In the competitive field of personal branding, Gregory Gorgeous is considered a champ. His vlogs (like blogs, but with video), which consist mainly of cosmetics tutorials, have generated 25.6 million YouTube views, presumably by people who want to look like a Real Housewife of Orange County. I’ve watched the tilt of his Carol Brady hairdo and the gloss of his Kristen Stewart lips as he offers a lesson on thermal hair spray. “Stay gorgeous!” he says. I’ve also witnessed his account of the night he lost his iPhone in a club, a story that wends, for eight unbearable minutes, along a road to nowhere. Weakly leveraging the “born this way” message of the times, he makes paid and unpaid endorsements (though there’s never any distinction) for his “favourite things,” such as sparkly fuchsia platform pumps and a line called Swedish Skin, in his videos and on officialgregorygorgeous.com.

One of the countless young Canadians seeking fame and fortune in “lifestyle blogging,” Gorgeous kick-started his YouTube semi-celebrity as a bored sixteen-year-old in 2008, then followed a well-worn path to semi-riches: launch a YouTube channel, tweet about yourself (he counts more than 48,000 followers), secure sponsorship from advertisers, bask in the attention. He is part of a digital black hole that’s sucking up the most superficial minds of his generation, including a phalanx of aspiring PR girls who spend all day photographing themselves, a fraternity of party-hearty amateur rappers who hoist red plastic cups in a kind of ne’er-do-well salute, and platinum blondes who go by names like Raymi the Minx, and Lauren O’Nizzle (real name: O’Neil). On Lauren Out Loud, the latter blogs about dyeing her cat’s tail green, and her love of “kitty-cat videos”; this recent Toronto Star intern is now qualified to be, in her words, an “instructor of online journalism at a local college.” At twenty-six, she has a modest 6,200 Twitter followers, but she is a leading Blondebot (also her word) of the personal blogging scene, with a creative signature that does little more than establish how cute she looks in a tank top.

Gorgeous and O’Nizzle are only two of the attention-seeking asteroids careening through the universe of personal branding. What these kids have in common is a goal: to become a new order of quasi-socialite. What they stand for, sadly, is nothing.

This alone should irk the hell out of anyone who is older than they are, and it frequently does, particularly the glib fortysomethings of my peer group, who revel in damning shallowness. My people also profess to distrust all conspicuous self-promoters. So we can find no better target for our ire than kids who self-promote without so much as a product to sell.

But I’ve learned a few things about this axe we’re grinding: First, that protesting their inanity on the Internet is as futile as spearfishing with a toothpick. Second, that lifestyle bloggers haven’t cornered the market on being inane. And finally, that they weren’t just “born this way.” Okay—they were. But all little monsters were spawned by something. And that particular something is my Gen X. That’s right—it’s kind of our fault.

Grown-ups, here are the harsh tokes: We are the ones who made brands out of every nostalgic pop culture totem from Tootsie Rolls to Beavis and Butt-Head. We are the ones who started the irrational obsession with the concept of branding, by reading our copies of No Logo and lobbying for bike lanes while driving our Subarus to Starbucks. (It’s embarrassing when the worst cliché about your peer group is actually true.) We are a generation of both thumb-twiddling and eye-gouging ambition, who spent half of the ’90s resenting the boomers—for soaking up all of the riches and leaving us the scraps—and the other half thrashing around in the deep end of online enterprise.

Our resulting self-obsession encouraged the Millennials’ worst narcissism, yet still we scoff.

By many accounts, the concept of the personal brand was first introduced by marketers Al Ries and Jack Trout (both my parents’ age, as it turns out), with their 1987 book, Positioning: The Battle for Your Mind, in which they advise corporate cogs to use a “positioning strategy to advance your own career.” I was in my twenties when that notion received a major public airing, in a 1997 article in Fast Company, then a new business magazine with its lens tightly focused on tech-driven start-ups. The dot-com universe was booming with overvalued companies that would soon implode, and although most of us didn’t have a clue what the Internet meant, we hoped it would result in gainful employment. The author of the Fast Company piece, management thinker Tom Peters (or “tompeters!” as he brands himself) exhorted readers to develop an indelible mark, like the Nike swoosh or the Starbucks siren. “It’s time for me—and you,” he wrote, “—to take a lesson from the big brands, a lesson that’s true for anyone who’s interested in what it takes to stand out and prosper in the new world of work.” Today his essay reads like Orwellian fiction, an eager fist pump for the commodification of the self. As for the locus of branding’s next boom, Peters identified the Internet.

