Lu Chekowsky reveals how decades in advertising and personal challenges inspired her powerful memoir, Don’t Buy What I’m Selling.
Lu Chekowsky reveals how decades in advertising and personal challenges inspired her powerful memoir, Don’t Buy What I’m Selling.
This week on Book Gang, Emmy-winning ad creative Lu Chekowsky joins us to talk about her bold memoir, Don’t Buy What I’m Selling. You may not recognize her name, but you’ve definitely felt her influence.
Lu pulls back the curtain on the world of advertising, sharing a journey that stretches from childhood poems about Levi’s to being part of a viral Michael Jordan campaign. Along the way, she confronts the invisible labor, personal costs, and body-image battles behind the scenes of an industry built on selling aspirational bodies that didn't look like hers. I promise, you’ll never see an ad the same way again.
In this week’s juicy episode, we discuss:
📚 Auditioning to Tell Her Own Story: Lu shares the surprising reality of having to "audition" to narrate her own memoir—and how voicing her story in the audiobook studio brought new power and intimacy to her journey, with a surprising starter job that not only helped with this job, but empowered her in the world of advertising.
📚 The Power and Pressure of Image: We explore Lu’s experience with body image, self-worth, and media culture, and how the memoir confronts the messages we absorb (and perpetuate) about beauty, acceptance, and enough-ness.
📚 Escaping the Sell: What Happens When You Break Up With Advertising? Lu shares the wild, sometimes surreal reality of life behind the world’s most influential campaigns, and what it truly costs to make a living selling other people’s dreams—plus what’s left of your own when you walk away.
FREE BONUS BOOK LIST: This week’s bonus book list features 21 Nonfiction November Books To Read Now—my most anticipated new releases and a handful of backlist gems to inspire your reading month. Patrons receive a printable list and a spoiler-filled chat with Lu Chekowsky, where we dig deeper into their memoir and the art of self-reinvention.
Meet Lu Chekowsky
Lu Chekowsky [she/they] is a writer and Emmy Award–winning creative director, and the author of Don’t Buy What I’m Selling: On Breaking Up With Advertising and Finally Learning to Love My Whole, Fat Self (Little, Brown, 2026).
Lu’s career has spanned creative leadership roles at Facebook, Comedy Central, MTV, and Wieden+Kennedy, shaping campaigns for everything from The Daily Show and Broad City to Nike and Delta. Their essays and poetry have appeared in The Rumpus, Pigeon Pages, Autofocus, Ad Age, and Muse by Clios. A 2023 NYSCA/NYFA Fellow in nonfiction, Lu lives in the Hudson Valley.
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Don’t Buy What I’m Selling by Lu Chekowsky
Returns & Exchanges by Kayla Rae Whitaker
501 Blues: A Look Back at the Levi’s Ad Campaign
How Sex Work Prepared Me for a Career in Advertising
Woodworking by Emily St. James
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Book Gang Podcast Transcript:
Lu Chekowsky (00:01)
Hi, I'm Lu Chaikowski. I'm the author of Don't Buy What I'm Selling on Breaking Up With Advertising and Finally Learning To Love My Whole, Fat Self.
Amy’s Warm Intro:
Hey, Book Gang! You have unknowingly been impacted by the words of Lu Chekowsky, and that was by design. For the first time, in Don’t Buy What I’m Selling, Lu takes us on her hero’s journey—from the seeds of crafting poems to her Levi’s with her mother as a child, to reaching career milestones like writing copy for a Michael Jordan campaign that became a viral sensation. The trajectory, just like life, is a bumpy one, as she navigates personal struggles with disordered eating, obesity, financial issues, and the loss of her mother.
Chekowsky begins her story on set at MTV, as she navigates the sticky work of convincing an actor to continue participating in a campaign that increasingly objectifies him. She coos and coddles the star with promises of whole milk, double-stuffed Oreos, and an Xbox with games. It's not uncommon for her to be surrounded by stars (even sharing a sandwich backstage with Britney Spears or witnessing Beyoncé’s reveal of her pregnancy from close quarters), but she goes largely unnoticed because she is overweight in a world obsessed with beauty standards.
She writes, “No one can know I exist. In fact, to remain invisible is one of my main responsibilities. This is for the best because I’m not the kind of person anyone’s supposed to aspire to be or want. I’m more of a cautionary tale of what can happen when a person doesn’t buy the products that run during the commercial breaks, the ones for diet pills and Doritos (in moderation, of course). My body has disqualified me from being seen in the ads I spend my days making, and that’s why I’m so great at making them. I know what’s good because I have what’s bad.”
Raised by a mother who faced the same body struggles, Rose encourages her to see how ads work in her everyday life at a young age and not fall for them, coaching Lu to stay alert to the perils of false marketing. But even she can’t resist the pull of the new advertisements featuring a man named Walt Stack, which appear to show Nike finally aligning its brand with the everyman. To Rose, it mattered less that she could never wear anything from Nike because it wasn't size-inclusive. The allure of “Just Do It” signaled that everyone should do what they say they can’t. Whether it is auditioning for a play, a slice of cheesecake, or telling a boy you have a crush on them, Rose fully embraces this mantra, and the two of them use it to navigate the big and small choices of their everyday lives.
