become my friend and teacher. Over time, I learned that Destiny was a talented soul with a flair for writing poetry that’s insightful and heartbreaking. A deeply painful childhood had given her profound insight into the human mind and the roots of self-destructive behaviour. I often wondered what Destiny might have become had she been offered a stable home and a loving parent.

After this inaugural presentation, Penny gave me a permanent Tuesday gig, a room with no view, and an assistant to help with setup. I was granted carte blanche to research, write, and deliver on any topic that I deemed appropriate and prison-worthy. Each lesson was to be accompanied by a supporting booklet about the corresponding life lessons.

This demanded an enormous time commitment. But it was worth it, because, as I came to learn, many of the women at Vanier treasured these little handouts. And when a woman left prison, she would sometimes share her materials with a troubled friend or a little sister.

It must be said, though, that Vanier contains an ample number of insecure women who suck up to guards—typically for self-serving reasons that involve ratting out your bestie. If you’ve watched Orange is the New Black, you know something about Vanier. The Netflix series’ depiction of lesbian loves and miserable bullies is realistic. (Unlike the character Red in the TV series, however, our cook was supervised, and less likely to poison her least favourite guests.)

Preparing for “Tuesdays with Phyllis,” as I called these meetings, began with Destiny as my informal prison consultant. In the early days, I needed her to translate prison language, and explain how these women tick. My learning curve seemed endless, but Destiny never lost patience. In fact, she seemed to find me refreshing. We became friends, and her honest feedback gave me a reliable sense of my progress.

Studies show that leading a meaningful life is necessary to achieve happiness. When you shine a light on others, they often shine one back. I have also learned that those who’ve experienced the most pain are often the best teachers. The person I am today is largely a product of Destiny and the many women like her who put their trust in me and showed me kindness.

As we got better acquainted, Destiny explained that she was born in a biker house. I wasn’t quite sure what that meant. She explained that her father was unaccounted for, and that her biker mama literally gave birth to her in a Hells Angels clubhouse—and then left. It seemed that her mom needed a fresh start.

The clubhouse was no place for kids. Destiny said she was raised by bikers “doing Mom a favour.” Sadly, this favour led to abuse on every level, including sexual abuse. Deviants often prey on the most readily available victims. But Destiny was a survivor.

Destiny told me that she would give anything for a brief conversation with her mom. She’d enjoyed a few visits with her in past years, and learned that she now lived in Vancouver’s East Side, where she was dealing drugs. Since then, Destiny had lost touch with her mother, but hoped to find her once she left prison. When she told me this story, we held hands and cried for a long time.

One afternoon, Destiny didn’t make it to class. I later learned that she was experiencing severe depression and wanted privacy. This also happened to be the day that I was teaching intimacy and relationships—and, more memorably, the day that I spotted two inmates fondling one another during my presentation. That’s right, fondle. Front row centre.

I stayed calm, and lived to regret it. With absolutely no idea how to handle the development, I did nothing. After class, I reported the incident to Penny during our debriefing. After listening intently, Penny looked at me as if I were missing a brain.

“Do you do that in public?” she asked.

A soft “no” slipped from my lips.

“So why did you allow them to do it?” she asked, in a respectful but firm tone. I explained that I had frozen and, before I could thaw, they’d stopped fondling one another.

Penny gently insisted that next Tuesday I discuss classroom boundaries and appropriate group behaviour. When the day arrived, I did just that. Despite the ladies’ quiet demeanour, their sideways smiles turned it into my most awkward prison moment.

Such episodes aside, I found there was seldom a session that didn’t have me learning as much as I taught. As a result, I began loving more deeply, listening more intently, striving to exude kindness, and enjoying more meaningful relationships. I began to see that in researching benevolence and teaching compassion, I, too, was healing. I’m still a work in progress, with various weaknesses, someone who makes mistakes and screws up. But every life, including mine, is precious, and deserves a second chance.

I was humbled when, after two years at Vanier, I was named “Volunteer of the Year.” My daughter Melanie escorted me to the award dinner, which made it the proudest professional day of my life. It felt surreal to have her enter a prison with me, but it gave Melanie an opportunity to speak with several of the inmates.

As many readers will know, there’s a prison inside every prison. You may have heard it referred to as “the hole,” “segregation,” or “solitary confinement”—more formally known as protective custody. A few years after I began working with Vanier’s general population, I was offered an opportunity to work with the women confined to this isolated area.

These inmates are kept apart because they’re either high-profile targets who might be victimized by other prisoners, or, conversely, they are a danger to themselves or others. Most of these women have received their final sentence, but some are merely in custody pending trial. The majority suffer from intellectual and emotional shortcomings, along with a lifetime of abuse.

My Tuesday schedule had me spending afternoons with the women in “gen pop,” then enjoying an ice cream dinner at McDonald’s, and heading back to prison in the evening to teach the residents of the protective-custody section.

My heart ached for them, and for the underprivileged groups within which family members had struggled to raise them. But though I came to love these women, my Tuesday evenings were brutal at first: Protective custody was a rough group, and the guards, in particular, treated me like the enemy.

