Peggy Olson

Peggy Olson

In a crowd of many, be Peggy Olson – with your perspective shining through. That's how you become a preference for your audience.

Published Sep 15, 2023
Reading time 5 min read

You know who benefits the most from all the “how to XYZ” content? Your competitors.

When your audience buys into the idea of solving their problem but fails to see your distinct solution, they go elsewhere – to the people who own their strengths and talk about what makes their solution a fit.

Nurturing on a problem alone benefits the industry and your established competitors – there’s little solace in “thank you for your service 🫡”, so let’s turn the volume up on your positioning and communicate what you have to offer!

Let me introduce you to the iconic Peggy Olson: A woman who made her mark in advertising in the 60s, against all odds.

Peggy Olson walking down the corridor, with black shades and a cigarette in her mouth.

And the story goes:

Is it even possible to breathe at Sterling Cooper without inhaling all that smoke? Men and their leisure-at-work.

Next to Don Draper’s office, there’s the desk of Peggy Olson. Just another secretary in the advertising agency, ready to bring ice for drinks and cover for a cheating boss.

Yet, Peggy is much more. She is a storyteller at heart. Overlooked – but she waited for the right opportunity to shine.

“A basket of kisses,” murmured Peggy bringing a box with used tissues after an internal focus group for Belle Jolie lipsticks.

“That’s cute. Who told you that? Where did you hear that?”

“I just thought of it.”

She wasn’t just another secretary anymore. Peggy Olson’s talent was seen – and the basket of kisses was just a beginning in her new copywriting career.

Character narrative at glance

🎞️ Story arc: From a naive and timid secretary to a confident creative leader.

💭 Thinking behind: Matthew Weiner, the creator of “Mad Men”, captured a pivotal time in American history through the lens of the advertising industry. Within that story, Peggy’s journey shows the gender dynamics in a male-dominated industry in the 1960s – the struggles, the biases, the small and big victories – where, against all odds, she makes her mark and becomes a copy chief. Peggy is also symbolic of a new era in the American workforce: The rise of talents that didn’t come from privilege but merit and determination. While Peggy is not directly based on any real person, there were women in advertising, like Mary Wells Lawrence (founder of the Wells Rich Greene agency, the highest-paid advertising executive by 1969), who certainly inspired the character.

🗺️ Narrative: Peggy is a character with a clear sense of self who grapples with external struggles, like workplace sexism; yet her ambition and efforts to find her voice struck a chord with the audiences.

🍋 Character deep dive: The focus of “Mad Men” is on Don Draper, the main character; but ultimately the hero of the story is Peggy Olson, a counterpart to Don’s anti-hero. I liked how someone put it as “Peggy is our eyes in this advertising-in-the-60s world.”

🗺️ Mapping Out The Narrative

No one could imagine the rise of a young secretary in the male-dominated advertising world of the 1960s. Certainly not with Peggy Olson. 

At first glance, she’s not likeable. There was no immediate “stand-out” quality – even visually, she just blended in with the walls, earning herself a nickname of a “mouse.” Yet, in the right situation, Peggy’s knack for understanding customers’ minds, wit, and thoughtfulness shined.

After the “basket of kisses” breakthrough, Peggy was promoted to a junior copywriter position. (I wish it meant recognition for Peggy’s talents and efforts – but her talent, unfortunately, didn’t solve workplace sexism.)

With every new account, in all the creative sessions, we still see Peggy underestimated: Her work benefits her boss and team members, yet she’s not on the same level as her counterparts. Does it stop her? Not at all.

Peggy is relentless in communicating her ideas and opinions, to the extent of being called bossy (cue in all the stereotypical attitudes when women – against the expectations – don’t behave all warm and fuzzy). The more she’s forging her spot among the creatives of Sterling Cooper, the more confident she becomes, the more her perspective makes her indispensable to the team.

The transformation is seen both visually – her clothing & fashion style becomes more modern and reflects her blooming inner boldness – and contextually. However, with little to no accolades and gratitude, taken for granted, Peggy makes a decision: To join the rival firm.

(Her relationship with the boss, Don Draper, at that point evolves to a mutual respect-based partnership and becomes a fascinating storyline – it’s so much deeper than just a boss-underling motive! Highly recommend watching Mad Men.)

At her new job, there’s just one more pitch that shows how Peggy found her place in such a crowded creative space – the “Burger Chef” campaign. Unlike other firms (including her former workplace, Sterling Cooper), Peggy delivers a concept that doesn’t just focus on the problem of changing family dynamics in the US but gives a solution – re-positioning Burger Chef as a place for families to come together.

(It’s getting meta because, look, Peggy as a copy chief did the same thing that I think is so brilliant about Peggy as a character: Talk about problems AND unique solutions you offer – that’s how you differentiate and demonstrate value to your audience.)

Welcome to Peggy’s renaissance. Make your mark and stand out, like you’re the only choice and preference in a crowded market.

🍋 Navigating To Your Brand

Not going to lie: Figuring out your position is not a one-time thing. This is something you make an assumption about, go out, communicate yourself, and iterate back at the drawing board every once in a while, with the new information & feedback you get.

There’s one question – perhaps trivial – that lets you kick it off:

📝 What sets you apart from your competition?

(And it’s not that you’re the most affordable or high-quality option – the differentiator lies in your perspective, an approach you hold that provides value to clients AND is different to what your competitors are doing.)

My example: I view personal brands as a platform for your narrative, ideas, and business. I draw parallels to iconic characters that are like fictional personal brands and believe great customer experience is a must. My skill set is that of a generalist – and all of that dictates how I communicate myself and what kind of experience I provide to my clients.

That’s the kind of thinking that brought Peggy into the spotlight – and a way for you to stand out (and not lose your potential clients to other distinct competitors).

With a bookmark at the end of this chapter,

👉 Did Peggy's story resonate with you? (I'd love to hear your takeaways – I reply to all messages, so welcome to our nerd club table.)

P.S. Do you want to attract the right people to your brand?

With a clear Big Idea, vision, and key messages to your audience, that trickle down into your voice and actions – your ideal client gets the value you hold.

🍋 Reply "Peggy" and let's chat about your personal brand!

Seeing Through Stories

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Every week, I will send you a TV or book character breakdown and what made them iconic – and how you can apply those insights to your creator brand.