The Strategist's Shame

An essay from The Work series

Introduction to the Series

When I published The Work, I knew it wasn't going to be an easy read. It wasn't designed for skimming on LinkedIn or half-reading between Zoom calls. It’s long, dense, layered - which means it’s supposed to be sat with, argued with, digested. I knew that would put some people off.

And it did. Some loved it, some told me it landed like a punch in the gut, some never got past page ten. That's fine. It wasn't meant to be universally popular. It was meant to be honest.

But I also realised something: for those who did read it, it opened up conversations. And for those who didn't, it left a gap. The Work was never supposed to be a takedown. It’s constructive - sometimes painfully so. It was an act of love for strategy, because I care about this practice and I want it to be better.

The report did what it was designed to do: map the breakdown and sketch the breakthrough. But maps aren't the same as territory. And some truths need to be told as stories, not systems.

So this series is my way of carrying The Work forward, but differently. Not summaries. Not bite-sized versions for busy strategists who want the insights without the discomfort. Think of these as entry points that are more personal, more narrative, more willing to sit in the messiness before rushing toward solutions.

Each essay cuts into the same body of thought from a different angle. Where The Work was comprehensive, these pieces are specific. Where the report was systematic, these are more lived experience.

This is the first entry. And it begins where it has to begin, with shame.

The Strategist's Shame

I'm sitting in a glass conference room on a fairly non-descript building in Victoria, watching twenty-three Post-it notes get arranged into something that will supposedly unlock human behaviour. The client - a woman in her forties with the particular alertness of someone who's been in too many meetings like this - leans forward as our pontificating CSO points to a cluster of yellow squares and announces that we've identified "the key cultural tension."

The tension, apparently, is that parents feel guilty about their kids' nutrition. The yogurt brand we're all working for, it seems, can heal this wound - for a price. Revolutionary stuff.

I watch faces around the table light up with that specific brand of professional satisfaction that comes from watching complexity get tamed into a neat little framework. The account director nods with the authority of someone who's about to invoice six figures for this insight. The creative director looks relieved - now he has something to sell up the line. The client pulls out her phone to take a photo of our Post-it masterpiece.

And I'm sitting there thinking: what the fuck are we actually doing?

This is Droga5. One of the most celebrated agencies in the world. The room is full of genuinely smart people. The brief is from a brand that millions of people interact with daily. The research behind those Post-its represents weeks of cultural analysis, consumer interviews, and trend synthesis. On paper, this should feel important.

Instead, it feels like an elaborate game of professional make-believe. We're performing insight. Choreographing intelligence. Acting out the ritual of strategic thinking while somehow avoiding the actual work of strategic thought.

I've always felt like this, that uncomfortable nagging voice in the back of my mind saying, “is this just performance art?” Because that's how it feels - not just in pitch (though we call it pitch theatre for a reason), but in every context. The creative check-ins where we perform strategic rationale. The brand planning sessions where we perform cultural insight. The quarterly reviews where we perform progress. It's all theatre, every moment of it.

The Post-its come down. The client says she's "excited to see where this takes us." We schedule a follow-up. Everyone shakes hands with the particular vigour of people who believe they've accomplished something meaningful. I pack up my laptop and walk out into the London afternoon, carrying the quiet weight of complicity.

This is the strategist's shame: the knowledge that you're very good at performing intelligence, and increasingly unsure whether you're actually practicing it.

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The shame started early. Maybe it was always there, waiting for the right conditions to surface, like a bruise that only shows up in certain light.

I've worked at some of the best creative consultancies in the world, and I've felt this at each and every one of them. A constant nagging whisper - what are we actually doing here? What are we producing that matters and that has any meaning? I think that's why I've always felt like an outsider in this industry, staring at the emperor's new clothes while everyone else nodded along, applauding the fabric choice.

For one particular brief, I spent three months researching why teenage girls drop out of sports. Three months. I interviewed girls across the United States about their relationships with coaches, their confusion about their changing bodies, their anxiety about performance and belonging. I mapped the cultural forces that make them turn inward - from social media comparison to the particular loneliness of feeling misunderstood by male coaches who meant well but couldn't bridge the gap. My heart broke listening to these girls describe how sports, which should have been a source of strength and community, had become another place where they felt isolated and inadequate.

It was fascinating work. Genuinely illuminating. The kind of cultural investigation that could inform policy, therapy, education, real interventions in real problems.

Instead, it became thirty-seven slides about "empowering the next generation of female athletes" and a campaign about "finding your inner champion." Months of genuine cultural analysis about isolation, body shame, and the failure of adult institutions to understand teenage girls - reduced to advertising copy that would run for six weeks and be forgotten.