The tech boom was about young people propelling themselves into the future, but unfortunately we were conditioned to our very core to wait our turn—for a tap on the shoulder that meant we could join the boomers in the traditional job market. Waiting had become a way of life; fearing unknown consequences, we practically invented putting things off. So our response to Peters’ call to arms was conflicted. First, inspiration (“I have to figure out my brand”), followed by panic (“I have to figure out my brand!”), followed by embittered defiance (“Who needs a bloody brand anyway?”).

In the decades after the Fast Company story, we became further discouraged by fear of failure: as people, at work, and eventually as parents. Instead of doing things, we jabbered on about our lives to anyone who would listen, voicing our “takes” more than any previous generation had, a penchant that gave birth to a ubiquitous breed of personal, confessional writing, from “young gal in the big city” columns in print to “young mom coping with Chardonnay” blogs online.

When a new generation appeared on the scene, with new media at their fingertips—and brimming with self-esteem, thanks to their poor, well-intentioned parents—they deftly realized the concepts we struggled to wrap our heads around. The supersize personas that emerged, kids who were self-assured and style obsessed, invited damning generalizations. But I’m looking for reasons to understand the monstrosities we created, and maybe even to cut them a little slack.

Toronto’s Casie Stewart is a pixie blonde with an ardent audience—50,000 unique visitors to her blog, This Is My Life, and a Twitter following of over 7,000—that consists of 60 percent young girls. That crowd, she says, tells her all the time how much she inspires them to be “positive” individuals whose purpose is to enjoy “the VIP life.” This entails attending openings and junkets, and promoting products (be they Puma shoes or Virgin America flights), often in return for free stuff. Air New Zealand recently sent Stewart to cover its fashion week, where she drank in the experience of riding around with a car and driver. When we meet, just after the Halloween weekend, she tells me she spent the day working at her friend’s vintage fashion store in downtown Toronto, in exchange for free clothes.

Stewart seems sunny and rather sweet, a twenty-nine-year-old who blogs about going to the gym, hanging out with her friends, and sunbathing topless—though she says she prefers not to “show my boobs” as others in her peer group do, “because my mom reads my blog.” (In her teens, she posed in a not-so-fashionable bikini as a Sunshine Girl in the Toronto Sun.) When I check Klout, a company that “identifies influencers on topics across the social web,” I find her score is a healthy fifty-eight out of 100. The Klout score is an entirely scary invention that quantifies registrants’ ubiquity and audience reach by looking at their social media profiles and interactions. Gregory Gorgeous ranks a sixty-one. Lauren O’Nizzle, a friend and digital soulmate of Stewart’s, scores a sixty-three. Kim Kardashian’s hovers around ninety-two.

I see where Stewart is coming from. For someone with small-town roots (Cambridge, Ontario), living large in the big city of Toronto is a thrill. She runs her personal brand as a full-time job, having been fired from a marketing position at Much mtv for excessive blogging on the job. She employs a paid intern, and has managed to climb out of a tuition-fuelled $30,000 debt through an appearance on the W Network’s financial makeover show, Maxed Out. She now makes bank by speaking to companies about ramping up their social media strategies.

“The brand,” she says, “is bigger than me now.” When she describes how she built it, I’m reminded of an interview I read with marketer Hubert Rampersad, author of the bestseller Authentic Personal Branding: A New Blueprint for Building and Aligning a Powerful Leadership Brand, part of a recent pack of books instructing us all to self-market. Branding, he writes, is about controlling the impression people have of you, and making that impression desirable (which is not, of course, the cakewalk these authors make it out to be). Building an authentic personal brand is a way of “improving yourself continuously.” Though we’re obsessive about improvement, my generation might feel almost as embarrassed touting Rampersad’s advice as we would be donning folk costumes and dancing the mazurka. But because Stewart’s peers have not known self-doubt as much as we have, and because they’re so much better at manoeuvring in the digital age than we were, they feel perfectly at ease. “I think to myself,” Stewart says, “that I created all this by putting out positive thoughts and accepting things into my life. I dreamt about doing this—getting the star treatment—and now I am.”

