When a Simple Date Night Becomes High Stakes
This December, Jen and I decided to get intentional about spending quality time together—no easy task with a one-year-old keeping us on our toes. Jen, always full of great ideas, suggested we have a “paint night.” I thought, Cool, Painting with a Twist vibes.
Nope! She came home with blank canvases and said, “Let’s paint each other.”
Now, I’ve closed real estate deals and taken big risks, but this? Zero experience, no instructions—it was straight-up anxiety written all over it. I found myself more stressed about this painting than selling a multi-million-dollar deal. The fear of failure, the lack of control, the messiness—it all felt overwhelming.
The True Lesson: It Wasn’t About the Art
But you know what? It wasn’t about the painting at all. It was about the laughs, the creativity, and the connection.
I won’t be expecting my art to be in a gallery anytime soon, but the memory of that night is worth more than any work of art. What I learned was that marriage, like entrepreneurship, is about being intentional and stepping outside your comfort zone.
This little experiment reminded me that the best moments in life and business aren’t scripted—they’re created when you embrace the unexpected and choose vulnerability over perfection.
Your Challenge for the Week
So here’s my challenge for you: Try something new this week with someone you care about.
It might be messy, you might feel anxious, and you might get covered in paint, but the connection you’ll build is absolutely worth it.
