Failing Upward: The Secret No One Told You
June 21, 2025
You know when you get an exciting idea you want to share and the thing standing in the way of bringing it into the world is fear that it’s different?
I was there. Really good at what I did, but always flooded with ‘different’ ideas. Not feeling brave enough to start the climb of a new and unfamiliar mountain.
Failing upward are two words I never felt could sit next to one another until one day a mentor explained to me that a fail is only a fail if you add a period at the end.
In other words, it means that you never tried again…
Failing upward is how you get to the peak of the mountain.
The Real Reason You Haven’t Started Your Climb Yet…
I always walked around the base of my mountain. Sizing it up with a clipboard in hand finding all the ways that I could fall and hurt myself.
I thought that if I took enough notes, I could learn to climb it in the most seamless path.
I watched others often in groups approach the mountain, backpacks full of excitement and courage ready to begin their ascent.
I wondered how they could begin such a terrifying climb so…fearlessly. Without having spent much time researching all the ways they could slip and fall.
I knew that if I could just speak to those who had made it to the top of the mountain, I could get a roadmap to avoid all the dangerous areas,
The thing is, I waited for them to come back down to the base and share their stories with me, but they never did. I waited and waited and kept taking notes of more dangerous areas. And guess what? The more I looked, the more I found…
Then, during a trip to Thailand in 2023 at a dark time in my life, I made a promise to myself on the last night. A promise to go all in on my business and hire my first mentor when I got back to Canada.
One mentor quickly turned into two, then three. Before I knew it, I was surrounded by a network of deeply supportive, vulnerable, and confident female business owners. A side of women I had never been around before.
I learned from eight different mentors around the world specializing in areas I had never been taught, from mindfulness and manifestation, to trauma and healing, to therapeutic arts and business.
And then one day, it finally clicked. Those at the peak WERE sharing their stories and roadmaps, but I couldn’t hear them from all the way down where I was cautiously standing.
They were shouting it from the mountain tops and those who were close by would hear it and pass it on to those below. This continued and echoed all the way down to those who had just started their climb.
But I never heard these echoes because I was too busy taking notes at the base, focusing on how I could fail instead of how I could succeed, that I never even started the climb…
Since starting the climb, I’ve met all sorts of inspiring people
With different stories, but familiar pain.
With different goals, but similar fears.
AND with an unstoppable ability to place one foot in front of the other and forge a new path for themselves EVEN through uncertainty.
I know there will be many more mountains to climb that I can’t yet see from where I’m standing, but I now know that the real reason I’ll continue to overcome challenges is not my grit, my passion, or my relentless desire to continue to grow, rather the community celebration that emerges every time we choose vulnerability over fear.
I can confidently trust my decision to sit and rest whenever I need to and continue the climb when I’m ready because I’m no longer chasing something outside of myself that will forever be unattainable.
My promise to you is that as I get more insight from those at a higher altitude, I will continue to share it with you and anyone starting their climb.
Because the most rewarding part of it all is that I can now get to help those with similar versions of myself who’ve also been searching for guidance.
When you can finally understand the purpose of the climb, you win the lottery of life.
So I want to leave you with these three lessons that have moved me from feeling stuck to taking action (even in fear).
- There will never be any shortcuts to where you want to get to.
- Sometimes the longest feeling path becomes the necessary pivotal one to your success.
- You can trust that there will always be people reaching out a hand to pull you up onto their level…(IF you’re willing to ask for help). It took me 31 years to ask for help, but only two years to realize I had been playing a completely different game of life…
So what’s been preventing you from starting your climb?
