Whatever the Cool Girls Are Doing, Do the Opposite

October 6, 2025

Hello and welcome to The Financial Diet's weekly newsletter!

We'll be in your inbox every Monday sharing our best tips to keep your money, career, and life in order. Today’s newsletter was written by Chelsea! She’ll be taking over the newsletter over the next 3 weeks in celebration of her upcoming book, Having People Over!

Don’t forget to scroll down to the Events section of this newsletter and join us at one of our upcoming FREE workshops!

Thank you for being a part of this special little corner of our community!

❤️ TFD

By Chelsea Fagan

As of this writing, I'm on day 22 of my 30-day social media series to celebrate my new book, Having People Overnot to be confused with my full-length YouTube series of the same name. (If you haven't already, please consider preordering the book or requesting it from your library, as it's the single most helpful thing you can do for an author!) Maybe unsurprisingly, the process of creating so many videos to support the launch has been much more labor-intensive than I initially expected: even for someone who has been in the business of making content her whole adult life, putting something out every single day is a lot! And the videos range in topics, from straightforward hosting content to mini-rants on the communication or finances of friendship. Fortunately, the response has been pretty universally positive, in part because I think social media has us -- or, at least, me -- feeling starved for this kind of content.

I made a TikTok a few months back about the idea that whatever the Cool Girls are doing, at least as it pertains to social media, we should do the opposite. And doing this series -- focusing on the home, on personal connection, on the things we create rather than purchase -- has had me thinking about that video a lot. 

I'm a New Yorker, for example, which means that social media is constantly apprising me of fabulous new restaurants where I can spend my money. Every week, it seems, there are a dozen new "it" restaurants I've never heard of, ones where you can wait in line for hours before opening or speed dial the reservation number at the crack of dawn, a month before you wish to get a table. These are the places the Cool Girls eat, you see, with low lighting and branded matchboxes and various snack foods you can optionally order with a tin of caviar to dollop on top (for the low, low price of two hundred US dollars). They serve martinis and orange wine and revisited diner fare that feels mostly indistinguishable from an actual diner, except for the price point. And everyone who is anyone is eating there, so why aren't you?

There are also the clothes the Cool Girls wear -- I've heard on good authority that ballet flats are back, as is a certain rollneck sweater from J.Crew! They are loving "uptown punk," according to Vogue, but also bringing back a sense of "modern prep," perhaps typified by the aforementioned J.Crew sweater which has gone nothing short of viral this season. The way we dress has always been a means of signifying a million different micro-statements, but combined with the speed of social media trends, the production cycles of fast fashion, and the endless churn of influencer culture, now what separates an "on-trend" versus "dated" outfit changes on an essentially week-to-week basis. 

Even in my beloved space of home decor, the Cool Girls have decided what is or isn't worth doing. Are you thinking of doing a gallery wall? Many designers say they are over! Love the look of an accent wall? I regret to inform you that those are no longer chic. (This was tough to read, as someone with both in her apartment.) And I certainly hope you didn't tie up the majority of your savings in a modern farmhouse you purchased during the style's high point, as designers are now saying the look has lost its appeal. Guess it's time to tear your house down and start over, because apparently the It Girl has her own interior design style, and your place probably doesn't have it. 

For anything a woman wishes to do, be, or purchase, there is a Cool Girl version of that thing being relentlessly marketed to us. I'm not a mother myself, but I'm well aware that there is even a strong market for Cool Moms, and if you don't know who to follow on that front -- fear not! There are always roundups of the right moms to follow if you want to emulate their simultaneously breezy and hyper-curated version of motherhood. 

The reassuring thing to tell ourselves, of course, is that the Cool Girl doesn't exist. But I think it's better to embrace the reality that they do, and always have. There have always been, and will likely always be, a certain class of woman from whom endless style envy and shopping trends flow downstream. Much ink has been spilled on how unsatisfying the photos look from the set of the new JFK Jr/Carolyn Bessette series, in part because what made Bessette in particular such an enduring style icon is essentially impossible to recreate using anything but the original materials (including the woman herself). She was a Cool Girl, even if her life was far from perfect -- because contrary to popular misconception, being Cool doesn't necessarily mean being fulfilled, or even being happy. 

We've always had these Girls, we now just have exponentially more of them with the explosion of social media and its attendant influencer culture. You don't have to search very hard to find women who are wearing the Right clothes, eating at the Right restaurants, looking the Right way (and, let's be honest, weighing the Right amount). I'll never forget the night a few years ago, when I was eating with friends at a then-quite popular restaurant, and looked up from my table to see that almost every single woman in the place -- young, well-heeled, beautiful -- had her hair in the exact same style: pulled back, lacquered to the head with styling gel or pomade, twisted into a clean little knot at the nape of her neck. 

I know that trends existed when I was their age, and I'm sure I participated in them. But it was the first time I truly felt the flattening effect of an algorithm play out in real life: everyone was perfectly on-trend, everything looked sort of the same. 

Much of my book is about this very topic, about what it means to escape that algorithmic flattening and reclaim our own tastes and desires. Of course, part of that is just logging off our apps and experiencing the world through our own senses, which is why the in-person aspect of gathering is so important. But we don't necessarily need to be with other people in order to experience life fully. I have a whole chapter called Curation versus Consumerism, attempting to separate the important act of being inspired and moved by the world around us, as opposed to the common impulse to purchase something in order to feel like we draw value from it. A question I often ask myself, particularly when drowning in messaging about what the Cool Girls are doing, wearing, eating: do I need to own this thing in order to appreciate it? Is a painting I love in a museum somehow less a part of the tapestry of my experience and taste because it does not hang in my own living room?

(It is at this moment I should reiterate that, while I hugely appreciate anyone who preorders my book, it is just as valuable to request it from your library -- and that is super easy to do!!)

