Meet Cassandra Wilder

We recently connected with Cassandra Wilder and have shared our conversation below.

Cassandra , we’re thrilled to have you on our platform and we think there is so much folks can learn from you and your story. Something that matters deeply to us is living a life and leading a career filled with purpose and so let’s start by chatting about how you found your purpose.

I’ve discovered my purpose through trial and error.

At eight, I was inspired by my social worker mother and a child psychiatrist who helped a case she deeply cared about. I was determined to follow that path. After a decade of hard work, I shadowed my mom and saw firsthand the emotional toll of her job. With love, she told me I wasn’t built to leave that kind of work behind—I’d never be able to separate from the horrors. She was right.

So my purpose shifted. Raised by a single mom with three older siblings, I knew struggle. I wanted stability—a middle-class life, a family, and a way to give back. I married an amazing man, had a son, built a stable career in banking, mentored, coached, and volunteered. Life wasn’t always happy, but I was content.

Then, after my second son was born, my employer broke the promises they made to bring me back from maternity leave. I accepted the demotion—until they expected the same effort without the recognition. When I refused, I was fired. I was crushed. I had worked through feeling like a failure as a woman after experiencing four miscarriages between my first and second born, only to now fail professionally.

For a while, I drifted. I loved my kids, volunteered, and helped family, but I felt unfulfilled. My husband, ever supportive, worried I’d go back to work for the wrong reasons. Instead, he encouraged me to start a business. I was terrified of failing again, but he was persistent. After a couple of drinks, I jokingly named a business—by morning, he had filed the paperwork. He knew I needed a purpose before I did.

That business was seasonal, and I still wanted more. When my husband asked what would truly feed my soul, I surprised myself with the answer: fostering. It had always been something we’d discussed for the future, but suddenly, it felt right. We prepared to be a temporary foster home—no plans to adopt, just a safe place for kids in transition.

Two weeks before our certification was finalized, we got a call. Two little boys needed us. That August, I met two of my sons for the first time. Raising my four boys became my whole world. It was exhausting and hard, but it was good. I loved my life.

Then life threw another curveball. We fostered a child temporarily (who I will love forever), and I told my husband five kids was too many. He scheduled a vasectomy consultation—only for us to discover I was already pregnant. What followed was the darkest period of my life. Antenatal depression hit me like nothing I had ever experienced. Every day was a battle, and my husband was my lifeline.

During one of my worst moments, he reminded me of an old idea I had tossed around: an indoor play space. He believed I could build something meaningful, a community for parents who felt alone. So I added a purpose. At nine months pregnant, I toured spaces. I signed paperwork while rocking my newborn. Our boys’ adoptions finalized, lifting a weight I hadn’t realized I was carrying. I balanced motherhood and business ownership, and for the first time in a long time, I felt like I was thriving.

Now, I have multiple purposes. I use my business to support other small businesses and give back to the community. I serve on my local council, finding ways to improve our little corner of the world. I mentor other female business owners, building a network of support. My marriage, my health, my friendships—they are all priorities, all pieces of my purpose.

For years, I believed I had to find one singular purpose, and when nothing ever felt quite right or lasted, I felt lost. But we are multifaceted people—how could one thing ever be enough for all the pieces of who we are?

I no longer search for one grand purpose. Instead, I embrace the many that shape me.

Appreciate the insights and wisdom. Before we dig deeper and ask you about the skills that matter and more, maybe you can tell our readers about yourself?

I own two businesses. The first is Wilder Party Supplies, which offers party supplies, bounce houses, slides, and more. It’s a seasonal business, and my role is to ensure everyone is properly trained, that we meet all safety standards, and to oversee customer service and community projects. We’re the only bounce house company that automatically applies a discount for non-profits, and we’ve worked closely with several community organizations to give back—something I’m extremely proud of.

My second business, That Play Place, is my sixth baby. It’s an indoor playground that I designed from the ground up to create a fun, safe space for kids while also keeping parents in mind. I’m there six days a week, handling everything—planning, customer service, operations, and all the behind-the-scenes work. It’s both exhilarating and terrifying—no one prepared me for how personal it would feel to create something and then open it up to the world to love or critique. But I love it.

