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Leadership Lessons: Stepping Outside the Comfort Zone and Embracing the Unknown

November 28, 2024

5-minute read
Post Contributed by Kasia JamesExecutive Director, Legal Help Centre
Leadership Winnipeg Class of 2024-2025


Working at the Legal Help Centre, a downtown non-profit charitable organization that helps low-income community members access free legal and social service supports has given me a unique perspective on the opportunities and challenges within our downtown community.  I was eager to dive into the latest Leadership Winnipeg session focused on other city-centre organizations and the work they’re doing to improve the social health of our downtown.

From hearing about the YMCA-YWCA of Winnipeg plans to grow their role in positive downtown impact, to the different ways that End Homelessness Winnipeg is trying to help realize their vision, to hearing about the tangible difference that the Downtown Community Safety Partnership is making everyday, there was no shortage of valuable leadership insights.

Perhaps the notion that struck me the most throughout the day was the idea shared by Jim Ludlow,  President of True North Real Estate Development, that to succeed, you must venture outside of your comfort zone. That this concept, often summarized as “get comfortable with being uncomfortable,” is essential to make a significant impact in our community.

Throughout my career in the non-profit sector, I’ve often heard the idea that while your comfort zone is a pleasant place to be, it’s not where growth happens. When we push ourselves beyond our usual limits, we encounter new challenges and learn new skills. In the context of downtown revitalization, staying within the comfort zone means perhaps sticking to familiar strategies and avoiding risks. However, revitalizing a downtown area requires innovative thinking and bold actions. It involves exploring new ideas, engaging with diverse stakeholders, and sometimes making difficult decisions. Stepping outside our comfort zones is not just beneficial but necessary for meaningful progress.

Another key takeaway that resonated from what was shared was the importance of not being afraid of the unknown. As leaders, there is an expectation of planning, execution and measured results, but sometimes there is value in embracing the adventure of not knowing what’s around the corner.

Sometimes uncertainty should not be a deterrent but a motivator. As hard as it can be, when we approach the unknown with curiosity and openness, there is an opportunity for discovery and learning. This mindset can be crucial for leaders in any field.

The session on exploring Winnipeg’s downtown provided invaluable insights into the current opportunities and challenges faced by those who are actively striving to make a difference in the complex and dynamic process of downtown redevelopment. The insight that stood out the most was the importance of venturing outside of our comfort zones, embracing discomfort, and facing the unknown with confidence. These principles are not only essential for revitalizing downtown areas but also for personal growth and leadership development. By being open to this mindset, we can drive meaningful change and create strong, thriving communities.


Thank you to our sponsors for making the Leadership Winnipeg program possible.

Vision Partners: Canada Life, Johnston Group, The Winnipeg Foundation
Proud Partner: Assiniboine Credit Union
Proud Supporters: Boston Pizza, Change Innovators Inc., Honest Agency, University of Winnipeg

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