After her untimely death, this beacon of optimism propels Lu into the world of advertising, but she struggles to pay her bills. Working banker’s hours, she becomes a phone sex operator and finds community in an underground world, bouncing from job to job until, it seems, a magical scholarship becomes available: a job with the very company that crafted the Nike campaign that inspired her mother. In this unpaid position, she learns hard lessons and the truth about advertising. As the stress builds, she eats through the pain until her body begins to reject this form of creature comfort, and she must decide to finally, for the first time, choose herself.
Given her background, it's not surprising that the audiobook experience is pleasant, and that Lu creates soothing ad interludes, complete with music, that pull back the Oz curtain on the mindless choices we think we make, choices that are, in fact, all corporate design.
After you finish this book, you will likely never see advertising the same way again—or the people who craft them. This week, as the glow of ads for Botox, boob jobs, and anti-aging creams rolled across my television screen, I found their power over me had dimmed in an indescribable way. How freeing to no longer participate in the insanity. I just needed Lu to pull back the curtain. This memoir is punchy, powerful, and life-changing. I am so excited to introduce you to this icon in advertising.
If you’re new here, hi, I’m Amy Allen Clark, and this is Book Gang—the podcast dedicated to debuts, backlist favorites, and under-the-radar gems.
In today’s episode, we’re joined by Lu Chekowsky—Emmy Award–winning creative director, writer, and now the author of Don’t Buy What I’m Selling. Today we’ll talk about what it’s like to literally audition to narrate your own story as an audiobook narrator, the deep work and team involvement that go into crafting a memoir of this scope, and how to spot the billion-dollar “hum” of advertising in your own life.
As always, you’ll find a themed bonus book list in the show notes—this week: 21 Nonfiction November Selections to kickstart your reading month, including new releases and backlist gems. Patrons can download a printable list and unlock a spoiler-filled chat with Lu.
If you’re new to Nonfiction November, you’re in for a treat—this community reading challenge, created by Olive Fellows of the A Book Olive YouTube channel (who joined us for a special episode which I’ve linked to in today’s show notes), is all about exploring and celebrating nonfiction in all its forms. Whether you’re a memoir lover, a true crime devotee, or just curious to break out of your usual reading routine, Nonfiction November invites readers everywhere to try new voices, tackle big ideas, and share discoveries with fellow book lovers. It’s the perfect time to pick up a true story you might not have reached for otherwise, and our curated list and conversation will help you dive right in.
A quick reminder: our next Jane Eyre meeting will be on December 3rd at 8 PM ET, and new book club guides will be issued in November. Thank you to everyone who joined the incredible One Yellow Eye chat with Leigh Radford and our latest Jane Eyre discussion. Voting for next year’s book clubs is now closed—stay tuned for the big announcement on December 1st! Membership is $5 a month (or save 10% by prepaying for the year). This multigenerational book club needs your voice.
Now let’s meet this week’s guest: Lu Chekowsky [she/they] is a writer and Emmy Award–winning creative director and the author of Don’t Buy What I’m Selling: On Breaking Up With Advertising and Finally Learning to Love My Whole, Fat Self [Little, Brown 2026].
In Lu’s most recent job in the advertising industry, she was lead creative director for video at Facebook. Before that, Lu was the SVP of brand creative at Comedy Central, where they developed campaigns for shows like The Daily Show with Trevor Noah, South Park, Nathan for You, and Broad City. Previously, Lu was VP, creative director at MTV, where they made ads for Teen Wolf, Jersey Shore, The Real World, and the Video Music Awards. Before working in entertainment, Lu was a creative director and copywriter at Wieden+Kennedy, where she oversaw work for brands such as Jordan, Noxzema, Delta Airlines, and The National MS Society.
Lu is a 2023 New York State Council on the Arts / New York Foundation for the Arts Fellow in nonfiction literature. Lu lives in the Hudson Valley.
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Now, let’s get chatting…
(TRANSITION MUSIC)
Amy- Book Gang (00:10)
Good grief, Lu. I'm so excited to talk to you about this book. I have already set readers up for what is in store in the story. I don't do a ton of nonfiction. It really has to grab me. And I have to say, your audiobook narration is spectacular. Can we talk a little bit about that before we get started?
Lu Chekowsky (00:27)
Thank you. Yeah, please. Thank you so much. I really appreciate that.
Amy- Book Gang (00:31)
What was that experience like for you?
Lu Chekowsky (00:34)
I loved recording the audiobook. It was such a special experience. And when I sold the book, it wasn't a home run guarantee that I would get to it. It's its own process. I had done a reading in the city that was recorded, and luckily my editor forwarded it to the audiobook team as sort of like an audition of sorts to read your own book. It's a funny thing. But of course you want the audiobook to resonate for readers, so whatever it takes. But I was thrilled when I found out that I would be able to do it and I did it over about six or seven days at a studio not far from where I live. It was thrilling. It was wonderful.
Amy- Book Gang (01:04)
Oh my gosh. Did you know they were gonna do like musical interludes with the ad portions or did you come up with that concept?
Lu Chekowsky (01:11)
We spoke about it together. My production team and director on the book were incredible. But I did suggest that as an idea as a former ad person. I had a few ideas about how that might work and I was glad that they responded and moved ahead with that.
