How Rosie & Raven Found Its Way to Oprah

There are certain moments in life that are so improbable, you almost have to laugh when you look back at all the tiny decisions that led you there.

This was one of them.

When I started creating Rosie & Raven, I put Oprah on my vision board.

It was a wildly aspirational thing to do. At the time, I didn’t have a publisher. I didn’t have an agent. I didn’t have a marketing team. I had an idea for a children’s book unlike anything I had seen before, and a very strong feeling that somehow, someday, it was going to reach a lot of people.

What I didn’t know was how.

First, a lot of people said no.

When I finished the first version of Rosie & Raven, I genuinely thought publishers would be excited by it.

Instead, I was told it was difficult to categorize. Too unusual. Not quite what the children’s market was looking for.

For a while, I wondered if they were right.

But I also knew what I had created. So rather than changing the book to make it fit more neatly into an existing category, I decided to publish it myself.

That meant figuring out everything—from printing and production to distribution, technology, sales, marketing and publicity.

There were many moments when I questioned whether I had completely lost my mind.

But I kept going.

Then I booked one more trade show.

By the summer of 2025, the finished edition of Rosie & Raven was finally out in the world.

I had spent almost two years creating it, and now came the completely different challenge of figuring out how to get people to actually see it.

So, as one more attempt to get the book in front of retailers before the holiday season, I decided to exhibit at a gifting trade show in New York.

My expectations were pretty straightforward: stand at my booth, demonstrate the book approximately one million times, talk to buyers, hand out information, and hopefully convince some stores to carry it.

That was the plan.

And then something very strange happened.

Right place. Right moment.

During the show, my booth was being featured live. 2 people stopped by, and the show director asked me to demo the book. It was only after I did the demo that I realized who I was talking to. 

It was the creative director for O magazine. The next day, his team contacted me. They wanted the book brought to their office for an important meeting—and they were sending a messenger to the trade show to pick up a copy.

Okay. That felt big.

I knew they published holiday gift guides, so of course my mind started racing. Could Rosie & Raven possibly be considered for one? Even being included in an Oprah holiday gift guide felt almost too exciting to imagine.

The messenger arrived, took the book, and brought it back to their office.

And then...

Not much.

I didn’t know what had happened in the meeting. I didn’t know who had seen the book. I didn’t know if they liked it, if it was still being considered, or if the opportunity had quietly disappeared.

So I did the only thing I could do.

I waited.

Five weeks later, an email arrived.

For five weeks, I tried not to get my hopes up.

I knew something had happened. Someone important had seen the book. It had been specifically requested for a meeting. I was quietly hoping that maybe—maybe—it would make one of their holiday gift lists.

What I had never even considered was Oprah’s Favorite Things.

That possibility wasn’t even on my radar.

So when the email finally arrived telling me that Rosie & Raven had been selected as one of Oprah’s Favorite Things 2025, I almost couldn’t process what I was reading.

Not just a gift guide.

Oprah’s Favorite Things.

The list I had seen year after year. And somehow, my little independently published book was going to be on it.

Oprah herself had been on my vision board from the beginning—not because I had some master plan to make Favorite Things, but because she represented the kind of reach and impact I dreamed this book might someday have.

I just never imagined the path there would look like this.

And it was real: Rosie & Raven appeared in the Kids & Families section of the official 2025 list, alongside Oprah’s description of the book’s augmented-reality experience. Oprah Daily

The part of the story I love most

It would be easy to tell this story as though it were one miraculous stroke of luck.

And obviously, there was luck involved.

The right person really did walk down the right aisle at the right moment.

But that moment could only happen because of the hundreds of much less glamorous moments that came before it.

The publishers who said no. The hundreds of cold emails. The endless rewrites. The months spent developing new technology. Finding a printer who could make the book the way I imagined it. Walking into bookstores and gift shops. Dragging heavy boxes to fairs and pop-ups. Showing up over and over again when I had absolutely no idea whether any of it was going to work.

And then booking one more trade show.

That’s the part I’ve thought about the most since it happened.

We tend to see someone’s big break as the moment everything changed. But we don’t see the hundreds of tiny decisions that put them in the room where that moment was able to happen.

If I had listened to the publishers, there would have been no finished book sitting on that table.

If I had decided the trade show wasn’t worth the expense, there would have been no booth.

If I had given up during any one of the countless moments when giving up would have been completely reasonable, there would have been nothing for Oprah’s team to discover.

And knowing what I know now makes that random encounter feel even more extraordinary. 

A very Rosie & Raven ending

There’s something about the whole experience that feels almost suspiciously appropriate.

Rosie & Raven is, at its heart, a story about trusting something before you can see exactly how it’s going to unfold. Apparently, I needed to learn the same lesson while making it. I couldn’t have planned the path that took this book to Oprah. I certainly couldn’t have predicted it.

All I could do was keep making the next decision that felt right, keep putting the book in front of people, and keep believing there might be a place in the world for something that didn’t fit neatly into an existing box.

Then one day, someone walked past my booth.

And everything changed. Watch the full video here.