A Leadership Anchored in Earth and Sky
I shared a dark secret with someone recently and now everyone knows that I’m a double water sign. Cancer Sun. Scorpio Moon. Which honestly explains a lot.
The Cancer Sun is warm, compassionate, deeply creative, and wants everybody to feel emotionally safe at all times. The Scorpio Moon, however, can smell bullshit from three boroughs away. Inauthenticity physically exhausts me. Corporate babble? Makes my eye twitch.
It’s a very confusing combination to live with professionally. On one hand, I can walk into a room, read the emotional temperature in under thirty seconds, identify who’s uncomfortable, who feels unseen, and which team member is quietly carrying the entire operation on her shoulders. How quickly I tend to identify those archetypes in a room is truly a super power.
On the other hand, I’m also wildly creative, charismatic as hell when I’m comfortable, and still very much connected to the first grader who almost got held back because he refused to color inside the lines. True story. Apparently it’s important for leaves on a tree to be green, or red, or yellow.
I very clearly remember asking: “but why?”
Maybe the leaves are purple today. Maybe they’re blue. Maybe there’s a unicorn in the background because honestly the forest feels emotionally incomplete without one anyway.
The point is: My heart is anchored in earth and in sky. So, I have always had a complicated relationship with structure of any kind. After all, I’m the son of a flower child day dreamer and a militant super intelligent steelworker.
This is ironic, considering I somehow built a career in operations - the land of timelines, KPIs, P&Ls, and conversion percentages. Yet… I love it all so much. Deeply. You see, underneath all the structure, spreadsheets, and logistics, leadership is actually about Human Beings.
If earth is strategy then sky is imagination. The problem is that most workplaces teach leaders to surrender one for the other. Leadership culture through the years has treated professionalism and emotional honesty like star-crossed lovers. A bit of a Montagues v. Capulets situation.
I know people who have never experienced a truly vulnerable leader before. Where real openness is paired with real accountability. Vulnerability does not weaken standards. It strengthens trust, and trust is where the most impactful ideas live.
I’ve seen it happen at the end of twelve-hour event days when everyone is physically exhausted and slightly delirious. Hospitality people know exactly what I’m talking about here. There’s this magical moment after the guests leave where the entire team starts laughing uncontrollably over something objectively stupid.
Someone becomes unhinged.
Someone’s eye starts twitching from exhaustion.
And suddenly everybody is crying laughing in the middle of a freight elevator or a backstage staircase.
My favorite boss of all time was tough as nails with crazy high expectations. He was also the most beautifully vulnerable leader I’ve learned from. His example of leadership is one I’ll carry with me into every project and every and coaching session.
The most meaningful leadership moments in my career were birthed somewhere between structure and softness, accountability and imagination, earth and sky.
And maybe that’s the whole point.
The best leaders aren’t the ones who force everyone to color inside the lines.
They’re the ones who create environments safe enough for someone to ask:
“What if the leaves are purple?”