What Failure Teaches us That Success Doesn’t
Lessons from a big swim…
I think we get the idea of learning through failure, but the reality is, most of us would probably prefer not to fail. Despite knowing the value and insights gained, given the choice, I’m picking the glowing success every time…
I recently got a reminder of failure’s value. As you may have seen, I attempted the 10km Bondi to Watsons Bay swim, but didn’t make the 8km cut-off times and had to hop on my support boat. We skipped about 800m, before I jumped back in for the final stretch.
This was uncharted territory, having never swum that far. Coming into it, I knew there were no guarantees I’d make it, and I had to be ok with that (and did keep reminding myself). That it wouldn’t be a reflection of me or who I am. Yes, my pride and ego would take a hit (it did). But I would always be able to come back and try again (I might).
Why We Avoid Failure
From early on we’re conditioned to equate failure with being bad and a sign of shortcomings. Red crosses on schoolwork or failing an exam. Performance reviews that focus on gaps. Jobs that we don’t get, goals that we didn’t achieve, and competitions we didn’t win.
We aren’t taught how to fail well. We might know the importance of what psychologist Carol Dweck termed a ‘growth mindset’, which includes being open to learning from failure, knowing that we grow through it. But the preference to quickly sweep it under the rug and pretend it never happened can be favourable. Or maybe that’s just me.
We might link our self-worth to achievement and success, so when we fail, our identity feels threatened, and our self-image can take a hit. There can be feelings of shame and embarrassment. We fear judgment, rejection, and repercussions. No one is going to search for all of that!
Why That’s a Problem
The problem? At its worst, we don’t even try things for fear of failure. We let self-doubt take control. We don’t try new things, experiment, take risks and head into the unknown. We can stay stuck in sub-optimal situations and stagnate. We play it safe and risk setting ourselves up for regret.
In the workplace, it can feel like there is even less space for failure. But without it, creativity, productivity and innovation can be stifled. Talent can be lost. People's potential remains untapped. Different, and potentially better ways of doing things are ignored.
The irony is - success rarely teaches us as much as failure can.
The Benefits of Failure
Failure builds cognitive flexibility
When things go wrong, especially in unexpected ways, it forces the brain to shift gears and problem-solve, switch strategies, and adapt. This cognitive flexibility is a critical skill in an unpredictable world. It’s the foundation of creative thinking, decision-making under pressure, and innovation. We learn to trust our ability to respond and adapt to what gets thrown at us. We are then more confident to try new things.
In this fast-changing world, adaptability is a leadership superpower. Teams that fear failure stay rigid. Teams that embrace it flex and evolve.
Failure strengthens emotional agility
Experiencing the emotional discomfort of failure and moving through those feelings (rather than avoiding them) and extracting the learnings, builds emotional agility. When we avoid failure, we often do so because we’ve collapsed what we do with who we are. If we can reframe failure it helps us uncouple the two. Yes, it can be a humbling experience with egos taking a hit, but through positive reflection, we learn that these events don’t define us.
Emotional agility combined with cognitive flexibility helps us become antifragile and grow through the challenges. We are less likely to shy away from things we are not sure we will succeed at, because we know we can deal with those feelings and emotions.
Resilient leaders and teams accept failure and grow back stronger. They create cultures where others feel safe to do the same. If leaders want innovation, adaptability, and resilience in their teams, they need to actively de-stigmatise failure.
Failure shows us the right path
When we unpack what went wrong we can see what we need to avoid, and where the gaps are. It could be skills we need, more training that’s required or a different approach. By digging into the mistakes, we potentially avoid a bigger problem in the future. A failure can also end up being an opportunity. Being fired from a job, could end up leading to something better.
Risk managers collect issues, errors, failings and even near misses like they’re collecting Pokémon. Why? Because there is something to be learned. A minor incident can uncover a bigger problem or a systemic issue. Project post-implementation reviews (PIRs) are all about looking at the lessons from the project to make the next one better. A positive review after something has gone wrong, not only helps avoid a repeat, it can lead to better ways of doing things.
How to get better at failing
Like anything, it takes deliberate practice.
1. Be a beginner or try something new
As a beginner, we’re like a kid learning to walk, there are going to be the equivalent tumbles. Put down the stick you might be tempted to beat yourself with, and instead, be kind to yourself. Reflect on what you are learning as you go.
2. Look at past failings.
If there are failures in the past that got swept under the rug, go back and have a closer look at them. With the distance of time and less heightened emotions, we can practice digging into what happened and extracting lessons. There could be some nuggets of gold waiting to be unpacked.
3. Change the perspective
It can be tempting to automatically associate failure with being bad. What about shifting that perspective to being more neutral? In his book The Obstacle Is the Way, Ryan Holiday points out the objective and subjective in the phrase, “it happened and it’s bad.” We are being objective when we say ‘it happened’, but subjective when we say ‘it’s bad’.
“Choose not to be harmed, and you won’t feel harmed. Don’t feel harmed and you haven’t been.” Marcus Aurelius
4. Extract the lessons.
We love the highlight reel, but every big success is rarely a linear path. Thomas Edison is the regular poster child for this. As he famously said on his path to inventing the lightbulb, “I have not failed. I’ve just found 10,000 ways that won’t work.” Think of elite athletes or startup founders. For them failure is baked into their progress. It’s not a detour from the path. It is the path. I’ve launched many things in my business that haven’t been a commercial success. That’s ok. I trust I will find ones that will and learn from those that haven’t.
Making Space For Failing in Corporate Environments
In these environments, failing can be costly. But it doesn’t have to be.
Many corporate environments still reward perfectionism and risk-aversion. When leaders show that failure is accepted and there isn’t a blame culture, teams are liberated to experiment and take calculated risks.
When I was at Macquarie, ‘freedom within boundaries’ was like the corporate battle cry. There were guardrails in place, like policies, budgets etc, but it created space for teams to experiment. It was a big part, I believe, in making it such an innovative (and profitable) organisation.
Environments that tolerate smart failure improve problem-solving and future performance. Those who punish it create a culture of fear and stagnation. If you’re in a leadership role, your response to failure sets the tone.
Share your setbacks, not just your successes
Reward smart risks, not just flawless outcomes
When things go wrong, focus on what can we learn, not who’s to blame.
Create space for experimentation. Celebrate the effort, not just the result.
Innovation happens when people feel safe enough to try and fail.
Failure Can be Fuel (if you let it)
It can be incredibly liberating when the fear of failure loses its hold. And a powerful driver when we unpack the lessons and carry them forward.
I didn’t finish the 10km swim the way I hoped. I learned a hell of a lot more from the attempt than I would have from a straight swim to the finish line. I realised several incorrect assumptions and got some perspective. Friends and people I shared it with on socials celebrated what I had done. It helped me focus on that rather than what I hadn’t done. And there were parts of my preparation that paid off better than expected. Without the testing conditions, I wouldn’t have had that appreciation.
Yes, success feels better. But failure is more formative. It doesn’t just show us what didn’t work. We get to grow, adapt, strengthen and (if we choose) go again, wiser than before.
