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Writer's pictureLindsay Sheldrake

Diary of a Leader: Embracing Failure as an Entrepreneur

Welcome to "Diary of a Leader" - Real Stories, Leadership Lessons, and Personal Growth

 
A Leader reflecting on the leadership lesson: Embracing Failure
"Diary of a Leader" - Embracing Failure as an Entrepreneur


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.






And today, I’m serving up part two of my lesson on failure. Last week, we talked about helping our teams become comfortable with failure. This week, we’re turning the lens inward—how as leaders and entrepreneurs, we can learn to embrace failure ourselves.

 

The Entrepreneurial Reality: Failure Is Everywhere


When I worked as a traditional leader and manager, I’ll admit, I struggled with the idea of failure. There was constant pressure to get things right the first time—after all, mistakes impacted not only me but my team as well. But here’s the thing: becoming an entrepreneur taught me that failure is unavoidable, and resisting it only holds you back.


In fact, I’ve learned that being afraid to fail will literally paralyze you. Entrepreneurship is full of failures. It’s a game of ten no's for every yes. There’s always more you can do, more you can improve, and fewer traditional feedback mechanisms to guide your wins and losses. If you try to avoid failure, 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 went for lunch with a friend who’s thinking about taking the leap into entrepreneurship. She confidently shared her business idea and product concept, and it all sounded amazing. But I asked her the same question I’ve been asked before:


“Have you reached out to your ideal client and asked them about the challenges they’re facing in their business?”

This question brought back memories of my own early entrepreneurial days. I had enrolled in an incredible program at Platform Calgary, where they pushed us to talk to potential customers—not to sell them on our ideas, but to understand their pain points. We were encouraged to ask open-ended questions, validate assumptions, and refine our solutions based on real feedback.


When you start a business, it’s often because you’ve spotted an opportunity to solve a problem. But here’s the trap: we fall in love with our ideas. We get so attached to our solutions that we forget to ask whether they truly align with what people need.


My advice to her was simple: get out there and talk to people. But she hesitated and opened up to me about her imposter syndrome. Then, she said something that stopped me in my tracks:


“I see you as someone who doesn’t make mistakes.”


The Truth About Leadership: We Go First, Mistakes and All


I was stunned. Me? Someone who doesn’t make mistakes? Clearly, she hadn’t seen the times I cried my eyes out over a project I didn’t win, or when I sat on my office floor, completely unsure of my next step.


But here’s the reality of leadership, especially as an entrepreneur: we are often the ones who have to go first.


As John Maxwell says, “Leaders see first and see far.” That means we’re the ones who step into uncertainty and take risks before anyone else does. We lean into the possibility of failure—not because we enjoy it, but because we know 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 just 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’s not an endpoint but a stepping stone. Failure teaches us, refines us, and helps us see new opportunities we might have otherwise missed. It’s not just something to accept—it’s something to celebrate.


As they say, you’re either winning, or you’re learning. And 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 are a few ways to lean into failure and use it to propel you forward:


  • 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 team members. Hearing a “no” or “that’s not a good idea” might feel like failure, but ignoring feedback could lead to something much worse. Embrace the lessons these conversations bring—they’re the first steps toward creating something better.


  • Take the First Step - As leaders, we have to go first—whether it’s stepping into uncertainty or trying something no one else has done. Yes, you might fail, but you’ll also learn.


  • Reframe Failure as Progress - Every failure is an opportunity to grow. Celebrate what went wrong as a necessary part of building what will eventually go right.


  • Let Go of Perfectionism - Failure doesn’t mean you’re not capable; it means you’re human. The sooner you let go of the need to be perfect, the sooner you can make real progress.



Wrapping Up (Because Time is Precious)


Here’s the takeaway: Failure is not 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—and remember, every step into uncertainty brings you closer to success.


Leadership
I can honestly say I may have failed on this half marathon without my sister leading the way!

Stay tuned for more reflections and lessons from the trenches of leadership in the next installment of


"Diary of a Leader"






 

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