Hey Legend,

 

 

It involved wine, a dress, and a very confused Officeworks employee…

 

But first, let me give you some background. 

 

I’d been working with this millennial couple for the past three months. They’re both business owners in the ‘Allied Health’ space and they have a 6 month old daughter (she’s a cutie!). 

 

During our first 90 days working together, we built a strong relationship and achieved some great results. 

 

From previous experience, I know I can help my clients get the best results when we work together for the long-term. 

 

So I made them an offer to extend our coaching relationship for another 12 months. 

 

After some back and forwards, the husband texted me back:  

 

“We’re in. But I want to be wined and dined”. 

 

Curiously, I replied:  

 

 

This is what he said.

 

 

But then… I had an idea. A ridiculous one. One that involved me wearing a dress. 

 

So I asked Kaci to explore our wardrobe. 

 

She pulled out a nice black number from the rack. 

 

I slowly squeezed my arms through the tight sleeves. 

 

Somehow, they managed to get through without tearing the dress. 

 

But my chest and nipples were severely exposed… 

 

Kaci poured me a glass of red, she lit a candle and I sat down at the dining table. 

 

The first few photos Kaci took, I looked like a complete psychopath.

 

But we managed to land a shot that wasn’t quite as creepy… 

 

 

When Kaci got there, the person gave her a weird look. 

 

They must have been thinking, 

 

 

All I can say is I’m glad I wasn’t the one picking up the photo. 🤣

 

Turns out, one of my clients was sick so I didn’t need to rush the order through… 

 

Oh well. 

 

Kaci & I had a good laugh about it.

 

—  

 

On a wet-cold Sunday afternoon in Adelaide – I drove to my clients house to hand-deliver the gift.

 

The moment I’d been waiting for.

 

He opened up the gift bag, picked up the bottle of red, then the book, and then finally – he pulled out the card with the image of me in my wife’s black dress. 

 

His reaction was priceless! 

 

He was in stitches. He rushed down the hallway to show his wife. She couldn’t stop laughing too. And just like that – we went from formal coaching agreements to a deeply supportive alliance.

 

This experience reminds me of something I deeply believe.

 

 

It’s about real relationships. It’s about understanding someone well enough to have a laugh together and talk about money with honesty.

 

When you work with me, you’re not just getting financial & life guidance – you’re getting someone in your corner. 

 

Someone who celebrates your wins, challenges your blind spots, and occasionally – puts on his wife’s dress to make you smile.

 

If this story made you smile, reply to this newsletter and let me know.

Have a fantastic day,