If Failure’s Wrong, We Don’t Want To Be Right

When you think about failure, what’s the first thing that comes to mind? 

Does it bring up feelings of regret, shame, or embarrassment? 

Perhaps you associate it with a lack of success or falling short of expectations. 

The fear of failing can feel more daunting than actually failing because of its perceived impact on our self-worth. For example, if you start a business and it fails after a few years, it’s easy to think, “I’m a failure,” rather than, “My business failed.” No judgment here — we’ve all felt this way at some point. But the best part is, we have the power to redefine failure and the stories we tell ourselves about it, approaching it in a way that fosters growth and learning.

At Venture for Canada (VFC), we see failure as a key part of creating impact. High stakes and a wide network mean our failures can affect many, but we view these moments as chances to learn, innovate, and adapt, rather than being paralyzed by shame.

To illustrate this mindset, we turn to the insights of Jessica Lee, our Learning Design Manager and Fail Forward facilitator, whose expertise in navigating and learning from failure has been invaluable. Jessica’s approach to failure combines storytelling with practical strategies, and has led sessions for individuals (like our very own Fellows) and organizations alike. 

Her sessions, including one recently held with The Good Growth Company titled “10 Things Social Purpose Organizations Need to Know About Failure,” focus on how to embrace failure in ways that foster learning and growth, even in high-pressure environments where resources are tight, and public scrutiny is high.

Jess’ guidance on how you and your team can embrace failure:

1. Redefine Your Relationship With Failure: Shift your perspective on failure from being wrong or bad to a natural and necessary part of growth. Help your team reframe failure by replacing the word “failure” with terms like setback, hurdle, or learning opportunity.
2. Reflect on Your Failure: Speaking of learning, if you want to move on from blame and focus on actionable solutions it’s essential to reflect on what went wrong by asking, “What can we do differently?” and “What was the most valuable lesson we can take from this experience?” Learn from failure, don’t rush past it and use it as a catalyst for innovation.        
3. Normalize Failure:  It’s easy to feel alone after a failure, thinking everyone else has it together while you’re the only one struggling. The antidote to this is sharing your failure when we’re in a psychologically safe environment.      
4. Create Psychological Safety: Building an environment where team members feel safe to admit mistakes and speak openly without fear of judgment is crucial. This takes time, trust, and vulnerability, especially from leadership. At VFC, we create psychological safety by addressing “sticky” or challenging tasks in one-on-one meetings. This allows both managers and team members to share what’s feeling difficult or stressful, fostering a culture of openness.
5. Lean into Compassion: Understand that failure is inevitable, and perfection isn’t the goal. Be kind to yourself and your team when setbacks happen. A useful framework for responding to failure is the “gratitude-reassurance-process.” Thank your team for their openness, reassure them of their value, and collaborate to analyze and address the issue.

Clearly, failure itself isn’t the issue —  it’s how we perceive it and what we do after we fail that matters most. In fact, we’d argue that failure can be a good thing. Yes, we said it. 

An organization that fosters a culture of risk-taking, where learning from mistakes is valued, is one that drives innovation and resilience. So, remember, don’t fail fast; fail thoughtfully.