To me, it is obvious that this intentional conflation of appreciating and owning is why Cool Girl culture is so valuable to our current marketing moment. We've always been able to see a glamorous, affluent woman doing something and want to be more like her, but never have we been more able to directly own a piece of her, often without having to leave our own sofas (or even close the app we're watching her on). If we want to wear the adorable ballet flats that are firmly back in style, they're linked in her bio. If we want to eat the baked potato topped with caviar at that chic, dimly-lit bistro, there are entire third-party websites that scalp reservations to the hottest restaurants. If you love the way she does her no-makeup makeup, fear not, as she has filmed a step-by-step tutorial on how to recreate it (step one: be born with a perfect bone structure and pore-free, dewy skin). If you like it, you can buy it, and in the process feel just a little bit worse about the things you already had.

One of the downstream effects of filming so much content in my home, and organizing even more gatherings than usual to film, has been a significant reduction in the amount of going out I do. I go to fewer restaurants, I'm shopping much less (save my weekly visit to the flea and farmers markets), and have been so consumed with the stuff I have to produce that I've barely been paying attention to what else is happening on my feed. I've noticed a significant change in my budget -- as I've always said, hosting is usually the cheaper option! -- and found that a few of my friendships have been strengthened by the increased time allocated to nurturing them. Although I'm under a lot of pressure, I feel less anxious, in part because I think I have less bandwidth to worry about what I'm doing wrong, or how "perfect" everything might look. 

And my manifesto in this book, when you take away all the fun little recipes and DIYs and practical hosting advice, is just that: The more we fill our lives with the people and things that have actual meaning for us, the less time we have to worry about what everyone else is doing. A home that looks perfect on a screen is vastly less valuable than one that feels warm and welcoming to the people who enter it. One outfit that you love, keep, and re-wear for years is worth ten that happens to be perfectly on-trend. And no matter how popular a new restaurant happens to be -- no matter how many foods they can find to top with caviar! -- it will never hold the same meaning as a homecooked meal shared with someone you love. 

It is perfectly healthy to be inspired, and to even sometimes envy the things we see. But we do not have to transmute those feelings into purchases, nor is the value we offer in life something enhanced by imitating through consumption. The more we take back our identity and self-worth into what we already have, and the things we can create rather than consume, the more we will feel secure in the person we are -- regardless of whether or not we're on-trend. It takes so little to make another person feel seen, valued, and special. We don't have to be rich (or Cool) to create experiences for ourselves and others that life beautiful. A home that is good is one that is loved and lived-in, regardless of what some designer might say is out of style. And the more we remember that, the happier we'll be. Or, at least, I will.

October 16th: Join us for The Art Of Being An Adult hosted by Chelsea! In this FREE workshop to celebrate her upcoming book, Having People Over, Chelsea will deep dive into many of the more underrated aspects of growing into yourself as a well-rounded adult. She’ll cover the basics you need to start hosting more regularly, the rules for creating a beautiful, personal, and functional home on a budget, how to create and live by a well-balance calendar, and more! You’ll also receive a free bonus workbook and exclusive content from the book. Register here.

November 12th: Wealth-building workshop alert! Join Chelsea along with Financial Planner and friend of TFD, Kellen Thayer, for How To Put Your Money To Work! This will be an info-packed 90-minute immersive workshop to learn the must-know wealth-building techniques for after you have covered the basics. Chelsea and Kellen will cover everything from the basics of real estate, mastering investments beyond the 401k, side income, entrepreneurship, and so much more! Click here to register! *Please note we’ve been having some technical issues with the registration quiz, please email [email protected] if you have any issues!

While this section includes products and services from our paid partners, we only feature brands we genuinely like and use—and think you would, too.

FINANCIAL ADVISORY — Advisor.com: Dozens of people in the TFD community already trust and use Advisor! They’re one of the only financial advisory companies offering their services for a fixed, flat annual fee. Their team of advisors work for you, not commissions, and help you to achieve your financial goals through planning, investing, and more, no matter where you’re starting from.

INVESTING — Betterment: If you’ve been wanting to start investing but feel overwhelmed by where to begin, Betterment makes it super simple—even if you’re not a financial expert. With automated investing and goal-based planning tools, they’ll help you grow your money responsibly and sustainably over time. It’s a great option if you want to take control of your financial future without having to become a full-time market expert.

BUDGETING — Monarch: Our recommended Mint replacement! As we already shared in the main section of this newsletter, we highly recommend using Monarch to take the guesswork out of managing your money — use it to budget, set goals, and actually understand where your money’s going. Even better: there’s no ads, no selling your financial data to third parties, and no "premium only" upsells — just a clean, secure app that makes managing money feel way less overwhelming (and actually kinda fun?).

The Society at TFD is our members-only community with access available on both YouTube and Patreon. Joining The Society is the best way to directly support TFD! The Society offers the exact same things on both platforms, so choose whichever one you prefer!

We offer 3 tier options:

The Society at TFD Lite: $2.99/month

  • Monthly office hours with Chelsea to chat and get your personal questions answered

  • Access to our monthly book club hosted by TFD Creative Director, Holly

  • Illustrated tech backgrounds every month

  • Access to Society Discord

The Society at TFD: $4.99/month — includes everything in the $2.99 tier plus:

  • Monthly ad-free extended director's cut videos from Chelsea

  • Exclusive members-only events and workshops

  • Complete post archive (including exclusive members-only videos of Chelsea ranting on different topics)

The Society Premium: $9.99/month — includes everything from the previous tiers plus:

  • Weekly newsletter from Chelsea

  • Monthly multi-page workbook/guidebook on a different topic each month

  • Members-only capsule podcasts