What Would You Still Do Even If You Knew You Were Going to Fail?

Imagine standing at the edge of a venture, knowing with absolute certainty that you'll fail. Not the kind of failure that leads to an unexpected success story, not the "fail forward" corporate speak, but genuine, unavoidable failure. Would anything still be worth pursuing? This question, posed by coach Jason Jaggard in a recent podcast I listened to, cuts through our success-obsessed culture to something far more fundamental about human nature and purpose.

It's a query that makes most of us squirm. We're conditioned to believe that everything worthwhile must have a positive outcome, that effort should always equal reward. The entire self-help industry, with its promises of "guaranteed success if you follow these steps”, has reinforced this notion. Yet history offers us profound examples of people who chose to act despite knowing they faced certain defeat.

‍
The White Rose resistance movement in Nazi Germany stands as one of the most powerful examples of this principle in action. In 1942, at the University of Munich, a small group of students and their professor decided to resist the Nazi regime through the power of words. Led by siblings Hans and Sophie Scholl, along with their professor Kurt Huber, the group wrote and distributed leaflets exposing Nazi atrocities and calling for passive resistance against the regime. These weren't naive young people unaware of the consequences. Sophie Scholl, just 21 years old, had already seen her father imprisoned for criticising Hitler. Her brother Hans had witnessed the brutality of the regime as a medical student on the Eastern Front. Professor Huber had decades of academic experience and fully understood the Nazi state's ruthless efficiency in crushing dissent.

‍
Yet they acted anyway. Between June 1942 and February 1943, the White Rose produced and distributed six leaflets. Each time they did so, they knew it could be their last act. The fourth leaflet spelled out their clear-eyed understanding of their situation: "We will not be silent. We are your bad conscience. The White Rose will not leave you in peace!" When Sophie Scholl was finally arrested on 18 February 1943, after being spotted dropping leaflets from the university's atrium, she knew what awaited her. During her interrogation, she declared,

"Somebody, after all, had to make a start. What we wrote and said is also believed by many others. They just don't dare express themselves as we did." Sophie Scholl

‍
Four days later, after a show trial, Sophie, Hans, and Christoph Probst, another member of the group, were executed by guillotine. Professor Huber and other members of the group would soon follow. Their "failure" was inevitable from the start - a handful of students could never hope to overthrow the Nazi regime through leaflets alone. Yet their actions, which appeared futile in the moment, have echoed through history. Those same leaflets were later dropped in their millions over Germany by Allied aircraft. Today, the square where Sophie Scholl was arrested is named after her, and schools and streets throughout Germany bear the names of White Rose members. Their "failure" has inspired generations to consider what they might stand for, even in the face of certain defeat.

This isn't about romanticising failure or promoting futile gestures. Rather, it's about understanding what drives us beyond the binary of success and failure. It's about identifying those pursuits that hold inherent value, regardless of their outcome. In our metrics-obsessed world, where everything must be measured, tracked, and optimised, this concept feels almost revolutionary.

The question becomes particularly relevant in our current context. We're navigating a world where AI promises to outperform humans in increasingly complex tasks, where social media creates impossible standards of success, and where the pressure to "win" has never been more intense. Yet paradoxically, this might be exactly why we need to understand what we'd do even if failure was guaranteed. I also want to contextualise this in a story about my youngest daughter, Martha.

Martha is a born winner. She is as sharp as a button, can engage any adult in conversation and never misses a trick. She is top of the shop in pretty much every subject. And she hates getting things wrong. Just like her dad. So when she was presented with the superstar award at school for her application of the Austin’s Butterfly model, I was intrigued and over the moon.

The video above shows the process of descriptive, specific feedback that helps learners to improve their work, in this case, epitomised by the brilliant Ron Berger from EL Education (who, by the way, has been the subject of many Edufuturists conversations with the late, great David Price OBE.)

