The Art of Losing: How Failure Shapes the Person You Become

... So what's your biggest failure in life?

One of the most heartbreaking responses I've ever heard to this question was from a parent who believed they had failed their child. They told me how, just after meeting their family at the airport as their wife and children were returning from a family holiday, their child suddenly went limp in the backseat of the car and couldn't be saved. They carried the unbearable thought that if only they had been able to take leave and go on the holiday instead of meeting their family at the airport, things might have been different.

Failure is something I ask about often - not to catch people off guard, but because it reveals something deeper about who we are. I ask this question in interviews, when mentoring, and even in conversations where I want to understand someone’s motivations. Sometimes the answers are light, sometimes they show incredible personal growth, and sometimes they make me feel truly honoured to bear witness to someone's story.

Failure is an unavoidable part of life. No matter how intelligent, accomplished, or prepared we are - or think we are - we have all had moments where we have fallen short of our expectations. If we haven't experienced failure directly, we have certainly seen its effects through others, and are failing in more implicit ways by avoiding potential problems.

When was the last time you felt like you truly failed at something?

Yet failure is so often treated as something shameful, something to be avoided, denied, or spun into a palatable “learning experience” that removes the sting. When I burned out, I told myself it was just another lesson in resilience, but the healing only started when I admitted the truth - I had failed. Failure is not just a stepping stone, it's part of the process of being human.

When I ask candidates about their biggest failure, I can usually tell within seconds who is engaging with the question and who is trying to spin a weakness into a hidden strength.

I'm not looking for a rehearsed answer. I ask because failure is one of the greatest tests of self-awareness. It shows how we process setbacks, how we frame our own growth, and ultimately, who we are becoming over time.

Those who claim their biggest failure is being too good at what they do are unlikely to get a call back from me. The human experience is complicated, messy, and real - and anyone who refuses to acknowledge their own struggles is either deeply unaware or unwilling to be vulnerable.

Failure and the Stories We Tell Ourselves

One of the biggest traps people fall into is tying their self-worth to things - job titles, relationships, achievements. I explored this in my last article, reflecting on my own experiences as a successful person in my twenties. At the time, I felt untouchable, but looking back, I realise that confidence was na?ve at best and reckless at worst.

When our identity is built on external success, failure feels like losing a part of ourselves. However, self-awareness comes from understanding that failure is something that happens to us, not something that defines us.

How do you usually respond to failure? Do you let it define you, or do you use it as fuel for growth?

Of course, we have to balance vulnerability with risk. Just as you wouldn't give someone your house keys after a first date (unless you're one of my long-time friends who shall remain nameless - it didn't end well), you also wouldn't expose yourself completely without considering the consequences.

The real danger is when we internalise failure so deeply that we start to believe we are failures. That belief is incredibly damaging - like carrying burning coal in our hands, convinced we have no choice but to hold on.

Pain is unavoidable, but suffering over it is a choice.

I know this because I've done it myself. 've clung to my failures and the pain they caused, replaying them in my mind as if doing so would change the outcome. I've experienced both the loss of control and the loss of hope, and I would argue that the latter is even more destabilising. When we lose hope, we struggle to move forward because we no longer believe progress is possible.

So if failure is inevitable, what then? Do we just accept it as a necessary evil and keep moving, wrapped in layers of metaphorical armour?

Failure often feels wrong, but feelings are just that - powerful emotional states that can either strengthen or derail us, depending on how we respond. A friend of mine has spent decades living solely by how she feels, but often finds herself frustrated by life and the associated outcomes when she lacks the tools to balance emotion with logic.

With that said, failure is not always bad. Sometimes it's a sign that something valuable is coming - something that, paradoxically, may even make us better.

The Tension Between Comfort and Growth

The secret to becoming the best version of yourself is not about avoiding failure, but about learning to manage the tension between your comfort zone and your aspirations.

Comfort feels good. It's warm drinks, soft blankets, and familiarity, but it's also limiting. Growth requires challenge - enough to stretch us, but not so much that it breaks us.

I tell my team: you wouldn't learn to swim by jumping into the middle of the Atlantic Ocean, but you also wouldn't learn by never stepping into the water at all.

Even as I write this, I know comfort is enticing. Many of us pursue feeling good as if it is the goal, without asking whether it is actually serving us in the long run. Some of the nicest things in life - pleasure, familiarity, predictability - can lead to dysfunction when overindulged.

At the same time, nobody should suffer unnecessarily. I've often told friends and colleagues alike, there's no reward for living a harder life than needed, yet I've struggled to follow my own advice. Many times, I've avoided the better option out of fear - fear of being hurt, of losing money, or of experiencing danger.

I have also realised that many of these choices are deeply rooted in subconscious beliefs. For years, I convinced myself that I couldn't be defined simply by existing - I had to do to be worthy. This belief only became clear to me through years of meditation and reflective writing.

Growth happens in the space between comfort and challenge. I tell my mentees that a 10 to 20 percent stretch beyond their current ability is enough for structured growth. Whether it's learning a new skill, progressing in a career, or asking out the person you see on the train every morning, small steps lead to big change.

Comfort is not a reward. It can be the thing that holds us back from the life we are meant to live.

What Does “Good” Failure Look Like?

Failure in the right environment fosters resilience, creativity, and problem-solving. However, failure in a culture of fear does the opposite - it teaches people to play small, avoid risk, and seek safety over growth.

I've spoken to companies that claim to embrace a "fail fast" culture, yet reprimand employees when things go wrong. That's not an iterative culture - it's a fear-based one. If people don't feel safe to fail, they will eventually stop trying altogether.

I know this feeling well. As a high-achieving child, I built up an intense fear of failure. My neurotic perfectionism made me believe that even though I had succeeded ten times in a row, the eleventh attempt might be the one where I finally failed. If I did, what then, young Matthew?

Good failure is controlled failure - failure that leads to learning, not punishment.

The Courage to Fail, The Strength to Continue

When I was younger, I thought bravery meant feeling no fear. Later, I read Wilfred Owen’s poetry during English class and saw bravery for what it really was - moving forward despite fear.

The soldiers Owen wrote about were not Hollywood action heroes. They were ordinary young men, facing horrors beyond imagination, terrified of never seeing home again. Their courage was in continuing, not in feeling fearless.

Failure is not the opposite of success. It is part of it.

So what's my biggest failure? Worrying about a future that has not happened, because of scars from the past. I don't want to feel pain, but I also don't want to reach the end of my life burdened by regret - I can't have my cake and eat it, though.

What I have learned is that whatever failure I have faced to date, it hasn't stopped me from having the chance to try again today.

Maybe, in the end, the art of losing is not about never failing - but about learning to fail well.