Amy- Book Gang (01:26)
Oh my gosh. Well I loved this experience. I was thinking, you know, for us to kick off, ads are so interesting right now. It's really funny because I had interviewed an author who wrote a book in the 1980s. It's called Returns and Exchanges. Her name is Kayla Rae Whitaker, and it's about a department store and they have to do their own advertising. And she was talking about how the ads were so sentimental and warm and, you know, almost a little hokey in some ways. Like we were they were giving us this idea of an American dream and how in contrast what the ads are doing right now, I wanted to ask you, do you have a favorite ad that's running right now?
Lu Chekowsky (02:03)
Oh my gosh, do I have a favorite ad that's running right now? I wish I could answer that. I don't. I feel like so much of my life is like blocking ads on my apps and I spend a lot of time trying to avoid them. And then I do make content, which we might talk about about advertising, which is often pretty cynical and calling out the way they work. It's been a long time since I've seen an ad. You know what? I'm actually gonna correct that. I saw an ad on a trade journal this morning. Etsy is doing a campaign where they went to find all the people named Jeff that are selling things on the site as a counter to Jeff Bezos's Amazon. I thought that was quite a lovely insight. So they follow different Jeffs who make artisanal products and things out of their home and sell on Amazon. Sorry, sell on Etsy, not on Amazon. I thought that was pretty smart and a great insight.
Amy- Book Gang (02:53)
Okay, I love it. Well, I love that you are rejecting the ads and then we're gonna get to talk about, you know, making ads. Of course, the story really starts with you crafting, for me a very pointed scene, I should say, is you crafting your first poem to Levi's Jeans with your mother. And I wanted to talk about how those early experiences ended up teaching you about the power of advertising, especially as it influenced Rose, your mom.
Lu Chekowsky (03:20)
Thanks for asking. What a cool thing. I and other memoirists bringing people who aren't alive anymore back to life in their book. It's really special to have you ask about my mom who's been gone thirty years at this point, and is a main character in my book. The time we did spend together, she was incredibly media savvy and you know, I was a young girl when she first got cancer, I was eleven years old. I think the idea of her maybe not being around forever was introduced really early on in our relationship and with that she wanted to arm me with all kinds of lessons about how to navigate the world.
And I was born in the early 1970s. I grew up in the 70s and 80s. Our television was always on in our home. So there was like this backdrop of not just programming and shows, but the commercial breaks. And my mother spared no expense to let me know at every break, you know, don't pay attention to that. They're selling you a line here. This is why that's not right. And it's, you it's funny now to be here talking with you about the same subjects.
And it's, I think the book tries to tangle with that, you know, the things we're given early and how they send us on a trajectory in life. But thank you for calling out that one scene. I was a writer from a very young age. Words were, you know, my passion and fell out of me. And there is a scene in the book where I write about a very famous Levi's 501 campaign that ran for several years in the mid-80s that showed very cool people on city streets wearing their jeans in New York City and being, you know, the coolest kids in town. And I just emulated them.
But I wrote a poem sort of untangling that what I saw there wasn't real. And I read it from my mother who was really proud of me for that observation. And that really, I think, lifted me up to believe that this was my place was to question these things. I have the poem actually handwritten it from a box. I'm very fortunate as I was writing this book, like I still have it. I thought about framing it. It's pretty it's called Hidden Persuasions, which might also be another subtitle for my book in another iteration of that.
Amy- Book Gang (05:16)
Oh my gosh, I love this so much. You know, that scene really stuck out to me as a reader. And, it it was fascinating to me that, you know, you pen this together, right? And I do think you should frame it because it is such a special moment. I feel like that's, you know, when you've run across things like that from your childhood, it is so special to be able to give a little homage to it. But, one of the things that blossoms or evolves, I think, with you and your mother and those ads plays in to a Nike ad, which really strongly influenced her, but also like influenced your way of life. Can we talk a little bit about that Nike ad?
Lu Chekowsky (05:54)
Yeah, yeah. This is one of the very first Nike ads I think argue there was a campaign, so whether it was the first one that aired or the second, but in the mid 1980’s, like 1988, I believe, it was called the Walt Stack ad, it's features an 82 year-old man running over the Golden Gate Bridge at in like five o'clock in the morning. And the joke of the ad is that people ask him what he does with his teeth when he runs in the morning, you know, do his teeth chatter in the morning and he he they don't chatter because he leaves them at home in a glass because he's so old he's wears dentures.
And my mother and I saw this ad during an episode of Oprah, which we watch religiously every day. And it was the only ad that my mother gave a hall pass to. She burst into tears and said, I'd never thought I'd live long enough to see an old man in an ad. Like her belief about advertising was that it was all aspirational and perfection. And here was this left-of-center, just one of the first just do it ads from the ad agency, Wyden and Kennedy, that she loved and without giving too much away, my career path took me straight to the front door of Wyden and Kennedy where that had originated later many years later and it was difficult to not believe there was some kind of supernatural pull from that moment to the front door of that place.
Amy- Book Gang (07:14)
I think I found it so interesting because even though it was tapping into this very aspirational aspect of life, what you detail is that a lot of the well, almost all of the garments that were made by Nike were not actually for someone like Rose, right? And so to latch on to a brand in which she's not included was really fascinating to me as you are unboxing what you were dealing with within your own body and also witnessing your mother.
