The Imperfectionists

How do you make confident decisions when the future feels impossible to predict? In Strategic Mindsets for Uncertain Times, Robert McLean and Charles Conn argue that the key to thriving in chaos is not to chase certainty, but to embrace imperfection. They introduce the concept of the imperfectionist—someone who acts decisively without needing perfect information, who learns through experimentation, and who continuously adapts in an ever-shifting world.

At its heart, the book suggests that most traditional strategy is fantasy. You cannot plan with precision when technologies, markets, and global systems evolve faster than your five-year forecast. Instead, McLean and Conn call for a new way of strategic thinking, grounded in humility, curiosity, data-driven experimentation, and courage. They blend insights from philosophy, behavioral science, and decades of advising organizations—from Amazon to Patagonia—to explain how leaders can master uncertainty rather than fear it.

The World Has Changed—But Our Thinking Hasn't

The authors open with a sobering truth: uncertainty has exploded. Unlike the slow, predictable changes of the pre-industrial age, today's challenges—from artificial intelligence to pandemics—unfold at dizzying speeds. They cite staggering data: more new knowledge has been created since 2010 than in all prior human history. The lifespan of companies in the S&P 500 has plummeted from 61 years in 1958 to just 18 today. In this environment, traditional strategic planning, with its base-case forecasts and static assumptions, is doomed to fail.

And yet, many organizations still cling to outdated models—either making reckless, overconfident leaps (think Bank of America’s disastrous acquisition of Countrywide Financial) or freezing in risk-averse paralysis (like Blockbuster’s fatal failure to respond to Netflix). Imperfectionism, McLean and Conn argue, rejects both extremes. The sweet spot lies between betting the farm and doing nothing: the space where you experiment intelligently.

The Six Mindsets That Power Imperfectionism

The authors unveil six interconnected mindsets—curiosity, dragonfly eye, occurrent behavior, collective intelligence, imperfectionism itself, and show and tell—as the essential tools for navigating volatility. Each mindset reframes how you approach risk and uncertainty:

• Ever Curious: Ask bold questions that challenge assumptions, like Edwin Land wondering if instant photography was possible after his daughter asked to “see the picture now.”
• Dragonfly Eye: See problems through multiple lenses, combining different perspectives to find hidden opportunities, as Amazon did when widening its view to cloud computing.
• Occurrent Behavior: Experiment relentlessly and rely on real-time data, not outdated reports or unreliable expert opinions.
• Collective Intelligence: Tap into the wisdom of crowds and machines instead of relying solely on in-house expertise.
• Imperfectionism: Make strategic small moves, tolerate ambiguity, and evolve through trial and error instead of waiting for complete certainty.
• Show and Tell: Use storytelling and demonstrations—with evidence, visuals, and emotion—to drive action and convince others of change.

Together, these mindsets form a powerful operating system for uncertain times. They teach you to experiment like a scientist, think like a systems designer, and communicate like a great storyteller—a potent combination for any modern leader.

Why This Matters to You

You can’t predict the future—but you can prepare your thinking for it. Whether you’re a CEO facing technological disruption, a teacher navigating hybrid learning, or a nonprofit leader tackling social crises, imperfectionism invites you to exchange fear for curiosity. McLean and Conn call it “strategy in action”: not planning from the armchair, but testing, learning, and building resilience step by step.

Ultimately, Strategic Mindsets for Uncertain Times is both a toolkit and a mindset shift. It’s about seeing uncertainty as an opportunity for creativity instead of chaos. By blending data with humility, experimentation with empathy, and storytelling with strategy, imperfectionists don’t just survive disruption—they harness it.

Curiosity might seem like a soft skill, but in McLean and Conn’s world, it’s the beating heart of strategic thinking. The first mindset, Ever Curious, is about continuously asking “why,” even when everyone else assumes the answer is obvious. Curiosity doesn’t just generate ideas—it reduces uncertainty by revealing what’s possible.

Curiosity as a Catalyst for Innovation

When Edwin Land’s young daughter asked to see her photograph instantly, she triggered a domino of innovation that led to the Polaroid camera—a multi-million-dollar invention born from a child’s simple question. Similarly, Nobel laureate Barry Marshall’s curiosity about stomach ulcers pushed him to challenge medical orthodoxy by infecting himself with bacteria to prove that ulcers were caused by microbes, not stress. These examples show that curiosity is more than a mental habit—it’s a radical act of questioning what others take as truth.

