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Diary of a Leader: Embracing Failure as an Entrepreneur
Updated: Jun 19
Welcome to "Diary of a Leader" - Real Stories, Leadership Lessons, and Personal Growth
Ah, leadership! The thrilling, heart-racing journey of ups, downs, and all the delightful chaos in between.
Welcome to "Diary of a Leader," where I peel back the curtain on the good, the bad, and the downright awkward moments of being a leader.
This is part two of a two-part lesson on failure. In part one, we talked about helping teams get comfortable with it. This week, the lens turns inward: how leaders and entrepreneurs learn to embrace failure ourselves
The Entrepreneurial Reality: Failure Is Everywhere
When I worked as a traditional leader and manager, I struggled with the idea of failure. There was constant pressure to get things right the first time, since mistakes impacted not just me but my team too. But becoming an entrepreneur taught me something different: failure is unavoidable, and resisting it only holds you back.
Being afraid to fail will paralyze you. Entrepreneurship runs on failure. It's a game of ten no's for every yes. There's always more you can improve, and fewer traditional feedback mechanisms to tell you when you're winning or losing. Avoid failure too hard, and you won't just limit your growth, you'll stop yourself before you even begin.
The Importance of Talking to People
A few weeks ago I had lunch with a friend thinking about taking the leap into entrepreneurship. She confidently laid out her business idea and product concept, and it all sounded great. I asked her the same question I've been asked before:
"Have you talked to your ideal client about the challenges they're actually facing in their business?"
That question took me back to my own early days. I'd enrolled in a program at Platform Calgary that pushed us to talk to potential customers, not to sell them on our ideas, but to understand their pain points. We were trained to ask open-ended questions, validate assumptions, and refine our solutions based on real feedback.
Most businesses start because someone spots a problem worth solving. The trap is falling in love with your own solution before you've confirmed it actually matches what people need.
My advice to her was simple: get out there and talk to people. She hesitated, and admitted to imposter syndrome. Then she said something that stopped me in my tracks:
"I see you as someone who doesn't make mistakes."
We go first, mistakes and all
I was stunned. Me, someone who doesn't make mistakes? She clearly hadn't seen the times I'd cried over a project I didn't win, or sat on my office floor completely unsure of my next step.
But here's the reality of leadership, especially as an entrepreneur: we're often the ones who have to go first.
As John Maxwell puts it, leaders see first and see far. We're the ones who step into uncertainty and take the risk before anyone else does. We lean into the possibility of failure, not because we enjoy it, but because it's the only way to build something meaningful.
Why we must embrace and celebrate failure
Here's the good news about failure: it's not only about the possibility of things going wrong, it's also about the possibility of creating something incredible.
When you learn to embrace failure, you realize it isn't an endpoint, it's a stepping stone. Failure teaches you, refines you, and surfaces opportunities you'd have otherwise missed. It's not just something to accept, it's something worth celebrating.
You're either winning or you're learning. Since I love to learn, I've become surprisingly comfortable with failure along the way.
How to embrace failure in your own journey
Whether you're a leader, an entrepreneur, or both, here's how to lean into failure and let it move you forward instead of holding you back:
Talk to people, not just yourself. Your ideas are only as good as the problems they solve. Get out there and talk to your customers or your team. A "no," or a "that's not quite right," might feel like failure, but ignoring the feedback entirely leads somewhere much worse.
Take the first step. As leaders, we go first, whether that's stepping into uncertainty or trying something no one's done before. You might fail. You'll also learn.
Reframe failure as progress. Every failure is a chance to grow. Treat what went wrong as a necessary part of building what eventually goes right.
Let go of perfectionism. Failure doesn't mean you're not capable, it means you're human. The sooner you let go of needing to be perfect, the sooner you make real progress.
Embracing failure as an entrepreneur: common questions
Why is embracing failure as an entrepreneur different from embracing failure as a team leader? As a team leader, your job is to make failure safe for other people. As an entrepreneur, you're usually the first one taking the risk, with no one ahead of you to make it safe. That's a different kind of exposure, and it requires a different kind of comfort with uncertainty.
How do you get comfortable talking to potential customers about your idea? Go in to learn, not to sell. Ask open-ended questions about the problems they're already facing rather than pitching your solution. The goal is to validate whether your idea solves a real problem, not to get a yes.
What does "leaders go first" actually mean in practice? It means founders are often the ones stepping into a decision, a market, or a risk before anyone else on the team has to. That's not about being fearless, it's about being willing to take the first failure so the path becomes clearer for everyone who follows.
Wrapping up (because time is precious)
Here's the takeaway: failure isn't something to fear, it's something to embrace. Whether you're starting a business, leading a team, or navigating your own career, failure is what helps you learn, grow, and build toward your highest potential.
Catch you next time, fellow leaders-in-training. Every step into uncertainty brings you closer to where you're trying to go.
Stay tuned for more reflections and lessons from the trenches of leadership in the next installment of
"Diary of a Leader"