Sidling up to every willing PR agent, then, is a Millennial way to present the authentic self, about as awkward and disingenuous as New Age was thirty years ago. Yet Stewart seems blissfully, radiantly, ear-to-ear happy.

But not everyone finds their bliss in doing dumb stuff: not style and society blogger Nolan Bryant, who is about to turn twenty. Though his mini-fame resulted from his smart use of digital resources, he is nothing like Casie Stewart. For him, the star treatment is a beast of a different stripe. A follower of fashion since childhood, he is known for his long hair and his six-foot-five stature, and for wearing capes. Those who follow his personal brand assume he comes from money. In truth, like the Factory crew orbiting Andy Warhol, or Truman Capote orbiting Babe Paley and Slim Keith, he is enthralled with the rich and famous. His budding career is as a social chronicler/new media socialite, and he’s good at it.

Another small-town kid (from Newcastle, Ontario), Bryant belongs to a WASP family, he says, but not a society one. His father worked in corporate communications, promoting hotels for Fairmont. As a boy of six, he would find himself sitting rapt in the Library Bar of the Royal York Hotel. “I believe the socially affluent in Toronto to be fascinating,” he says, paraphrasing a Herb Caen quote about “cockroaches and socialites being the only things that can stay up all night and eat anything.”

Bryant began attending Toronto Fashion Week shows when he was in grade nine, via an aunt who worked at CBC and had a connection to the television show Fashion File. That was the era, he says, when “everyone worked in magazines or was a buyer.” Now, he observes, “everyone is a blogger. Everyone has a Twitter account. So many of them hang around outside at fashion shows, taking pictures of people in weird outfits. That’s not for me.” He had bigger aspirations. Through a friendship with Marissa Bronfman (of the Seagram Bronfmans), whom he met at Fashion Week, he became well known to the right PR people, was photographed for the party pages, and found himself in the front rows alongside the reed-thin elite. He took their pictures, which provided much of the content for nolanbryant.com, which he launched in 2008. The exposure brought him attention, including an invitation by Hugo Boss to shoot the company’s collection at Berlin Fashion Week in 2010.

When we meet for coffee, I find it remarkable that he is only nineteen; he is so self-confident and measured. “I wear the fun clothes, I blog about it, and I socialize,” he says when I ask him to describe what defines his personal brand. He also understands the line between self-promotion and exploitation. “When you’re photographed by the party pages, they always list your name and where you work. In the beginning, it was just my name. I wanted to go to events and have something else people could say about me.”

What he was really doing, like so many others, was looking for a way to present his identity—which is, in the end, the purpose of youth. It’s just that he started with a baseline the teenagers of my era lacked. As well as the digital tools, he possessed an uncannily solid sense of himself. Like all socialites on the ascent, confidence became his key. His generation lives out life in public; my generation chose to lurk in the shadows, scared shitless about what others thought of us. To paraphrase Henry Rollins, we spent half of our lives screwing up, and the other half making up for it. Bryant and his peers strode purposefully out of the gate. This, at the very least, is admirable.

I find no new media arriviste more sure of herself than Sarah Nicole Prickett, a brand who craves some distance from the Blondebots of the world. She doesn’t consider herself a style blogger, although she blogs about style (and happens to be blond). That label would put her in the wider concentric circle of online personalities whose ambitions are shallow, whose observations are generic, and whose writing is poor.

Meanwhile, she struggles with a few categories of her own. “I’m a Millennial, right?” she asks me. “I keep reading about how unhappy we supposedly are.” One such piece happens to appear on the cover of New York magazine the week she and I meet in a downtown Toronto restaurant called the Böhemian Gastropub. (When she points out how awful the name is, and I agree, I’m left wondering which of our generations has the bigger compulsion to comment on everything.)

The New York cover shows a guy I can only describe as an emo—which is probably no longer a Millennially correct designation—shot in black and white and looking nobly tragic. The line across his chest says, “Sucks to Be Us.” The story is about children of over-praising parents, kids who grow up to Google Chat and live in angst in Brooklyn. Held up as symbols of “post-hope America,” they are described as “screwed, coddled, self-absorbed, mocked,” yet “surprisingly resilient.”