The cognitive dissonance was crushing. Not because advertising can't be meaningful, it absolutely can. But because the entire apparatus seemed designed to take genuine insight and flatten it into vacuous commercial messaging. The research was never meant to deepen understanding; it was meant to decorate a predetermined creative strategy.

Maybe I should have just kept quiet, because this was my livelihood, my career. I should have been grateful, sucked it up, kept my head down. And yet it all just felt so ridiculous and superficial.

The economic pressure made it worse. There’s a particular kind of self-betrayal that comes from trying to maintain intellectual integrity when your mortgage depends on performing strategic insight whether you believe in it or not.

So you develop a split self. The professional you that gets excited about consumer insights and brand territories and cultural tensions. And the private you that knows most of it is elaborate busywork. You learn to code-switch between true curiosity and strategic performance, until you're no longer sure which one is real.

And God, I always felt like such a fraud doing all of that research, all of that quasi-intellectual can-can dancing and jazz hands and diving deep into philosophy, economics, and overthinking and over-reading and over-intellectualising, only to package all of that up into a proposition for how to sell soap, or a microwavable burger, or how to shame young girls into buying more deodorant by dressing it up as self expression and empowerment.

All the moves of serious intellectual work, but instead of building toward understanding or intervention, it all got packaged into brand strategies that leverage yoghurt to capitalise on parental guilt.

Isn't that crazy, when you think about it? All that analytical sophistication, all that cultural research, all that deep digging into human behaviour - deployed not to answer the complex questions it could actually illuminate, but to justify conclusions that were predetermined and decorate decisions that were already made.

And that's why I always felt like such an imposter - because I was doing all this rigorous work on a fundamentally dishonest premise - being pushed to perform as an intellectual entertainer, whilst being quietly discouraged from doing the actual work of strategic thinking.

The most shameful part wasn't the waste of intellectual capacity, though that stung. It was the recognition that everyone in the room knew exactly what was happening, and we'd all agreed to pretend otherwise. The client knew they weren't buying genuine strategic intelligence; they were buying the performance of it. The creative director knew the "insight" was reverse-engineered from the brief. The account team knew the cultural tension was invented to justify work that was already sold.

But we all played our parts, we all nodded along, we all pretended that this was something, but I'm not sure it ever really was.

We'd become complicit in our own analytical diminishment. Smart people agreeing to think less rigorously in exchange for steady income and professional advancement. The shame wasn't just personal, it was collective. An entire industry of brilliant minds voluntarily participating in the systematic trivialisation of critical thinking, cultural analysis, the capacity to sit with complexity, the willingness to challenge assumptions.

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But what makes it particularly insidious is that the machinery of performance is genuinely sophisticated. This isn’t amateur hour. The strategic frameworks we use, the workshop methodologies, the presentation formats - they are all elegantly designed to create the impression of rigorous thinking.

Every agency has its own flavour of the same fundamental performance. "Disruption ladders" and "cultural codes”, "human truths" and "ownable territories." Different vocabulary, same underlying choreography: take complexity, run it through a framework, emerge with clarity that feels both inevitable and proprietary.

The workshops were particularly theatrical. Twenty people in a room covered with small neon-coloured rectangles stuck to the walls, everyone deeply focused on the serious business of insight generation. The strategist at the front, facilitating with the practiced authority that comes from having done this exact workshop twenty-seven times before. The client, taking photos because this feels like Important Work Happening.

I remember one session where we spent four hours mapping "emotional territories" for a financial services brand. Four hours. We identified that people feel anxious about money (groundbreaking), that they want security but also growth (paradoxical!), and that they trust institutions that feel human (who knew?!). By the end, we had a beautiful diagram showing the "tension between security and aspiration" with our brand positioned as the "confident guide."

The client was thrilled. Finally, someone understood their customers' deep psychological drivers. The creative team was energised - now they had emotional permission to make the work more interesting. The account director could see the path to a long-term retainer. Everyone’s a winner.

And I walked out of that room knowing we'd just spent four hours discovering things that any competent adult already understood about people and money, then packaged those obvious truths into language sophisticated enough to justify our insane fees.

This is the heart of strategic performance: taking common sense and making it sound like specialised knowledge. Using the language of insight to describe the obvious. Creating frameworks complex enough to seem valuable, but simple enough to be easily consumed by clients who don't have time to think deeply about anything.

The "strategic pyramid" with its hierarchy of truths. The "tension ladder" that transforms everyday contradictions into ownable positioning territories. The "cultural cartography" that turn basic human needs into proprietary insights. All of it designed to create the illusion that complexity has been mastered, that something fundamental has been decoded, that the strategic challenge has been solved.

And this performance seduces everyone involved, including the performers. The client leaves feeling smarter, more confident about their brand strategy. The creative team feels like they have a solid foundation for their ideas. And the strategist - especially the strategist - gets caught up in the showmanship of their own expertise.

