Crossing: A Memoir

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We have read the stories of those who have "crossed" lines of race and class and culture. But few have written of crossing—completely and entirely—the gender line. Crossing is the story of Deirdre McCloskey (formerly Donald), once a golden boy of conservative economics and a child of 1950s and 1960s privilege, and her dramatic and poignant journey to becoming a woman. McCloskey's account of her painstaking efforts to learn to "be a woman" unearth fundamental questions about gender and identity, and hatreds and ...
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We have read the stories of those who have "crossed" lines of race and class and culture. But few have written of crossing—completely and entirely—the gender line. Crossing is the story of Deirdre McCloskey (formerly Donald), once a golden boy of conservative economics and a child of 1950s and 1960s privilege, and her dramatic and poignant journey to becoming a woman. McCloskey's account of her painstaking efforts to learn to "be a woman" unearth fundamental questions about gender and identity, and hatreds and anxieties, revealing surprising answers.
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Editorial Reviews

Maxine Kumin
A highly readable, dramatic account.
New York Times Book Review
Publishers Weekly - Publisher's Weekly
Transsexuality has fascinated mainstream readers since 1953, when former U.S. serviceman George Jorgensen went to Sweden and, to banner headlines, returned as Christine. Since then, there has been a string of notable memoirs of gender crossing, including Geoff Brown's sincere I Want What I Want (1966), Jan Morris's meditative Conundrum (1974) and Holly Woodlawn's campy A Low Life in High Heels (1994). McCloskey's own odyssey from Donald to Deirdre is closest to noted journalist Morris's, in that it charts the life change of a highly regarded public figure--McCloskey is a world-famous conservative economist--who finds fulfillment as a woman after four decades of living as a man. McCloskey forthrightly describes her upper-middle-class youth in Boston, her early and lifelong interest in cross-dressing, her education and eventual success as an academic and her marriage and children. In her late 40s, McCloskey decided that she was not simply a heterosexual cross-dresser but a transsexual and decided to undergo a series of operations to become an anatomical woman. Her memoir effectively details the pain involved: a bitter divorce, insurance companies' refusal to cover surgeries and her sister's repeated attempts to block the process legally. McCloskey's proclivity to jump around in time, her tendency to disrupt the flow of her story with social and political digressions and the constant placing of additional thoughts and ideas in bold text throughout the narrative distract from her story--but her courage nevertheless shines through. (Nov.) Copyright 1999 Cahners Business Information.
Library Journal
McCloskey, married for 30 years, the father of two, and an economics and history professor, was a secret cross-dresser for 41 years, as "Jane." At 52, he realized that his real identity was as a woman and began transitioning as "Dee" to become "Deirdre." At the heart of this fascinating and poignant story, told in the third person, are the two years (one in Holland) of hormones, multiple surgeries, electrolysis, and a legal name change, all part of the physical and emotional "crossing" from male to female. The big-boned Deirdre describes the joy of "passing," the fear of being "read," and the occasional loving support she has received in contrast to painful estrangement from family, friends, and colleagues. At times revealing, humorous, and provocative, this often overwrought and self-righteous book is marred by minor mistakes, includes gross generalizations about gender differences, and inconsistently employs italicized bold type to represent internal thoughts. For larger public and academic libraries.--James E. Van Buskirk, San Francisco P.L. Copyright 1999 Cahners Business Information.
Some conservative economists proved to be gender libertarians, whereas some feminists proved to be gender authoritarians. So Donald McCloskey (economics, U. of Iowa) found out when the married father sought his true gender identity as Deirdre. Includes b&w photos of stages in the transition. Annotation c. Book News, Inc., Portland, OR (
Kate Bornstein
Deirdre McCloskey's brave, witty, dizzying autobiography positively drips tears, sex, danger, and courage with each sashaying step.
Peter Skinner
Deirde McCloskey tells a searing tale of the traumas and rewards of gender change. This book is a powerful indictment of legal, medical and institutional obstruction to gender change.
Kirkus Reviews
A testimony to her struggles and courage, Crossing invites the reader to enter Deirdre (formerly Donald) McCloskey's mind as she decides to become a woman after a lifetime as a man, husband, and father. A renowned professor of economics at the University of Iowa, Donald McCloskey had to fight tenaciously to realize his inner call to become a woman against such foes as his sister (who had him repeatedly committed against his will for psychiatric evaluations) and his marriage family (who, in the book's most heart-wrenching scenes, renounce their father and former husband). Mixed with this trauma, however, is McCloskey's blossoming sense of self and her discovery of a true community of friends who love her for the woman she is, not the man she was. The cantankerous halls of academe provide the setting for many of the memoir's intriguing political debates: feminists argue that McCloskey is not a women and therefore should not join female faculty groups; conservative economists accept McCloskey's new self with libertarian nonchalance. Oddly enough, though, McCloskey's views of gender seem to become more strongly reified through her experiences. Men are combative; women nurturing. Men barter for gain; women give for comfort. One is left wondering how a woman brave enough to undergo the tribulations of losing a family and to face the possibility of professional contumely could have emerged from a man so self-parodically timid of his femininity that he could not bring himself to describe his car as "dark blue, with cream trim." This Trojan horse of a memoir approaches under the guise of sexual equity yet closes with gender stereotypes still firmly entrenched. Crossing remains a tribute tothe power of resisting society in order to realize personal fulfillment, but McCloskey would have done so with a more incisive voice if she did not seem to believe so strongly in the many gender stereotypes she attempts to undermine. (10 halftones)
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Product Details

