Building Confidence – Fail First

by | Blog, Executive Coaching

When my son was in high school, he announced he had decided to try out for the school golf team. I said, “Great, but Liam, you have never played golf in your life”. To that he replied, “No worries, I’ll figure it out; how hard can it be”? Having been a hack golfer my entire life, I wanted to convince him not to try so he wouldn’t be disappointed. But who am I to shout down his dream and chip away at his confidence? I admired his fearlessness. I think we both knew he wouldn’t make the team, but I knew that if he tried, failed, and then recovered, he would be better for it. His innate confidence and fearlessness were leadership traits I needed to nurture.

Fail First

The fact is everything we accomplish in life comes first at the foot of failure. I did not get into my college of choice, I did not get every promotion I expected, and I did not get the client upon the first ask.

For example, I was first rejected by several leadership programs for which I applied. Ultimate acceptance to these programs came because I knew that there was a chance I would fail. The first try was like a trial, a test, experiences from which I needed to learn. I knew that I could overcome the consequences of these failures. I would be lying if I said I didn’t feel disappointed, but I also knew that the outcome of the failure belonged to me. It seems counterintuitive, but each time we fail, overcome, and ultimately succeed, our confidence skyrockets. Leadership is built on failure, recovery, and a slow building of confidence. The key is to first try.

Confidence to Try

To be clear, confidence begins with the try. However, it is realized, ultimately, with accomplishment. Failure is our signal that we need to learn and experience more. Once we put ourselves out there, we need to accept the path of learning that will follow. That means hard work, perfecting our approach, and practicing our skills.

Even when we perfect our abilities, life will present new challenges and failures which continue to enrich our abilities. It’s in knowing ourselves, our limitations, and then driving to stretch our goals. If you examine every success you have had, you will recall the path of struggles and challenges that you kept working through. Think of any leader you know or from history. You will find their struggle and growth of confidence. Abraham Lincoln, Steve Jobs, Oprah Winfrey, and Elon Musk all built their success on the back of failure. So can we.

Failure to Try

If we examine our most troubling failures, it sometimes is the failure to try. Not trying feels worse. If Liam had not tried out for the golf team, he may have not ever tried out for theater, which turned out to be one of his biggest successes. He found his passion because he tried without fear of failing.

What if Steve Jobs gave up upon Apple’s biggest failures, or if Oprah gave in because she was told someone like her could never make it in broadcasting. I think they all would have felt much worse if they had not tried. Eventually, they experienced the joy of overcoming failure. They all failed, we all will, but the trying and the ultimate reward is confidence.

Let’s talk about building your confidence.


About Sojourn

Sojourn Partners is a results-driven executive leadership coaching firm that empowers the professional workforce to think differently in order to realize the full return on investment in themselves and their companies. Professional leadership thinking and intervention, based on years of research and experience, place Sojourn Partners at the forefront in executive leadership coaching, organizational development, strategic planning and culture and climate change.


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