Because it does feel good to be the person who can take a mess and make it clean. To transform confusion into a path forward. To walk into a room full of uncertainty and emerge with a framework that makes everyone feel like they understand what the fuck is happening.

The performance works because everyone needs it to work. So we all conspire to maintain the illusion. Until one day, you're sitting in that conference room and something inside you breaks just enough to let the truth leak in: this is a farce. This is all absurd. Maybe even grotesque. And we're all pretending it's not.

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But how did we get here? How did strategy - once the art of navigating life-and-death decisions - become this elaborate performance of professional insight?

The story starts with Sun Tzu, writing about deception and terrain in 500 BCE. Strategy was about survival. About reading the field of battle accurately enough to avoid annihilation. The stakes couldn't have been higher, and the thinking had to match the existential reality. Get it wrong, and you’re dead. Cities fall. Empires collapse.

Clausewitz understood this when he wrote about war as the continuation of politics by other means. Strategy was about power, consequence, the careful orchestration of force and intelligence to achieve outcomes that mattered more than anything else in the world.

These weren't abstract intellectual exercises. They were tools for navigating survival-level complexity.

Then something happened. The stakes dropped, but the language remained.

Post-war business schools began importing military frameworks into corporate contexts. The Boston Consulting Group translated battlefield terminology into market dynamics. McKinsey turned strategic thinking into a methodology that could be taught, packaged, and sold. What had once been the desperate improvisation of commanders became the systematic optimisation of consultants.

This wasn't necessarily wrong. Business competition does involve strategic thinking. Market dynamics can be usefully analysed through frameworks borrowed from military theory. The problem was what got lost in translation: the life-and-death urgency that made strategic thinking necessary in the first place.

In war, bad strategy kills people. In business, bad strategy might hurt quarterly earnings. The feedback loops got longer, softer, more forgiving. You could be wrong about market positioning and still collect your fee. You could develop strategies that failed spectacularly and still get promoted, as long as the failure was sufficiently sophisticated and the presentation was impressive enough. And contained enough pie charts, graphs and powerpoint wizardry to feign certainty.

Meanwhile, advertising agencies watched the consulting boom with envy. Why should McKinsey get all the high-margin strategic work? Why shouldn't creative agencies offer strategic thinking alongside creative execution? After all, who understood human behaviour better than the people whose job it was to influence it?

So agencies began hiring "planners" and "strategists." They developed their own frameworks, their own methodologies, their own versions of strategic thinking. But agency strategy was never about survival. It was about selling. About making creative work feel more intelligent, more defensible, more worthy of investment.

This wasn't how agency planning was supposed to work though. The original idea, pioneered by people like Stephen King at JWT, was genuinely valuable: understand the audience before you create the message. Research the cultural context before you craft the communication. Let insight drive creativity, not justify it.

Somewhere along the way, that got inverted. The consulting firms, for all their flaws, were at least trying to solve genuine business problems. But very quickly, agency strategy became something else entirely - a way to justify creative decisions that had already been made. The insight came after the idea, not before it. The cultural tension was reverse-engineered from the creative brief.

And this is where I found myself, twenty-two years into a career that began with genuine curiosity and excitement. Sitting in conference rooms at Naked and Droga5, watching centuries of strategic thinking get compressed into slides about soap and deodorant.

But the tragedy isn't that Sun Tzu's ideas ended up selling scented candles. The tragedy is that they ended up selling them badly. That all the intellectual sophistication, all the cultural analysis, all the philosophical heavy lifting got filtered through systems that had no use for genuine strategic insight.

Because there probably are genuinely strategic questions to ask about selling "Positano Vibes in candle form." Questions about resource allocation, market dynamics, consumer motivation, cultural change. Questions that might benefit from the kind of rigorous thinking that actual strategy requires.

But those questions are harder to answer than "people want their homes to smell like Mediterranean holidays they can't afford." They require longer research timelines, more complex analysis, less certain conclusions. They might suggest uncomfortable truths about wellness culture as consumer manipulation, the environmental impact of luxury lifestyle products, or why people seek emotional comfort through purchasing objects that promise experiences they can't actually access.

And that kind of strategic thinking doesn't fit neatly into campaign timelines or client expectations, or the performance rhythms that keep agencies profitable.

So we developed a bastardised version of strategy. All the language, none of the stakes. All the methodology, none of the consequence. All the intellectual sophistication, none of the practical analysis.

We took the tools designed for existential complexity and used them to optimise the sale of unnecessary products to people who probably couldn't afford them. We turned frameworks meant for life-and-death decisions into templates for creative justification.

And as a result, we forgot that real strategy isn't about having a clever answer. It's about asking a question that matters enough to stake your career on getting right.