Martha was given the award because she doesn’t always take critique or criticism well but, after her teacher explained this model, she has been working hard at embracing getting things wrong and then doing her level best to act on the feedback. This is well and truly a process and, although it is in the context of school here, I think there are loads of lessons we can learn.

The Psychology of Guaranteed Failure

We've talked about failure before, referencing Steven Bartlett's Head of Failure and his focus on failing fast and often but our conventional understanding of this is remarkably narrow. We tend to view failure as a simple negative outcome: the business that doesn't turn a profit, the relationship that ends, the project that doesn't meet its objectives. But this definition betrays a deeper bias in how we think about human endeavour.

Unsurprisingly, Carol Dweck's research on mindset offers a crucial insight here. While her work is often oversimplified into "growth mindset good, fixed mindset bad", her more nuanced findings suggest something profound about how we view failure. Those with a growth mindset don't just see failure differently; they fundamentally reject the idea that outcomes alone determine value.

This connects directly to what psychologist Viktor Frankl termed "tragic optimism" - the ability to remain optimistic despite acknowledging life's tragic nature. Frankl, writing from his experience in Nazi concentration camps, argued that meaning could be found even in guaranteed suffering. He wasn't suggesting that suffering was good, but rather that purpose transcends outcomes.

The cognitive bias known as outcome bias is particularly relevant here. We tend to judge decisions based on their results rather than the quality of the decision-making process itself. This bias leads us to overlook valuable pursuits simply because they don't guarantee positive outcomes. As Daniel Kahneman notes in his work on decision-making, this can lead to systematically poor choices about what's worth pursuing.

“We think, each of us, that we're much more rational than we are. And we think that we make our decisions because we have good reasons to make them. Even when it's the other way around. We believe in the reasons, because we've already made the decision.” - Daniel Kahneman

Categories of Worthy Failure

We will explore six distinct areas where guaranteed failure doesn't negate the value of the pursuit. Each of these categories reveals something fundamental about what makes us human and what gives our actions meaning beyond their outcomes.

1. Moral Imperatives

Some actions are worth doing simply because they're right, regardless of their chance of success. Think of Chiune Sugihara, the Japanese diplomat who spent his final days in Lithuania writing transit visas for Jews fleeing the Nazis. He knew his career would be ruined and that he couldn't save everyone, yet he kept writing until the very last moment, throwing visas from his train as he was forced to leave.

This kind of moral action aligns with Kant's categorical imperative - the idea that certain moral duties are absolute, regardless of consequences. When faced with systemic injustice or moral wrongs, the act of resistance itself carries inherent value. It's not about winning; it's about standing for something.

2. Relational Investments

Perhaps nowhere is guaranteed "failure" more evident than in our deepest relationships. Every parent knows their efforts will be imperfect. Every close relationship will end, either through death or separation. Yet we pursue them anyway. It’s hard to say but it's very true. 

Consider palliative care nurses, who build relationships with patients knowing that every single one will end in loss. Or parents of children with terminal conditions, who pour everything into caring and loving, knowing the inevitable outcome. These aren't failures in any meaningful sense - they're profound expressions of what makes us human.

The philosopher Martin Buber's concept of I-Thou relationships helps explain this. These genuine encounters between people have intrinsic value that transcends outcome. The relationship itself is the point, not its longevity or "success”.

“Every real relationship in the world rests on individuation, this is its joy – for only in this way is mutual knowledge and acknowledgment of being different given – and this is its limitation – for in this way the complete acceptance of otherness is denied.” Martin Buber

3. Creative Expression

Art in its purest form isn't about success or failure - it's about the act of creation itself. Samuel Beckett captured this perfectly with his famous directive: "Ever tried. Ever failed. No matter. Try again. Fail again. Fail better”. This isn't empty encouragement; it's a fundamental truth about creative endeavour.

Think of William Blake, who spent years producing works that hardly anyone saw during his lifetime. Or Vincent van Gogh, who sold just one painting before his death. They created not because of guaranteed success, but because the act of creation was essential to their being. For all of us who care passionately about creative pursuits, we know we will fail but create regardless. 