  • ISBN-13: 9780226556697
  • Publisher: University of Chicago Press
  • Publication date: 9/28/2000
  • Edition description: 1
  • Pages: 282
  • Sales rank: 1,262,005
  • Product dimensions: 6.00 (w) x 9.00 (h) x 0.90 (d)

Meet the Author

Deirdre N. McCloskey is University Professor of the Human Sciences at the University of Illinois, Chicago. She is the author of nine books, including The Vices of Economists and If You're So Smart, the latter published by the University of Chicago Press.
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Read an Excerpt


A Memoir

By Deirdre N. McCloskey

University of Chicago Press

Copyright © 2003

University of Chicago
All right reserved.

ISBN: 0-226-55668-9

Chapter One

Before Deirdre there was Jane

The big event of that half week was on the way home from the East Coast to
Iowa City. Donald had arranged to stop in a Chicago suburb for Saturday
night, going to a motel to meet his crossdressing friend Lucy. Then they
planned to navigate the parking lot of the motel next door to attend their
very first crossdressing meeting.

The meeting was for the Chicago chapter of Tri Ess, the national
crossdressing sorority, which Donald had joined through his Chicago BBS
girlfriends. He had been excited for weeks and planned it like a military
campaign, lugging from Iowa City to Philadelphia to Baltimore to Chicago a
big suitcase filled with his outfit for the evening and his Philadelphia
loot. He chose his Marilyn Monroe wig and a black crepe dress inherited
from his wife.

Lucy arrived already dressed, and Donald complimented him, as women do:
"You look great!"

"I found a cosmetician in my suburb who does makeovers on crossdressers."
Lucy looked like a suburban housewife, not a drag-show star. Later Donald
bought some dresses at the woman's store and had a makeoverhimself. The
cosmetician's youngest son was a drag queen and competed in beauty

Lucy got anxious and wanted to go, and Donald/Jane agreed as he struggled
into the dress, a little small: "I'll come over when I'm ready. Zip me up,
will you?" Better to go by myself, he thought. The probability of being
read rises with the square of the number of crossdressers in a group. (One
is "read" like a book, detected in the wrong gender.) The man on the
street reads the least convincing one of a group and then notes that all
these women seem large.

Stepping out into the hallway of his motel half an hour later he was
frightened, imagining detection and the punishment of scorn. On the stairs
going down, avoiding the elevator with its long looks, he walked by a
couple coming up, but they didn't appear to read him. Clicking in heels
around the back of his own motel, he walked into the open toward the other
one. It was Donald's first time out-of-doors as a woman, apart from a very
few nighttime walks in empty streets in Princeton and Chicago. It felt
natural. He hitched up his skirt and leaped over a little stream between
the two motels, scuttling through the other parking lot in full drag in
the glare of the late afternoon sun. Still outside, as he approached the
entrance to the meeting room he encountered a woman: Oh, oh; she'll read
me. Wait: no.
It was another crossdresser on his way to the meeting. Easy
to read when you're looking for it.