Today’s organizations often stifle curiosity with bureaucracy. Professor Francesco Gino’s survey of 3,000 employees found that only 24% felt curious at work. McLean and Conn suggest using structural practices to rebuild curiosity, such as dedicating “15% time” for passion projects, as 3M and Google famously do. Google’s innovation culture—where Gmail and AdSense were born from side experiments—illustrates how institutional curiosity drives growth.

The Science Behind Curiosity

Psychologist George Loewenstein describes curiosity as a “drive state,” much like hunger—it arises when there’s a gap between what you know and what you want to know. McLean and Conn highlight research showing that moderate uncertainty sparks the most curiosity. Too much chaos overwhelms; too much certainty bores. The sweet spot lies in the middle—where something is just uncertain enough to intrigue you. This finding is crucial for managing innovation teams: problems should be challenging but not paralyzing.

Creating Environments Where Curiosity Thrives

For curiosity to flourish, two conditions must exist: novelty and safety. Novelty breaks patterns, while safety allows risk-taking without fear. The authors tell the story of Eric Favre, the intrapreneur who invented Nespresso. Given freedom and time by Nestlé, Favre applied his background in rocket science to coffee-making—literally experimenting with air pressure and piston mechanics—until he cracked the “crema” formula that turned coffee pods into a $7 billion industry.

Safety, meanwhile, prevents curiosity from being crushed by hierarchy. McLean and Conn share the idea of “structured curiosity,” pioneered by Professor Robert Wood, where teams anonymously log questions during the week to discuss later without fear of judgment. The message: psychological safety isn’t just a moral choice—it’s an innovation engine.

Curiosity, the authors conclude, is the antidote to paralysis in uncertain times. When you treat each unknown as a question rather than a threat, you shift from needing control to seeking insight. It’s curiosity—not certainty—that keeps leaders resilient when the world won’t sit still.

The second mindset, Dragonfly Eye, teaches you to see problems through multiple lenses. Just as a dragonfly’s compound eye perceives the world in thousands of simultaneous perspectives, great decision-makers learn to look beyond their narrow view—from different disciplines, stakeholders, and even competing industries. This multidimensional vision helps prevent the dangerous myopia that blinds incumbents to disruption.

Anchoring Outside: The Case of the Peterborough Bond

The authors recount Sir Ronald Cohen’s creation of the Social Impact Bond in Britain—a novel financial instrument that tied returns to reductions in prisoner reoffending. Cohen wasn’t a criminologist; he was a venture capitalist. By applying an investment lens to a public problem, he saw what experts missed: social outcomes could be financed through market incentives. His ‘dragonfly gaze’ rewired how governments think about social finance and inspired $1 trillion in sustainability-linked bonds worldwide.

Widening the Aperture

McLean and Conn describe widening your “aperture”—looking broadly before zooming in. They praise Amazon’s leap into cloud computing as a textbook case: originally a retailer, Amazon widened its scope to see the potential of selling its own digital infrastructure. That outside-in view, cultivated through experimentation, gave rise to Amazon Web Services, now a half-trillion-dollar business.

Similarly, Stanford students Kelsey Wirth and Zia Chishti revolutionized orthodontics by looking at dentistry through an outsider lens. Their startup, Invisalign, sprang from noticing how a retainer could subtly move teeth—an insight that traditional orthodontists dismissed. Their lens turned embarrassment into opportunity and birthed a multibillion-dollar category.

Avoiding the Analogy Trap

But changing lenses isn’t just about creativity—it’s also a defense against bias. The authors warn against “analogy traps,” when managers mistake superficial similarities for truths. WeWork, they argue, collapsed because its leaders viewed real estate through the lens of a tech startup, convincing themselves they were a “network company” like Facebook instead of a landlord with leases. When your lens doesn’t match the problem, you magnify risk instead of insight.

By training yourself to alternate between zoom and panorama, inside and outside perspectives, you begin to see what others overlook. Dragonfly vision, as McLean and Conn define it, isn’t about omniscience—it’s about humility: knowing that no single frame contains the whole picture.

The third mindset, Occurrent Behavior, is about seeing reality as it unfolds—not what was planned, predicted, or past. Great problem solvers, the authors argue, rely on fresh experiments and live data rather than static models. It’s the difference between driving with a windshield and staring into your rearview mirror.

Experimentation in Action

McLean and Conn share vivid examples of experimentation as strategy. Two consultants at the Federal Reserve tested whether bundles of cash could be weighed instead of hand-counted. Their experiment revealed that weighing was not only faster, but more accurate—saving millions in labor costs. The key lesson: small tests, big payoffs.

