Winging It with Wendy · Episode 3

Belief, Doubt, and the Signs That Change Minds

Real people. Real stories. Real Angels.

Winging It with Wendy, Episode 3: When You Ask, True Stories of Angels Showing Up

Welcome back to Winging It with Wendy.

Listen to Episode 3
When You Ask... True Stories of Angels Showing Up.
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This episode is a little different from the first two, because today I want to tell you about the people in my life who didn't believe.

Not the ones who were quietly open, or gently curious, or willing to sit with the idea. I mean the real sceptics. The eye-rollers. The ones who looked at me across a lunch table and said... you seem so smart, and yet.

Because here's what I've learned: the people who push back the hardest are often the ones the Angels are most eager to reach. And these four stories are proof of that.

So if you're sitting there right now a little uncertain... maybe a little suspicious... you might just be exactly the person this episode is for.

Let's get into it.

Story One: The Ring

I was down in Arizona with my company, World Tree, at the Jeff Wilmore Autonomy Course. If you've never been, it's an extraordinary thing, the kind of experience that holds your feet to the fire and asks you to really look at who you say you are.

I had my whole team there. And at one point, in the middle of a classroom session, I ended up going toe to toe with one of the coaches about my belief in Angels. He had a problem with it. We went back and forth, and I can tell you right now, there was no way on this green earth I was giving up my Angels. They have been with me every step of building that company. I count on them. I know they're real.

Well. That classroom debate caught the attention of a woman in the room. She is, honestly, one of the most impressive people I've ever met. She manages the wealth of very, very wealthy people. Extremely accomplished. Extremely classy. And over the lunch break, she came up and asked if we could sit together, just the two of us.

I said of course.

We sat down, and she looked at me and said something like... you're so together, you've built this incredible company, you have this amazing team... but you believe in Angels.

She wasn't being unkind. I could tell she genuinely didn't understand. And I've heard some version of that sentence more times than I can count. People look at me and think... woo-woo. Too fairy. Off her rocker.

But here's the thing. I believe in something more than us... something beyond us. And no amount of side-eye has ever changed that.

Why Do People Find It Strange That I Believe in Angels?

So I asked her: are you interested in meeting your Angels?

She looked at me like I had three heads.

But she said yes.

I walked her through everything I know about how to reach out and what to ask for. And the most important piece is this: make the ask big. Make it specific. Make it the kind of thing that could only show up as a miracle, so that when it does, you can't explain it any other way.

She thought about it overnight. The next day she came back, arms folded, and said... okay. I've got my thing.

She and her husband had moved four or five times in the past couple of years. And somewhere along the way, she had lost her engagement ring. She wanted it back.

I told her that was a wonderful ask.

She said, you really believe I can actually get my engagement ring back?

I said: Angels can do a lot.

When we said goodbye at the end of the course, I told her: the minute you get that ring, you send me a photo.

She laughed. But she said she would.

About ten days later... my phone buzzed.

A photo. A gleaming diamond ring, close up, right there in her hand.

I got on the phone with her immediately. It turned out she had a collection of briefcases, she'd built up quite a few over the years and had decided to donate them to a women's shelter, for women re-entering the workforce. She was cleaning them out, going through each one, when she found it. Sitting at the bottom of one of the cases.

She had gone through those same briefcases many times before. It wasn't there. And then, the day she decided to give them away to help someone else... there it was.

A little miracle. And just like that... she was converted.

Remember the Non-Believer? She's Converted.

Story Two: The Vision Book

I used to be a big believer in vision boards. You know the ones, the giant boards covered in magazine cutouts of dream houses and airplanes and abs. Very nineties. Very committed.

But I moved a lot, and hauling a giant board from place to place started to lose its charm. So I decided to make a vision scrapbook instead. Something I could take with me wherever I went, flip through whenever I needed a reminder of where I was headed.

At the time I was dating a man who... let's just say he was not a believer. Every time I mentioned my Angels, his eyes would do a full rotation. I had parking Angels, and he found that particularly baffling. We'd go out and I'd say, I always get a spot, I've got my parking Angels working on it, and he would just... stare at me.

So one day I told him I was heading out to find the perfect scrapbook, and I'd put it out to my Angels that it would be exactly right.

He said: any book you pick is going to be the perfect one. I don't know why you think your Angels are going to give it to you.

I said: because that's what they do.

He said he was coming with me.

And here's where it gets good. Instead of going to the store I had planned on, he decided mid-drive to take a detour. Another store entirely, in another part of Scottsdale. His logic was: if your Angels are so good, it doesn't matter where I take you. The book should be there.

I said: absolutely. Take me wherever you want.

We walked into the craft section. He started pulling scrapbooks off the shelf. What about this one? This one? Nope. Nope. Nope. Not that one either.

And then I turned down one aisle and I stopped.

There it is.

Now, one of the things he knew about me was that I love daisies. I have exactly one tattoo, and it is a daisy. So when I pointed to the book, he said: that's just because it has daisies all over it.

I said: look at the name.

On the front of the scrapbook, printed right there in the included sticker sheet, the kind you use to personalise it, was the word: Burton.

His jaw dropped.

I said: and that, dear man, is how your Angels work.