When Jane came into the meeting room it was filled with crossdressers, and
his first impression was, These women are huge! They were a third bulkier
than a roomful of genetic women. It seemed to him that the average
crossdresser was above average in height. Can't be. (It can, though. If
there is a deficiency of testosterone in adolescence the bones do not
close off early in their growth. That's why boys who mature early tend to
be short and why the castrati playing women's roles with women's voices in
early opera were unusually tall for men. Not that there's any evidence of
testosterone deficiency in crossdressers, mind you. Just guys.) Still, the
clubs ordinarily do not have really big men in them, which makes one
wonder how the bigger crossdressers and gender crossers are able to
express themselves. Perhaps in football.

Most everyone was cordial, though some of the prettier ones seemed snooty.
Jane later met one of the snooty ones in Atlanta at a conference
discussion on gender-crossing life for professionals and found him shy and
uncertain about his future. They all had name tags, and Jane spotted and
hugged Suzy, one of the BBS friends he had not met in the flesh. Suzy was
"Susan Roberts," which is to say that in the convention of choosing
feminine names among crossdressers he was "Bob" as a man. He was tall,
thin, blond, breaking up with an intolerant wife whom he still loved, and
struggling with his identity.

"I went to therapy for two years with my wife," Suzy said.

"Two years. Did it help?"

"In a way. We're getting divorced. The therapist finally said to me,
'Look: your wife is unable to adjust. Some women can handle it, others
can't. She has her own reasons.'"

When the official meeting broke up Jane was standing next to a vivacious
crossdresser named Robin, a little taller than he was, with a
Chicago-accented voice. He was brassy, intelligent, extroverted,
complaining knowingly about the administration of Tri Ess. (Jane learned
later that it was his first meeting too.) He proposed that he, Jane, Suzy,
Jane's friend Lucy, and another crossdresser go out on the town. Lucy
demurred, and the remaining four musketettes set out for a lesbian bar.

The tougher straight bars are good places to get killed. Gay bars also
have the undercurrent of lethal violence that is the male condition. The
lesbians are more civilized and don't mind having crossdressers around,
regarding them as harmless. The first place was quiet, though enlivened by
the crossdressers (ten of them, others from the Tri Ess meeting, crowded
along a set of bar tables like a typing pool out for an after-work drink)
and then by an ineffectual fistfight between two lesbians in a love
triangle. Jane danced the way the kids do, by himself, different from the
lovely paired regularity of square dancing. A butch dyke paired with Jane
for a while on the dance floor, and Jane gave himself over to ecstasy.
"Just dance!" the dyke said, "Don't come on to me." When he had to go to
the bathroom Jane had the others take a picture of Suzy and him outside
the "first ladies' room." Pictures are big among crossdressers. How many
crossdressers does it take to go the ladies' room? One hundred: one to go
and ninety-nine to take pictures.

They went to a much hotter lesbian bar called Temptations on Grand Avenue
in the Chicago suburbs. It was in a strip mall next to a tire store, and
when the stars came out it glittered. Robin had been to the place before,
as everyone else had too. They regarded Jane as bold to go with the girls
barhopping on her first night out. What made Jane run? Square dancer,
middle-aged college professor, father of two, thirty years married, pillar
of the community shook to the beat of the drum with a hundred others of
assorted genders and sexual preferences. The cool dance the kids were
performing turned out to be steps that Donald had learned the year before
at a square dance in Iowa City. The company was diverting, and each set
was long.

Robin introduced Jane to a lesbian sitting at a little table crowded with
others. She looked like a suburban woman. Kids. Van. She was in her
forties, dressed butch but not too. Acceptable in the mall. Though women
can get away with more.

"I was married and have grown children," she told Jane. "I only figured
this out a few years ago."

"How have they adjusted? I mean your family?" Jane was always interviewing
people, gathering data like some sort of anthropologist, an anthropologist
who could go native.

