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Crossing the Water: Eighteen Months on an Island Working With Troubled Boys -- A Teacher's Memoir

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It's a rare pleasure when a new author shows not only notable talent, but the skill and chutzpah to go where no one else has gone before. Daniel Robb takes a subject that many have considered but few understood--juvenile delinquents--and writes about it with rare insight. For a year and a half, Robb was a teacher on Penikese Island, off Cape Cod, where teenage boys are sent by the courts and social services to put six months between themselves and their chaotic daily lives. During this time they experience safety, a routine, hard work, and the decency and constancy of adults better adjusted than the ones they've known. The place is less a school, Robb writes, than "a family, or a way of life, a rhythm, a discipline, a music, with many voices of boys competing with my own for ownership of the tale." The boys have varied résumés: Mose shot a man who threatened him one night; Edward torched a boat for money; Alan is the king of substance abuse; Burt's parents have both been in jail since he was 7. But Robb finds that they all have a number of things in common--childhoods fraught with so many uncertainties that they never learned cause and effect, the lack of a father's guidance--the same things, it turn out, that plague Robb's own heart.

Robb has a gift for evoking their natural surroundings on the island in a language that resembles poetry while capturing the cadences and tribulations of his surly yet charming students with perfect pitch and clear-eyed sympathy. Not only does the dichotomy make for compelling reading, it works on the kids as well: Ned, the longhaired metalhead, gives CPR to a mouse and actually revives it; Wyatt, who stole cars out of boredom, considers his absent father's legacy after reading a Gary Snyder poem. Robb is a literary voyager in the most unlikely of places, and, in the end, reveals that even boys such as these have a poetry all their own. --Lesley Reed

288 pages, Hardcover

First published May 1, 2001

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Daniel Robb

2 books

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Displaying 1 - 22 of 22 reviews
Profile Image for Joey.
262 reviews55 followers
January 6, 2016
I have been teaching Koreans for seven years. There are times that I also teach non-native speakers from Asia and Africa. I have not taught my fellow Filipinos yet although I dream of it.

There is a big difference between teaching other foreign students and teaching my countrymen: It is a matter of cultural differences. When it comes to Korean educational system, Korean students, especially in these days, have academic competition. Their parents work their butts off to make sure that their parents can afford to send them through expensive academies and schools. In fact, it is a quite common thing to do that they are supported in school overseas. In other words, what all students are supposed to do is to focus on their studies while their parents are away, busy with their jobs. Consequently, based on my observation, students tend to experience psychological and physiological effects. Physiologically, they are always tired and sleepy during class because they always stay up very late , busy pulling an all-nighter. Also, some of them tend to have short attention span. Meaning to say, they can easily lose patience under slow circumstances. I have learned that students, or I guess my student then and I coined it ourselves , “ Bali-bali syndrome”, an expression in Korean which means, “ Hurry up!”Psychologically, without offense, some I have taught have delinquent behavior. Some were rude to me. Some discriminated against me. Some played tricks on me. Some tended to get uppity because they reason that Korea is richer than my country. So, within seven years, I always have had a hard time teaching my students. Nevertheless, I have known it all along that it has been a big challenge for me until I have learned that the best way to build a harmonious student-teacher relationship is to adapt their culture. I found that this kind of approach somehow works.

Daniel Robb, the author of the book, is an English teacher too. He wrote in his memoir about his teaching life on an island which is Pekinese where juvenile delinquents are sent to be rectified. He, along with the other staff on the island, lived with many kinds of handfuls whose lives have been complicated. He taught them academics, particularly English which is his forte, carpentry, and other household chores. The big challenge for Mr. Robb was how to catch his students’ interest, for they were predisposed to anti-social behaviors. How would you teach students who keep on cussing you? A student who is always making a fool of you? An arson student who can risk your life while you are asleep? A student who likes to get in high? A student who likes to play hit-and-run? A sexually preoccupied student? Or even a psycho student? Fortunately, Mr. Robb somehow managed to handle them. He tried to be tough and empathic at the same time. However, there were times that he could no longer put up with them alike. But the longer he stayed on the island, the more he had heuristic insights into his life. There ,on the island, he learned to understand the students’ abject misery. Like them, Mr. Robb also grew without a father figure.

