Want Deep & Hilarious Connection in 1 Minute?
The Art of Awkwardness, In Action
"In order to design successful habits and change your behaviors, you should do three things. Stop judging yourself. Take your aspirations and break them down into tiny behaviors. Embrace mistakes as discoveries and use them to move forward." - BJ Fogg
Why looking silly might be the shortest path to authentic connection
Scare Your Soul Challenge: The Blind Portrait Experience
Bottom line: Sometimes the worst art creates the best conversations
Dear Courageous Souls (and Reluctant Artists),
Picture this: 50 college interns, eyes glazed over, mentally counting the minutes until their farewell happy hour.
And there I am, the keynote speaker - the final human roadblock between these young professionals and their well-deserved margaritas.
Talk about a tough crowd.
But then, magic happened.
Armed with nothing but paper, pens, and what I call "strategic silliness," I watched a room transform through an exercise called "Blind Portraits."
Within seconds, these screen-weary professionals were giggling, gasping, and genuinely connecting.
It was like watching a group of strangers become lifelong friends in the span of 60 seconds.
This brilliant exercise (created by the amazing Jenny Sauer-Klein) works because it hijacks our natural fear of looking foolish. When everyone's creating equally terrible art, those carefully constructed professional personas crumble. Real connection rushes in.
Here's what fascinates me: Research shows that vulnerability and shared laughter create deeper bonds than traditional "networking." When we laugh together at our wobbly lines and wonky portraits, we're actually activating the same neural pathways that build trust and empathy.
Think about it - when was the last time you really looked at someone?
I mean, really looked?
In our world of fleeting eye contact and constant screen time, this exercise forces you to see the person in front of you.
It's like a mini-vacation from our disconnected reality.
This Week's Scare Your Soul Challenge: The Blind Portrait Connection
Let's get delightfully awkward together. Here's how:
The Setup:
Find your drawing partner (friend, family member, or brave stranger)
Grab two pieces of paper and pens
Set a timer for one minute
The Rules (they're simple but scary):
Draw your partner's face WITHOUT looking at your paper
Keep your pen on the paper the entire time
No peeking! (Yes, it will be terrible. That's the point.)
The Magic Moment:
After one minute, reveal your "masterpieces"
Share three positive qualities you noticed while really looking at your partner
Let the laughter and connection flow
Here's the beautiful thing about this challenge - there's no way to fail. The worse your drawing, the better the connection. It's like anti-perfectionism therapy wrapped in a 60-second art class.
In a world where we're all hiding behind carefully curated social media posts, there's something revolutionary about creating something terribly, wonderfully, authentically imperfect - together.
With courage, creativity, and questionable artistic skills,