 4. Personal Growth

Some pursuits are valuable precisely because they push us beyond our current capabilities. The British mountaineer George Mallory's famous response when asked why he wanted to climb Everest - "Because it's there" - speaks to this human drive to push boundaries, even when success isn't guaranteed.

As we have mentioned previously in other newsletters, the Stoic philosopher, Epictetus argued that the true value of any challenge lies not in its outcome but in how it develops our character. This view suggests that ‘failure’ in pursuit of growth is more valuable than ‘success’ that teaches us nothing. It is certainly true when it comes to learning too - we won’t always ‘complete’ our education; it should be an ongoing iterative process. 

5. Social Change

There are those who pursue social change knowing they might not live to see results. The suffragettes who went on hunger strikes, knowing they might not live to vote themselves. Climate scientists work tirelessly, knowing they can't guarantee policy change. These efforts aren't measured in immediate victories but in their contribution to the arc of history.

As anthropologist Margaret Mead noted, "Never doubt that a small group of thoughtful, committed citizens can change the world; indeed, it's the only thing that ever has”. The key word here isn't "can" - it's "committed”. The commitment itself holds value, regardless of guaranteed outcomes.

6. Physical Exercise

Whilst there are finite elements of sport and exercise, such as the end of a season or a specific competition, the nature of true physical fitness is rarely a pass-fail pursuit. As someone who is trying hard to make a habit of lifting weights, I know all too well the need for ‘failure’. Rather than lifting the same weights each session and making little progress, most of my training focuses on increasing load and/or repetitions, as well as improving form and stretch. But it is definitely interspersed with pushing (or pulling) until there is nothing left in the tank.

This concept is backed by exercise science's understanding of "training to failure”. Research by Dr. Stuart Phillips at McMaster University demonstrates that muscular failure - the point where you physically cannot complete another repetition - triggers optimal protein synthesis and hormone release for muscle growth. The body literally requires failure to adapt and strengthen. Elite athletes deliberately incorporate failure into their training cycles through concepts like ‘periodisation’, where planned phases of intentional overreaching (temporary performance decline) lead to subsequent performance peaks. 

Philosophical Frameworks

To understand why certain pursuits hold value despite guaranteed failure, we need to examine philosophical perspectives that challenge conventional success metrics. 

Friedrich Nietzsche's concept of amor fati ("love of fate") offers a compelling starting point. Rather than just accepting failure, Nietzsche advocated for embracing all aspects of life, including its inevitable defeats. His famous directive to "become who you are" suggests that authentic self-realisation requires facing certain failure rather than avoiding it.

This connects to Simone de Beauvoir's ethics of ambiguity. For Beauvoir, human freedom lies precisely in our ability to pursue meaningful projects while fully acknowledging their inherent uncertainty and potential for failure. She argued that authentic living requires embracing rather than denying this fundamental ambiguity of human existence.

Psychologist James Pennebaker's research on expressive writing reveals something seemingly counterintuitive: people who write about their failures, not just their successes, show improved immune system function and mental health. His studies suggest that engaging with, rather than avoiding, our failures literally makes us healthier. How crazy is that? Contemporary psychologist Tania Luna's work on "surprise literacy" offers a different angle. Her research shows that people who deliberately seek out situations where failure is likely develop greater cognitive flexibility and emotional resilience. It's not about learning from failure, but about developing comfort with uncertainty itself. 

The emerging field of "uncertainty management theory”, pioneered by Dale Brashers, suggests that choosing to engage with guaranteed failure actually helps people develop more sophisticated coping mechanisms than those who only pursue likely successes. Healthcare professionals using this framework help patients manage chronic conditions not by promising cures, but by finding meaning in the management itself. Uncertainty isn’t something to be avoided; it’s likely something to press into. 

