We Develop and Grow When It Feels Safe To Fail

Confidence grows when we feel safe to fail and make mistakes.

Sports people typically attribute confidence to believing they can beat anyone. So I was surprised when an England cricketer linked the team’s recent historic success to their willingness to lose games.

The England test cricket team has been playing a completely different brand of cricket. It’s expansive, exciting, and “fearless“. As a result, it comes across as extremely confident. But is that confidence built on what they can expect to happen when they fail instead of simply believing they can beat everyone?

In this episode of The Gentle Rebel Podcast, I explore the idea that confidence (and excellence) can be grown in unlikely places when people, things, cultures, and processes make it feel safe to mess up.

The Three Little Pigs

Do you remember the story of the Three Little Pigs? It’s a perfect tale to help us consider different sources of confidence in everyday life.

Confidence And The Desired Outcome

We often think about confidence in broad and general terms. When we do this, very few of us would not wish we had more of it, making us susceptible to products and services advertised with a promise of helping us become more confident and self-assured in life.

As such, we will always come up short again. So it’s far better to consider our confidence in particular situations, environments, and projects.

The three pigs had an objective. They needed to build strong, resilient houses that withstand adverse winter weather and keep the big bad wolf at bay.

Misplaced Confidence

The first little pig wanted to build his house as quickly as possible so he could play. He had confidence that there was nothing to worry about.

The second little pig wanted to build a better house but was distracted when he saw his brother playing. He had confidence that if there weren’t any storms or wolves, things would probably be okay.

The third little pig wanted to build a house that he could trust. He had confidence that if he did the job properly, his home would protect him from the weather and the wolf.

Confidence is The Safety to Fail

The third little pig creates a safe environment. WHEN the winter weather hits and WHEN the wolf comes knocking, he knows he can rely on the house he’s built to keep him safe from what would otherwise be harmful.

The environment that the current English cricket leadership have built is similar. Rather than saying, “we won’t lose”, like the first two pigs, they have created an infrastructure around the safety TO lose.

Safety is a source of confidence. It means you’re free to focus on what matters more than worrying about what happens when things go wrong.

Good Leaders Show It’s Safe To Fail

We are often so afraid of failure that we try to deny its inevitability. However, in many industries, if you’re not failing, you’re not succeeding. Failure is a by-product of taking risks. If you work in intelligence, innovation, or any industry that makes predictions, if you’re not getting things wrong, you’re not taking the necessary risks to get things right.

Certainty is only possible when it’s too late.

The best leaders show us that it’s safe to fail. Not to encourage sloppiness but to reassure us that it will be OK on the other side. So we have the freedom and confidence to grow without fear when it feels safe to fail.

Playing It Safe Is a Failure of Safety

We protect ourselves, keep things small, and avoid waste when we play things safe. This is NOT the kind of safety we need. But playing BECAUSE things are safe is a different matter. It’s underpinned by the assurance that: “We will figure out what to do if it goes wrong.”

The safety of making mistakes isn’t the elimination of accountability for them. Our failure doesn’t become someone else’s problem to clean up. But we are given a clear sense of process and support to be confident if things go wrong.

We might need to go and have some difficult conversations and fix whatever broke. But we know that the consequences are not fatal. We will not be exiled, thrown out, or banished from the social order. And a good leader makes taking responsibility for failure more attractive than keeping it secret.

Bringing vs Burying Failure

Just because the implications of mistakes can be bad, it doesn’t stop them from occurring. Wherever uncertainty exists, so too does the possibility of human error. And there will be less-than-perfect solutions where humans must make judgement calls.

If we are told that “whatever we do, we must not fail”, then we have to hide it when we do. So we hide, cover up, blame, dig deeper holes, and worsen the problems.

Healthy cultures bring failure early and know that when they do, it will get worked out…rewarding ownership and responsibility – met, not with passivity, but with action. A safe leader doesn’t just abandon or disown someone who makes a mistake; they use it as an opportunity for growth. Taking responsibility feels more rewarding, secure, and attractive than covering up or pretending it didn’t happen.

What Happens When We Run Out?

Our relationship with the idea of scarcity can affect our confidence. If we’ve been taught to fear squandering and wasting resources and opportunities, our focus can be consumed by a feeling of scarcity. This can be a source of anxiety about running out, losing out, or missing out. As a result, we might become miserly, hoard, and resent others.