Lu Chekowsky (07:44)
Yes, and thanks for saying. So to just underscore that, my mother was an obese woman over three hundred around three hundred pounds. A wonderful example of body positivity before it was a hashtag. She wrote a zine about body acceptance, she wrote an op-ed for a local newspaper about being beautiful at any size. And your observation is really keen. She embraced the Nike sentiment, even though to your point she couldn't go to a store and buy any clothes in her size. The message of living as you are, living on your own terms, seizing the moment was a message that resonated deeply with her. And she almost seemed to forget the inaccessibility of her like not being invited into the party of the brand with the purchase. It was almost like a secondary, irrelevant detail of her love of that line and the brand.
Amy- Book Gang (08:35)
Yeah. I loved the playfulness of how she embraced that, you know, where she's like, you know, you want a piece of cheesecake? Just do it. You wanna go to the store? Just do it, you know? And I love that because I think we all can relate to maybe different aspects of mother daughter journeys where our moms are kind of conspiring with us as children and it really brought a lot of levity, I think, to your life. Would you say that's true?
Lu Chekowsky (09:01)
I do think so. Yeah. My mom and I had a really secret shorthand of communication. In the book I talk about this. We talked in taglines from ads. We you know, we talked about what we saw and and sort of parroted the language of the times back onto each other. You know, good to the last drop, we would say when we finished our, you know, coffee or whatever. You know, it was like the ads were sort of the soundtrack to our life. And she and I had a secret conversation, which I think in the book I unpack both the very positive implications of that and also some negative what we pick up from our parents that we sort of internalize and maybe don't understand, maybe isn't always the best for us.
Amy- Book Gang (09:40)
Yeah. Well, I wanna talk a little bit about how candid you were about the financial struggles that you were dealing with, that you were under as you were, contemplating, breaking into this industry and really creating a name for yourself within it. Can you take us back to what your day-to-day reality looked like, you know, between this season of being with your mom and then moving on as a grown-up out into the world?
Lu Chekowsky (10:08)
It was a profound struggle. So my mom passed when I was 22. I talk about my father as well in the book and our complicated relationship. But by and I adored and loved him and also complication. And some of the complication was about, you know, you're eighteen, you're out of the house, you have to find your way. And the implications of that for me were, yeah, how do I find my way? And how do I survive? And how do I piece together a living? And I was desperate to be in New York City and to live this life. I grew up in Florida and I moved to New York right after I graduated grad school. And it was a chaotic time, it was a desperate time. Money did not come easy. I had a, you know, a few jobs, which I write about in the book in the early days of media. but I would say without any additional support and help, which in retrospect I'm glad for, it made me who I am at the time was a real struggle. And it had me trying to piece together a living from all kinds of realms.
Amy- Book Gang (11:07)
Yeah. So one of those realms that you do talk about and that I just wanna talk a little bit about was operating as a phone sex operator, which is a world that's very far removed from like corporate advertising suites you would later enter. Is it?
Lu Chekowsky (11:22)
Or it or is it? Or is it?
Amy- Book Gang (11:25)
Or is it? Or is it? Fill me in. So but I do think, being a storyteller, which is in a sense what you were doing in that role is telling a story to someone on the phone, you know, you do have to learn different techniques like persuasion and giving people what they want, right? Can you talk a little bit about maybe some surprising overlaps that people might not expect from those two worlds?
Lu Chekowsky (11:51)
Definitely. And thanks for asking me about it because it actually is sort of joyful when I think about that time of my life and the skills I was really using to survive and scrape by and what they meant. And as a sort of sidebar, there was an essay I was very fortunate to publish about five years ago in a wonderful lit mag called Pigeon Pages. I won their nonfiction contest that year with an essay that was called How Sex Work Prepared Me for a Career in Advertising, which was sort of like a seed of what ended up in the chapters in this book, where I draw even more close parallels between these two lines of work.
And so, yes, creativity, storytelling, but even more than that, keeping people wanting more, returning to a brand that they can trust, knowing they're gonna get a positive experience for their dollar, customer satisfaction in terms of how you treat them as a customer and respect and communicate with them on where the brand is going. Like it's and also I think the chapter where this subject appears in my book is called I Am My First Brand. And I think that probably sums it up best to say, without my knowledge, I was packaging this version of what was me, but was also very much not me, the best parts of me, the parts of me that I thought were sellable, which in this case was my voice.
I also struggled with my weight and my body. And at the time felt like using my voice in sex work was the way to work in that realm because as I say in the book, my body didn't inspire fantasy. It ruined it, which was, you know, my take at that time about my place and that kind of work. So this is all to say I did that job for years. It financed my life. I learned a lot, but I think in the process of writing the book, I really was able to see and maybe I'm giving this away your next question, but it was the job I was doing right before I landed in the advertising business. And so the parallels are kind of impossible to ignore.
Amy- Book Gang (13:48)
Mm-hmm. As an observer, of what you've created, I was laying on the Planet Fitness Hydro Massage bed listening to your audiobook while I was like, clipping coupons of kind of doing all these things simultaneously. But I was like, her voice is so soothing. Like there's something very special about her voice. And then of course, as I dig deeper into the book, I'm like, well, that makes sense. Like that makes perfect sense. I feel very soothed. I'm entertained. You know how to tell a story in all the different mediums.
And I do agree. I think there is some surprising amounts of overlaps that I think people will uncover as they start to dig into your story to see, you know, the parallels. Being a storyteller takes a lot of gifts. And yeah, being able to give you a nice like cliffhanger, right, to bring somebody back to something applies in a lot of different, you know, mediums, not just in that line of work.
