Thank you for joining us for the very first episode of Winging It with Wendy.
Before I share this story, I want to tell you a little about what this podcast is all about.
Winging It with Wendy is a place where we explore real stories from real life that make you pause and wonder if something more might be going on around us. I share moments from my own life, along with stories from listeners, about those times when comfort, guidance, or something that feels a little magical shows up exactly when it's needed.
Because if you're anything like me, you've probably had a moment or two where you thought... was that just a coincidence? Or was something actually helping me out?
The idea behind this show is simple. For the next little while, just stay curious. Imagine that maybe, just maybe, our Angels might be walking alongside us as we figure life out.
And the story I'm about to share is the moment that made me start believing that might actually be true.
The Day Everything Fell Apart
How I first met my Angels happened at one of the lowest points of my life.
At the time I was a real estate agent, a single mom, and I had two young boys who meant absolutely everything to me. Business had been slow. No deals had closed. And on this particular morning I had exactly five dollars to my name.
Now normally that might not sound like the end of the world... except for one thing.
My boys had hockey that day in the next town over, about a forty-minute drive away, and I had promised them something that I took very seriously.
No matter what was going on in my life, I would always show up for their games.
But there was a problem. My car was almost empty. And five dollars was not going to get me very far.
The night before I had done what I think many of us do when life feels impossible. I cried. I yelled. I complained to the universe. I basically said, somebody better show up and help me right now.
When I woke up the next morning my eyes were swollen from crying, and I remember sitting on the couch feeling completely defeated. And then something shifted inside me. I suddenly felt calm. I looked up and said something out loud that changed everything.
Okay... I give up. I surrender. You figure it out.
At the time I didn't even know who I was talking to. But I said it anyway. Then I grabbed my keys and got in the car.
The Gas Station Moment
I drove to the closest gas station with my five dollars. If you've ever been in a situation like that, you know the feeling. You walk inside a little embarrassed and ask the cashier to put the smallest amount possible on the pump.
Five dollars on pump eight, please, I said.
And then something strange happened. Bells started ringing. Loud bells. The woman behind the counter looked at me, smiled, and said, Congratulations! You're our 100th customer.
It turned out the gas station had just opened that day. Because I was the 100th customer, I had won a prize package. I stood there stunned while she explained everything.
A full tank of gas, she said. Check.
A gift certificate for a family-size bucket of Kentucky Fried Chicken with all the sides. Check, check.
Two bottles of Coke. Can you believe it?
And a chocolate cake. Every single thing two young boys and their mom would love for dinner.
Outside, someone was already filling my car with gas and even washing the windshield. I stood there thinking, wow... I needed this.
But then another thought crept in. Was this really luck? Or had someone actually heard me?
Lunch in the Car
When I picked up my boys later that day, I remember feeling like mom of the year. I told them, you are not going to believe what I have in the car. When they saw the bucket of Kentucky Fried Chicken they were absolutely thrilled.
But the magic of that day wasn't finished yet. Just as we started driving, the rain began to fall. And not just a little rain either. It came down in sheets, the kind that makes the whole world feel like it's wrapped in water.
My car had bucket seats that folded all the way back, so we pulled over, laid the seats down, spread a blanket across the car, and turned the inside into a little fort. We sat there eating chicken, talking about our week, laughing together, and watching the rain come down.
And then we saw something that stopped us all. Through the rain there was a beam of light. And perched in that light was the tiniest yellow bird, singing its little heart out.
We just sat there quietly, watching. It was one of those moments that feels bigger than the moment itself. And I remember thinking very clearly: something is happening here.
The Question That Changed Everything
Driving home that day, one thought kept coming back to me. If someone heard me... then maybe I could talk to them.
That idea was new for me. I had never thought about Angels in a personal way before. But something about that day, the timing, the specific details, the little yellow bird singing in the rain, made it impossible to just shrug off and move on.
So the next morning I tried something I had never really done before. I sat down quietly, took a breath, and I asked. I had been reading books like The Celestine Prophecy and Conversations with God, so the idea that there might be more to life than what we see with our eyes wasn't completely foreign to me. But asking directly? Talking out loud to someone I couldn't see? That was new.
I said: if I have a Guardian Angel... what's your name? And the name that came back was Tilly.
Now here's the funny thing. I didn't know anyone named Tilly. No relatives, no friends, nobody. But that was the name I heard. So I kept going. Okay, Tilly, I said. If you're real... how do I know?
And the answer surprised me. Ask for three things.
The Three Asks
The idea was simple.
If something happens once, we usually call it coincidence. If it happens twice, we start wondering. But if it happens three times? That's when it becomes much harder to ignore.
So I spent about ten days thinking about what those three things should be. They needed to be specific. Something tangible. Something that would make me stop and say, okay, that's impossible.
The first ask came to me while I was vacuuming one afternoon with the television on in the background. A country music video came on from a singer I had never heard before, John Berry. His voice was so beautiful it gave me goosebumps. Right then and there I said out loud: I want tickets to see John Berry live in concert. But not just any tickets. They had to be VIP tickets, and they had to be given to me as a gift, because I didn't have the money to buy them.
The second ask came a few days later while I was getting ready to go out. I opened my closet, stared at everything hanging there, and said the thing so many of us have said: I have nothing to wear. What I really wanted was a pair of jeans. Not just any jeans, new to me, tags still on them, and when I put them on they had to feel like butter and make me think, wow, I actually look good in these. And of course... they had to show up without me having to pay for them. There was definitely a theme there.
The third ask came during a moment that pointed toward what would eventually become my next career path. I had been helping a group of people launch a company, and while I was hosting an open house one day they called me from a boat on a nearby lake and asked me to find a telescope in the house and look out at them. When I did, something clicked. Looking through that telescope felt symbolic, like I was seeing further into my future. So I asked for a telescope, not necessarily brand new, but still in the box, and placed directly in front of me as a gift.
Those were my three asks. And after I made them, I did something that felt important: I said thank you. The same way you say thank you when you order something online and you trust it's already on its way.
What Happened Next...
Those three things each showed up in ways I never could have planned. But I think I'll save those stories for the next episode.
Because the moment at the gas station, the bucket of chicken, and that little yellow bird singing in the rain were the beginning of something much bigger for me. They were the moment I realized I might not be walking through life alone.
Your Turn
If this story stirred something in you, that's worth paying attention to.
In the next episode of Winging It with Wendy, I'll share how each of those three asks showed up in my life, and why that experience completely changed how I see the world.
Until then, I invite you to try something playful. Ask for three things. Make them specific. Make them a little unusual. And see what happens.
And if you have a story about a moment that felt like more than coincidence, I would truly love to hear it.
Because the more we share these stories, the more we begin to realize something beautiful: we might not be winging it alone.
Have a story to share? Send it here.
Listen to the full episode on Spotify, YouTube, and Apple Podcasts.