Many of these adjectives might seem appropriate—but not “screwed.” Prickett strikes me as neither unhappy nor disadvantaged. Her red lipstick is too flawless, her five-inch wedge platforms imperially high. By her own account, she is right where she wants to be, and is far more in control of her personal image at twenty-six than I was of mine at thirty-six. She has a career as a freelance writer for the National Post, the Toronto Standard, and Fashion magazine. She confidently calls herself a “good writer.” (I wouldn’t have had the guts to say that about my own writing at twenty-six—or forty!) And she has something her 5,000 or so Twitter followers consider significant: a growing status as a new media personality and party fixture. Strangers refer to her by the abbreviation SNP, and when visitors read her site, snprickett.com, which has seventeen sections, like a lifestyle magazine, they will assume she is the centre of a magnificent universe. It’s more accurate to call her a big fish in the medium-sized pond of Toronto fashion.

Later today, she will attend a charity runway show featuring outfits modelled by dogs. Let that not paint a picture of her erudition. She’s reading Haruki Murakami, which she notes on her Twitter feed. On her site, she quotes Baudelaire and writes about Nellie Bly. In person, she is articulate, likeable, and smart. She is also comfortable with public exposure. “Self-promotion used to be reviled,” she says, referencing my era. “Kurt Cobain said, ‘I don’t want to be on MTV,’ and then he was on MTV. This was sneakier—pretending you didn’t want the attention in order to garner more of it.”

But the idea of a brand leaves her uneasy: “People have said that to me, in person at parties. ‘You have a great personal brand.’ I mean, who says that to someone?” The idea makes her feel so disingenuous that “someone should pull my hair back so I can vomit.” That’s because her plan was to self-express rather than to self-brand. (If she could write about any subject, she says, it would be “my feelings. But there’s not a huge market for that.”) She was raised in London, Ontario, with four younger siblings, by deeply religious parents: “We went to church five times a week. I didn’t have a computer until I was ten, and no Internet until sixteen. My parents didn’t like popular or secular culture. You read the Brontës but didn’t read The Baby-Sitters Club.”

As a form of rebellion, she began buying fashion magazines and writing an online journal. After she moved to Toronto, the whole thing grew, aided and abetted by her apparent enjoyment at having her picture taken and broadcasting her thoughts. To illustrate the generational divide I’m feeling when I listen to her, my friends and I would find putting our faces, clothes, hair, makeup, boots, penchants, partners, and reading lists out into the world terrifying.

I don’t want to moan over Gen X’s lot in life, as we have nothing to feel sorry for. My peers are educated and successful, own property, and are usually pleasant to be around. However, many of us grew up feeling like hapless bystanders to the extraordinary events of our time. Over the years, we honed a diagnostic, eyebrow-raising pose on the sidelines, but it’s just a cloaking mechanism for our own insecurities. In the end, my anxious group’s greatest setback might be our dread of any scrutiny or derision; maybe that’s why we scrutinize others and sit in judgment ourselves. I’m now in a position of envy: neither Prickett nor any of her peers, frivolous or thoughtful, boob flashing or not, suffers from that growth-stunting trepidation.

“I just thought,” she tells me, reflecting on the plans she made in her youth, “who do I want to be?” Her decision was: “I can make myself. I have all the resources here in this city at my disposal. And now, when girls like the one I used to be—shy, sheltered girls from small towns—write to me and say I helped them understand something, or they don’t feel as weird now, or that they want to move to the city to have my life, even though I understand that my life is kind of bullshit, I think that’s good. I needed people like that when I was young.”

The rest of us, the elders of the kind who swore never to join Facebook or Twitter (and then did), are only now, through gritted teeth, starting to ask the question.

What’s my personal brand?

I haven’t the foggiest.

This appeared in the March 2012 issue.

Maryam Sanati

Maryam Sanati is editorial director of Toronto Life magazine.

Michael Byers

Michael Byers (michaelcbyers.com) is an award-winning artist based in Hamilton. His clients include Sports Illustrated, the New York Times, Wired, Variety, and the Wall Street Journal.