Lu Chekowsky (14:42)
Yes, and I think my point about sharing that story and that part of my history, you know, in a book about advertising, is to give readers the possibility of finding connections for all kinds of things in their own way. I feel like that's part of what the mission of the book is, is to show some of the underpinnings of how these things work. And by making that analogy, I'm hoping to sort of empower people to, you know, there's this idea of sex cells as an ad trope of you know all time. And I think it might be shocking to people to see the relationships of those two industries and how far those connections really go and it's such a part of our culture and we see it as this these two different things and one is sort of the seedy underbelly and one is sort of the pop and color of imagine Time Square with all the ads around. But when I see those two sort of realms I see things side to side. They're very parallel to me.
Amy- Book Gang (15:36)
Yeah. And I think too, as more information is given to us. I as a reader, you know, as someone who's consuming a lot of media myself, what I considered to be that kind of seedy underbelly is no longer in that realm in my mind either. And I also see the world in a much different way in that there's a lot of ways that we have to survive financial difficulty and sometimes those are the opportunities that are accessible to people to be able to pay their bills. And in this case, that's what, you know, kind of kept food on the table and kept you alive during that season. And you how lucky that that was available to you and that that was a skill set that you could use later into your career as you are persuading people through a different kind of medium, right? I wanna Yeah.
Lu Chekowsky (16:27)
Definitely. And I also just quickly want to say not to harp on the subject, but to your point also as the book grapples with various mental health challenges, emotional challenges, devastating grief. My mother was not gone for that long at that time when I picked up that job. And I talk about it in the book. What other jobs could I do from home? I mean the world has changed so much. Zoom exists, work you know, work from home exists. But at that time it was challenging to be in office settings or whatnot for myself. So in addition to the financial kind of opportunity, it really was a way to survive at a time when my life was floundering in a lot in a lot of ways.
Amy- Book Gang (17:03)
And then a magical scholarship became available.
Lu Chekowsky (17:06)
Yes, magical. Yeah.
Amy- Book Gang (17:10)
We will keep most of the scholarship like details as a fun fact to uncover as a reader, but you did stumble upon a scholarship. Now, where was the scholarship located? And tell us a little bit about your first initial days into what we like to call corporate quote unquote culture.
Lu Chekowsky (17:26)
Yes, well predating the scholarship was a line ad on the back page of The Onion newspaper, which was still printing on newsprint, that the headline read Talented, Directionless, with money and time to spare.
And I leaned in because I couldn't have been more that. And it was an advertising school. I've already said at Wyden and Kennedy, the ad agency still of record for Nike in Portland, Oregon, was launching an advertising school for 12 people. that could be, as even as the ad said, strange, weird, freak it was a freak show, like they wanted the weirder the better. There was a really kind of cryptic website I went to saying that whoever applied might even hate advertising. I was compelled.
Because I had been raised to hate advertising and I applied and was accepted in short order and to your point. It was a $13,000 a year program. I did not have that money. And I applied for a scholarship. And within about five weeks' time of going out there for an interview, I moved all the way across the country and woke up in the center of what is arguably the best advertising agency still in the world. measured by creativity and where people would wanna work. And I was, I had a key card to the front door and I was in school in Portland, Oregon. Snap, just like that.
Amy- Book Gang (18:44)
Oh my gosh. I'm sure you learned a lot about corporate culture in this environment. It definitely seems like a very bro environment where you're kind of thrown in and I'd love to hear just some initial impressions. I obviously I remember my first corporate job was incredibly exciting and now looking back on it I was like, hmm
Lu Chekowsky (19:05)
Well yeah, I mean it was it was a spectacular time and I do wanna say like I have great affection for that agency and it was corporate but also not like it was a the counterculture corporate and they really prided themselves on being a hotbed of creative people because at that time I think you know less now with AI and sort of the way that the industry is going, but it was a it it it was a driven by creativity and who better to do that than a bunch of weirdos. But to your point about bro culture, yeah, I mean I think there was it was a sporty culture just by nature being the Nike headquarters. There was a gym in the building. There was a basketball court in the building.
Amy- Book Gang (19:48)
I was gonna ask, what were the amenities?
Lu Chekowsky (19:51)
You know, I was not in that realm at all. It was totally lost on me. But I had a lot of, I talk about this in the book. I had a lot of shades of kind of that picked last for PE history that I had and being teased for, you know, being a fat kid kind of stuff when I rolled in the front door there because it was it was like a giant gymnasium sort of had exploded and I was suddenly in the middle of it.
Amy- Book Gang (20:15)
Yeah, that was kind of the height of, you know, really giving people these like crazy amenities. I remember my husband worked at Microsoft and you know, it's like the ping pong tables and like what they were offering for snacks was really exciting and like all these like built in breaks and like endeavors that the company was doing to try to build community that were kind of off the wall. So I totally understand that.
Lu Chekowsky (20:39)
Yes, just like that. Video games, you know, foosball, you know, all the rest like that.
Amy- Book Gang (20:44)
Yeah. Well, you have described yourself as a real world fortune teller, implanting obsessions and dreams into people's minds. Can you walk us through what it's really like to be behind the curtain, shaping what the public is desiring, and maybe some of the biggest misconceptions people have about advertising and the people who create it?