Given the book is powerful and deeply moving , I really liked it because I can relate to his pedagogical dilemma. Also, there are some parts in which he tells about some literary and historical pieces such as on Marxism and Mao Zedong. Furthermore, it is perfectly well-written giving the indication that Mr. Robb is a gifted writer. However, I just had a hard time reading some dialogues with various English accents since his students came from different regions in the U.S.

In the end, Mr. Robb and I , maybe even you when you read it , are in the same opinion that there are juvenile delinquents because of the familial problems which come into existence at home. After all, parents should be responsible for their kids. They should love their kids because love is a powerful element created in the universe.

Although Mr. Robb quit teaching on the island, he still represents all teachers who have the same passion for teaching regardless of money or environment elsewhere.

For the same theme, I suggest that you read Frank McCourt’s Teacher Man. His memoir deals with his teaching difficulties in a vocational and melting-pot school.

I love teaching! ^__^
Profile Image for Sunny.
151 reviews
August 23, 2021
I found this book from another book -- Why Fish Don't Exist and thought the premise sounded interesting. Since I've been having a lot of discussions recently about crime and whose fault crime is and how one should hold the people who commit crimes accountable, I thought it would be interesting to know the perspective of someone who deals with these questions on a daily basis. I can see that most of the other people who read this book were involved somehow in education or something -- I'm not, but I read it anyways.

I was disappointed by pages 30-80 or so. I was almost going to drop the book because there was a lot of descriptions and details but no real... purpose. I thought that this would be what the rest of the book was like, and didn't feel like reading 200 more pages of that. To make things worse, there were just so many boys and I could not keep them all straight.

Also, the way women were evaluated based on their appearance at almost every opportunity and encounter was sometimes more than a little off-putting.

Still, I gave this book four stars because it got better. A lot better. After hitting page 130 or so, I was hooked and finished the rest in two days. It wasn't so much that there was drama or an interesting plot -- there wasn't much of either. It was the way Daniel Robb wrote about these boys and captured perfect moments of dialogue that painted them in a light that felt fresh. It was also the way he wrote about himself. His candidness was apparent in every word he wrote, and you could really tell how human he was. He wanted to do a good thing but he was by no means a God. He had moments where he questioned the worth of what he was doing, where the isolation crept in, where he lost it with the boys. But he stuck with it, and every day, he really truly tried.

The boys, too, they tried. Much more than I expected them to. When I saw "troubled boys" I was expecting something different. I wasn't expecting boys that thought deeply. Boys that showed respect. Boys that cared. It was surprising, but nicely surprising, how they viewed the island and how they viewed Dan. Most of them, it felt like, genuinely wanted better for themselves. Most of them appreciated the help they were getting. Most of them just felt trapped. In my discussions about crime and criminals, we always talk about who is at fault. The boys themselves? Society? Their circumstances? Nature or nurture. Which triumphs? For a lot of people, nurture is the obvious winner. Man is nothing but a reaction to his circumstances. I liked, therefore, that there was an emphasis placed on "cause and effect" on the island. Not only would that (probably, hopefully) teach the boys that their actions have consequences, but also that they are a consequence of other people's actions. That it is not them who is the issue. Yet that blaming their circumstances only goes so far -- they have to recognize that by blaming the circumstances that were inflicted upon them, they also have to blame themselves for any negative circumstances they inflict on others. I'm not saying this as a moral lesson, more as a practical one.

