Note: I wrote this review back in 2006, when I still identified as “just a crossdresser” (and as a man), but I was recently asked to talk about the differences I’ve had living as a man vs. a woman, and I still think Norah Vincent’s book, despite some serious flaws, has some great insights. (Also, the references to “transsexuals” reflects the language used at the time.)

Norah Vincent’s experience in “Self-Made Man,” her account of posing as a man named Ned off and on for 18 months, is a lesson in what being careful what you wish for. Vincent successfully blends in, but instead of the world of male privilege she’d been expecting, the strains of “being a man” (and of her double-life) lead to a nervous breakdown. For anyone who’s lived life as a man, Vincent’s insights often fall into the “well, yeeaaah” variety, but I suspect (and hope) many women will find the book to be eye-opening.

I was particularly interested in Vincent book as someone who’s both interested in gender issues and one of the estimated 1 in 20 men who’s a regular crossdresser. If you’ll indulge me, I’d like to digress with a briefly primer on crossdressing, since it both colors my thoughts on Vincent’s books and because I’ll be referring to some of the parallels I see with Vincent’s experience. First off, I’m not gay—the vast majority of crossdressers are heterosexual and most of us are married. Second, unlike transsexuals, we’ve got no desire to become women, instead we’re just happy taking the occasional gender vacation. Finally, while in private crossdressers may engage in stylized femininity similar to our more flamboyant sisters, drag queens, those of who go out in public shun the attention that drag queens seek. Consequently, like Vincent our aim is usually to pass unnoticed in the crowd.

Like many crossdressers, Vincent seems to have a discomfort with her native gender. “Practically from birth, I was the kind of hard-core tomboy that makes you think there must be a gay gene.” That sentence points out one problem with the book and with Vincent’s conclusions: she fails to distinguish between sex identity (whether you feel biologically male or female), gender self-identity (whether you feel you’ve got a “masculine” or “feminine” personality) and gender role expectations (how others think men and women are “supposed” to behave). Vincent claims not to have transgendered feelings and I believe her. But Vincent herself makes clear her discomfort with gender role expectations for women and her belief that she’s got a “masculine” personality.

Ironically, Vincent assumes she’s butch enough that her personality won’t be a problem. Instead she frets about her physical appearance even though she’s got a physique (5’10” wearing size 11 men’s shoes) that female-to-male transsexuals would gladly kill for. Vincent spends several pages describing her physical transformation in the sort of loving detail one finds in postings on online crossdressing forums. But to Vincent’s shock, it’s her feminine personality that keeps comes bursting through the physical disguise. Vincent may successfully pose as a man, but she’s almost universally seen as a gay man—an example of society’s syllogism of “unmanly” = “effeminate” = “gay” in action.

Part of it that Vincent constantly stumbled over the subtle do’s and don’ts that men have incorporated into their behavior an unconscious level. (For example, one of the monks actually reprimands Vincent when she refers to another monk as “cute.”) As a crossdresser trying to blend in, I also find the hard part is less the physical transformation as much as trying to understand all the unwritten rules of behavior that women have also learned consciously or unconsciously growing up.

Crossdressers are often (and rightly) taken to task by wives and girlfriends for the assertion that feeling that one has a “feminine side” and putting on a dress somehow inherently understand those who are born and raised as women. And I confess I had the same reservations about Vincent’s experiment. The experiences she sought seem drawn from a rogue’s gallery of middle/upper-class feminist bête noires. The men’s hangout for working class stiffs. The strip club. Men-without-women (Vincent joins a monastery mainly because going undercover in the army or prison presented obvious difficulties). The Glengarry Glen Ross sales job. The Robert Bly-ish men’s movement weekend, beating drums in the wilderness. It’s only the chapter on dating where Vincent talks about something remotely like everyday male-female interaction.

Admittedly, choosing these sorts of extreme archetypes does highlight behavior seen elsewhere, and initially Vincent does caution that her experiences are a really a travelogue of carefully chosen outings, “certainly inapplicable to anything so grand as a pronouncement on gender in American society.” Which—for better of worse—doesn’t stop her from making exactly those sorts of pronouncements later on in the book. Many of those insights are dead on—if not exactly news—for this guy.

This is where Vincent’s lesbianism is advantage. She herself points out having dated men before she came out as a lesbian, she learned that romantic hurt gets inflicted by both genders in equal measure—whereas exclusively heterosexual woman often unfairly assign the blame for such hurt on the gender, rather than the morals of the person inflicting the pain. But more significantly, while a number of feminist writers have written sensitively and insightfully about the masculine psyche, as heterosexual women they’ve assumed that men’s relationships with women are the pivotal foundation of masculine experience. Whereas Michael Kimmel points out in his excellent “Manhood in America,” that American men define their masculinity, not as much in relation to women, but in relation to each other men. Not to say women are incidental to men’s conception of (and efforts to prove their) manhood—men do often take elaborate and extraordinary risks to prove themselves in the eyes of women. But it’s the fear that we won’t measure up in the eyes of other men that’s far more haunting.