I still have that scrapbook. I go through it every now and again. A lot of what's in it has already come true.

Don't doubt yourself. Even when the people around you do.

Story Three: The Purple Lace Bra

This one still makes me laugh.

Years ago, when I was living in Arizona, a girlfriend and I decided to take a road trip to San Diego. Just because we needed to see the ocean. No other reason. Sometimes you just need water.

On the way, she asked me about the Angels, she'd heard me talk about them and was curious. I'll call her Donna. And Donna, bless her heart, has what I can only describe as a very Dolly Parton-like figure. Absolutely beautiful. But she told me that because of her... voluptuousness... she had to buy industrial-strength bras. Not pretty ones. Not fun ones. Just structural ones, because, she said, they simply don't make beautiful lingerie in her size.

I said: well, why don't you ask your Angels for that?

She looked at me the same way everyone looks at me.

I said: I'm serious. Ask.

So she did. Quietly, on the way to San Diego, she put it out there: a beautiful, well-fitting, gorgeous bra in her size. We spent the day and hit a few lingerie shops along the way. Nothing. She was right, twenty years ago, the selection just wasn't there.

On our way home, something told me to stop into a Neiman Marcus. I couldn't explain why. I just felt called to go in.

We headed up to the lingerie department, and I went to ask the woman at the counter if they had anything in a larger size. But before I could finish the sentence, I looked past her shoulder.

Hanging on a rack, on its own, was one bra.

Considerably large. Absolutely stunning. Purple lace.

I asked what it was doing there. She said it had been a custom order, the customer had changed her mind.

I asked what size it was.

You already know.

I asked if it was for sale.

She said yes.

Donna tried it on. It fit the way those jeans fit me in Episode 2, like it was made for her. Because it was.

Before we'd even made it home, Donna was already testing out her new connection. The handyman had been at her house fixing the dryer. She quietly asked her Angels if he might not charge her. When she walked in the door, he told her it was just a sock caught in the vent... no charge.

That's how fast they can show up, once you let them in.

Story Four: The Endless Bottle of Wine

This one is the hardest to tell. And the most beautiful.

About twelve years ago, my father passed away. He was diagnosed with liver cancer, and from diagnosis to the end was just ten days.

I need to back up just a little, because there's a piece of this story that matters.

When I was 33, I took myself to the Hotel Del in California for a solo dinner. I ordered two bottles of wine, had a glass, and asked for the rest to be corked. After dinner, I walked out to the beach and wrote a letter to myself... to be opened on my 50th birthday. I tucked the letter in a little box with the second, unopened bottle of wine.

I want to tell you: do this. Write yourself a letter. It is one of the most extraordinary things.

When my 50th birthday came, I took myself to Italy instead of back to the Hotel Del. And who brings their own wine to Italy? Nobody. So I left the bottle at home, opened it when I returned, and sat in Italy reading a letter a 33-year-old version of me had written. It asked if I'd started the company I always dreamed of. If I was a grandma yet. If I was sitting at the Hotel Del... which I was not.

I cried. Obviously.

And while I was there, my sister called. Our dad had been diagnosed.

When I got home, my Angels were clear: go see him. Immediately.

I called my boys. Their grandfather was Candy Grandpa, that's what they called him. I told them I was leaving at six in the morning and if they wanted to come and say goodbye, they'd better be ready.

That morning, both of them were sitting on the veranda with their bags packed.

We drove to Vancouver Island. On the way, my sister called. He'd slipped into a coma. She held the phone up to his ear, and I called down the line and told him he was not allowed to leave until I got there. I told my Angels the same thing.

We made it. He heard us. The boys got to say goodbye. And within the hour, he was gone.

That bottle of wine, the one I hadn't taken to Italy, was still sitting in my car. I still don't know why.

My Angels Kept Telling Me to Go See My Dad

That night, the whole family gathered at my niece's house. No formal service, dad didn't want anything like that. So we did what felt right. We sat together and told dad stories.

I brought in that bottle of wine and said: let's open this and share it.

My dad, by the way, was not a drinking man. He thought alcohol was a waste of time and money. He'd take us out for dinner, but you bought your own. That was just how it was.

We poured the wine, told stories, laughed, cried, filled our glasses again, told more stories. Someone kept saying someone should run to the liquor store for more. Hours went by. More stories. More laughter. More glasses poured.

And then someone finally asked: did anyone ever go for that wine?

Nobody had.

Not one person had left. And yet we had been drinking all evening. One bottle. For a room full of people. Hours and hours of stories and glasses filled.

I thought... dad finally bought us our booze.

And somewhere in that, I believed he turned water into wine and gave us one last gift, the gift of time together. One more evening of his family, all in the same room, with nowhere to be and nothing to do but remember him.

What a way to say goodbye.

Your Turn

Four stories. Four people who started out somewhere between sceptical and completely unconvinced.

And four moments that changed everything.

I don't ask you to believe any of this. I just ask you to stay curious. To be open to the idea that something might be walking alongside you, waiting for you to notice.

In the next episode of Winging It with Wendy, I have a very special guest... and you are not going to believe the story she brings.

Until then, try something playful. Ask for something specific. Something a little outside the ordinary.

And see what shows up.

Because you 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.

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