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Failure Isn’t Fatal: A First-Hand Employee Wellness Journey and Call To Action for Leaders

Kayla Isabelle

CEO, Startup Canada

Businesses must embrace authenticity and transparency, supporting mental health and flexible work.

The business ecosystem – from community non-profits to the world’s most recognizable C-suites alike – too often uphold a public-facing employer identity rooted in notions of innate perfection, effortless balance, and faultless leadership. We have all seen it – the organization in the midst of a widespread retention crisis boasting their latest “Great Place to Work Award” in a press release, or your friend who works at a company infested with toxic management despite the office walls being plastered with innovative leadership recognition. Don’t get me wrong, it’s often necessary for organizations to safeguard their brand and public perceptions when faced with adversity – it’s how we maintain client trust, keep teams motivated, and how we protect triple bottom lines. However a complete, conscious absence of authenticity and transparency can do more harm than we may imagine – to our missions, customers, teams, and the larger business community. 

We learn from failure, period. Whether it’s our own failures or the observed failures of others, it’s how we identify and understand what didn’t work so we can adjust methods and approaches in the future. Learning from failure is also how we learn about ourselves, gain empathy for others undergoing a similar challenge, and foster community based on shared experiences. Very little, in my personal experience, has ever been gained from falsified, sugar coated stories predicated on instant success, over glamorization, and hidden realities.  

As a national convenor of small businesses and those that support them from coast to coast to coast, myself and Startup Canada know that entrepreneurship can be a hard, lonely journey – a journey that often begins in an echo chamber of self doubt, anxiety, and seeming isolation. What makes this echo chamber longer, stuffier, and nearly impossible to escape? The mutually upheld, unchallenged phenomena of unabated masking of hardships, cloaking of underperformance, and overvaluing of inflated optics.  

Too often romanticized, the reality is that business is hard. But, it could be slightly easier if we all swallowed our pride every once in a while, acknowledged this reality, and showed up for our community with a spirit of collaboration and mutual understanding. For this reason, and in this spirit, this piece is a first-hand  profile documenting Startup Canada’s employee wellness journey since 2020 – covering the good, the bad, and the ugly along the way.  

I began my career in change management and digital marketing consulting before packing my bags in 2019 and heading to Tanzania where I worked one-on-one with local entrepreneurs operating in the tourism sector. It was in Tanzania where my passion for supporting founders and the small business community was born. It was almost serendipitous, then, returning to Ottawa at 27 years old and finding my next role at Startup Canada where I was able to continue growing and evolving this passion for the startup support ecosystem.  

My first month at the helm in March of 2020 felt too good to be true – our team was welcomed to Parliament Hill where we spent the day with the Prime Minister for an International Women’s Day event, hitting the ground running with Startup Canada’s programming for women-identifying entrepreneurs. In hindsight, it was too good to be true as within 48 hours the country was in total lockdown as COVID-19 swept across the globe and the greatest economic crisis in recent history confronted Canada’s small businesses. 

Amidst the world’s most unforgiving crash course in crisis management, I was completely consumed by the sheer number of unknowns in front of us. When would things return to normal? Would the government step in to support founders? What in the world am I doing?! Is it normal to be this lost? How should we navigate previously committed to in-person conferences? Are we ready for remote work? Is the team safe? How do we pivot to better serve founders during this crisis?  

To be completely transparent, I nor anyone around me had any idea what would lay ahead or how to balance internal and external demands in those early days. It was entirely overwhelming. While most new CEOs use the first few months of their tenure to mark personal transition and catalyze institutional renewal, I inherited a central support role for a vital aspect of the national economy that was experiencing upheaval. Serving this community in need of urgent support, innovative solutions and constant adaptability was incredibly fulfilling, but this new reality simultaneously elevated pressure on our entire team to step up to the plate and deliver.  

Shifting roles and responsibilities, depleted capacity, and ceaseless change took its toll at times and, like most organizations operating in 2020, burnout and employee wellness challenges began to emerge. Faced with this make-or-break circumstance, I knew things needed to change but was unsure of ideal approaches to take. In the beginning, I’ll admit, I relied on toxic positivity and rationalized optimism – the notion that to succeed and persevere, hardship and adversity couldn’t be acknowledged to the team. A journey in and of itself, I quickly came to understand the true impact of authentic leadership and people-first action. Our team didn’t need high fives and incomplete solutions, they needed to trust that meaningful changes would be implemented and that the leadership team heard and appreciated them. 

Recognizing that flexibility and people-first leadership were non-negotiable, we took immediate action and implemented permanent remote work protocols, paid mental health days, half day Fridays, and a monthly wellness initiative coined “Health Over Hustle”. In addition to these new policies focus was also placed on transforming institutional culture, holistically, via consistent one-on-one check-ins, collaborative decision making, and relentlessly fostering psychological safety. Considering how many non-profits were shutting down during the onset of the pandemic, I also heavily prioritized transparency regarding the month-to-month finances of the organization and our respective standing with various partners to ensure the team didn’t experience any unnecessary, additional surprises along the way. The results since this shift have been undeniable. Since 2020 Startup Canada has gone from a team of as low as 3 to an engaged team of 14+, have launched and/or reinvigorated 9+ national programs, held over 300 events, engaged nearly half a million Canadian entrepreneurs, and continue to grow our impact every day. Internally we have seen increased retention by over 50% since 2019, a 32% increase in employee satisfaction, and hold an employee Net Promoter Score of 9.3 out of 10.  

Upon reflection, the last three years have been the greatest lesson in leadership I have yet to, and likely will ever, experience. Marked by both mountains of success and valleys of failure, this has been a beautiful journey of self discovery, organization-wide growth, and collective lessons learned. Leading during change is both a collective and independent exercise with differing nuances, contexts, and ideal solutions from organization to organization, and from team to team. However, a few key learnings are likely universal for fellow leaders:  

  1. You can do anything, but not everything. 
  1. What got you here might not get you there.  
  1. Don’t light yourself on fire to keep others warm.    

Failure is delay, not defeat and as famously quoted by Denis Waitley, “failure is something we can only avoid by saying nothing, doing nothing, and being nothing”. It’s inevitable, but if those in the business community can show up authentically for themselves, their teams and other leaders, we can all help in reducing the stigma and isolation that often accompanies the idea of failing. The real world does not exist in vetted press releases or glamorized LinkedIn feeds (seriously, do you think every person you’ve ever met is thriving 24-7?!). No, it exists in quiet moments of anxiety, loud moments of collective success, lonely moments of humble reflection, and in courageous moments of shared compassion and strength.   

About Kayla Isabelle 

Kayla Isabelle is the Chief Executive Officer at Startup Canada, the gateway to Canada’s entrepreneurial ecosystem that points you in the right direction, eliminates barriers, and champions your needs to private and public sector partners. Startup Canada’s mission is to connect Canada’s entrepreneurs with the tools, community, and support they need to start and build their businesses. Kayla has dedicated her career to supporting entrepreneurs, both in Canada and internationally. As an award-winning strategic communications consultant and change management facilitator, Kayla is passionate about leveraging the power of storytelling in the entrepreneurial community. 

To learn more about Startup Canada and to connect with the team visit

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