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By Darryl Stewart
a woman breaking free from chains

How to bust out of a leadership rut

Our days are filled with things we “need” to do.   Be it work or personal, the lists are never ending.   There never seems to be enough time to get it all done. How then do we challenge the status quo and go after an important goal?

Moving through the clutter takes a new state of mind. Every leader is faced with the same pressure to get all the usual things done, but the truly inspirational leaders are the ones who somehow rise above the busy-ness and find ways to move the most important things forward. Think of Winston Churchill, literally and figuratively besieged, but able to galvanize a nation to achieve what appeared to be an impossible victory in the Battle of Britain. Churchill defined a compelling victory condition saying that winning the battle would be remembered as Britain’s “finest hour”. In the same important address, Churchill went on at length about the many other issues facing Britain. He ended with the Battle of Britain, however, and he kept the country focused until the battle was won.

Perhaps it is not fair to compare ourselves to Churchill. In a way, he had no choice but to make sure the battle was won. It was literally a matter of life and death for the country. We, on the other hand, can choose to focus on what is right in front of us and never try to achieve anything of note.

I think part of the problem is that for the most part we all fear failure more than we desire victory. In other words, we are so afraid of dropping the occasional ball or letting anybody down that we don’t prioritize the stuff we really want to get done for ourselves.

Richard Mulholland, author of Legacide: Why legacy thinking is the silent killer of innovation, points out that there is a natural tendency inside all of us to fear failure and this is stronger than the drive to accomplish exceptional things. This explains our natural tendency to stick to the status quo rather than shake things up and drive down a new path.

Mulholland says:


Mulholland also delivers the antidote to this tendency. He points out that we fear regret far more than failure. If you probe your own psyche or think of the most profound feelings expressed by people you know, you often find deep pain around regrets. Regrets over relationships lost, opportunities not seized, and words never spoken. In contrast, failures don’t often carry such pain. We tried, we failed. We don’t dwell upon a failure like we dwell upon a regret.

For me, this has been a powerful revelation. As I plan my days, weeks, and months, I actively check for opportunities I might regret missing. I devote some effort towards exploring these new opportunities, even if it means making small sacrifices in the rest of my work. Of course, I don’t do this recklessly or in isolation. I try my best to share what I am up to with those who might be impacted by my plan to pursue new victories.

As a leader, husband, father, and friend, I don’t want to live with regrets.

IBEX Payroll extends our profound respect and immeasurable gratitude to all the ancestors and keepers of the land on whose traditional territories our work takes place. We acknowledge that we are on Treaty 1 territory, the traditional gathering place of the Anishinaabe, Cree, Oji-Cree, Dakota and Dene people and the traditional homeland of the Métis people. This land is sacred, historical, and significant. 

Every time we acknowledge this truth, we have an invitation and an opportunity to reflect on the wrongs of the past, what we do in the present, and what we can do to continually honour the people whose lands and water we benefit from today. 

This statement only acts as a first step in honouring the land we reside on and its peoples, and must be paired with education, understanding and informed action.