Lu Chekowsky (21:04)
Hmm. Well, I'll start with the biggest misconceptions about the people who create it. Again, I think we're really at an at an inflection point with AI, which I know we don't want to get into much on we're all sort of swimming in that conversation, but I was sort of following the Khan advertising festival, which just ended last week at this recording and vaguely sort of reading the headlines and just kind of the the move towards automation. Yeah, automation of the advertising industry.
But to your question about who's behind it, so it's hard for me to say 'cause I haven't worked in ad business since 2018. And I think this is just a way to sort of say a lot has changed. It's constantly changing. And my perspective is a little dated, I think, at this point from what I understand. But the people in advertising were some of, are some of the best people I've ever met. Some of my best friends still work in that business. were in my wedding, like in my wedding and my life are considered family. And so what I want to tell you about those people is they are often really highly creative, detail-oriented, caring individuals who are empathetic and empathic. And that's why they're so good at that business, because they can put themselves in the shoes of anyone and understand what might move them to action. And on one hand, you know, with the cynicism of the moment and the earned cynicism of the moment, that can sound really diabolical. And I believe that those instincts can be used in a diabolical fashion. But when you wander into an ad agency, a lot of times it's a lot of nice people who really like paying their bills and sending their kids to college and existing in our capitalistic structures with a decent pay by being creative. And I don't begrudge that at all.
And if I hadn't gotten as ill as I did, which forced me to leave the business, I might still be there myself. So it's a place filled with a lot of delightful, charming, creative people that would probably surprise a lot of people to hear that.
I also think, at least again from my dated ex ad adventures, when I was in this business, working on an advertising campaign was a problem to solve. It was compelling. It was like doing a puzzle. Putting the pieces together. So this is who we wanna meet in their homes, in their business, in their cars, on the radio. Like what where are we gonna be? What is the right thing to say in that moment? And you're just like all these moving pieces. And it was very rare to think of that as anything else but a puzzle, a joyful puzzle.
And it's sort of maybe to me complicated to admit that because it's like, well why, you know, why weren't you thinking more about it? And of course there's parts of the book where I was trying to change the business from inside. I'm sure we'll talk about that a little more. But you get caught up in the puzzle of it. And it's really exciting to think about how to communicate a problem in a creative fashion. It's a human kind of driver. So that might be surprising to people to think about.
Amy- Book Gang (23:56)
Yeah, I mean, I feel like when it comes to like fortune telling, who better to tell a fortune than someone who's empathetic and reading the room and trying to figure out how to solve a puzzle right for someone? So I can see that complete overlap. And you know, I have the experience of being hired for the campaigns which advertising companies were trying to put on.
And from that perspective of being someone who was creating the content, it was always how do we solve a problem for the consumer? What's going to make their life better? And you know, given the freedom with some ad agencies where I was able to actually address those things, I'm proud of the work that I did because I feel like I solved that puzzle or offered someone a solution that they wouldn't have, found on their own. And yeah, it's a complicated beast.
And I remember even, you know, in my earliest days, I got a lot of backlash for partnering with certain companies or, you know, those kinds of things. But in the end, it was about who is the consumer that is buying at this particular company. You know, it also has to match the frugality, the budget, what I was doing with my own business. So I can see all those complicated things and I always went into it with a lot of heart. So I do think that, yes, there are like evil villains in the story, and then there's also really good people that are just trying to make life better and also pay their own bills.
Lu Chekowsky (25:18)
Yes. And I think for me, yes, a hundred percent what you just said. And I also would say there was a large stretch of my career, which maybe we'll talk about again, where I was trying to, quote, change things from the inside. And I had this belief that using my more human, my humanity, my deeper human parts and infusing ads with those beliefs, reflections of different types of bodies and people, could move the needle for someone who might see it, who could see themselves in the work, might make their day a little brighter.
And let's be honest, you know, going back to the way I saw my mother respond to just do it. And I'm not just talking about working on Nike. I'm talking about any campaign I happen to work on. But I think because I had a front row seat to my mother's sort of internalization of that line, my eventual relationship to that company, I believed there was an inherent there could be an inherently good positive outcome.
And also in 2004 when I went to advertising school, there was a huge onslaught of what might we might now call greenwashing. But this belief that aligning brands with certain causes. I write about it in the book, The Live Strong campaign at the time launched in 2004. Dove Beauty was alive and kicking in 2004. There was sort of a group belief that through advertising, marketing, and branding we could support different kinds of causes in people. I think that there's more cynicism around that as it's proven to maybe not be so accurate. But when I showed up, it seemed like a fairy land of like I can move the needle of culture from inside this place and maybe even for good.
Amy- Book Gang (26:49)
Our overlap is crazy because I started in 2004 and I was like going on trips for Dove Beauty. And I remember going to like Hollywood movie premieres and all of these things where they were empowering women to come and see women directors do things. So I was completely embroiled in a lot of the campaigns that were running during that time. And also like inspired and proud to represent these products that were doing the things that, you know, people said that they were doing for us.