Modern Applications

These philosophical frameworks find practical application in various modern contexts. In some far-flung examples in education, for instance, we're seeing a shift away from pure outcome-based assessment toward valuing the learning process itself. Schools like Summerhill in Suffolk have long championed this approach, focusing on developing the whole person rather than just measurable academic outcomes.

The Climate Emergency Response Fund in Bristol finances local climate initiatives knowing that no single project will ‘solve’ climate change. Yet they continue because incremental action, even in the face of overwhelming odds, builds community resilience and inspires wider change. Their support of citizen-led projects, like community renewable energy schemes, demonstrates how accepting partial ‘failure’ can still drive meaningful progress.

In London, 4Day Week Global runs workplace trials where companies experiment with reduced working hours while maintaining full pay. Their October 2023 UK pilot with 61 companies demonstrated that even when the transition wasn't completely successful - with some companies reverting to traditional schedules - the attempt itself generated valuable insights about work culture and productivity. The companies that decided not to maintain the four-day model still reported lasting benefits from questioning traditional work patterns.

The Slow Food movement in the UK exemplifies another approach to worthwhile non-success. These artisanal food producers choose traditional methods despite knowing they can't compete with industrial agriculture's efficiency. They accept lower yields and higher costs because maintaining food heritage and supporting biodiversity matters more than market success. It’s an impressive two finger salute to the conglomerates who insist on speed, uniformity and processed obesogens. And who is the clown?

Psychological research from the University of Cambridge's Well-being Institute reveals something surprising about such chosen challenges. Their longitudinal studies show that people who deliberately engage in ‘impossible’ long-term projects - like habitat restoration or language preservation - report higher levels of life satisfaction than those pursuing easily achievable goals. It's the commitment to the attempt, not the outcome, that predicts wellbeing. The journey nor the destination, as some might say. 

This connects to neuroscientist Eleanor Maguire's research at UCL. Her team's studies of memory and motivation show that our brains process chosen challenges differently from imposed ones. When we consciously choose to pursue something despite likely failure, we activate neural pathways associated with meaning-making rather than just reward-seeking.

The Role of Process vs Outcome

Here's where we need to fundamentally reframe our understanding of success and failure. The traditional view treats process as merely a means to an end. But what if the process itself is the point?

I have been thinking about the UK's parkrun phenomenon. Every Saturday morning, thousands gather in parks across the country to run 5K. Most participants will never win, many won't even improve their times significantly, but they keep showing up. Why? Because the value lies in the participation itself, the community built, the commitment maintained. It’s not about winning; it’s about showing up. In fact, showing up is winning. Not winning is winning!

This shifts us from what philosopher Alasdair MacIntyre calls "external goods" (victories, achievements, rewards) to "internal goods" (character development, skill building, community connection). Internal goods can't be taken away by failure because they're inherent in the activity itself.

“The choice between the ethical and the aesthetic is not the choice between good and evil, it is the choice whether or not to choose in terms of good and evil.” - Alasdair MacIntyre

The Japanese concept of kaizen (continuous improvement) offers a useful framework. It's not about reaching perfection but about engaging in constant refinement. Toyota's manufacturing philosophy embodies this - they know perfection is impossible, but the pursuit of improvement holds inherent value. It’s why we have Kanban boards and Gantt charts after all! 

Practical Implementation

Moving from theory to practice, how do we actually implement this philosophy of worthy pursuit despite guaranteed failure? 

The late philosopher Mary Midgley's concept of "philosophical plumbing" is useful here - examining the underlying structure of our motivations before committing to action. Ask yourself:
- Does this align with my core values?
- Would I admire someone else for attempting this?
- Will I regret not trying more than I'll regret failing?

I also want to reference what philosopher Simon Critchley calls "active nihilism" - the idea that meaning comes not from guaranteed outcomes but from conscious engagement with meaningful pursuits. For instance, the Royal National Lifeboat Institution's volunteer crews embark on rescue missions knowing that not every attempt will succeed. Yet the commitment to try, irrespective of outcome, defines their service.

