Today we’d like to introduce you to Tiffany Glass.
Hi Tiffany , so excited to have you on the platform. So before we get into questions about your work-life, maybe you can bring our readers up to speed on your story and how you got to where you are today?
I actually started my career in the entertainment industry—working with companies like Interscope Records, Cartoon Network, and a few other amazing entertainment brands. It was an exciting time, but the irregular hours really started to take a toll on me, especially when it came to spending time with my son.
Eventually, I got my real estate license. I never really pursued real estate full time, though, because I naturally fell into home design and flipping properties—starting with my own homes. People began to notice my design style at open houses and started asking me to design their spaces too. That turned into something I truly loved and still do to this day. Even after 20 years, I continue to work in both real estate and home design. It’s a job that allows me to use my creativity and passion—but deep down, I still felt like something was missing.
Through it all, I’m most proud of being a mom. I’ve raised four children, and now that my sons are grown, I made the decision to be a stay-at-home mom to my two daughters, who are 14 and 11. I went back to photography, which is one of my original passions, and even explored creating a homeware line. But as I began taking photos of my daughters, I saw how talented they were at modeling, and that led us to try creating a clothing line together. It was a great experience, but I quickly realized I wasn’t quite ready for that path just yet.
Then, one day, I noticed my daughter was growing up—and it hit me: she might be getting her period soon. I panicked a little, unsure how to start that conversation. Was it too soon? What should I say? That’s when the idea for our first book, The Day I Saw Red, came to life. It started as a way to help my daughter, but it turned into something much bigger. I didn’t realize at the time how much it aligned with my true purpose—but now I do. And I can honestly say, I’m exactly where I’m supposed to be
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
It’s definitely been a rough road—and honestly, it still is sometimes. I was never someone who was into books or reading. I’ve always been on the go, and with ADD, it’s hard to sit still and stay focused for long periods. So writing a book wasn’t something I ever thought I’d do. It actually took me years to get it where I wanted it, and even now, I struggle to read it without thinking of all the ways I could’ve made it better.
One of the hardest parts has been working on other people’s timelines. This is my passion—but for others, like editors and illustrators, it’s something they get to when they can. I’ve waited weeks for responses, only to feel like nothing moved forward after all that time. It’s frustrating, but it’s part of the process.
Even with all the setbacks, delays, and even situations where people tried to steal my ideas, I still couldn’t walk away. You’d think I would’ve just given up by now—but I can’t. I love what I do, even when it doesn’t always love me back. It may not have been the path I planned, but being here—doing this—feels like home. It doesn’t feel like work. And that’s how I know this is not just my passion, it’s my purpose.
Appreciate you sharing that. What else should we know about what you do?
Like I mentioned earlier, it all started when I noticed my daughter might be getting ready to start her period. That moment kind of stopped me in my tracks—I didn’t know how to talk to her about it or if it was even the right time. That’s where the idea for our first book, The Day I Saw Red, came from.
What makes this book so special is that it’s written specifically for younger girls who are getting their periods earlier than expected. We’re talking about ages as young as 7, 8, and 9. I’ve learned that a lot of girls are starting their periods at 8 or 9 now, and most by age 11, even though many of us were taught to expect it around 12 or 13—I was almost 14 when I got mine!
This book gives parents an easy way to introduce the topic without the pressure of a big, awkward conversation. You’re simply reading a story together. It introduces the idea gently and makes it familiar before it even happens. It’s educational, but it doesn’t feel like a health lesson—it’s wrapped up in a fun, engaging, and age-appropriate story.
From The Day I Saw Red, we naturally moved into our next book, Chest Disease, which is about body development—specifically breast development—and is inspired by my other daughter, Skyler. That book walks young girls through what’s happening with their bodies, what to expect, and how to navigate those changes in a way that feels safe and comforting.
What I’m most proud of is that these books inspired us to start our nonprofit, Skyyz of Wynter. Since both books focus on body development and periods, our mission is to provide essentials like feminine hygiene products and training bras to girls in need—especially unhoused or low-income girls. We want to make sure no girl feels unprepared or alone just because she doesn’t have access to the basics.
What really sets us apart is that our books are geared toward young girls—children—rather than teens who’ve already started their period. Most books out there start after the fact. Ours prepare girls before it happens, in a way that’s approachable, comforting, and even fun. That’s the difference—and that’s the heart behind everything we do.
Is there a quality that you most attribute to your success?
For me, the most essential qualities have been determination, faith… and maybe a little bit of insomnia—just kidding! (But honestly, it does come with the territory sometimes!)
I’ve always said, I know God didn’t bring me this far just to let me fail—even in moments when I feel like I’m failing. There have been so many roadblocks along the way that sometimes it feels like I’m on The Truman Show, like the whole world is in on some cosmic joke. But I keep pushing forward because I believe there’s a dream on the other side of this that’s bigger than anything I could’ve imagined for myself.
At the end of the day, I’m doing this to break generational curses, to pave the way for my children—and for the children who come after them. I want to leave behind something meaningful. I want to leave a legacy. And I’m determined to make that happen, no matter how many twists and turns the road takes.
Contact Info:
- Website: https://www.wynterskyyz.com
- Instagram: https://www.instagram.com/adventureswithwynterskyyz/
Image Credits
Tiffany Glass
