Am I Pretty Enough To Sell The Dream?

October 14, 2025

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We'll be in your inbox every Monday (or Tuesday when there’s a holiday) sharing our best tips to keep your money, career, and life in order. Today’s newsletter was written by Chelsea! She’s taking over the newsletter this month in celebration of her upcoming book, Having People Over!

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By Chelsea Fagan

I went in for a plastic surgery consultation last month. I'm a bit embarrassed to admit this -- and, to be clear, the actual experience of being quoted a ludicrous sum of money while a doctor prodded at my face in a handheld mirror was enough to put me off the idea entirely -- but I think it's important to be honest about my brush with such a decision. In my defense, it had been a very rough week, a horrendous bout of PMS during which I was confronted with the most unflattering video of myself I'd ever seen. Even as someone who has spent the past ten years seeing herself daily on 4K video, it was a shock to the system harsh enough to book an emergency appointment with a very nice doctor on Park Avenue. (Farewell, sir, and don't spend my nonrefundable $250 consultation fee in one place.)

Part of me is glad I went, in the sense that seeing the details (and finances) of such a decision up close is a healthy dose of reality for our image-obsessed media environment, which has made cosmetic procedures so ubiquitous as to ostracize any public figure who dares to age naturally. It also led me to have several meaningful conversations with my husband and close friends about what I was feeling in the days surrounding the consultation, an acute level of physical awareness I'd never before experienced, even through a career that has constantly required me to be on camera. Talking through these feelings and anxieties, as well as giving my hormones a chance to settle, was healthy for me to do, rather than just keeping it to myself. 

But on the other hand, something about the experience has left me feeling distinctly nervous about the future. Part of my crisis came from the reality of being 36 years old, when things inevitably don't look quite as fresh as they did in your twenties. If I'm going to continue to have a public platform as I get older -- and for what it's worth, I think having older women in roles of media visibility is extremely important -- that's just going to be part of the deal. But I'm aware that another, less universal part of my recent appearance-related stress is due to the space I am now trying to enter, professionally. With the launch of my upcoming hosting book, and its ensuing tour with Williams Sonoma, there is no denying the fact that I'm entering the lifestyle space. 

For better or worse, the majority of my career has been in the personal finance space, where the expectations of visual appeal are... low. I'm not going to name names here, but most of the industry is very male-dominated and not aesthetically pleasing, to say the least. Your appeal as a financial creator is usually either based on your ability to make money (get rich like me!) or take down people for not managing their money wisely (don't be an idiot and get into medical debt!!). Though my content has never quite fallen into those categories, I have always felt like I'm edging out the competition just by wearing a shirt that fits reasonably well and brushing my hair before going on camera.

And even in writing romance, which is undeniably a much more feminine sphere, there is just not that much visual pressure put onto authors -- at least, not that I've experienced. I couldn't pick most of my favorite fiction authors out of a lineup, and many in the space go out of their way to use pseudonyms or hide their faces on social media, as their writing is to some extent in conflict with their day jobs. There are the Hot Girl Authors, of course, but I can say that they are very much the minority, and not usually the most successful. For all its faults, I can give the romance world big credit for never putting pressure on their creators to also be baddies, or to live ultra-fabulous lives on social media. (If anything, I think the latter might make them feel less relatable.)

But the lifestyle space? That's where the It Girls tend to congregate. I am once again not interested in naming names, but I'm sure you can conjure many of them from memory, or from your own feeds! These are the mostly-millennial, social media-famous queens who teach us how to cook a meal, style a home, or generally live a chic and aspirational life. Even the ones who start out as regular-degular home cooks in humble surroundings eventually, through dint of their success in the field, turn into something out of a magazine. Their kitchens undergo six-figure renovations, their bodies become sculpted by pilates, and their wardrobes benefit from the intervention of professional stylists. 

I've been made aware -- occasionally with less tact than I'm sure the person intended -- that appearances matter in this space. If you want to get booked on daytime television, grace bookstore end caps with your smiling face on covers, or be selected for aspirational magazine photoshoots, it helps to be a baddie. It's not enough to be good at your craft, or to have genuinely helpful tips to offer people. It doesn't even particularly matter if your content is geared towards the more affordable or lo-fi, the person (woman) delivering the message is supposed to be the kind of woman you want to be. And that has a lot of connotations in our society, some more healthy than others. (It's not lost on me that many of our most successful food influencers are quite thin, in a way that regular consumption of their own food would largely preclude!)

And I should say that these questions of my appearance -- am I pretty enough to be the kind of woman you want to watch prepare a meal? -- are not the extent of my newfound self-doubt. Now that my own home is more a focus of the content I'm producing, it's hard not to look at it with a more critical eye. As I'm showing the same items and angles over and over, although it is a very accurate and budget-friendly representation of how I actually host, it's easy to feel a twinge of wanting to upgrade. Would people like it more if I had nice new things to show, or upgraded my kitchen to look even more Instagram-worthy? My answer to these questions has been a resolute "no," but I would be lying if I said that they didn't cross my mind.

I grew up on the Marthas and Inas and Julias of the world, women who for all their talents and aspiration weren't baddies as we conventionally know them. (Martha Stewart did used to be a model, but by the time she was teaching everyone how to live at home, she was well past the age that standard media would consider It Girl-status.) But I do fear that the confluence of social media culture, youth obsession, and hyper-consumerist culture have made the pressure on women in the lifestyle space to be viable brands absolutely unbearable. There are a few exceptions, of course, but for the most part the women who rise to major prominence in these worlds now are women who have it all in the very old-school, Helen Gurley Brown sense of the word, right down to the adorable children most of them end up having -- only adding to their domestic goddess bonafides. 

When I spoke to my husband about all this, I came to two major conclusions about what this very real (if somewhat embarrassing) anxiety should mean for my future. One, I don't ever want lifestyle content to be my full-time focus. I'm always happy to share moments of hosting, cooking, or home decor when they organically happen, but just 30 days' worth of pressure to turn my actual life into content for my book series has been way more stressful than I ever anticipated. And two, I want to do more work that involves real, physical events and gathering, where people and moments can be experienced, rather than solely viewed (and judged) through a screen. I'm currently making some moves to set myself up for a more events-focused career in the years to come, and I'm extremely excited to share them soon! The fact that events are also a very good hedge against the encroachment of AI is a bonus, but my AI-related anxiety is for another newsletter...

In the end, very few of us will make it through life without feeling the pressure to look more beautiful, or have a more visually enviable life. And to some extent, I think making peace with this is good for our mental health. Like it or not, how we present ourselves will usually have an impact on outcomes, including in the professional sphere. But there are always going to be forks in the road at which we choose just how much the superficial will bear on our success, whether that means working in a certain industry or living in a certain rarified zip code. There are lives we could all be living which would make the way we look, the clothes we wear, the car we drive, or any other number of ultimately aesthetic choices very, very important to how we are perceived. And in flirting with the lifestyle space, I've realized that to forever hitch my success to the industry would mean living with such an outsize level of pressure to be aspirational that I would likely succumb in many ways, undermining my values in the process. 

Ultimately, I love hosting and wanted to write a book about it because having people over is not about how perfect we make things look -- it's about how we make people feel, the warm and intimate and welcoming experiences we can conjure in their presence. Perhaps selling this message on a massive scale will require looking like a model, or living in a home straight out of Architectural Digest. But I'd rather keep my expectations for success in this world reasonable, and focus more on the work I do that is less about how fabulous my life happens to look at a given moment. I may never be the next Martha, but I'll keep getting to be the me that I've worked very hard to become, and to love as she is. 

October 16th: Join us THIS THURSDAY 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!

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