We probably need a framework for identifying truly worthwhile failures, which I will outline below. 

1. Develop Clear Criteria

Before embarking on any potentially ‘worthy failure’, establish clear criteria for what makes it worthwhile. Ask yourself some questions such as:

• Is it that it serves a purpose beyond your immediate community? 
• Is it that it has long-term financial benefit, which you might not directly see? 
• Is it a small part of a bigger picture?

“A society grows great when old men plant trees in whose shade they shall never sit.” — Greek Proverb

2. Create Support Systems

Knowing that you aren’t alone in failing often helps in building confidence in trying uncertain things. We probably need to ask some more key questions here:

• Who do you need in your corner to help you navigate when things don’t always work out as you’d hope? 
• How do you know you can trust these people with your broken pieces?
• When do you know it’s time to call in the support crew?

3. Document the Journey

The Mass Observation Project, founded in Bolton in 1937, demonstrates the value of documenting ordinary experiences. Similarly, recording our own worthy failures creates meaning beyond outcomes. This might involve keeping reflective journals, creating resources for future attempts or vlogging your learning with others. Again, key questions might include:

• What did we learn at different stages of this process that meant it didn’t work?
• What do we keep, bin and tweak for next time?
• What were the red flags that we missed along the way?

The Role of Community

Individual pursuits of worthy failure don't happen in isolation. Success-oriented societies often drive people toward safer choices, but communities can create spaces where noble failure becomes possible, even celebrated. Local climbing groups exemplify this - experienced climbers actively encourage beginners to attempt routes beyond their current ability, creating an environment where falling (safely) is seen as essential to development. I have seen this firsthand when I worked in a school that built a climbing wall on site - what an opportunity!

The UK's amateur orchestras demonstrate another model. Rather than selecting only the most accomplished musicians, many deliberately include players of varying abilities, taking on challenging pieces knowing the performance won't match professional standards. The focus shifts from perfect execution to collective growth through ambitious attempts.

Often, failing as part of a group where more experienced members can pick you up, support you with how to do it differently next time, yet accept you as your unformed self, is just the tonic for embracing failure even when it’s painful. The polar opposite is also true of course - and that’s why we need to pick our tribe carefully. 

As we face unprecedented global challenges - climate crisis, technological disruption, social inequality - understanding worthy failure becomes increasingly crucial. So my final thoughts here come by way of some more tips and tricks:

1. Identify your non-negotiable pursuits: What matters so much to you that success becomes secondary to the attempt?

2. Reframe failure metrics: Instead of measuring just outcomes, why not track engagement, learning, and alignment with values?

3. Build failure-resilient systems: Create support structures that sustain you through guaranteed failure. What is the worst that can happen if this doesn’t work? 

4. Choose your failures wisely: Not all failures are equal - focus on those that align with your deepest values. What can we afford to get wrong?

5. Create space for others' attempts: Foster environments where worthy failure is respected. Who do you need to encourage to embrace uncertainty?

6. Share your stories: Normalise the pursuit of meaningful failure through open discussion. Who can you inform what went wrong for you?

Returning to Jason Jaggard's provocative question - "What would you still do even if you knew you would fail?" - we can now see it's not really about failure at all. It's about identifying what matters so deeply that success becomes secondary to the attempt. In our success-obsessed culture, this perspective feels almost revolutionary. Yet history's most meaningful endeavours - from the suffragette movement to the ongoing fight against climate change - have been pursued by people who couldn't guarantee success but acted anyway.

As we face increasingly complex global challenges, this capacity to pursue worthy goals despite uncertain outcomes becomes ever more crucial. The question isn't whether we'll fail - in some ways, we will. The question is whether we'll have the courage to pursue what matters anyway.

Perhaps failure, when in service of something truly worthwhile, isn't failure at all. As Samuel Beckett suggested, it's just part of the process of failing better. And in that continuous attempt to fail better, we might just find what it means to truly succeed.