How An Invitation To Paint Taught Me About Leadership Risk


The Safe Strokes


I hadn't picked up a paintbrush since I was in high school. But in my thirties, I received an invitation from a friend to try. 


At first, I played it safe - light strokes, predictable colours. Neat, tidy, contained. But everything I made looked... flat. 


It wasn't wrong. But it wasn't alive either. 


The Bold Pour


Eventually, I became so frustrated that I poured paint straight onto the canvas. There were no careful strokes - this was a spontaneous act underpinned by a single objective: learning to surrender. 


It was bold. Messy. Uncontrolled. 


And for the first time, it felt honest... and I felt free.  


Here's what I learned: 


The more risk I took, the more alive the work (and I) became. Not because it was perfect, but because it stopped trying to be. 


The Parallel With Leadership


Leadership is like that.


We're taught to stay inside the lines. To colour with the "right" shades. To make decisions that don't rock the boat. 


But the truth? Growth lives in the mess. Presence emerges in the risk. And sometimes, the most courageous act isn't holding onto control, it's surrendering to creative freedom. 


Why Emerging Leaders Struggle With Risk


For ambitious leaders, the instinct to play it safe runs deep. You want to prove yourself. To make the "right" call. To avoid mistakes that might undermine your credibility. 


But playing it safe often flattens leadership. It makes you cautious when boldness is needed. Silent when honesty is called for. Contained when presence is required. 


Risk doesn't mean recklessness. It means stepping into the unknown with clarity, and trusting that what emerges may not be perfect, but it will be real. 


What Painting Reminded Me


Painting reminded me of three things that leadership often forgets:


  1. Perfection isn't the goal. Aliveness is. 
  2. Control has limits. Some of the most powerful outcomes come from letting go. 
  3. Risk is necessary. Without it, nothing new emerges. 


And maybe that's what leadership needs most - not more polish, but more presence. 


My Gentle Invitation


If you've been playing it safe in your leadership - staying inside the lines, colouring with predictable shades, waiting for certainty before moving - maybe it's time to pour some paint. 


At Foresight, our coaching programs create space for that kind of risk. Not reckless leaps, but intentional experiments. Not mess for its own sake, but creative surrender that makes leadership more alive. 


Because the leaders who inspire aren't the ones who control the canvas, they're the ones who dare to let the paint flow. 

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