In Practice: Christina Monroe Is Three Weeks Ahead, Always

How a bridal shop job led to a career in worldbuilding, and why she's begging brands to stop being weird in the comments.

You can literally just do things! Earlier this week, I had the idea to bring an interview series to this newsletter. Well, here it is.

As we know, the branding world talks a lot about vision. Big ideas. Breakthrough thinking. But if you’ve actually worked in it, you know that what matters most isn’t just the idea; it’s how you practice. How you notice things. How you structure your time. How you build trust. How you stay curious, even when the work is exhausting.

In Practice is a series of interviews with the people who make brands move. Not the ones with the loudest voices, but the ones with the sharpest eyes. Strategists, marketers, creatives, researchers. People whose influence shows up in campaigns, in team culture, in how a brand behaves, not just how it looks on a slide.

I hope that this series can be a window into how people think. What they’re tracking. What’s shifted for them. What they’ve let go of, or started to hold more tightly. It’s a chance to see brand work not as hype or identity, but as practice—shaped by taste, context, media habits, self-awareness, and the systems we build around ourselves to keep going.

Introducing Christina Monroe

There was never a question who would go first.

Christina Monroe is my closest collaborator, one of my best friends, and one of the most gifted cultural strategists I know. She’s also the co-author of this newsletter, and the person I trust most when I want to know whether an idea’s actually hitting, or if it just sounds smart in my head.

Christina works at the intersection of strategy, storytelling, and internet culture. Her background spans heritage brands and digital-native upstarts, but her signature is the same across both. You just know if Christina did something. Her POV is part pattern recognition, part prophecy, and always grounded in a deep care for how people actually move through the world.

You might know her from All Caught Up, or from one of the many brands she’s played an instrumental role in. She’s fluent in screenshots, allergic to cringe brand behavior, and quick to cite a 2003 rom-com or a niche Tumblr post to prove a point. More than anything, she’s built a practice around staying close to what matters: meaning, connection, context, joy.

In this interview, we talk about the real story of how she got her start, what finally helped her let go of the need to take on everything, and the future she sees coming for brands.

1. What's the real story of how you got here? (Read: Not the LinkedIn version!)

Every opportunity I have had has come from someone taking a chance on me. Sincerely! My first real step into social (outside of college internships) was at a bridal shop in Manhattan. The owner posted an ad for a social media manager, and somehow, she ended up with me: very green, with zero bridal experience, hungry for anything fashion-industry-adjacent and ready to post.

I worked there for about a year — even sold a few gowns (!) — before meeting my future boss. She was in the market for a wedding dress and a SMM to help her revitalize a portfolio of heritage brands. Kinda kismet. Our store manager, who was a close friend of mine, introduced us. She ended up buying her wedding dress from the boutique and then setting up a meeting with me. The rest is history!

My ability to connect with people has moved me forward at every stage of my career. I think that's also what makes me a good strategist. I love people. I love connecting the dots. And I love connecting those dots when they actually mean something to people.

2. What's something that quietly rewired how you work?

During a drawn-out freelance phase, I reached a breaking point. Every bit of client feedback felt personal, like a direct hit. I am a sensitive person by nature, but for a long time, my sense of self was completely tied to my work. (Neptune in Capricorn, lol!)

This, plus nonexistent boundaries led to overwhelming burnout. Everything felt sooo heavy. Eventually, after a lot of time and some soul-searching, I came to terms with the fact that you can still care without carrying everything. Letting go shifted things for me. Highly recommend letting go!

Btw, fwiw —

Christina’s chart. She’s very brave for sharing this, imo!

3. What's a piece of media you've rewatched or reread an embarrassing number of times?

Let me be clear: I am not embarrassed by any of this! But I love movies and TV and have spent an ungodly amount of time watching both. Off the top of my head: 13 Going on 30 (peak Mark Ruffalo), Sex and the City, Game of Thrones and Curb Your Enthusiasm — all of which I've rewatched more times than I'd care to count.

4. What's an opinion or trend in the industry that makes you roll your eyes?
I am begging brands to stop hijacking the comment section. Not every post is an invitation! You don’t have to be weird. Or mean.

Case in point...

The Wendy’s official Twitter account, responding to Pop Crave’s coverage of Katy Perry in space.

5. What's a moment in your career that you felt totally in control? What about the opposite?

My first fashion week was monumental. Not only was it my first fashion week, but I was entrusted by a major company to travel abroad for nearly a month to capture and own content on the ground. It was a massive responsibility, but also an incredible opportunity that made me realize just how much I could handle. It was the first time I thought, "Wow, these people really believe in me. And I know I can do this."

On the opposite end of the spectrum, when I was laid off in 2020, it was abrupt, disorienting and completely out of my hands — especially during a time when the world already felt… insane. That moment taught me a lot about surrender. I didn't feel in control, but there is power in taking the next step anyway.

6. What's in your media diet right now that's actually influencing your work?
Chia Amisola immediately comes to mind. Their work — mainly around building a more personal web and writing as a form of self-preservation — has inspired me to get back into writing for the sake of writing. They describe it as a beautiful ode and capsule to the life you live, and that has really stuck with me.

7. What's a shift in tone, taste, or language that you think is coming—but hasn't hit yet?
Over-optimization fatigue. The feed has been flattened and while the internet works — it's so boring. People want to stumble and discover again. (I'm people!)

8. What's something you wanted early in your career that doesn't matter to you anymore?

Titles. They don't validate the work.

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I hope you enjoyed meeting

Christina Monroe

. You can find her on LinkedIn and Instagram, and on her website.