The Hardest Part of Any Job
On the fine art of not knowing what the hell to do
The sky from the Alexandra Battery bunker. Sandy Bay, Tasmania. September 2024.
At some point in any job dealing with real-world problems - policy, frontline services, leadership - you’ll slam headfirst into a wall. Not because you’re incompetent. Not because you lack vision. But because there is no right answer.
That’s not hyperbole. That’s what happens when you work on wicked problems. Drug and alcohol use. Mental illness. Intergenerational poverty. The kind of messes that don’t come with neat solutions: just trade-offs, collateral damage and time bombs waiting to go off.
Yet, despite knowing this, we still act like certainty is possible.
One of the hardest fights I’ve ever had in public policy was over substance use and mental health services. We had a model: yes it was messy, imperfect, but real. It let people make choices about their own lives. It upheld the dignity of risk. It wasn’t a utopia. People relapsed. Many continued to make terrible decisions. Some died.
But in between all that? Tiny victories. Self-determination. A sliver of autonomy for people who had spent their lives being told they had none.
Then, the higher-ups arrived. The ones who love a clean, linear solution. The ones who wanted something that looked good in a report. Something neat. A model that removed risk entirely.
And that’s when I had to say it: Certainty is a myth.
You can’t engineer recovery in a straight line. You can’t legislate people into neat, measurable outcomes. You can’t create a world where humans make perfect, rational choices.
But systems don’t want to hear that. Because systems hate ambiguity.
Ambiguity means mess. And mess? Mess gets people blamed.
The Emotional Cost of Ambiguity
Ambiguity in decision-making isn’t just a policy problem. It’s a human problem.
It doesn’t just live in reports and strategy documents; it lives in your chest. In that slow, creeping dread of not knowing what the hell to do next.
It feels like paralysis, knowing you have to make a call, knowing you’ll get ripped apart no matter what you choose.
It feels like frustration, trapped in an endless loop of if we just had more data, more resources, more time…
It feels like the urge to bullshit, faking confidence so no one realises you’re winging it.
It comes with the sinking realisation that no one - not you, not your boss, not the so-called experts - has a clear answer.
Yet, systems too often pretend otherwise. They demand certainty in situations where certainty does not exist. They want risk-free decisions in problems where risk is the entire point.
How People Fake Certainty (And Why It’s a Problem)
Ambiguity is a deeply unsettling thing. It makes people squirm, stall, panic, and, in extreme cases, send calendar invites. The human brain will do almost anything to avoid sitting with the discomfort of uncertainty, so when faced with the horror of a decision that has no clear answer, people don’t confront it; they contort around it.
Here’s how:
Option 1: Double Down on the Past
If a program didn’t work, but it’s been funded before, guess what? It’ll get funded again. Because the safest move isn’t fixing the problem, it’s repeating failure with confidence.
It doesn’t matter that the initiative produced no meaningful results. What matters is that it’s a known quantity. There’s a paper trail, historical precedent, an entire filing cabinet of past approvals to hide behind. A terrible but familiar failure is always preferable to an untested solution, because if a new idea flops, someone has to take responsibility.
So, instead of funding a new, innovative pilot that might actually work, the system says:
"Hey, let’s roll out the same broken model from five years ago. Maybe this time it’ll magically do what it never did before."
It’s the policy equivalent of banging your head against the wall and waiting for the bricks to collapse out of sympathy.
Option 2: Turn Meetings into Infinity Loops
Ah, the bureaucratic Groundhog Day. A single, difficult decision gets stretched, blurred, and diluted across committees, subcommittees, stakeholder engagement sessions, and “consultation workshops” until the actual choice dissolves into a fog of action items and follow-ups.
Nobody wants to be the one to put their name to a risky decision, so instead of just choosing a direction, they create a perpetual motion machine of professional dithering.
First, you need a preliminary discussion.
Then, an alignment workshop to clarify the key takeaways from the preliminary discussion.
Then, a working group to explore emerging themes from the alignment workshop.
Then, an advisory panel to assess the initial outcomes of the working group.
Then, an executive briefing to synthesise insights from the advisory panel.
Finally, an urgent meeting to determine the next steps.
At no point does a single, definitive decision get made, but by the end of it, everyone feels very busy.
This is the corporate art of looking productive while doing absolutely nothing.
Option 3: Hot Potato
Ambiguity feels like a live grenade, and nobody wants to be holding it when it goes off. So, when an unclear decision lands on someone’s desk, the first instinct is to get rid of it as fast as possible.
This can be done through a range of classic bureaucratic maneuvers:
Escalate it. ("This needs to be signed off by an executive panel.")
Defer it. ("We should wait for more data before moving forward.")
Reassign it. ("This actually falls under another team’s remit.")
Wrap it in ‘strategic oversight’. ("We need a task force to evaluate next steps.")
