Overcoming Fear of Failure

Photo by Goh Rhy Yan on Unsplash

In recent times, there’s been a lot of discussion around failures, with successful people sharing their “resume of failures.” While this has helped normalize failing, it often focuses on “big” failures that come before success. But when it comes to trying out new things — whether or not they’re life-changing — do we still give ourselves permission to fail?

A former client of mine decided to attend a 10-day silent meditation retreat (Vipassana). Though he was uncomfortable being alone and preferred social settings, our coaching had encouraged him to challenge his limiting beliefs. However, when he mentioned the retreat to his friends, they questioned how he’d manage without speaking for 10 days or eating simple food, causing him to doubt himself. He even considered cancelling. When I asked what changed, he admitted that it was the fear of not making it through the 10 days. His doubt stemmed from the possibility of failure. Through our discussion, he was able to shift his perspective, focusing on the experience itself as an experiment, curious to see what might come up. The goal then wasn’t perfection but the willingness to give it a try. This helped ease his anxiety, though self-doubt lingered until the retreat began. Later, he shared how he could reach such deep meditative states that he sometimes missed the announcement to stand up and go for meals.

The fear of not doing things perfectly often stops us from trying. We also hesitate to jump into things where there’s a possibility of failure or where we may need to reverse decisions in the future, worrying about being seen as wrong. This isn’t limited to challenging tasks like silent retreats. We often abandon new habits after missing a few days, where the pressure of consistency overshadows the value of simply starting again.

When I started this newsletter, the commitment to a weekly schedule felt daunting. But by shifting my mindset to “I’ll try to send it every week,” I gave myself permission to fail, easing the pressure. We hold ourselves to high standards, but that can prevent us from taking the first step.

The Cult of Done Manifesto includes a point : “Accept that everything is a draft. It helps to get it done”. This applies to people too. Some write “WIP” (Work-In-Progress) as a status on LinkedIn, but aren’t we all works in progress? We’ll never be the perfect, polished beings we aspire to be. Accepting ourselves as drafts, with flaws and all, makes the journey lighter.

In coaching, I often help clients design experiments to reach their goals. Framing them as experiments allows for failure and encourages curiosity and learning. Isn’t life an experiment too? After all, none of us have lived this exact life before.

Antonio Machado, a Spanish poet, once said, “Traveler, there is no path; the path is made by walking.” Taking action comes with the risk of failure, and we often play it safe out of fear — fear of embarrassment or being wrong. But would you really let that stop you? Are you willing to risk playing the fool?

As a leader, you must carve your own path. The unique combination of your team, the organization’s stage, the challenges you face, and your own style makes leadership an act of creativity — a way of expressing yourself to the world.

So, would you not want to express yourself authentically and walk the path that appears before you? Are you comfortable giving yourself permission to fail, to play the fool?

🤔Reflect: I invite you to bring a particular goal or desire to mind and consider the following questions:

• Where is fear of failure or embarrassment stopping you from taking action?

• What could be your first step in that direction, giving yourself permission to fail?

• Imagine yourself as a wise 95-year-old on your deathbed, having lived a fulfilling life. What advice would this older, wiser version of you give to your present self?

PS: Came across The Cult of Done Manifesto through Ed Batista’s writing.

If you’d like to read more from me like this directly in your inbox, you can head here to subscribe to my newsletter.