This approach mirrors SpaceX’s iterative philosophy: “fly, test, fail, fix.” By running constant launch experiments, Elon Musk’s team drastically reduced the cost of putting payloads into orbit—by over 90% compared to NASA’s historical costs. Similarly, platforms like Airtasker used A/B testing to fine-tune booking fees, learning in real time what customers would—or wouldn’t—pay.

Thinking Like a Bayesian

Behind these stories lies Bayesian logic. Derived from the 18th-century statistician Thomas Bayes, Bayesian thinking involves updating beliefs continuously based on new data. For instance, in policy-making, comparing Sweden and Norway’s contrasting COVID-19 responses acted as a real-world “natural experiment,” revealing the perils and payoffs of differing strategies. Bayesian reasoning helps leaders adapt to emerging evidence instead of clinging to outdated assumptions.

When to Stop Experimenting

Still, you can experiment too much. McLean and Conn caution against “pilot purgatory,” where endless trials replace real decisions—a trap that plagues IoT companies and startups alike. The goal isn’t perpetual testing but learning-driven execution. Once data shows a clear signal, move fast.

Occurrent behavior is essentially curiosity in action—turning questions into evidence. By measuring what’s happening now, not what used to be true, you stay grounded in reality—a crucial survival trait when the world keeps rewriting the rules.

If Occurrent Behavior is about generating new data, the fourth mindset—Collective Intelligence—is about harnessing more minds to interpret it. In a world where no one can know everything, McLean and Conn emphasize the value of collaboration beyond the corporate walls. The smartest solutions often come from crowds, not committees.

From Singular Experts to Global Networks

The authors revisit Bill Joy’s famous law: “No matter who you are, most of the smartest people work for someone else.” Sun Microsystems’ co-founder was right—modern innovation thrives on openness. The Nature Conservancy’s FishFace project, for instance, used a Kaggle competition to crowdsource algorithms that identify fish species from photos. Thousands of global data scientists contributed, producing a machine-learning system now helping preserve Pacific tuna stocks. One organization’s problem became the world’s puzzle.

Open Source and AI Partnerships

Collaborative intelligence doesn’t stop with crowds—it includes machines. Open-source frameworks like Unix and Apache have allowed small players to stand on the shoulders of giants. Software firms like Zetaris combine public algorithms with proprietary tweaks to outperform far larger competitors. Even Microsoft, once hostile to open source, now leads the GitHub ecosystem of over 70 million developers—a testament to how collective code outpaces closed genius.

Ancestral and AI-Enabled Wisdom

McLean and Conn stretch “collective” to include ancestral knowledge and hybrid human–machine learning. In northern Australia, Indigenous rangers revive “right way fire” techniques—early dry-season burning that curbs destructive wildfires. Paired with modern satellite analytics, this blend of ancient and digital intelligence reduces emissions and regenerates ecosystems. Conversely, platforms like TikTok illustrate AI-enabled collective intelligence gone viral—algorithms amplifying the crowd’s creativity faster than any expert curation could match.

The authors encourage leaders to “have more people toiling in your garden,” meaning to design systems—competitions, partnerships, open platforms—that invite outsiders to contribute. The future of problem solving, they argue, is less about genius lone wolves and more about orchestrating networks of curiosity.

Imperfectionism—the book’s namesake mindset—is the art of acting with incomplete information. It’s the antidote to both reckless risk-taking and paralyzing caution. Imperfectionists understand that in uncertain environments, the cost of waiting for certainty is far higher than the cost of small, reversible experiments.

Learning from Mistakes and Odds

To illustrate, McLean and Conn contrast Rio Tinto’s disastrous 2007 “bet the company” aluminum acquisition with Amazon’s smaller, learning-driven approach to financial services. Jeff Bezos’s team made low-cost moves—buying startups like TextPayMe, testing Amazon Web Pay, and hiring fintech talent. Many of those ventures failed, but each failure was inexpensive tuition that built capabilities for Amazon Pay’s later success. The message: progress depends on stepping into risk with humility and feedback loops.

Resisting the Risk Aversion Tax

Behavioral economist Dan Lovallo’s research, cited by the authors, calls excessive caution the “risk aversion tax”—the invisible cost of opportunities not taken. In their experiments, managers routinely demanded higher chances of success than math justified, effectively forfeiting 30–50% of potential value each year. Organizations can fight this paralysis by separating reversible decisions (“two-way doors”) from irreversible bets and empowering frontline teams to move fast on the former.