Lu Chekowsky (27:17)
And could arguably I don't wanna yeah, I don't wanna diminish the value. I think there was and is an important role that like that campaign, for example, because it was so large scale and prominent, you know, would we rather a world that didn't have that in it? Like I don't I think my answer would be no. Like I'm glad that those campaigns existed. I'm glad those conversations happened. But with the perspective of time, do I think it moved the needle on women's role in our culture, on our ability to have, you know, power in our culture? No. Do I think it changed the relationship to our self love and how products need to sell us things to fix imagined problems? No. You know, so it again. It's you continue to turn the prism and there's like all these different flavors and shades in it. But I don't want to give the impression that I of such great cynicism that I wish those things didn't exist. I'm glad they existed. I just feel like with the perspective of time, it wasn't the thrust forward that maybe culturally that we might have believed that it was at the time.
Amy- Book Gang (28:20)
Yeah, cosigning that all of this is building up to something, which is that you finally get to choose yourself. I wanna talk about the moment that you made that decision, Lu.
Lu Chekowsky (28:31)
Well, what I will tell you about that moment is that the decision was made for me in that my body and I had a falling out. I had put it to the back burner in service of big campaigns, big jobs, big travel schedules, big shoot schedules, big glamorous famous people I was working with, et cetera, et cetera. And I kept saying, I'll get to the business of my body later, I'll take care of it later, there will be later. And then later happened in 2018.
And it made it so that I could no longer work in the ways that I had been working. And I got so sick I had to leave my career. And that was when it became really critical for me to piece together the story that is this book. And how did that happen? And how did I get there? And and that was that was where the that's where the story fell out
Amy- Book Gang (29:28)
Well, we are lucky because we get to hear your story. And I'd love to dig into your experience selling this book, right? Because you have this incredible story. What was the process like with drafting? I mean, did you know a lot about storytelling in this capacity? How did that first draft look and how long did it take you?
Lu Chekowsky (29:49)
So I really and the book discusses this a little bit. I had started I had wanted to write a book my whole life. I had gone to undergraduate graduate school for creative writing. So I and then I fell into media business as the book grapples with and sort of lost my voice along the way for myself and sold it again as we've talked about endlessly to brands and big companies. So when I got too sick to work, I had no ability to harness my own voice and my own story in any way that felt true to me. I knew how to internalize a brand story as we've talked about, like spin it around, find the best parts.
Like chart it, map it, but I didn't know how to write from my heart. I used to know how to do that when I was a child, as we talked about in college. When my mother died, who was my biggest fan of writing. I think I just sort of gave that dream up. I was really unable to access my writing for a lot of years. So in terms of this book, I sat down and said I have to write what happened, but those first pages were messy. I wrote from second person endlessly. You, you, you. Well, who's the you in a memoir? The you is the me, is the I, right? but I had spent so many years making advertising that I was talking to the consumer and the you and it was striking. It was relentlessly difficult. I kept, I felt like I was throwing myself against a wall. Like it was so hard to write down these stories because what I had learned in advertising had changed how I thought. Everything needed to be fifteen seconds, thirty seconds, which of course is like an inordinate amount of attention at this point with how the world has gone and so who would stand stick around for a chapter about me or a whole book? Like and also why me? Why would anyone care about my story when there's all these other more beautiful people? Like the writing of the book for me is what's on the page.
Certainly, but it also is what happened behind, which was just an enormous process of trying to locate my own value and my own story. And that took a lot on the very pragmatic level and practical level. There was a proposal that went out in 2020 that was more centered around the book was called I Exist to Please You at the time. It was about the idea of people pleasing and pleasing an audience and pleasing culture and pleasing my mother. It was a blurrier version of what the book is now.
There was another proposal that never went out that was just really more focused on my relationship with my my mother, who's obviously folded into this book a lot. Anyways, that's all to say. It took about eight years from start to finish. And I'm really grateful now in retrospect because I believe that this version of the book holds the perspective necessary to hopefully make it resonant with readers. I think I was really close to the story as I was writing, writing, writing, and with just distance, there's more humor, there's more perspective, there's more ability to recount something without needing to double down on the trauma of it or the implications. It's like I can just let things be, it's been a very long process. As well as to say it's been almost a decades long process.
Amy- Book Gang (32:56)
Wow. Okay, well, I find this fascinating that it was not originally written in first person. That is so interesting to me. You know, we just as a book club had read a book called Woodworking by Emily St. James. It's about the trans experience, but it's told from three different perspectives. One person who's fully stepped into their story, told in first person, close voice, sometimes a a little aside, and then someone who hasn't fully gained into their story, and then one who's completely out of their story. So a first, second, third person kind of kind of experience and now I'm thinking about you because it's like it took you to go in from that place of distance to get into that first person voice to claim the story and then be able to tell it in that voice is really fascinating to me.
Lu Chekowsky (33:42)
Yeah, I really appreciate that. And I think, you know, in retrospect, I've said to a few people, and maybe I don't. I don't see this as a spoiler, but maybe maybe someone will. I believe that the book existing as an object is the proof of my journey through that process. And I'm so proud of that. Meaning without all of that sort of back and forth or my ability to locate myself in my own story, the book could never exist. And I love that it's an artifact of that process.
Amy- Book Gang (34:10)
So what did it look like then after eight years? How did you get your agent? What did that process look like for you and then the sale of this book?
Lu Chekowsky (34:17)
Yeah, I don't mind sharing. So I'll be very honest. I never had to do the query trenches insofar as I met my amazing agent, Monica Verma, at LGR in twenty seventeen and I had a bud of a book idea and we just really aligned and she saw a lot in me. And she traveled the last eight and some years with me as this book evolved. And so really believed that I would eventually crack it. And she's amazing, and that's I know that's a very unusual story. She was a friend of a friend. I was introduced. I'm thinking of writing a book, I said, in 2017. And then, you know, and on we go but with all the process and the and the ups and downs of the book, 2024 I sold the proposal as a lot of nonfiction sells with a very constructed first chapter, deep, deep, deep outline and I had a lot of it written but not all of it.