In fact the central lesson Vincent learns is how constrained and powerless men often feel. As Kimmel notes, the paradox of male privilege is that while men as a whole have benefited from it, individual men rarely feel the power that feminist critiques tell they have. As Vincent puts it: “Somebody is always evaluating your manhood. Whether it’s other men, other women, even children. And everybody is always on the lookout for your weakness or your inadequacy, as if it’s some kind of plague they’re terrified of catching, or, more importantly, of other men catching.” In a meat-grinder job of door-to-door sales, the sale manager taunts the sales team with the fear of failure. On dates she’s shocked by the power women have and the icy precision with which they wield it. She hates how emotionally constrained she has to make herself to be a believable man.

One gets the sense that her breakdown may not have simply been the strain of the impersonation and the inevitable lies required, but instead may have been just as much do, as another reviewer put it, that “it was just as difficult—particularly for a lesbian, feminist, former Village Voice writer—to handle the disconcerting realization that being a guy is, as she plainly puts it, “is really hard.’”

Men—particularly those in the men’s liberation movement—have been saying that for years. So one of the main values of Vincent’s book is that hopefully women will be more receptive to hearing about some of the downsides of masculinity—and differences in communications styles—from one of their own. Vincent notes that women have taken the attitude that their style of communication is the “correct” one and men are just incommunicative clods who need to be trained how to do so properly. And it’s true that many men are unable to analyze their feelings, let alone articulate them, not only lacking the years of training that women have in both skills, but also having been actively discouraged (by fathers and mothers) from developing them. But Vincent discovers there’s a masculine style of intimacy that women haven’t bothered to see is there, let alone understand. It’s more physical than verbal, it’s often more about letting someone know you’re there rather than overtly offering sympathy—but it’s no less caring. As Vincent says, she learned “about the respectful space a man often needs around him when he is vulnerable or in tears. It may be possible now to interpret the silences of men around me as something more than voids or standoffs, and to feel more comfortable about being present and available to them without always needs our exchange to be explicit or neatly resolvable in my language.”

But being a man isn’t all bad. In her sales-jobs-from-beyond-hell, nerdy Ned becomes a Big Swinging Dick. “Nobody ever thought this Ned was gay,” she notes. Vincent doesn’t comment on why the change occurred, nor is it really clear to me either. But in part it was the clothes. Ned finally gets to wear the blazers and dress slacks Nora had stocked up on. And in the hardscrabble door-to-door sales industry, Vincent in her sharp suits stood-out (as potential management material) from the other salesmen with little cash and less fashion sense, who looked like exactly what they were: hucksters in cheap suits. The other part is it seems Vincent learned the same lesson men learn: fake it until you make it. The interviewers for these high-testosterone sales jobs expected Ned “to brag about himself, to be smugly charming and steadfast, and so I did and I was.” (Ned ended up getting into Norah’s head so much that she ended up being mistaken for a man even out of disguise.)

That air of confidence—even if it’s sometimes actually whistling in graveyard bluster—is one of the few aspects of Ned that Vincent carried through her post-Ned “detox” and she’s appreciative that it allows her to expand her repertoire of behavior. In a similar vein, crossdressing at its best can allow men to flex the parts of their personalities that they feel they can’t express as men. Admittedly, as Helen Boyd, author of the excellent “My Husband Betty,” points out, crossdressers are expressing a man’s idea of what it’s like to be a woman, but again it can—especially for crossdressers who get out in public and interact with people—be an opportunity to step out of the “normal” constraints of masculinity.

Speaking of constraints, I enjoyed Vincent’s chapter where she joins a men’s lib group of the Iron John/Robert Bly mythopoetic variety where the men eventually get together for a weekend retreat out in the woods beating drums and getting in touch with their long-buried Wild Men. While Vincent sympathizes with the mostly broken men there—she says of one man: “you could see that his sense of self was in pieces all over the floor”— she’s a bit bemused by the “toothless mantra and aphorisms, or airy poetry that’s supposed to sound deep but usually isn’t.” As someone who flirted with the men’s movement years ago, but who was turned off for similar reasons, it was interesting to see Vincent also wishing the group would “offer a genuine obstacle, a real trial that would test the limits of a person’s character and sense of self” rather than their faux-Native American/pagan rituals.