The end result? Nobody actually decides anything.
If you ever wonder why some of the biggest problems in policy, business, and services seem permanently stuck in limbo, this is why. The moment ambiguity enters the equation, it begins an epic odyssey of being shuffled from one department to another, with each new recipient applying a fresh layer of delay tactics.
If done correctly, the original issue will eventually age out of relevance, meaning nobody ever has to make a call at all.
Option 4: Performative Certainty
You’ve seen it before. A senior leader stands at the front of a boardroom, delivering a PowerPoint slide deck filled with carefully curated nonsense, reassuring everyone that things are under control, even when they very much are not.
This is where ambiguity aversion goes fully theatrical: the art of disguising complete uncertainty with a thick coat of corporate jargon.
Watch in awe as they transform raw confusion into polished, professional-sounding declarations:
Reality: We have no idea what’s happening.
Presentation Slide: We are currently assessing multiple strategic pathways to optimise outcomes.
Reality: There is no plan, and leadership is stalling for time.
Statement to Staff: We are leveraging data-driven insights to ensure an agile, cross-functional approach to our evolving priorities.
Reality: This problem is unsolvable, but we need to sound proactive.
Media Release: We remain committed to ongoing stakeholder engagement as we explore sustainable, long-term solutions for future challenges.
Nobody leaves these meetings more informed, but they might leave feeling strangely reassured, because the leader delivered the ambiguity with confidence.
Why This Matters
The problem isn’t just that uncertainty makes people squirm. It’s that the fear of ambiguity keeps broken systems running. It kills innovation because safe choices feel better than risky, necessary ones. It reinforces bad policy because familiar failure is more palatable than an uncertain solution. It punishes honesty because admitting “we don’t know yet” is treated as incompetence instead of integrity.
Here’s the real headache: the people who need ambiguity the most - the ones who need us to sit in that discomfort and work through it - are the ones who suffer when we refuse to. Because real change means risk. And risk means sometimes getting it wrong before you get it right. Most people would rather do almost anything else.
But the ones who don’t? They’re the ones who actually fix things.
The people who struggle most with ambiguity are the ones paid to pretend they don’t. Leaders, policymakers at a distance from reality, executives; their entire professional existence depends on projecting confidence in situations where confidence is, at best, a bold miscalculation. Their authority hinges on the illusion that they have a plan, understand the landscape, and are absolutely not making it up as they go along.
At the top, admitting uncertainty is professional suicide. The expectation is simple: radiate confidence, have a strategy, steer the ship; even when the compass is spinning, the hull is taking on water, and half the crew is below deck Googling “how to fix a sinking ship.” Leadership isn’t about knowing what you’re doing; it’s about convincing everyone else that you do. Preferably with a well-timed statement about “navigating evolving complexities.”
Many policymakers don’t just struggle with ambiguity; they deny its existence outright. The fields they work in, whether social policy, public health or economic reform, are complex, unpredictable and deeply resistant to quick fixes. But quick fixes are exactly what politicians demand and voters expect.
So, ambiguity is quietly replaced with a neat, artificial certainty that looks good in a press release but collapses upon contact with reality. This is why bold, necessary interventions get scrapped in favour of shiny, palatable half-measures; because a failure that looks like progress is preferable to a solution that takes time.
Middle managers are not leaders in the formal sense of the word. They do not make decisions. What they do is absorb the fallout from bad decisions made elsewhere while pretending the strategy they’ve been handed isn’t completely detached from reality. Their job is to execute, not to question, not to push back, just to translate vague executive mandates into something that won’t immediately spark a workplace mutiny.
They don’t control the fire. But they sure as hell are expected to pretend it’s manageable.
For frontline workers, ambiguity isn’t an intellectual dilemma; that’s just Tuesday. They are given policies designed in boardrooms by people who have never set foot in their workplace, then expected to apply rigid frameworks to unpredictable, human situations.
Unlike leadership, they don’t have the luxury of faking certainty. They deal with actual people, real crises, and consequences that aren’t theoretical. Their job is to make broken systems work, all while being scolded for “non-compliant service delivery.”
Thriving in Ambiguity
There are people, MY people - strange, mythical creatures - who don’t just tolerate ambiguity but actively enjoy it. They move through uncertainty with an ease that suggests either deep resilience or mild neurological dysfunction. They aren’t necessarily the loudest in the room (those are usually the ones having a breakdown in real time), nor do they always hold formal leadership positions. Yet they’ve developed a rare ability: navigating chaos without curling into the foetal position.
Frontline Workers: Feral Adaptability in Action
Once sufficiently traumatised by years of bureaucratic absurdity, frontline workers develop a feral adaptability. Unlike those in boardrooms who attempt to impose order on the inherently uncontrollable, frontline workers don’t waste time demanding clean solutions because they know there aren’t any.