I began to appreciate the setting more and more as the book went on. It gave me strong Henry David Thoreau vibes. I was actually jealous of Robb, and how he was able to live on this beautiful secluded island, reading books in his free time, working in nature and doing a lot of physical activity, all the while doing something meaningful -- and the meaningful activity was basically psychoanalysis of other people and attempts to get them to better understand themselves and the world. I mean really, sounds great to me. (Of course I am romanticizing it to a certain extent.)

The last thing that I can think of right now that I enjoyed about this book is how it exposed my own prejudices. We always talk about racial bias or discrimination for one's sexual orientation, able bodidness, etc. People different than us. Something that isn't talked about as much is prejudices we hold against people with different personalities. As a self-proclaimed nerd, I've always held somewhat negative preconceived notions about people not like me ( aka "popular"-type people/heavy party people/rule breakers). I'm not proud of it, but for me, "coolness"? I guess you could say, more than race, sexuality, or any other politicized aspect of one's identity is what causes me to default to the "us vs them" mentality. I separate myself from "those people" similarly to how they separate from me. The boys, not surprisingly, made a lot of jokes that mildly hated on the broad category of people I'm just going to call "nerds." It seemed like they were so afraid of their social status being lowered -- which would happen if they were identified with characteristics present in nerdy losers -- that they had to constantly remind everyone that they were not like them nerds. Not only did they feel the need to prove to the outside world that they were cool, they also had to prove it to themselves -- to protect and affirm their masculinity and whatnot. Myself, I tend to make it pretty clear that I am not like "those idiots." I subconsciously tell myself that I have a handle on things, that I am somehow wiser or level-headed or more mature. Not a child. Like all "us vs them" mentalities, this kind of thinking only sustains prejudices and creates barriers. Both sides look at each other with a certain amount of disdain and scorn. And I'm not going to sit here and pretend like that'll go away any time soon -- it probably never really will -- but at least I am more aware of it now, and am more aware of how I can, in fact, connect with people (even if they are in a book) who are on the "other side". That I can relate to them, that I can see them for more than just a label. As Gandhi said, or basically said, "Be the Change You Wish to See in the World." That's the best I, or Daniel, or any of the boys, can do.
Profile Image for Douglas.
26 reviews3 followers
December 5, 2017
I bought this book 15 years ago and I'm glad I finally got around to reading it this week. Robb recounts the frustrations and joys of working with troubled boys whose criminal acts require special supervision and understanding--on a remote island off the Massachusetts mainland.
Additionally, it's about Robb's attempts to deal with his own childhood and resentment of his own absentee father.
Robb is on the island to teach and counsel. He uses literature to speak to the boys, and they journal a lot to sort out their feelings of anger and abandonment. I especially liked their outhouse haikus.
Profile Image for Sally.
Author 20 books404 followers
June 1, 2015
This book offers a simple solution that is extremely complex. I'm only glad that Daniel Robb did the work, wrote the book, and saw the simplicity and complexity of the island and the lives he touched.
Profile Image for Booknblues.
1,545 reviews8 followers
October 13, 2025
Two things drew me to Crossing the Water: Eighteen Months on an Island Working With Troubled Boys -- A Teacher's Memoir, one was the island setting and the other was I have always loved stories and movies about teachers as Good Will Hunting, Up the Down Staircase and To Sir With Love. There is that and working in the education field for forty something years, of course drew me in.

Daniel Robb, a teacher wanted to try his hand at working on Penikese Island School for juvenile offenders as he hoped to reach them with his skills. It was a much harder road than Robb expected and there were times when his skills were clearly tested. There were times indeed, where I did not find him all the way likeable.

