What a Rain-Soaked Dream Taught Me About Real Leadership
- Scott Mason
- Apr 29
- 5 min read
In Greek mythology, there was a cave -- its mouth on the floor of a grove in the forest -- that no sane person would want to enter.
It was the the Cave of Trophonius.
The Cave of Trophonius was cold. Dark. Deep. Those who dared to step into it had mysterious hands grab them by the feet, yanking them through a dark tunnel and into a cavern where they saw things that would leave them incoherent with shock.
Only when placed on the Throne of Memory could those who had stepped into the cave make sense of the things they experienced.
But what they did emerge with—if they were strong enough — was the truth. The truth about who they were. The truth about the lives they had lived. The truth about the challenges --and the possibles --that lay in their future.
Many were scared to step into that cave. But if you wanted real transformation—if you wanted meaning, purpose, and the pathway into your next chapter—you had go inside.
And just last week, I dreamed I entered that cave.
The Bike Ride
It started like many of my real-life adventures: with a bicycle.
I’ve lived in New York City for years, and if you’ve ever tried to get anywhere on time here, you know why I bike whenever I can.
It’s faster than the subway, less maddening than traffic, and gets me up close and personal with a city that most people only skim the surface of.
I’ve ridden to parts of Brooklyn where you can smell the Atlantic before you see it. I’ve cycled deep into Queens neighborhoods where street signs bend in the wind and bodegas sell mango slices like gold.
One of my favorite rides ever? Flying down the West Side bike path during a rainstorm, soaked to the bone, as the Hudson River roiled like Poseidon himself was stirring it with a trident. The sky was iron. The river frothed. But I couldn’t stop. It was too beautiful. Too raw. That moment was pure aliveness.
But that night’s ride was different.
I dreamed I was biking north through Harlem, into the Bronx. It had just rained, and for a while, everything felt familiar. The rhythm of the wheels. The echo of tires on wet pavement. Then—something shifted. The streets grew strange. Narrower. Dingier. Almost post-apocalyptic. Imagine a mashup between post-WWII Tokyo and the grimiest parts of Gotham. The rain had pooled into mini-lakes, flooding sidewalks and making the roads impassable.
I dismounted and walked. And then things really got weird.
A Tale of Two Tunnels
Eventually, I saw an old man sitting by a covered passage between two crumbling buildings. He pointed silently. No words. Just the gesture.
I entered.
The tunnel was dark, damp, and full of shadow. But on the other side? A completely different city. Towering skyscrapers. Bright lights. But the street numbers were all wrong — starting from the beginning again, but clearly not in Manhattan. (For the non-New Yorkers: our streets follow a logic. Numbers climb as you go north. If they restart, you’ve either changed boroughs … or something stranger is happening.)
The streets curled into strange loops. Skyscrapers connected by hamster-tube tunnels arched into the sky. It was disorienting. I just wanted to go home.
Then I saw it: a different tunnel. Square, not round. Lit from within. People were coming out.
I stepped in.
The tunnel twisted sharply left. A red glow pulsed at the far end.
Terrified — but resolute — I held onto my bike … and walked forward.
And that’s when I woke up.
WHAT THIS DREAM REVEALS ABOUT LEADERSHIP (AND YOU)
Trophonius was once a mortal architect—until he built a temple so divine, the gods struck him dead and took him as one of their own. Now, he lives in the silence of the earth. But if you’re brave enough to seek him out, he’ll give you visions.
The price? You must face what you fear most.
And this, my friends, is the ultimate leadership metaphor.
Because the true path to power—to real, authentic, transformational leadership—always demands you go into the dark. Into the cave. Into the parts of your life, your self, your habits, and your comfort zones that feel too scary to leave behind.
Most professionals — especially high-achieving lawyers and execs — live their lives on familiar streets. We know the map. We follow the rules. But one day, the storm comes. The roads flood. And the map no longer works.
That’s when the journey begins.
And it will always, always, involve the dark passage—the thing we don’t want to see. The red glow at the end of the tunnel we don’t understand.
We may call it burnout. Or career confusion. Or the gnawing, unspoken knowledge that we’re playing a role we no longer believe in.
But really? It’s the Call.
SO WHAT DO YOU DO?
Trust the Stranger Who Points the Way. You may not recognize the guides in your life—but when someone silently points you toward the passage, pay attention. Your mentors, your friends, your inner whisper—that’s your sign.
Enter the Cave Anyway. Yes, it’s terrifying. The route is unfamiliar. The outcome is unknown. But your future is not on the sidewalk. It’s through the tunnel.
Embrace the Red Light. We don’t know what’s at the end of the road. But if it’s glowing, it means there’s energy. And in energy, there’s life.
If you’ve felt the streets growing strange, if the old maps no longer make sense, if a red glow pulses at the edge of your consciousness — you are not lost. You are being called.
Tell me below: What tunnel are you afraid to enter?
Name the fears. Walk the path together. Seek out life.
Because:
I want your future to be EPIC!
I'm Scott Mason, The Myth Slayer. I am an attorney and former C-Suite executive, coach, speaker, podcaster, and Master of the Mythic. I graduated from Columbia Law School and have spent years drawing on the full depth of a background spanning the private, public, and nonprofit sectors to provide lawyers feeling stuck or stagnant in their careers or as leaders with a unique (and fun!) system to help them live a life that's epic.
Click here to discover more about me, my mission, and how it can help you.
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