Instead, they MacGyver their way through shifting disasters, focusing on what works right now, what might work next, and what will at least stop the bleeding until someone with a clipboard inevitably arrives to tell them they’re doing it wrong.
Researchers and Problem-Solvers: Chaos is the Method
Then there are the researchers and problem-solvers, the ones who understand that progress is not a straight line but more of a drunken stumble through failure, contradiction, and occasional bursts of insight.
These are the people who don’t panic when data refuses to cooperate or when a plan collapses under the weight of reality. Instead, they take perverse joy in asking better questions. They don’t see ambiguity as an obstacle to progress; they understand that ambiguity is progress.
They also know that while everyone claims to want evidence-based decisions, most people just want a number that confirms what they already believe.
Innovators: The Ones Who Make Everyone Else Uncomfortable
Then we have the innovators, the entrepreneurs, the disruptors, otherwise known as the people who make everyone else deeply uncomfortable.
These rare individuals look at uncertainty and see opportunity rather than an unavoidable prelude to bankruptcy and regret. They are willing to take unhinged leaps of faith with no safety net, knowing that even spectacular failure is still useful data.
What sets them apart isn’t just their willingness to take risks but their fundamental refusal to worship the false god of certainty.
The Real Divide: Certainty Worshippers vs. Builders and the Leadership Paradox
Because that’s the real divide, not between smart and dumb, not between competent and incompetent, but between those who understand that certainty is a fairy tale and those still waiting for a happily-ever-after that isn’t coming.
The ones who build, change, create, and actually lead aren’t the ones desperately trying to force ambiguity into a spreadsheet. They’re the ones who sit in the discomfort, embrace the unknown, and get on with it.
The great irony of leadership - aside from the fact that many people in charge should never have been trusted with a microwave, let alone a multi-million-dollar budget - is that the ones most responsible for managing uncertainty are often the ones most allergic to it.
The higher up you go, the more you’re expected to project unwavering confidence, even as the problems become exponentially more complex, unpredictable, and catastrophically unmanageable. Leadership is essentially a game of pretending you know what’s going on while secretly hoping no one asks follow-up questions.
This sets up a spectacular contradiction: leaders are expected to steer through chaos while pretending chaos isn’t real. They have to project absolute confidence while secretly calculating how long they can stall before everything goes to hell.
They make decisions that could burn through millions, torpedo careers, or accidentally trigger a minor diplomatic incident, all while knowing that if it blows up, their name will be the one stapled to the wreckage. The tolerance for hesitation? Nonexistent. The expectation of control? Total. In this environment, looking like you know what you’re doing matters infinitely more than actually knowing.
One of the crueller realities of leadership is accountability without control. A leader is often blamed for the failure of a policy that required six different departments to magically cooperate. They’re held responsible for a strategy that was doomed from the moment it met budget cuts, stakeholder resistance, or plain old incompetence.
When things go well, success is communal, shared across teams, departments, and carefully worded PR statements. When things go badly, failure is personal, and someone’s name will be attached to it with a bullet point in an executive summary.
This is why so many leaders default to the safest, least controversial option, not because it’s the best one but because it’s the easiest to defend when the pitchforks come out.
The result? Problem-solving is subsumed by risk management. The goal isn’t to fix things; it’s to avoid blame. Institutions grind to a halt because trying something new means owning the fallout if it fails. Decisions aren’t made based on what works, but on what can be justified when it doesn’t.
And yet, effective leaders who actually move things forward refuse to play along. They don’t pretend ambiguity isn’t real; they use it.
They make decisions based on learning, iteration, and adaptation rather than rigid, consultant-approved delusions of certainty. They know that most of the best ideas start as a confusing mess, that real solutions don’t emerge fully formed, and that nothing worth doing comes with a neat 18-month rollout plan.
The paradox of leadership will never disappear. The demand for certainty will always exist, even when certainty doesn’t. But the ones who actually make an impact? They’re the ones who stop pretending.
Leadership was never about eliminating uncertainty. It was always about figuring out how to function in a world where certainty never existed to begin with.
The Cowardice of Certainty
Ambiguity aversion isn’t just an annoying psychological quirk, like avoiding eye contact with your barista because you forgot their name. It’s one of the great engines of systemic failure. The pathological preference for the known, even when the known is demonstrably useless, harmful, or decades past its expiry date, is why:
Governments keep funding the same broken programs
Organisations cling to rituals that make everyone miserable
People stay in jobs, relationships, and rental agreements that actively erode their will to live
The refusal to engage with uncertainty doesn’t actually reduce risk. It just replaces it with the slow, predictable failure of inaction, the kind that’s easier to defend in an annual report.
In policymaking, ambiguity aversion presents itself as the relentless pursuit of certainty in a world that does not provide it. If a promising new approach lacks a 20-year dataset or the right ideological branding, it is immediately discarded in favour of whatever we were already doing, even if it’s clearly failing.