Stepping Stones to Growth

The authors’ model of the “growth staircase” visualizes how small bets compound into major advances. Each step adds knowledge, assets, or partnerships that prepare you for bigger moves. The Commonwealth Scientific and Industrial Research Organization (CSIRO) exemplified this by methodically defending its Wi-Fi patent—starting with one modest lawsuit, building legal precedent, and scaling to billion-dollar settlements. Imperfectionists don’t sprint—they climb steadily, learning with each foothold.

To be an imperfectionist is to balance courage with calibration. You don’t need to know everything—you just need to know enough to begin. In a chaotic world, the imperfect move made today outperforms the perfect plan made too late.

The final mindset—Show and Tell—brings problem solving to life. McLean and Conn argue that even the best data fails to inspire without compelling storytelling. To lead through uncertainty, you must communicate visually, emotionally, and ethically—connecting logic to human values.

Stories that Stick

The authors open with the daring self-experiment of Barry Marshall, who drank bacteria to prove his ulcer theory—an unforgettable story that overturned medical convention and won a Nobel Prize. Great communicators, they argue, do more than present facts; they demonstrate truth vividly. Florence Nightingale’s rose charts on army deaths in the Crimean War transformed statistics into moral urgency, leading to a national health reform. Richard Feynman’s iced glass demonstration before NASA’s Challenger Commission made cold physics visceral and changed how space risk was managed.

Seeing Is Believing

Show-and-tell techniques rely on props, visuals, and concise narratives. When The Nature Conservancy sought funding for marine reef restoration, its team placed 17 empty buckets before bankers to symbolize the 170 liters of water an oyster cleans daily. The unusual visual startled, delighted, and persuaded the audience—winning the grant. McLean and Conn note that surprise and novelty reignite curiosity, cutting through “PowerPoint fatigue.”

Speaking to Values and Frames

Citing cognitive linguist George Lakoff and psychologist Jonathan Haidt, the authors stress that facts alone rarely shift minds—values do. Climate communicator Katharine Hayhoe exemplifies this by connecting science to shared moral frames, like parents’ concern for their children’s future. To influence change, leaders must frame ideas within what their audience already cares about rather than preaching dissenting facts.

Show and Tell turns strategy into movement. It’s the culmination of all the mindsets: curiosity sparks questions, experimentation yields insights, and storytelling spreads belief. In an age crowded with noise, clarity with humanity is the rarest strategic advantage of all.

In their epilogue, McLean and Conn offer a humbling conclusion: no matter how data-driven or disciplined you are, every strategy is still a wager. They draw on Blaise Pascal’s famous philosophical “wager” to illustrate that decisions under uncertainty are unavoidable—and the cost of not betting can be as high as betting wrong.

Understanding the Game

The authors reinterpret Pascal’s matrix as strategic thinking: if you act and win, the payoff is large; if you act and lose, you learn; if you do nothing, you guarantee stagnation. The challenge is to understand your “game structure”: who the players are, how reversible decisions are, and what learning opportunities exist between plays. Amazon, for instance, separates one-way-door decisions (irreversible investments) from two-way-door experiments (reversible trials)—ensuring agility without recklessness.

Weighing Stakes and Estimating Odds

Every decision carries stakes—both for doing something and for doing nothing. McLean and Conn urge leaders to quantify both “Type 1 errors” (mistakes of commission) and “Type 2 errors” (missed opportunities). Risk, they note, can often be priced—like Wimbledon’s 17-year pandemic insurance, which paid off spectacularly when COVID-19 canceled play. The secret isn’t avoiding bets; it’s structuring them with asymmetric payoffs: limited downside, unlimited upside, and built-in learning.

Epistemic Humility

Above all, imperfectionists cultivate what economists call epistemic humility—the awareness that your knowledge is always incomplete. Former U.S. President Barack Obama described governing as “constantly dealing with probabilities,” rarely above 70%. There are no perfect moves, only adaptive ones. McLean and Conn argue that by viewing every strategy as an informed bet—guided by curiosity, experimentation, and reflection—you turn uncertainty into a field for disciplined learning rather than fear.

The final message is simple but profound: you can’t eliminate uncertainty, but you can learn to play it well. Strategy, like poker or life, rewards those who act boldly, learn humbly, and iterate faster than the rest.