How To Fangirl All Over Your Boss Without Becoming Unbearable (With Examples From Last Week’s Episode of Mad Men)

20 Oct

by Janday Wilson

We’ve all been there: The uncomfortable pauses in conversation, the cagey disposition in the presence of a boss you want to be just like, the desire to do everything perfectly under her gaze.

I cringed during last week’s episode of Mad Men, watching eager beaver secretaries Meredith and Dawn fight so hard for approval from Joan, the Queen Bee of SCDP. I was embarrassed for them and I’d be lying if I said that I didn’t totally identify with them. See, I used to be that earnest assistant who wanted nothing more than to please her fabulous boss, and I learned a few lessons from those first steps up the ladder.


I don’t blame the women at SCDP for being stunned into silence by Joan’s mere presence. In that Sunday’s episode, she woke up from an all-night bender with a torn dress and smeared makeup and still managed to look glorious. Joan’s that put-together woman in every office who exudes a quiet confidence.

My Joan was the fashion director of the magazine where I had my first internship. She did not have to be my boss to catch my attention. “Sidney” (her real name is so dope that it only makes sense that it belongs to her) was the epitome of a fashion director of a brash, startup lifestyle magazine. In a word: fly.

She was adept at mixing street wear with high fashion and her shoe game was always exclusive. Her cadre of creative friends handmade the one-of-a-kind jewelry she wore and her makeup was always a tasteful, understated complement to her natural beauty.

Weeknights I struggled to select what to wear to the office the next day. I never came close to even halfway near Sidney’s level, but thinking so carefully about what Sidney would wear actually improved my own style. And when you look good, you feel good. My chicer look helped to raise my confidence level, and I feel I even did better work in the office.

I wish I would have given Sidney some compliments, though. Let her know how much she inspired me. But much like the Mad Men secretaries, I admired my Joan from a distance.

Since then I’ve added compliments — always genuine, of course — to my workplace arsenal. My comments on a lovely pair of shoes and exclamations of “Where did you get that dress?” have helped break the ice with many female colleagues I’ve admired, and have won me some allies in the workplace.

Poor Meredith may have gotten a smile out of Joan during Sunday’s episode if she had told her how nicely her violet ensemble complemented her hair. But who wouldn’t need courage to say something — anything — to Joan?

Joan stalks the hallways of SCDP in the way my mother always taught me: head up, shoulders back. Her ice princess/vixen/mother hen demeanor commands your attention through the screen and certainly seems to intimidate the ladies in her office, while enticing the men.

Sidney seemed to glide through the hallways at the magazine. Her face was always unreadable but I assumed she was reserved rather than evil, and treated her accordingly. I always greeted her with a simple ‘”Hello.” And that was all it took. I let our relationship form naturally.

When the magazine sent around an email inviting everyone to an event where Sidney would be performing spoken word, I leapt at the opportunity to go! After the event she hugged me and thanked me for coming. Mind you, we had never had a full conversation up to that point. But Sidney beamed as we chatted, visibly thrilled that I made an effort to show my support.

Thank God I had spared myself from having a conversation like the following from Sunday’s Mad Men episode:

Meredith: “How are you?”

Joan: “Busy.”

One of Sidney’s articles –- a thoroughly unique story about the history of manicures and “ghetto nails,” of all topics –- was why I’d applied for an internship at her particular magazine in the first place. Of course, I never told her any of this. I just envied her ability to marry her professional and creative life, read and reread her pieces, and hoped I would develop a fresh writing style of my own someday.

In addition to pulling together impressive fashion spreads for the magazine, Sidney was also a nationally recognized poet. To paraphrase Joan’s friend Kate, from where I was sitting Sidney’s accomplishments were “damn impressive.” But instead of tip-toeing around her, like the SCDP girls tip toe around Joan, I showed my respect without being obsequious.

And she noticed. A few weeks after I saw her show, Sidney personally requested that I accompany her to an interview with a notable Project Runway alum. That meeting shaped my personable approach to interviewing subjects and inspired my tendency to over prepare.

Dawn came the closest to revealing her admiration for Joan at the end of Sunday’s episode but she should’ve taken it a step further. An invitation to lunch could not hurt. As SCDP’s only female partner (let’s pretend we don’t know how she got there), Joan has a wealth of information about surviving in the treacherous advertising business that Dawn can learn from.

And Dawn has already proven that she has the courage to initiate a one-on-one conversation with Joan.

I could completely relate to the scene in which Dawn threw herself on her sword to make amends for punching in Scarlet’s time card.

I never had the soul-crushing experience of disappointing Sidney, but at my second editorial internship, my fellow interns and I got reprimanded by our editor “Courtney” for neglecting to deliver a package, a task that her colleague requested.

My heart immediately dived down to my stomach as I read her rightfully harsh email. “You NEED to do ALL of our duties as interns, no matter how HUMBLE,” Courtney reminded us. She stressed that every single task assigned to us was meant for that purpose.

I was particularly distressed because I had just grown from silently admiring her striking, signature look — bright pink lipstick and a striking buzz cut — and studying her professional path, to actually bonding with her over our shared love of The xx; I also knew that she was taking notice of my work ethic, as she had begun to compliment my work.

In my apology email, I probably typed “sorry” at least five times in two paragraphs. From that point forward, I always completed any request made of me with a smile on my face. So I saw myself in Dawn when she jumped at the opportunity to prove herself to Joan after screwing up.

Chilllllll Dawn. You’re a little too hype about that supply closet.

Chilllllll Dawn. You’re a little too hype about that supply closet.

When Dawn left Joan’s office with, “Well I don’t care if anybody hates me here, as long as you don’t,” Joan replied with a curt, “We’ll see.” But I know I did not imagine that slight smile on Dawn’s face. Well played.

Courtney never responded to my maudlin email, and it was never spoken of, but later she told me that I was her favorite intern. When she eventually moved on to a different publication, I was the only intern who she reached out to with several freelance opportunities.

It’s been years since I’ve seen Sidney, my Joan, but I did stumble on her Instagram account a few weeks ago. And I am not ashamed to admit that I spent a half hour scrolling through her photos, and followed that exercise in fangirl-dom with a quick Google search that confirmed that she is still as bossy as ever — and I mean that in a good way.

Sidney and Courtney may never know that I still think about their incredible ease with words whenever I sit down to write or that I am still striving to match their sartorial tastes.

My hope is that Joan will have the same impact on Dawn. Who knows, maybe her new found supply closet power will lead her to create a “petty dictatorship” of her own. Or perhaps before the season’s out Dawn will start strutting around SCDP with her head up to the sky.

xo jane

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