Their life was much like that of the pioneers, wood stoves, kerosene lamps. They raised pigs and chickens and planted a garden. They repaired boats, built a stone wall, set lobster traps. Doing all this they were taught academic lessons as well as keeping journals

He did present the boys and their dialogue quite well. Robb appreciates the flora and fauna of the island and describes it nicely:

"BIRDS are coming home. Yesterday I saw my first osprey, which looked like a seagull until I looked. It was more stolid in flight—less buoyant on the wing—and had patches of white on the underside of its wing up under the shoulder. It should build a nest soon, if it has a mate. But what a bird. Any being who can make a living pursuing swift fierce bluefish in the cool waters of the bay, stalking, hovering, then stooping down to strike with talons in a great splash, then fly home with a four-pound flapping fish held beneath its chest—and from this grow feathers, live only in the tallest trees, and winter in Costa Rica—this is a rare being, a being of discernment. "

He often veered off into stories of his life and as a reader, I wanted him to be more focused.
255 reviews7 followers
March 20, 2025
I am not quite certain how I can across this book but I am grateful that I have had the opportunity to read the work of such a talented and gifted writer as Daniel Robb. Given the background to the storyline and understanding how much it contributed to the authenticity of the book, I overlooked the language because it just seemed to fit right into the lives of the young boys Daniel was working with. It was the story itself, telling it from the notes in his own journal, his memories of events, the sensory descriptions of times, places, living quarters, food, the animals, residents, weather and other staff, all told in such a way that leaves you with no doubt about what it was like to live on an island, with kids sent their by the courts, for various crimes, in the hope that through your teaching these young boys could be rehabilitated in some way. There was an underlying theme throughout the book that had me wondering how it would work out. For the youths sent there and for Daniel.
Profile Image for Paul.
136 reviews5 followers
August 27, 2021
I originally decided to read this book because Penikese Island kept popping up in other things I had read. it is a fascinating journal of working with juvenile delinquents who had been sent to a program on isolated Penikese Island to attempt to turn their lives around. I ended up learning about the island, its early history as a leper colony, and gained a much better understanding of troubled youth and the potential to turn their lives around.
Profile Image for Derek.
31 reviews13 followers
May 2, 2010
Well, I guess I don’t agree with Publisher’s Weekly (“Robb… captures the humanity of each boy, thus avoiding Blackboard Jungle clichés”) and the other publications with good reviews for Daniel Robb’s "Crossing the Water: Eighteen Months on an Island Working with Troubled Boys – a Teacher’s Memoir" (The Washington Post, Library Journal, Booklist). I didn’t like it much at all.

I should have known from the start. The cheesy dedication -“Thanks be to every soul who has worked at Penikese. Thanks be to the island, for being. And thanks to every boy whom I knew, and those I didn’t. May you fly.” – should have been a warning. The contradictory prologue - “This book is about a small and specific school… on a small and specific island… It is not about every boy… There is something of me in every American, and the other way too” (16) – should have been a warning. But I, entranced by premise of an island that serves as a jail “with water for bars” (23) where dedicated teachers offer vaguely Amish educational experiences to troubled kids in hopes of turning them from “potential murderers into car thieves” (34), kept going.

After all, the kids chop wood. They discuss violence and non-violence. A tough kid offers a dying mouse CPR. Another tough kid hosts a burial for a dead barn swallow. The teachers offer consistency to kids with “arbitrary” lives: “What we try to teach on the island,” Robb’s mentor says, “is that there is a direct relationship between what one does and the reality one experiences as a result” (35). Really, I thought, how could this not be a good book?

At parts, it was pretty good, and I learned a few things. Robb provides specific descriptions of physical locations and objects: “There is also an oak desk which sits in front of a window facing the sea,” he writes, “and one other dark wood chair. A small kitchen butts off the east side, as does a small bathroom in which there is a massive clawfoot bathtub which is always very cold” (64). My writing could benefit from more of this. Also, Robb is great at dialogue. By my own estimate, about two-thirds of the book is dialogue, a lot of it interesting. It might be that Robb loves capturing authentic-sounding conversation, or it might be that there isn’t much for the kids to do on the island but chop wood and converse. Throughout, we hear the voices of Robb’s troubled students – “This stuff is the balls, yo” (39) – many of whom do not pronounce their “r”s: “odor” is “odah”; “cars” is “cahs”; “where” is “wheah”; and, “there” is “theah” (40-46).