The book does have some definite downsides. The chapter on sex is by far the weakest. For starters using a strip club to investigate men’s attitudes toward sex is both spurious and offensive. (I can only imagine the reaction I would get if I posed as a woman and hung out with strippers to gauge women’s attitude toward sex.) Moreover, the two clubs Vincent hangs out at sound like something out of the lower levels of Dante’s Inferno, but Vincent seems naively shocked to see the amount of sleaziness. Vincent’s attitude toward the male libido itself seems oddly Victorian—men are just horny beasts who can’t really help themselves. Now I’ve seen enough male-to-female and female-to-male transsexuals to have a healthy respect for the impact testosterone has on the libido, but the story isn’t quite that simple. There’s definitely truth in Vincent’s assertion that men on the whole think more from the groin and a better at separating lust from love, but on the other hand she wasn’t likely to meet the guys who take a more “womanly” approach to intimacy (i.e. attraction on more of an emotional basis) at a strip club.

The chapter on dating omits Ned’s dates with gay men, which Vincent has mentioned in interviews, which would’ve have provided an interesting contrast. Vincent did mention that they had far more sexual overtones than her dates with women and that the gay men immediately lost interest in her once they found out who she really was. But Vincent didn’t mention whether she also told them she was a lesbian—which obviously might have been a factor. A fair number of female-to-male transsexuals end up as gay men and manage to find partners even without genital reassignment surgery, so I’m not sure the picture is as clear-cut as Vincent might think it is.

In her chapter on her stay at a monastery, I think Vincent actually captures some of the problems of intimacy men have among each other and the sort of hazing that occurs as a new man seeks to proved himself to other men. But Vincent fails to look at how much of the hazing and emotional constriction is due to the environment rather than the gender. From what I recall of a ex-nun’s account of her time in the convent, a similar process of weeding out potential candidates went on, as well a tamping down on intimacy (also to prevent potential homosexual encounters as well as ensure each nun’s attachment remained on God), etc.

But it’s the conclusion of the book that for me is especially problematic. On the one hand, I’m glad she sums up the downsides to her experience. Vincent herself says that she became the “tired and prototypical angry young man” who she used to hate for droning on about his problems. “But after living as a guy for even just a small slice of a lifetime, I can really related to that screed and give you one of my own.” But Vincent is unable to move past the pain. Perhaps it’s too new to her. As men we’ve grown up with these constraints and as “Brokeback Mountain’s” Ennis Del Mar says, “If you can’t change it, then you gotta stand it…” So we may chafe it our constraints but they’re not as raw as they are for Vincent. And Vincent’s lopsided forays into the world of men might have something to do the pain she feels about being a man—ironically the final bits written after temporarily checking herself into a locked psychiatric ward are written in a clipped tone that reveals almost nothing about what’s going on in her head (maybe Vincent hasn’t shed Ned as thoroughly as she thought).

For transgendered people (in the broadest sense of the word, including not only transsexuals, but crossdressers, drag queens, etc.), it’s heartening to hear that Vincent— who wrote some notoriously trans-phobia things a few years ago—has developed a deep sympathy for us. (This isn’t explicitly mentioned in the book, but Vincent has mentioned on the talk show circuit.) However, Vincent does talk about the ever-increasing difficulty she had trying to sustain simultaneously maintain male and female personas—“this cognitive dissonance essentially shut down my brain.” Ironically, for someone who’s an advocate of androgyny, Vincent decides she needs to banish Ned entirely to maintain her sanity. “I could not live in both worlds at once, so I chose the side to which habit and upbringing have accustomed me….”

Unfortunately, Vincent generalizes from her personal experience that “I can’t help almost believing, after having been Ned, that we live in parallel worlds, that there is at bottom really no such thing as that mystical unifying creature we call a human being, but only male human being and female human beings, as separate as sects.” I’m reminded of Mark Twain’s adage that a cat having sat on a hot stove will never again—nor a cold stove either. Vincent has burned herself (perhaps deeper than she realizes) with her gender bending, and in talk shows she’s shown an unfortunate tendency to warn others against “messing with gender.”

Which is probably one reason Vincent doesn’t seem like she’s a found integrated sense of manhood. On the one hand, she sees men as the sorrier sex. On the other, she still seems to harbor “gender fantasy” ideas about masculinity—such as her rhapsody to the “authenticity” of the male handshake. Girlfriend, lemme tell ya, men’s handshakes may not involve the fake smiles that women-to-women greetings can have, but there’s also a lot of subtext going on there too. Believe me, I’ve endured more bone-crushing let’s-see-who’s-top-dog handshakes than I care to remember. That said, if Vincent has contradictory attitudes toward masculinity, it’s undoubtedly in part because society also does.

Had Vincent participated in more “regular Joe” male pursuits, she might have discovered that there many times when being a man isn’t “a series of unrealistic, limiting, infuriating and depressing expectations constantly coming over the wire”—in fact it can be a joy (and not just from the privilege of being the cock of the walk). Or why, although I enjoy putting on a dress and taking a gender vacation from time to time, I’m happy to remain a man.

Or so I thought at the time…