"Poorly." It was not unusual news. In the gay and lesbian community, Jane
read later, they spoke of 80 percent: 80 percent of your family and
friends eventually adjust, perhaps after years of rejection, and go on
loving you after a fashion. That leaves 20 percent. As they talked about
rejection and acceptance Jane warmed to her, and he found himself flirting
as the femme. They danced for a while to the throbbing music, then she
bought Jane a beer. In his three later visits to Temptations Jane looked
for her, a regular it was said, but never saw her. Jane/Donald was still
unclear about his preferences. Gender crossing is a matter of identity,
not affectual preferences. A third of post-op transsexuals go on loving
he would remind himself out of his new learning. Not that I'm a

He went to Temptations only those three more times. Chicago is 240 miles
from Iowa City. (Deirdre would explain to Dutch people where Iowa City
was: "Near Chicago." Oh, how far? they would ask, supposing she meant 50
kilometers. "It's 500 kilometers due west, as far as Amsterdam is west of
Berlin. Not too far.") Donald never did go to similar places closer to
home. Fear, security, the closet.

Robin said later that he was struck that first time by Donald's reaction
as Jane to the unbuttoned scene. Jane came up to Robin and gushed, "Lord,
I just love this!" The gushing seemed to Robin significant, signaling more
than a guy in a dress. Robin was coming to terms with his own gender
crossing and went full time the next month, just before Donald's dam
broke. Robin had the operation in Montreal a couple of months after
Deirdre had it in Australia. Deirdre called Robin afterwards and they
talked about how they just loved this.

He got back to the motel room at 3:00 a.m. and had a 10:00 a.m. flight
home. That afternoon in Iowa he was teaching business economics in his
macho, I'm in charge style. As men brag about their little exploits, he
dropped hints to the kids about his wild night at a bar in Chicago. He
left out the detail that he had danced through it in a cocktail dress.

He went to the first meeting of his local club, Iowa Artistry, thrilled
and frightened. The meeting was held in a big motel out by the interstate.
He was pleased to drive across town dressed-This is how it feels to be a
-but nervous about coming into the motel as Jane. In fact respectable
motels are cordial to crossdressers, because they are good customers.
Aside from makeup on the towels, they are no trouble. They don't drink
much, and they don't do sex or violence.

Iowa Artistry was forthrightly Iowan. The meeting was like a Kiwanis Club
in drag, with reports from the treasurer and mild quarrels about
governance. Jane had long, earnest talks about living with crossdressing.
His attention was held by a thirty-something gender crosser named Anna who
worked as a technician in a corporation south of Iowa City. She had been
full time for a year and had finished electrolysis on her beard down in
Dallas, which he quizzed her about. She was intelligent and sympathetic,
once married, kids. Donald was deliberating, unaware. But of course I am a
heterosexual crossdresser. Just wondering.

Donald's wife dreaded people's finding out and was appalled that after the
meeting a group of fifteen or so went on to a local bowling alley. Nothing
happened, no one found out. One attempt at rolling the ball left
Donald/Jane's false thumbnail halfway down the alley, and he had to walk
out to retrieve it, amused and embarrassed. He watched closely another
crosser, very effeminate. She was there with her male lover, the two
making an ordinary husband and wife. Three years later she had her
operation and they were legally married. She worked as a telephone
operator. The daily practice and her determination had made her voice
good. The heterosexual crossdressers, by contrast, were breezily male in
their voice and behavior. Jane didn't think much about where he fit in.

There was only one other group in the bowling alley, at the opposite end.
Eventually one of them came over to see what was going on, and a
crossdresser replied with a smile that they were a "mixed league" of
bowlers-a man and a woman in the same body. When crossdressers meet
straight people in a group it works fine. Crossdressers call it "gender


Excerpted from Crossing
by Deirdre N. McCloskey
Copyright © 2003 by University of Chicago.
Excerpted by permission.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
Excerpts are provided by Dial-A-Book Inc. solely for the personal use of visitors to this web site.