But ultimately there were things I couldn’t get over. 1.) There wasn’t a plot. Because students only stay on Penikese for short stints of rehabilitation, none of the “cast,” as Robb calls them, make it all the way through the book. They come and go. He is the only constant variable. 2.) He only describes people by their hair color and weight. And how tall they are. This gets annoying. 3.) He ends many of his vignettes with smug or sentimental lines, like, “I think I’ll never know” (199), or, “I am not yet healed” (193), or, “I shall say my good-byes” (283). 4.) There’s some kind of weird “savior” narrative here. “I’m elated to be here, on the front lines,” he writes of his desire to help. “Maybe I can pry one of these guys up, help him see the light, breathe the thin air...” (49). Seems noble. But then this:

"A couple of years later I read a book by a family friend named John Hough called A Peck of Salt, about two years he spent teaching for VISTA in the ghettoes of Detroit and Chicago in the late sixties. It was one of the finest books I’d come across… with lines about his students like, 'He was fifteen and last night he’d seen the blood of his father on the hands of his mother.' Jesus, I thought then, to teach kids like that, who were going through so much, to try and help them on their way… - that appealed to m" (61).

... combined with this:

"I pictured [my students:] witnessing, in the corner of a dim room in a seedy apartment, their drunken mother beaten by their drunken father, or raped by a new boyfriend who never came around again, or I saw the drunken mother or father coming for the small boy, and felt the blows, what those must have been like, the flat of a hand against a cheek..." (113).

... combined with the conversations about violence and non-violence in which Robb continually and cryptically alludes to a moral code his students must “come to” on their own, left me feeling ethically and pedagogically icky, as if Robb was writing himself into a teaching narrative he read in books and saw on made-for-television movies. For me, these clichés cheapened and invalidated the authenticity promised by the book’s original premise. I thought "Crossing the Water" was going to be a new kind of teaching book with a new kind of narrative. It wasn’t. Apparently our cultural notions of do-gooder-teachers, these self-perceived saviors (myself, ahem, included), can land even on the shores of a small windswept island called Penikese off the coast of Cape Cod.
Profile Image for Chris.
266 reviews25 followers
March 24, 2014
Anyone who plans to work with teens or troubled teens needs to take the time to read this book. The stories of the boys the author meets on this island are enough to make you wish more people appreciated the children they have and took better care of them.

The boys that live on this island are considered by the state to be unsafe to be in any other state run facility. This makes it the island with the most dangerous boys around. The life on this island is kept basic, the boys are taught that if they want to eat, they need to learn to take care of their garden and learn to cook. They have rules and chores to follow everyday. Everyone lives in the same house and each boy has his own bed, where many other boys before him have slept. This is made obvious by all the scratches and markings on the walls around and under each bed.

Working with troubled teens is difficult, but the one thing most adults in all forms of social services don't get is that they just want someone to love them, appreciate them, and care for them even if they are not perfect. Because of the rules for how teens are to be treated in any state run facility, that makes it almost impossible for any state employee to follow. If any love or attention is shown on one boy, the employee is questioned for inappropriate behavior. And they wonder why most boys never get better. They are simply fed, told to follow the rules, don't talk unless spoken to and keep to yourself.

Social Services for any program have to be improved, the rules changes, and more care and attention placed on the kids and teens. This place puts everything under a microscope and brings to live about the feelings of what these boys, the ones no one else wants, wish for but no one will give them. It can be a hard book to read at times, but more care and attention need to be placed on any program for troubled teens both girls and boys. State agencies love rules, and its those strict rules that help lead them to a life later on in prison where things only get worse for them.
Profile Image for Kim.
141 reviews23 followers
April 27, 2016
I read this book for a Professional Book Club reading at the high school. We have an Alternative High School for students who are high high-risk. Working with any teenager, I think it is important to have a perspective on students who have a traumatic past or are troubled, stressed, committing crimes, etc.

