The Wrong Guy

Once upon a time, I very nearly landed a job running a magazine I had no business running. A story about wanting something for all the wrong reasons.

Photo by Heng Films on Unsplash

As I type this, Anna Wintour’s inbox is filling up with emails from editors who think they can be the next editor-in-chief of Vanity Fair. Some of the emails will be wildly ambitious, touting not just qualifications (“I’ve led ten consecutive quarters of sustainable, multi-platform audience growth while our reporting has relentlessly held truth to power and set new standards in creative…whatever, whatever, whatever.) And while news of the job opening, once the most plum of positions, will probably attract fewer candidates than it once would. And it will definitely attract fewer qualified candidates.

Honestly, anyone you’d want to hire to lead Vanity Fair in 2025, should know better than to want the job. An editor’s most crucial, elemental attribute is judgement, afterall, and resurrecting Vanity Fair from it’s decade-long slumber, on a fraction of its former budget in the current media hellscape, is objectively a brutal job at which anyone is poised to fail.

But that won’t stop a hundred ambitious editors, content hustlers, and luxury grifters from crafting a door-stopping memo for Ms. Wintour to dismiss with a perfunctory “thank you for your interest” email one of her assistants has already crafted. I should know because I used to be one of those people who threw their hat in rings they had no business shooting for. No, not Vanity Fair, but lesser jobs, and plenty of them.

When I was younger and more recklessly ambitious, I very nearly got a job running a magazine I had no business running. I was a senior editor at GQ, when Conde Nast announced its intention to launch a male version of its semi-revolutionary shopping magazine, Lucky. (if you don’t know Lucky, it basically foretold the future of ecommerce and created a digital shopping model that would have saved at least some of Conde Nast’s bacon if they’d and adopted it back then.) The magazine had been a hit because it focused on things: which things to acquire, where and how to acquire them, how to store them, what other complementary things to acquire with them to maximize your enjoyment of them. Lucky was definitely not for me, and not just because it was created by and specifically for young women.

But that didn’t stop me from writing a multi-page memo outlining my vision for a male version of the shopping magazine, a word doc I probably code named Lucky Guy. (I mean, what would you call it? Lucky Dogg?) Anyway, who knows how much cortisol and calories I burned up in the weeks I spent writing, rewriting, and overthinking that memo. I think it’s all I thought about for the better part of March 2003.

I couldn’t tell you where the memo is now, as I’m sure it exists on some server or unexplored corporate cloud somewhere, and I have no idea how embarrassing or obsolete some of its ideas would be, but whatever I wrote was good enough to get me a meeting, and a follow up meeting, and finally, a meeting with a septuagenarian billionaire in a drab grey sweatshirt and elastic waist pants, who put an end to the folly.

This was a job I wanted for all the wrong reasons—salary, stature, perks—and a few of the right reasons, mainly about the uniquely satisfying process of building a magazine from nothing. It was all about hiring great people, then channeling and combining their creative energies to make a unique and compelling glossy thing that young men would recognize as novel and necessary in a world of overwhelming consumer choice. I was careful to avoid the word ‘metrosexual’ in my memo (except maybe mockingly) but that’s precisely who this magazine was meant for.

At the time, being the editor-in-chief of a mainstream magazine—even one as vapid as this aspired to be—would have doubled my salary, paid for a leased car and garage, given me access to a car & driver, and, if things wet well enough for long enough, an interest-free mortgage to apply to the overpriced dwelling of my choice. And, it would have come with hordes of generous PR ass-kissers who would flatter and cajole on behalf of their clients in the hopes of getting their things in this men’s magazine about things.

The job came with the kind of low, superficial, ephemeral power that only a real twat would mistake as genuine anything. I was not that twat. But since I’m essentially powerless in every other aspect of my life, lording over a legion of tech and fashion and grooming PR people, is better than nothing. Sure, I will consider your skater pants, your portable phone chargers, your electronic organizers, and your hybrid bicycles. Bring me your things and I will cast judgement upon them.

The only problem was that I’m not that good at things: I don’t choose them particularly well. I don’t value them enough. I don’t pay enough attention to what separates one from another. And I don’t take particularly good care of them. I’m not saying I’m not materialistic. [See above.] To be clear: I covet and admire objects of all types and values and purposes. I just don’t think about them in a way that’s elevated or unique enough to justify my leading a magazine about them. For one, I’m just not the best steward of the materials I am able to acquire.

Case in point: the other night, the oven that I use two or three times a day (and have cooked countless meals on and in) recently stopped heating as it should. So Monday morning came and I headed off to the office trying to remember to find someone willing to repair it. But then I realized that, despite the fact that this was a stove I researched and purchased, I have no idea what brand it is. No clue.

We all forget stuff, but I’m just saying the person who edits a magazine that’s essentially a guide to stuff, would know the brand of the stove he bought and uses like I use mine. A guy who doesn’t know the name of his stove, just isn’t the right guy for the job. But I didn’t recognize that back then.

Only the old man knew the truth.

Which, finally, brings me to mine, but it’s less a truth than a regret. Looking back on my thirty-five years of professional life—the years working and the year not working—I regret the times when I talked myself into being a good fit for a job opportunity. And not just: Am I qualified for this role, but is that who I am? Does this job actually play to my strengths? Will my weaknesses be an obstruction? Does it match at all with my worldview? I’m a realist—and what’s more, I’m a realist who was unemployed while I had two kids in college—and I’d never promote the precious, ludicrous idea that you should wait around for your dream job. I’m merely saying that when ambition and desire to improve your lot—to accumulate a few Paul Smith suits and a leased Volvo wagon—colors your idea of who you are and what you’re capable of, the universe will punish you, however mildly. If you’re lucky, you just won’t get the job and will come to appreciate the one you have a little more, and throw yourself into it a little more deeply. But if you’re still intent on writing that memo, don’t forget the underscore in the email. It’s anna underscore wintour at Conde Nast. Good luck.