This isn’t just an institutional problem. It’s a deeply personal one. People stay in jobs they hate, relationships they’ve outgrown and cities that drain them, not because they’re happy, but because at least they know what kind of suffering to expect. The human brain, in its infinite wisdom, fears uncertainty more than pain, which is why so many people choose familiar misery over uncertain possibility.
The question “Will this decision make my life better?” is, in practice, far less important than “Will this decision introduce new, unpredictable problems I can’t yet visualise?”
It’s a clever trick of the mind, convincing yourself that your stagnation is actually a rational, considered decision rather than what it really is: passive inertia disguised as caution.
Like people, systems that refuse to take risks don’t stay just the same; they deteriorate, becoming more disconnected from reality with each passing year. Individuals who refuse to embrace uncertainty don’t avoid hardship; they just resign themselves to a slow, numbing version of it.
This is how you get institutions that do not work, leaders who do not lead, and people who wake up one day and realise they have spent a decade waiting for something to change that was never going to happen.
How to Stop Letting Ambiguity Aversion Ruin Your Life (and the World With It)
If ambiguity aversion is what keeps bad systems running, broken policies funded and people stuck in cycles of hesitation and regret, then breaking free from it isn’t just a personal challenge; it’s a survival skill. The instinct to cling to the known, even when it’s failing, is deeply ingrained. But it’s also completely optional.
Step One: Recognise When You’re Bullshitting Yourself
People love to tell themselves they’re waiting for more information, for better timing, for some grand sign from the universe. But in most cases, this is just procrastination in a trench coat.
Ask yourself: Am I avoiding this because it’s actually a bad idea or because I don’t know exactly how it will turn out?
If someone told you a job you’re considering has a 60 per cent chance of being better than your current one, would you take it? If yes, then the only thing stopping you is the discomfort of not knowing, which, frankly, is a ridiculous reason to stay miserable.
Step Two: Reframe Uncertainty as Potential, Not Danger
Left to its own devices, the human brain defaults to treating unknown outcomes as risks rather than opportunities. This is why people obsess over what could go wrong, even when the unknown actually has a higher probability of success.
The only way to fight this? Force yourself to consider the best-case scenario. Your brain will happily loop worst-case simulations all day long, but you have to actively interrupt the cycle. If your default reaction to uncertainty is panic, at least make sure it’s competing with possibility.
Step Three: Abandon the Myth That Certainty Equals Success
The best leaders, problem-solvers, and generally functional human beings do not wait for perfect clarity before making decisions. They make educated, strategic bets, knowing that some will fail, but the ones that succeed will actually move the needle.
In policymaking, this means testing new models even when the data isn’t perfect. In frontline work, it means prioritising human needs over bureaucratic rigidity. In personal decisions, it means understanding that a life spent avoiding risk is often just a life spent avoiding growth.
Step Four: Accept That Discomfort Is Not a Stop Sign
The people who thrive in uncertain environments aren’t fearless. They’re just used to acting despite uncertainty. They’ve learned that waiting for clarity often means waiting forever. And they understand that the unknown isn’t something to be feared; it’s where every real opportunity begins.
Get Comfortable Being Uncomfortable
The most transformative decisions - whether in policy, business or that particularly ill-advised text you’re about to send at two in the morning - are made without guarantees. The people who actually shape the world aren’t the ones with all the right answers; they’re the ones who move forward while everyone else is still refreshing the data.
Ambiguity aversion is an evolutionary relic, a safety mechanism from a time when the unknown often contained large, carnivorous animals. But modern life has changed. The greatest threat is no longer a tiger in the grass but the slow, soul-crushing inertia of playing it safe.
Clarity doesn’t come before action; it comes after it. Yet, because the human brain is an exceptionally cautious idiot, we continue to act as if waiting long enough will make the unknown kindly present itself with footnotes and a detailed risk assessment. It won’t.
This isn’t an argument for recklessness. It’s not an excuse to hurl yourself blindly into bad decisions with the enthusiasm of a man investing his life savings in crypto eight beers in. But it is a reminder that certainty is a scam, a feel-good illusion peddled by consultants, self-help authors and anyone else profiting from your existential paralysis.
The pursuit of certainty does not lead to wisdom or safety. It leads to hesitation, stagnation, and the slow, bureaucratic rot of never trying anything new.
If you wait for perfect conditions, perfect timing and perfect data, you will be waiting forever. The people who build things, change things, disrupt things - the ones who drag the world forward, often kicking and screaming - are the ones who are comfortable being uncomfortable.
They understand that the unknown isn’t the enemy. It’s the only place where anything new actually happens.
So, next time you find yourself hesitating, ask: Is the risk real or just unfamiliar? If it’s the latter, step forward anyway. Because everything worth doing starts with not knowing how it will turn out.