The author of this book describes the challenges and successes of dealing and living with juvenile delinquents on an island of Cape Cod. (Do we still call them juvenile delinquents??, for some reason this sounds out of date to me). The teachers live intimately with their students on a Penikese island (which was once a leper colony) for a period of time as a last resort help for the kids who may otherwise be incarcerated.

Unfortunately, his writing wasn't always very engaging and he wrote about so many different kids, it was hard to make a connection with any one student on the island. The author wrote beautifully about the Island's environment and its surroundings, but wrote back and forth between his own life and the experiences with his students, that I sometimes got confused about what was happening.

I think the concept is a great idea to connect with students by isolating them out of any outside influences to change their behavior; however, it was no transition when they were put back into their environment once they left the island.

Take home message.. never give up on kids.
Profile Image for Mark Valentine.
2,105 reviews28 followers
March 16, 2016
Robb has such a natural gift of expression that it is very easy to settle into his memoir and enjoy its sentences and be informed by it. His story, however, is difficult to read because he writes about the struggles in teaching the teenagers who are on the fringes (incarcerated on Penikese Island, hidden in the Buzzards Bay in Massachusetts), marginalized, and at high risk for a life of crime and social failure.

I especially appreciate Robb's focus on the epic, Beowulf, and how that text in particular was beneficial in reaching teenage boys who are struggling against authority. The juvies immediately identify with Grendel and their animosity and rage against the social machine of conformity is a clarion call for all of us to reconsider. Clearly, this memoir is a "sleeper" but I believe it is very beneficial to read.
Profile Image for Cape Fisherman.
17 reviews1 follower
October 12, 2012
Robb's report of his year long journey on the remote Penikese Island tells the story of a man who learned as much from the troubled youth as he taught them in the classroom. A humbling goal of rehibilitating 'last hope' teens, the Penikese School takes a different approach in reaching out and connecting to it's students. A recommended read for anyone interested in children, solitude and the ocean.
Profile Image for Heather Pighetti.
21 reviews1 follower
July 10, 2014
I teach at-risk teenagers, and I was excited to read this book. However, the writing style is incredibly boring and the author somewhat annoying as a person. I have been trying to get through this book for a few months now, but it is not holding my attention at all. It is like torture every time it picked it up. I have read several other books while trying to get through this one, and I don't know if I will ever make it to the end.
Profile Image for M. Lynne.
34 reviews1 follower
January 30, 2008
This is one of those books which makes me want to
call up the author and thank him for his honesty.
This is a true and very realistic account of working with
mostly angry teenagers, all of whom have every reason to be.
What makes this book good is the author does not sugarcoat his own feelings about the various kids he has to live with, and yet he remains mostly able to keep helping them.
Profile Image for David.
403 reviews
February 22, 2009
Fantastic. Contemplative.

I learned about the challenges of the author dealing and living with juvenile delinguents on an island of Cape Cod. It also seemed like her learned a lot of himself, and he exposed me to that journey.
Profile Image for Emily.
7 reviews
May 29, 2016
Very moving, fascinating, grating and a pro pos to the teaching position I currently hold. Highly recommended to both educators and anyone who struggles to understand "lost" or "free-range" children.
84 reviews1 follower
April 22, 2008
This took me over a year to read, usually I give up on books that take me that long. Had some very good parts and some slow parts.
Profile Image for Cathy.
239 reviews7 followers
June 6, 2008
18 mos on penikese island working with troubled boys. Moving but I was unconvinced that they had figured out the best variables for success. 2001.
478 reviews7 followers
June 28, 2010
Highly recommended for people parenting/otherwise dealing with teens with a trauma history. It may not be anything new, but there are lovely insights and it's written beautifully.
2 reviews
September 18, 2015
Heckuva read. Get's right to the heart of the matter. Guy can really write, and the subject is important.
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