Instead of greeting me with the gratitude I’d come to enjoy in the prison’s general-population area, several of the protective-custody guards seemed to resent my wanting to work with violent offenders at all. They’d rudely ask why I’d bother wasting my time on, by one memorable description, “such pigs.” They assured me that I would never make a dent with this group, because they were low-life criminals, sentenced to life and “goin’ nowhere.”

The guards’ attitude was shocking and disturbing to me. But I didn’t complain, for fear that I would be seen as too soft. Instead, I decided to win them over. It should take only a week or two, I thought. I would treat the guards to a strong dose of motivational kindness and before long…

Well, that didn’t work. So I decided to simply ignore the guards and focus my attention on the women of Vanier.

There was one guard who was different, though. Respectful and amiable, Sheila was the only one to check in with me and ask how I was doing. She seemed genuinely curious as whether I could reach anyone.

“It’s rough,” I said. “But even prisoners need someone to care.”

The other guards were annoyed when I visited, she told me, because it meant they had to give up their slack-off shift to babysit me in the “fishbowl”—their nickname for the glass-walled meeting room. I began to understand the animosity. Still, there was no easy fix.

While working in protective custody, I was allowed 10 attendees in my group. The women were delivered to me one at a time and patted down in my presence (an embarrassing spectacle that I think some guards enjoyed). I was locked into this “fishbowl” with a succession of dangerous offenders, a stack of unstapled booklets, and a big blue panic button that was located under the table where I sat. I was assured that upon pressing the button, a guard would appear and save the day.

Several guards watched these proceedings from outside the room. Although it was comforting (for me) that they watched over us, it also felt like I had a hostile audience. Then it dawned on me that the room was soundproof, so the guards couldn’t hear a damn thing. I would smile at the guards from time to time, hoping to impart a sense of confidence while assuring them that everything was fine.

The stories I heard from these forgotten and forsaken women—their in-prison and out-of-prison tales alike—were very sad. To be honest, it wasn’t easy working with them, since many had deeply rooted issues and limitations. But for years, they came to look forward to my visits, shared their struggles with me, and searched for a reason to hope. Being locked up today with no hope for tomorrow is devastating. With expressionless faces, they called themselves lifers. There but for the grace of God, thought I.

Meanwhile, back in gen-pop, Destiny had served her sentence and was preparing to leave Vanier. On what would be my final Tuesday with Destiny, she called me aside after class and told me to take a seat in the laundry area. We needed some quiet time. Destiny had something private and important to say.

“I need to explain something,” Destiny began with a seriousness that I’d never seen before. “I care about you, and I need you to understand a few things. When we’re in here, everyone is clean, and everyone is sober. We’re not looking for our next fix. We’re not gonna hit ya up for anything in here.”

“But when we get out, we don’t even trust ourselves. We turn a trick for a cabbie home. If we’re lucky, we’ll get home on a [blowjob]. So here it is: if you see me on the street, just run. Run away and ran away fast.”

And then she added, without a trace of irony: “Trust me.” And we hugged.

Destiny explained that when a woman leaves prison, she is given some donated clothing and the standard bus fare. The bus fare doesn’t usually cover the ride home because she’s often headed for a distant town. So, resourceful cabbies park outside the prison awaiting a new release. When the happy cabbie scores a “fare,” he’ll take her anywhere she wants, in return for anything he wants. Women prisoners find performing a homeward bound trick safer than hitchhiking.

This is one of the reasons why women who leave prison can seem fated to fail. They’re systematically put at risk of victimization by a cycle of crime, incarceration, and release that encourages predatory behaviour.

My role is to create a safe and sacred space for women to share stories about their past and dreams for their future. For some of them, it’s the first time they’ve ever received respect, caring, or kindness. Together, we learn that there is a path to healing, which is critical to effecting change.

Seven years later, I found Destiny again—and, despite what she’d told me, I had no reason to run. While at Vanier, she’d been working on her GED (General Education Diploma). Now living outside of Toronto, at age 46, Destiny had managed to raise the money necessary to return to school, where she’s studying to become a veterinary technician.

I had the chutzpah to ask Destiny, now clean and sober, how she felt about finding romance.

“Fuck the guys, Phyllis,” she told me. “What I appreciate now is sunshine and school.”

A few years ago, Destiny even managed to reconnect with her mom, who now lives in Alberta. Apparently, she, too, had “cleaned up her act.”

Despite Destiny’s rough start in life, she wanted to assure me that there’s good and bad everywhere—even a biker home. While she endured rottenness at the biker villa, many of the folks there were kind: “I just had some bad luck with the Hells … please don’t give [all of] them a bad rap.”

It was a memorable lesson in forgiveness—from this extraordinary Destiny.

Adapted, with permission, from The Prison Lady: True Stories and Life Lessons from Both Sides of the Bars, by Phyllis Taylor. Copyright © 2022 by Phyllis Taylor. Published by Sutherland House.

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