Recently, I returned to my old prep school, Moulsford, to give a talk on the seven key lessons I’ve learned from the latest season of my podcast.
In the talk, I shared one lesson from each guest, introducing the boys to different mindsets and approaches to life. We explored a variety of ideas, from pursuing something you love and remembering the importance of play, to prioritising self-care before helping others and defining what happiness means to you.
However, one topic struck a chord with both the students and teachers—the idea of not being afraid to fail and, more importantly, not feeling embarrassed by failure. I hadn’t expected this point to resonate the most, but as we discussed it together, I realised just how impactful it was.
When I asked the group who had ever felt embarrassed by failure, nearly every hand shot up. As more boys raised their hands, even the quieter ones felt comfortable enough to do the same. This simple act of sharing made the lesson even more powerful, illustrating just how universal the fear of failure—and the courage to overcome it—truly is.
I’m not entirely sure why I didn’t anticipate that this point would resonate so deeply. My only conclusion is that over time, I’ve developed a thick enough skin to not worry about what others think. I definitely remember having similar fears at their age, especially in an all-boys environment where competition was fierce, and judgment quickly fell on anyone who stood out or was different.
For me, failure has become a natural part of growth. Once I embraced this, the fear of its consequences diminished. I now approach everything with the mindset that every experience offers a lesson—whether it's success or failure. If failure is part of the process, then it’s likely there’s an important lesson to learn from it.
This talk made me realise just how powerful the fear of embarrassment is as a driving force in many people’s lives, especially for the younger generation. It can be incredibly limiting.
I’ve often wondered why more people don’t start their own businesses or pursue their passions as a way to make a living, and maybe this is the crux of it—people are too afraid of failure and, more specifically, too concerned with what others will think if they fail.
Judgment from peers and your wider circle can be difficult to accept, especially when it isn’t positive. But developing the ability to stay comfortable with yourself, regardless of the outcomes in your life, becomes a true superpower—particularly when you’re making bold and ambitious decisions.
What many people don’t realise is what lies on the other side of taking risks. When you can take risks without being paralysed by the fear of the outcome, you open yourself up to the possibility of great success. The biggest successes often come from those who take the biggest risks.
We frequently focus on mitigating risks, especially in financial decisions, but what if we learned to filter risks and identify which ones are truly worth taking? Once you reach the point where the opinions of others no longer matter, you unlock the ability to take far braver and bolder steps—steps that have the potential to truly change your life.
I am Will Flindall, host of the Valley of Outlaws Podcast where I speak to those who have decided to take control of their life and follow a passion or instinct.
If you feel like you could be getting more from your life, then maybe one of the conversations I’ve had with the Outlaws might help you kickstart a change.
Peace x
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