At That Play Place, we do more than just play. We host mom nights where moms bring drinks, craft, and connect with others who also wonder why the laundry fairy never shows up. We’ve helped build friendships—not just between kids, but between parents and grandparents too. We encourage conversations about mental health, the importance of building a village, and supporting local businesses. I’m always looking for ways to collaborate with other businesses so we can lift each other up.

One of the things I’m most grateful for is how this business allows me to give back. We donate, put together baskets, host events to help recruit foster families, and are currently working with a local women’s shelter to provide birthday celebrations for kids who might not otherwise have one.

My youngest comes to work with me half the time, and all my boys have played a role in setting up and running the business. It means the world to me that they’re growing up watching their mom build something, give back, and help others in a way that just feels normal to them.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

The three qualities that have been most impactful on my journey are empathy, a problem-solving mindset, and self-awareness.

I have a strong sense of empathy, for better or worse. I can’t look at another person without recognizing that they are someone’s loved one. I can’t see a child without wanting for them everything I want for my own sons. While this has caused its fair share of challenges, it also keeps me from getting caught up in minor frustrations. There are far bigger problems in the world than whether my businesses succeed or if the laundry is ever finished. This perspective helps me adjust my course, find balance, and focus on ways to help others.

My drive to solve problems seems to come from the intersection of my empathy and competitive nature. My instinct is to believe I can do anything—until I convince myself I can’t. When I saw that local government wasn’t advocating for families like mine (and that I wanted chickens), I convinced my husband to run for council. He won but kept getting outvoted, so I ran the next time a seat opened. Now, we’re constantly pushing for common-sense changes against a majority of retirees who resist them, but I’d rather fight for solutions than sit on the sidelines and complain. Approaching problems with a solution-oriented mindset—rather than letting them drain me—helps me stay engaged without burning out. That, my support system, and a night routine of loud music and showers hotter than lava keep me going.

I’ve always been self-aware, even when imposter syndrome creeps in. This has served me well because I can recognize when I need help—and I know that needing help is normal. I understand my strengths, my limits, and when I’m out of my depth. When I hit a wall, I ask myself what advice I would give a friend, remind myself to be kind to myself, and make a plan. At That Play Place, I constantly seek input because I know I’m not the most creative person, I only have sons, and we’re simply better when we work together. I trust myself, and when I don’t, I know to lean on my support system. That ability to ask for help and trust in others is crucial in everything I do.

Who has been most helpful in helping you overcome challenges or build and develop the essential skills, qualities or knowledge you needed to be successful?

Here’s a cleaned-up and polished version while keeping your original tone and message intact:

My husband has been the most helpful person in overcoming challenges and finding success. I know that sounds cliché, but his perspective and experience are so different from mine in every way. As a middle-class white man, he moves through the world differently—he has never been afraid to ask for what he wants because, to him, the worst that can happen is someone says no. Meanwhile, I often assume the answer is already no and that everyone will think I’m awful for even asking.

He walks into every room expecting to be liked, to get what he needs, and to figure things out. He has insecurities like anyone else, but for the most part, he is always sure of himself, of me, and of our abilities. Because of that, we never fear we won’t land on our feet.

When that kind of confidence shines on you for years, you start to absorb it yourself. No one wanted to rent me a space—so he just kept calling people and talking me up until someone agreed. When I feel like I’m failing, he points out everything I’ve already accomplished and calls it winning. If I don’t know how to do something, he reminds me that even Hermione couldn’t read tea leaves, but I know how to find the right person to get it done.

I wish everyone could embody his level of confidence and faith—or, at the very least, that they have someone like him in their life.

Contact Info:

• Website: https://Www.thatplayplaceerie.com
• Facebook: https://www.facebook.com/share/1Bba4Bz1LA/?mibextid=wwXIfr

Image Credits

The professional photos were done by Chris. Zdarko at Zdarko photography.