The Fear That Points to What Matters
How Buying Coffee for Strangers Became My North Star for What Matters
This Week’s Courage Newsletter
💡 Big Idea: “We can live without religion and meditation, but we cannot survive without human affection.” - Dalai Lama
⚡ This Week’s Scare Your Soul Challenge: Buy coffee for a stranger. Yes, really. Yes, today. Yes, even though your brain is already listing 47 reasons why this is a terrible idea.
❤️ Bottom Line: Your fear of rejection isn’t a bug. It’s proof you’re about to do something that matters. The stranger behind you in line might be waiting for exactly the connection you’re scared to offer.
Dear Courageous Soul,
I’m in Miami. 7:23 AM. Starbucks line.
My workshop starts in two hours. My anxiety is already at a solid 7 out of 10. This is when my brain decides: “Hey, you know what would be fun? More anxiety.”
The man behind me is 6’7”. A full foot taller than me. Built like someone who actually uses his gym membership. I have to crane my neck just to make eye contact, which means if this goes badly, I can’t even pretend I was talking to someone else.
My mouth goes dry. My prepared speech—the one I’ve said a hundred times—becomes word soup in my brain.
“Hi, my name is Scott Simon, and I’m involved in a courage movement, and I’ve challenged myself to buy a coffee for a stranger... would you be OK if I bought your coffee this morning?”
The words tumble out like I’m reading terms and conditions at 2x speed.
Monte—that’s his name—looks down at me. One second passes. (Eternity passes.)
Then he smiles. “Yeah, man. That’s really cool.”
And just like that, the universe cracks open a little.
Here’s What No One Tells You About Buying Coffee for Strangers
It’s not about the coffee.
Monte is an HVAC contractor. Was an HVAC contractor. Dreams of being an AI programmer now. We end up sitting at one of those long communal tables that Starbucks has.
The ones designed for people to ignore each other while staring at laptops.
Except we’re not ignoring each other.
We’re talking about real things. The kind of conversation you usually only have at 2 AM with old friends or never. About reinvention. About being 45 and starting over. About how courage isn’t the absence of fear—it’s showing up with your fear as your plus-one.
The barista—who overheard me mention my courage workshop—writes “YOU GOT THIS” on my cup.
Monte tells me about getting laid off. About his dreams. I tell him about standing in front of rooms full of strangers, teaching courage while my hands shake in my pockets.
“So you’re scared too?” he asks.
“Every. Single. Time.”
The Truth About Living at our EDGES
I need you to know something: I am anxious before EVERYTHING that matters.
Before workshops. Before keynotes. Before hard conversations with my kids.
Before asking a 6’7” stranger if I can buy his coffee.
Some would call this “anticipatory anxiety.” I call it my North Star.
Because here’s what I’ve learned: The fear isn’t a stop sign. It’s your compass.
It’s our internal GPS pointing directly at what matters.
Why This Challenge Breaks People (In the Best Way)
Buying coffee for a stranger is terrifying because:
1. They might say no. (Rejection at 7 AM hits different.)
2. They might think you’re weird. (You are. Embrace it.)
3. They might say yes and then you have to... talk? To a human? Before caffeine?
4. You might stutter, stumble, forget your own name. (I once introduced myself as “Scott Scare Your Soul.” Not my finest moment.)
5. Everyone in line is watching. (They’re not. But tell that to your amygdala.)
But here’s the thing: The disaster scenario your brain is screening? It never happens.
What happens instead: Connection. Surprise. A moment where two strangers remember we’re all just humans trying to figure it out.
Sometimes you get a “Full Monte”—a full conversation about life and dreams and fear.
Sometimes you get a quick “thanks” and that’s it.
Both are victories.
This Week’s Scare Your Soul Challenge: Buy the Damn Coffee
Here’s your mission:
1. Go to a coffee shop. (Tea counts. Juice counts. It’s not about the beverage.)
2. Get in line behind someone. Or beside someone. A human someone.
3. Feel the fear. Notice it. Thank it for trying to keep you safe.
4. Say these words (or your version): “Hi, I’m [YOUR NAME], and I’m challenging myself to do small acts of courage. Would you be OK if I bought your coffee today?”
5. Whatever happens next, let it happen.
6. Email me immediately: scott@scareyoursoul.com Subject line: “I bought the coffee”
Tell me everything. Did you stutter? Did they smile? Did you run away immediately after? Did you end up talking about AI programming and existential reinvention? I want it all.
The Plot Twist Nobody Expects
Here’s what Monte said before we parted:
“I’ve been coming to this Starbucks for two years. You’re the first person who’s ever really talked to me here.”
Two years. Hundreds of mornings. Surrounded by people. Completely alone.
Your coffee offer isn’t just about courage. It’s about reminding someone—maybe yourself—that we’re not supposed to do this alone.
The fear you feel? That’s just your humanity showing. The same humanity that makes the connection possible in the first place.
One Last Thing
My workshop that morning? I told them about Monte. About being scared.
About doing it anyway.
Your fear isn’t disqualifying you from courage. It’s qualifying you for it.
Now go buy someone a coffee. I’ll be doing the same, somewhere, scared out of my mind, remembering that the fear is just proof that it matters.
With courage, caffeine, and connection,
Scott