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Table of Contents

Part 1: Doubt
1. Boy to Man
2. Marriage
3. Internet, 1995
4. Professor Dressed
5. Clubs
6. In the Ladies' Room
7. Boldness
8. Epiphany
9. Losing Family
10. Academic Drag
11. A Day You Feel Pretty
12. Premarin
13. Sweet October
Part 2: Struggle
14. Outed
15. "Welcome"
16. The Cuckoo's Nest
18. Then Why Are You Doing This?
19. Chicago
20. Changing
21. Sister's Last
22. Professional Girl Economist
23. Farewell Speech
24. Dutch Welcome
25. The Worst Days in February
26. Passing
27. Yes, Ma'am
Part 3: Across
28. Vriendinnetjes
29. Women's World
30. To Make Up for God's Neglect
31. Merry May
32. Starting
33. Finishing
34. A Post-Menopausal Woman on Hormone Therapy
35. Facelift
36. This Is How We Live
37. Dutch Winter, 1996
38. Going Home
39. Costs
40. Iowa Drag
41. Professora Traveling
42. Second Voice
43. Makeup
44. Getting There
45. Differences
46. Christ's Mass 1997
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A renowned economist and historian, a husband and father, Donald McCloskey (now Deirdre) had crossdressed for years without wanting more. But at age fifty-two a sense that he was denying his real identity grew to the point where he knew he had to become a woman. Crossing is the poignant story of this realization and its consequences.
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Customer Reviews

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( 4 )
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Sort by: Showing all of 4 Customer Reviews
  • Posted March 5, 2014

    more from this reviewer

    ¿Being a woman is what you do... not what your wear. Caring, wat

    “Being a woman is what you do... not what your wear. Caring, watching, noticing.” So says Deirdre N. McCloskey, quoting lessons learned when she was still Donald. He contrasts “the self-deprecating style women use when charming others of their tribe” with “the boasting of my tribe.” And he realizes, like a New Yorker whose heart is really in the South, that he wants to be someone else.

    I was an adult when I became an American. My husband and I forced a whole new world and culture on our children. There were times we wondered if family and friends would forgive us. But for Deirdre, the change is even bigger, and forgiveness can be hard to find. Doctors might easily offer a nose-job to woman who wants to change her face, but when a man wants plastic surgery to seem more womanly, the psychiatrists have to be called, and sometimes even lawyers. After expensive legal procedures (oh yes, we had those to become American) and stays in mental wards (we had none of those, but we did have to be physically examined to prove we were healthy), Deirdre finally embarks on a long series of operations. Insurance won’t pay, claiming she’s either ill, but not treatable, or mad and shouldn’t be treated. Complaining that “gender crossing is not a psychosis, and there is no medical evidence that it is...” Deirdre finally concludes “Identity is both made and not made,” while making for herself a very human, very normal new identity.

    As an economist, Deirdre is well-established, multiply published, very observant and very learned. One thing I particularly enjoyed about this book was her recognition of differences between male and female points of view of economics in relationships. “People have two ways, exchange and identity. Men can grasp only exchange,” she says, illustrating her point with a lovely scene where a wife recites who gave her each ornament in the collection around her house. To a man they’re just items of property; to a woman they stand in for the friends who gave them.

    The biggest surprise for me in this book was the author’s faith. I wasn’t expecting to see a connection drawn between finding gender and finding religion, though “rebirth” certainly makes sense in both realms. Faith does too; when he couldn’t imagine continuing as he was, Donald had the faith (and the money) to embark on his journey to Deirdre. While some readers might find it hard to imagine why, and some people of faith might find it hard to accept, Deirdre’s advice to “try to think of Jesus as a God of love” is wisely given and well-taken.

    A fascinating, absorbing memoir, Crossing invites us to examine who we are, and how much we care for our neighbor, in the light of someone who learned who s/he was not.

    Disclosure: I was lucky enough to get a free ecopy of this book.

