"Until he defines himself as an addict," Carlos replied, "you'll never teach him to read. It's not like when you have a cold and then get better or break an arm and it heals. If you're an addict, you're an addict. This will be with Al his whole life. It's just a fact."

"So what do I do?" I asked. "Al's starting to come to school. He's starting to make a connection to me. You're right that he isn't actually doing anything to read better. Most likely he'll fail the class. That can't be good for him, to have another failure—and this one coming from a teacher whom he seems to like."

"You can't stop him from failing." Carlos said this with a mixture of resignation and compassion. "It's his right to fail. Al is going to have to fail many times to change his life. Your job is to help him have a useful repetition of his failure. Many addicts have to have 100 repetitions of getting fired from jobs, getting sick, losing girlfriends and boyfriends, and failing a class before they know what they have to do. Your job is to let Al know you'll hang in through his failures."

What It Takes

One hundred repetitions—100 useful repetitions. This notion has guided my work in alternative education programs for almost 20 years, dealing with the most challenging students, from addicts to conduct-disordered adolescents to traumatized 5th graders. There are no magic tricks. Our role as educators is to align with the healthy potential in each student and hang in while they gradually find shelter in our expectations and caring, in our structures and hopes. It's not a straight line. It may take 100 repetitions.

One mantra from the world of special education is, "Again and again and again and again." Many students cannot internalize a new behavior just because you've told them to or by practicing it once or twice. They need repetitions. But—and this is crucial—providing those 100 useful repetitions does not mean rigidly providing students with exactly the same experience 100 times.

When we teach reading, we use a variety of texts. When we teach art, we use a variety of media. When we teach history, we use a variety of primary documents. The deep goal of all the activities may be the same, even if the materials look different. For challenging students, the deep goal is to rekindle a belief that trying will be worth it. That goal is woven into every task we ask of students.

I couldn't stop Al from using drugs. I couldn't teach him to be a better reader when he stumbled, hungover, into my class. What I provided him with was an emotionally safe place to land. I reminded him what I was willing to do for him, and I clearly told him what I couldn't do for him. I told him I thought his substance use was interfering with his learning. Every time he did something good, I let him know I'd seen it. When he failed my course, I talked to him one-on-one.

What Teachers Need to Do Along the Way

Schools play a crucial role in supporting challenging students as they go through their 100 repetitions of struggle. It's most important to

• Preserve relationships. Don't make students' struggles a personal issue. They have not failed you. Let them know you're strong enough to withstand their struggles on the path to success, however long that path may be.
• Be genuine in your emotions. You can repeat the most tired clichés and homilies, as long as they come from the heart. Your authenticity—your ability to integrate your concern with your expectations—helps students integrate those expectations in themselves.
• Help the student accurately understand the consequences. The student has already failed the course, lost a friend, been kicked out of the house. You don't need to be punitive in your actions or tone. The world is already supplying the natural consequences for the student. Clarify those consequences, and talk about ways things could be different next time. In particular, help the student keep the degree of damage done in perspective. Young people can think they've just ruined their entire future when they've tried and failed, so a teacher's realistic weighing of the situation is a necessary antidote to resignation.
• Highlight every bit of growth. It can take a long time to reach the 100th repetition. These students need many pats on the back for what they tried to do right. It's a rare failure that's without a redeeming moment of good will and effort.
• Listen to the student. After a couple dozen repetitions, most students have heard every well-intentioned speech. What they may most need from adults is help articulating what they themselves are now coming to understand about their efforts. Ask questions to help them think more deeply about their own construction of the situation. Reflect back their ideas. Identify where you agree or disagree.
• Let them feel their feelings. Sometimes the best thing we can do for students is bear witness to their feelings. When students are feeling low, the intervention they may need most is for you to say, "This is a sad moment." Then sit quietly so the student can experience that feeling. For many students, the genesis of problem solving is found in the quiet opportunity to feel.

Pulling for 100

I frequently use the "100 repetition" phrase as I work with teachers and school staff who serve our most challenging students. Adult professionals can feel beaten down. They can overlook the positives along the way. I often say,

You're doing great work. You've taken this student from repetition number 20 to repetition 35. If you hadn't done that work, this student would still be stuck at number 20. You may not get to be the one who does number 100; if you're doing repetitions 20–35, it's likely you won't be there at number 100. But the work you're doing is essential, so the next teacher can pick it up at number 36.

That brings me to the story of Martina. She's one of my all-time favorite students. When she enrolled in my literature class, she was angry at adults and avoided hard work, and she had no clear goals. Combining my work with the efforts of her therapist, her mother, and other school staff, I supported Martina as she went from what I would estimate being repetition number 30 to repetition number 75. I don't think I've ever mentored a student through so many useful repetitions. This was Martina's arc of development:

1. Martina storming out of the room when the work was hard. ("Martina, thanks for not bothering students on the way out the other day, because you could have done that, and you didn't. I'm glad you're back here today. That takes courage.")
2. Martina complaining that the work was "stupid." ("Martina, I'm glad you're telling me that and not leaving the class, even if it's hard for me to hear that you don't like the lesson. Let me know if you want me to explain the task again and help you get started.")
3. Martina coming to class without her homework. ("I'm happy you came to class and stayed, and we can make plans to catch up on the homework. You're far from failing the course. What do you think?")
4. Martina getting a low grade on a test and in despair because "I had actually studied this time." ("Martina, you stayed in the classroom for the entire test, you made an effort to study. Thanks for letting me know you feel bad about it. Feeling bad is what we humans do at these times.")
5. Martina angry at herself because she didn't make time to do her homework. ("Martina, you're always working in class these days, you're doing some of the homework, and you're not blaming me, so it's easier for me to listen. I'm so glad you let me know that you care. Tell me more.")

Martina continued to periodically have bad days, though far fewer. At the end of my year with Martina, I handed her off to her next teacher. We all could see her blossoming and assuming more responsibility for herself. She still could not completely forgive and forget the hard moments of the earlier repetitions with me, when I needed to call her mother, when I required that she redo a poorly done task, when I sent her to the principal's office on a particularly difficult day.

Martina's next teacher was the one who saw her through to graduation, to her triumphant repetition number 100. Martina loved this teacher. She respected me, but she loved him.

"Thanks," he said to me the night of graduation. "I know I did good work with her this year, but you did the heavy lifting last year. We're all dependent on one another to do these useful repetitions. Some of us are the lucky ones who get to do number 100."