And then I spent the last year before publication writing it in real time with my editor, Vivian Lee at Little Brown, who's amazing and generous and beautiful. and I love her. so I would deliver maybe every six weeks a new pages. So the book sort of, it was a lot of work, very close. The outline really ended up being mostly how the book worked. It was a really tight, tight, tight outline. but then spent a year sort of pushing the boundaries of the pages.
Amy- Book Gang (35:38)
Can we talk a little bit about the structure of your book and how you played into that? You know, I mentioned earlier that there were these ad interludes. You also kind of start in the height of things a little bit with MTV, where you're coaxing a star to participate in an ad that he's not really excited about, frankly. And then we work our way into childhood and then kind of go back to the you know beginning almost of where you were with your journey. Why did you choose to structure your book that way?
Lu Chekowsky (36:11)
Yes, so the first chapter is told in present tense. It's the only well, maybe the epilogue a hair, but yeah, it's told in very urgent, in you know, in action moment. I wanna, you know, look, I think that's the T V in me. You know, I worked in television marketing for a long time. I didn't make television shows, but I marketed them and understood how they worked. And I think there was a little bit of trying to set the scene of some high stakes, you know, hook hook the reader, bring them into the scene.
And have them with me. And then the book is chronological, although there are these beats. I think as you noted, they're called ad breaks. not formally in the book, but the shorthand for me, and they're written as sort of fake ads. They reveal maybe a little bit of the underpinning of how ads might work, but also move the story along. I think having the book mirror a content experience broken up by ads just seemed hilarious to me. And I'll I love you know, it's it's it's obviously the book is called Don't Buy What I'm Selling and I do hope people buy it. So I think it's a little bit of the meta in me where I like to not just participate in what I'm making but acknowledge that it's being made. I think that's a fascinating stance and it's a powerful stance. And I also I wanted to tell the story chronologically for the most part, because again, I it was a in my own journey of writing it was a mystery story and I do think the pieces start to fall together in chronological order in a way that that's important for the understanding of it.
Amy- Book Gang (37:38)
Hm. I loved it. Well, I wanted to ask what advice you might give to someone who's considering embarking on their first memoir.
Lu Chekowsky (37:47)
Yes. I have so much advice. Well, one, further to how long it took me to write this, I would say it's going to take as long as it will take. And it is worthwhile to keep pushing, even when it seems like you're not making headway. Your work is taking you closer to where you want to be. And that feels really critical to me to communicate to any potential author. If I had given up my process years ago, I wouldn't have this book. And, you know, cut to me sitting around piles of pages where I don't know how they fit.
And how they come together. I also would just reiterate something I said about in writing memoir, at least in my experience, and I'm not saying this has to be everyone's, but in my experience, understanding my relationship from a personal and spiritual and human point of view made my writing that much better and clearer. And I'm so much prouder, I think, of the work than had it had been published a few years ago. And so what I mean by that is I see memoir writing as what's on the page, but also the personal sort of endeavor to understand it. And those two things where those two things meet, I think is what makes a quality book.
Amy- Book Gang (39:00)
I love that. Well, we are going to be closing out on the main show here. And for those of you that are patrons of the show, it's $5. And that keeps us independent, commercial free, and gives space to people like Lu to tell their story. You'll get to get all the spoilers on the back half, but we always end our show the same exact way, which is what's making you feel proud right now, Lu, whether it's with this project or with life in general. And I just get to tell you, I was so moved by this book.
Also, I'm just gonna be honest. All the GLP 1 ads, the plastic surgery ads, the you know, body morph the you know morphing that we are trying to push onto people, I suddenly feel a lot less detached from it because I read your book and I now understand ads in a very different way. So I want to say thank you. And I've been like giving this information to my daughter. I feel like you are helping future generations understand, you know, that we don't have to be under the pinnings of other people's advertisements and what they want and desire for our life. So for me it's been a really impactful book. But I'd love to hear what you're feeling proud of right now.
Lu Chekowsky (40:09)
Thank you so well, first of all, what you just said, I couldn't I'm on cloud nine from that. I mean that's the greatest wish I have to have this book have impact and resonance. So thank you for sharing that. Thank you for saying. I mean, that's number one on the pride department. But also secondarily, I'll just say I'm so proud that I didn't give up on myself and that I located the voice inside of me that is actually mine and that I have now used with my own name on the cover of my own book. After years and years of supporting people from behind the scenes in the dark, uncredited, which again is part of what advertising is. That's the deal. I never thought in a million years I could get to this point and I'm I'm I'm proud to be here and to share my story and hopefully it will resonate with readers like it has with you. And I just I'm very grateful. Thank you.
Amy- Book Gang (40:58)
Yes, well, you must follow Lu on all social channels. She's a TikTok delight. I always look forward to all your storytelling over there. You can get some like short form great stories from her career as well as definitely check out this incredible book. I am so glad that we got to share space with you. And listeners, if you're a patron, I'll meet you on the other side.
Lu Chekowsky (41:21)
Thank you for having me.
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