How to Avoid "What-Could-Have-Been" Leadership Remorse


What would happen if you went too far?

I watched my son dodge waves at the beach this chilly winter morning.   He’d watch a wave come in, let it get within a metre or so of him, and then he’d run up the sand until he was beyond the reach of the water.

Eventually, he was waiting until the water was barely inches from his running shoes before commencing his retreat.  And with each progressive wave, he got even bolder and cheekier, pushing his luck until inevitably the waves lapped over his shoes and he got a soaker.

He looked down at his wet shoes, socks and pants, laughed, and went right back to dodging waves.

Playing it safe

Canadian hockey great Wayne Gretzky said “You miss 100% of the shots you don’t take.”

As a leader, if you don’t take any “shots” then you’re not doing your job.

Risk is inherent when you lead people, whether it’s taking a chance on delegating an important task to someone who may or may not be ready for it, or agreeing to speak to a bigger group than you ever have before.

The speed of learning

The fastest way to learn something is to experience it, mess it up, and go again.

Just as a pendulum swings past the centre line many times before finding equilibrium, the best way for you to build your leadership skills is by taking things too far.  You need to make mistakes. You need to aim for Personal Bests.

You need to challenge your limits.

Progress is happiness

There’s a joy that comes with stepping further than you ever have before.  There’s a thrill in taking on challenges that are just beyond what you think you’re capable of.

Reach for them.

I’m not talking about diving into the water, fully dressed, on a chilly winter day.

I’m saying get your feet wet.



One thought on “How to Avoid "What-Could-Have-Been" Leadership Remorse”

  1. Got me thinking this did! Your son was making calculations about risk with each step he took closer to the waves. These judgement calls are the building blocks of leadership. In so many organizations though there are risk management strategies which make judgement calls not possible. Have we tried to rationalize risk and used our left brains too much when ultimately what is needed is a simple intuitive judgement call. Not sure – but you are right: we need to get our feet wet and to do that we have to take risks and trust our judgement. Thought provoking post!

Leave a Reply

Your email address will not be published. Required fields are marked *