What Is The Opposite Of Imposter Syndrome? Because I Think I Have It.

October 20, 2025

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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! This is the final installment of her newsletter takeover this month in celebration of her upcoming book, Having People Over, which drops tomorrow!

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By Chelsea Fagan

My book comes out tomorrow. At this point, I don't think there is much I could say to convince you that I haven't already said, but I think I'm legally required as an author to ask, one last time, that you consider ordering a copy. It's called Having People Over, it's about hosting, making friends, building community, and just being a more self-actualized and happy adult. I think it's really useful, and I also think it's beautiful to look at, and it's a pretty reasonable price for the kind of book it is. So there is my final sales pitch to you, thank you for listening.

Today, I'm sitting in the familiar mix of nervousness and excitement that precedes any significant professional moment you've been preparing for a long time, the moment when all the work you've done must speak for itself. I have my own personal goals for the book, of course, but I find myself strangely calm at a time when I would usually be riddled with second-guessing and self-doubt. This time, I can say without any qualifiers that I did my absolute fucking best to make a really great book, and to promote it to the absolute best of my ability -- more marketing than I've basically ever done for anything else I've created. And that, in many ways, is the victory already.

I have been thinking a lot about the curse of ambition: fellow financial diva Stefanie O'Connell is actually working on a book about the way women get punished in life (and particularly in relationships) for having too much ambition. And while I don't feel punished in my marriage for pegging so much of my identity to achievement and productivity, I do often feel punished in my own brain. I think a confluence of growing up poor, not having a college degree, starting my writing career in perhaps the most un-prestigious way possible, and never quite feeling like I had the bona fides of my fellow authors has always left me with a seemingly endless need to prove myself.

And I want to be clear that what I experience is not imposter syndrome -- in fact, if anything, I feel more qualified than many people with objectively more impressive careers or credentials. I know that positions of power are riddled with incompetence, people whose trajectories were essentially determined at birth through a combination of connections, elite upbringing, and genetic lottery. (I said it the other day on Instagram, but it bears repeating: basically every Fortune 500 company has at least a handful of overgrown SEC frat boy executives who failed upwards into their job despite barely being able to open an email attachment.) One only needs to read Reddit threads from overworked executive assistants to see how little the people at the top are often doing.

In creative industries like mine, a level of competition and scarcity only drives this dynamic to a sharper point -- just the other day I fell in love with a woman on TikTok whose style seemed so effortless, and whose leather goods business was thriving despite being fairly new to the endeavor. Two clicks of a Google search informed me that she is descended from Hollywood royalty, her dad having directed one of my favorite 90s thrillers. Oh, well, I thought. That's par for the course.

So I don't feel like an imposter against such a backdrop: if anything, I feel an acute resentment at how hard so many otherwise-talented people have to work never to break through at all. I feel grateful for having achieved the foothold I have, imperfect as it may be. But the fact of having started behind the eight ball seems to have implanted a never ending level of expectation for myself, and how much I should be prepared to do. I am ambitious in some ways because I feel I have beaten the system and found myself in a role I was never intended to have, so it is a kind of cosmic duty to make the most of it. I think a lot of people feel this way, like it would represent a kind of ingratitude to not always be pushing yourself, always be producing, always be showing up in ways that many people (including, often, people in your own family) never had the opportunity to.

Ambition, in my brain, feels like constantly spinning gears, interlocking and propelling me forward with their endless motion. It is very difficult for me to accept that I have done enough, tried hard enough, left it all on the court (so to speak). No matter the project, I often find myself come showtime with a feeling of insufficiency, focused more on the opportunities I missed or ways than the things I accomplished. Marketing something is a great place to torment oneself, because there is always more self-promotion one could be doing. But this can happen over anything, a feeling that you owed just a bit more to yourself than you lived up to. (My friend recently described having this feeling during an important presentation at work, with each slide suddenly feeling like a display of her imperfect preparation once under the gaze of her potential new client.)

I told myself -- and several of my friends -- that with this book, I would set out a certain number of things to do to promote it, but that when those things were complete, I would be at peace. I did my 30-day social media series, my 4-week YouTube series, this newsletter series, an initial 8 book tour stops to which we're adding another 5-6, and a few other press hits here and there. That would be my big marketing drive, and after that, I will relax in the knowledge that I did my absolute best. It was a promise I made to myself knowing it would likely be very difficult to keep, as the permanent itch of ambition can always creep in at the last minute to remind us of what we didn't do enough of.

But strangely, today, I find myself really happy. Perhaps it's because the holidays are coming up, and for once I have plans to stay in New York City and just enjoy the tiny, beautiful life I've built there. That feels really exciting in a cozy, relaxing way to me. Or maybe it's because I have a lot of friends who've published books this fall, and their own anxieties about doing enough reminds me that we are all in a perpetual struggle with our own desires for ourselves. But I think, deep down, that I know I tried really fucking hard, and something that is blessedly coming with age is a little more gentleness with myself. I've never really felt like an imposter, as such, but I have sometimes felt an overabundance of "just really happy to be in the room."

I'm not happy to be in the room anymore, I think. With each passing year, this is just starting to feel like the room I belong in. I take care of it, and take pride in doing a good job while in it, but at the end of the day I get to turn off the lights, sweep the floors, and go home.

And after this book comes out and the tour is finished, I'm ready to go home. 

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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