Confidence is grounded in assurance that even if “there’s no more once that’s all gone”, we will still be fundamentally okay. This gives us a platform to build sustainability into our relationship with life.

Fear of Being Misunderstood (Bad Faith Is Unsafe)

We can lose confidence when we fear the consequences of our words and actions, especially when we can’t be sure how they will be received and interpreted.

This happens through “bad faith” when we filter what we hear through a desire to confirm something we want to hear. It takes courage and bravery to speak up despite being misunderstood. They may or may not be consciously aware they do it, but people make it their mission to misunderstand others. They receive and interpret the actions and words of other people with bad faith.

In The Courage to Be Disliked, Kishimi and Koga write about Adler’s definition of freedom, which isn’t the absence of something undesirable but the acceptance and willingness to face it. This is the fundamental principle behind having the courage to be disliked. We will be disliked by someone whether we like it or not. It’s a trap to dedicate ourselves to trying to be liked.

Likewise, confidence can grow when we accept that we will be disliked, misunderstood, and interpreted in bad faith. Or, like the England cricket team, freedom is being willing to lose.

This kind of freedom is a deep source of strength and confidence. It liberates us from the games people play and from fear of what might happen if we don’t play correctly.

The Team Makes It Safe To Fail, The Crowd Not So Much

The crowd is not a source of confidence. On the contrary, it’s fundamentally unsafe and volatile. It can turn on you without warning.

But the team is an environment we can control with a clear and unified vision. And while you may lose your place in the group when better players come along or you reach the end of your career, you will forever be a character in its story—part of the history. No one can take that away.

Confidence comes from accepting that no one individual is bigger than the team. No one will be here forever. It’s nothing personal. It’s just life. But you are forever written into the story of this thing.

Arrogance (“Over-Confidence”) is a Lack of True Confidence

Confidence is built on the safety of failing, whereas arrogance is built on fear of failure. Therefore, an arrogant person has been taught to believe that failure is not an option because it’s about them as a person. It is intrinsically linked to their value and worth as a human.

We can recognise the difference between confidence and arrogance in others by understanding how they leave us feeling.

When you spend time with a confident person, you feel positive about yourself. Conversely, when you spend time with an arrogant person, you have lower self-esteem and self-worth. Confidence lifts us; arrogance presses us down.

Arrogance rolls its eyes when you make a mistake. Their judgement is a distracting thorn, reminding you that failure is not okay. On the other hand, confidence shoots a reassuring look that tells you it’s safe to give it a go, reminding you that whatever happens, you are fundamentally okay.

Safety To Fail And The Road To Excellence

Arrogance nurtures average.

It is afraid of failure because it’s unsafe to make mistakes. If we are so scared to fail, we play it safe. We protect ourselves, blame others, and hold back from taking the necessary risks for the rewards we want.

Conversely, when we encourage failure and get more comfortable and better at it, we pave the way towards excellence.

This safety can’t be nurtured alone, though. It’s hard, if not impossible, to think yourself confident. But we CAN gradually build confidence as we recognise where this kind of safety to fail comes from. We can start to surround ourselves with people, things, approaches, processes, and stories that show us that it’s safe to fail.

Hunting For Confidence (A Courtyard Workshop)

Most of us would like a bit more confidence at times.

But what does it mean to be confident?

We often think of it as a feeling in itself. We hear people talk about “faking it ’til you make it” and the power of self-talk and mindset to help us feel more confident. And while these can be useful to consider, they are only a tiny part of the big picture because confidence is usually a by-product of other feelings.

When we think we want to feel confident, we might be saying we want to feel safe and be able to trust in something or someone outside us. In other words, we are confident when our need for security, acceptance, belonging, connection, authenticity etc., are met.

We talk to people in confidence (assured that they won’t tell others what we say), and we place our confidence in leaders (assured that they will work in the interests of their followers). We put confidence in objects, resources, and tools (assured that the car will get us from where we are to where we want to go).

In this workshop, we build on this idea in practical ways. It’s a chance to think about an area of life you want to feel confident in and look at it through different lenses of confidence. You will end up with simple ways to build confidence in your situation or project.