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  • Anonymous

    Posted July 5, 2008

    A reviewer

    I enjoyed this book immensely. Crossing is a fine memoir of an economist who underwent sex reassignment surgery in order to become a transsexual woman. McCloskey begins in childhood and shows the reader how his cross-dressing 'hobby' grew more intense through adulthood, marriage, career, and life. In middle age, McCloskey decided that it was time to get serious, so to speak. After consultation with his therapist, serious rumination, and research, McCloskey began the long, difficult physical and emotional process of transition. His family (wife and kids) seemed to be against it, and apparently tried to talk him out of it. He did it anyway. His wife divorced him, as a result of his transition. Many of his friends supported him, however, including his colleagues and dean. His mother also seemed supportive. What effort was required to become a woman! Surgery, hormones, travel, consultations, huge fees. Some physical changes were obviously required---e.g. genitalia and breasts. But he also need to correct a very masculine-looking face and a masculine voice. Since he did this mid-life, aging also needed to be addressed. Much of the book deals with the lengths to which McCloskey went to 'pass.' When McCloskey transitions to a woman, the book's focus shifts to what it is like to be a woman in a man's world--especially, a late middle-aged woman. McCloskey is most insightful in explaining what it means to be a woman after a lifetime of manhood. The book's biggest weakness is the relative inattention to sexuality. Pre-transition, one gets the impression that Don 'got off' dressing up as a woman--and viewing transsexual pornography. He seems to acknowledges the weirdness of it all. I didn't see anything wrong or problematic with his sexual behavior, pre-transition. Nevertheless, this aspect of his pre-transition life--sexuality--could have been more detailed. After Don becomes Deirdre, sex more or less disappears from the equation. This was disappointing because Deirde, female in every sense, including breasts and genitalia, surely has sexual feelings. What are they? And why are they mostly missing from this great memoir? Maybe this topic was too private, but this is a memoir and this reader wanted more. This is a poignant memoir, well written and highly readable. Despite the weaknesses noted above, I recommend this book to readers of memoirs, transsexual memoirs and memoirs in general. It's a unique book and exceptional memoir. I would welcome sequel.

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  • Anonymous

    Posted January 26, 2001

    You Go Girl!

    Admittedly I hate change. I despise it in any form in my life and often catch myself looking at it through the negative lens rather than the positive. Reading Deirdre's account provoked in me therefore a huge knot in my stomach, as the changes she keenly steered her life through are just downright amazing! If only I could have just a drop of her courage it would be enough to get me through a lifetime of change. Amazingly I felt changed as well when I finished with the last line and astoundingly I felt comfortable both for Deirdre and for myself. I have a new understanding of what it is like for those who go through this process and the gender defining issues involved. I did not find Donald to be selfish or narcissistic. I saw a man with courage to live the truth as he defined it to be. Admittedly the third person narrative was at first irritating to my reading. But as I read on I began to realize that she could not have written this a better way to bring home the understanding from her perspective. There are enough transgender accounts and texts out there that present someone's view of another's crossing. It is only through this fine writing style in third person that I was able to see the same traits in his transition to Deirdre, much like a butterfly spreading its wings after a long hibernation. And WHAT a beautiful butterfly she is! I feel terribly sorry for her families who were unable to cope with her journey of change or understand it. However, because of my dislike of changes their apprehension and grief makes sense to me. They grieve that they have lost a father and in a gender sense they truly have. Unfortunately they can not see what they have or could gain from Deirdre. I feel very sad for them and anyone else that does not completely understand.

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  • Anonymous

    Posted April 13, 2000

    A transgender bildungsroman

    Deirdre McCloskey's story of her mid-life transition from male to female is a suspense thriller, anthropological study, academic novel, and bildungsroman all in one. With candor, wit, joy, pain, feminine sexiness, and intellectualism, Deirdre brings the reader along with her as she describes her journey, from hints of transgender identification in early life, to the realization, at 52, that this is about more than simply cross-dressing. Through its internal style, which reminded me often of Madame Bovary, the book takes the reader along, pondering the logistics of combining public cross-dressing holidays with academic business trips, finding the doctors and deciding on the surgeries, suffering the fear and humiliation of being incarcerated for wanting to be a woman, and feeling the exhilaration of acceptance by friends, colleagues, and clerks in stores. Most remarkably, Deirdre McCloskey gives frequent insight into differences between male and female behavior in the same setting--including her own past and present behaviors. That's a thought-provoking gift to the reader, and a unique advantage for anyone to have. Ultimately, this book is about the journey to liberation of the self--like Joyce's Portrait of the Artist as a Young Man or Walker's The Color Purple. And we root for Deirdre just as we did for Stephen and Celie.

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