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The personal cost of this performance is hard to articulate without sounding overdramatic. But there's a particular kind of exhaustion that comes from spending your days in service of work that feels intellectually sophisticated but ultimately hollow.

It's not just job dissatisfaction. It's deeper than that. It's the slow erosion of your own sense of what your intelligence is for.

When you spend months developing genuine insights about cultural change, only to watch them get reduced to taglines that will be forgotten after someone scrolls right past it, something inside you starts to wither. When you have conversations with clients about "consumer truths" that you both know came from a Google search rather than genuine human understanding, you begin to lose faith in the possibility of meaningful work.

The shame isn't just professional disappointment. It's about complicity. About the recognition that you've become skilled at something you don't believe in. About the quiet compromise you make every time you present insight you know is thin, or nod along with strategic thinking you know is performance.

What a fucking waste of time and energy and resource and money and brilliant minds.

And this waste is staggering when you really think about it. All those sharp people in all those conference rooms, applying all that analytical horsepower to problems that don't actually need solving. All that cultural research that could inform policy, education, social intervention - instead reduced to rationales that exist primarily to make clients feel smart about their media budgets.

But the personal toll goes beyond professional frustration. When your daily work requires you to perform expertise about things you don't think matter, you start to lose touch with your own sense of what does. When you spend eight hours a day crafting strategic ‘plans’ for decisions that were already made, you begin to doubt your ability to think strategically about anything that actually counts.

The split self becomes more pronounced over time. The professional you gets better and better at the performance - more fluent with the frameworks, more comfortable with the theatre, more skilled at generating insights on demand. Meanwhile, the private you watches all of this with growing discomfort, wondering what happened to the curiosity that made you want to think strategically about anything in the first place.

So you tell yourself that advertising can be culturally valuable, that consumer insights can lead to genuine human understanding, that strategic thinking in these contexts is still strategic thinking. You focus on the craft elements - the elegance of a well-constructed matrix, the satisfaction of an insight that lands just right in the room, the pleasure of solving even artificial problems with faux-intellectual precision.

But underneath all the rationalisation, the shame accumulates. Not just professional disappointment, but something closer to moral injury. The recognition that you're complicit in a system that consistently takes human intelligence and channels it toward trivial ends.

And the isolation is crushing. Because everyone around you seems genuinely excited about the work that leaves you cold. Your colleagues get energised by cultural tensions that feel invented to you. Your clients light up over insights that strike you as utterly obvious and banal. Your creative partners build beautiful work on strategic foundations that you know are shakey as fuck.

You start to wonder if something is wrong with you. If you're the only one who sees the emperor's naked state, or if everyone else is just better at pretending not to notice.

Then you realise: it's not just you. This is collective performance, but recognising that doesn't make it less painful - it makes it worse. Because now you see that hundreds of smart people are caught in the same system, all carrying the same private doubt, all wondering if they're alone in questioning whether any of this actually matters.

And so the shame isn't individual pathology. It's systemic feedback. A signal that something fundamental has gone wrong with how we understand and practice strategic thinking in commercial contexts.

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But here's what I've come to understand: the shame is not the problem. The shame is the beginning of the solution.

Because shame, at its core, is the feeling that emerges when your deepest values are misaligned with your daily actions. It's the emotional signal that tells you something needs to change - not just in your career, but in your relationship to the work itself.

The shame I felt sitting in those conference rooms wasn't personal weakness or professional inadequacy. It was recognition. Recognition that the intelligence I was applying to strategic problems was real, but the problems themselves were mostly artificial. That the frameworks I was using were sophisticated, but they were being deployed in service of outcomes that didn't justify their sophistication.

The problem isn't strategic thinking itself, it's what we've allowed strategic thinking to become. We've created systems that reward the performance of strategy over the practice of it and that sucks, because strategic thinking is one of the most valuable capabilities humans have developed. The ability to hold complexity without reducing it prematurely. To see patterns across different domains and timescales. To navigate uncertainty without paralysis. To design interventions that account for systemic effects rather than just immediate outcomes.

These capabilities are desperately needed. Climate change, technological disruption, social inequality, democratic fragility - all the challenges that define our historical moment require exactly the kind of thinking that strategy, at its best, can provide.

But instead, we've been using it to justify decisions that were already made, to solve problems that don't really need solving, to create the appearance of rigour around work that's fundamentally decorative and most often, trivial.

We've deliberately chosen shallow over deep, and comfort over truth. We've taken tools designed to wrestle with difficult questions and used them instead to create the illusion of understanding where none exists.

And that recognition is shared by so many strategists who feel the same mismatch, the same complicity, the same hunger for work that actually requires the intelligence they're bringing to it.

Which means the shame isn't something to be overcome or ignored. It's something to be honoured as valuable information about what needs to change.

And once you feel it, you can't unfeel it.