What Winners Take All taught me about fixing things inside broken systems

I picked up Winners Take All a few years ago without much expectation. And then it made me rethink pretty much everything I thought about the world, life, systems, and what it even means to do “better”.

Anand Giridharadas asks: what if we get very good at making things better within a system without ever asking whether the system itself is the problem? What if all we do is learn how to survive inside it rather than expose it and make the people who designed it feel uncomfortable?

Winners Take All: The Elite Charade of Changing the World is a book that criticises the people and institutions that have come to dominate the language of social change: billionaires, consultants, philanthropists, social entrepreneurs, TED speakers, foundations, business leaders and the wider ecosystem around them. Giridharadas calls this whole world MarketWorld.

And his argument is pretty uncomfortable. You see, from the outside, you’d think that MarketWorld really wants to change the world. There are plenty of people in it who are sincere, intelligent and doing things that genuinely help other people. They create non-profits, foundations, charities and even companies to solve real-world problems. But the problem, Giridharadas argues, is that the kind of change this world tends to support is constrained by the interests and assumptions of the people running it.

If you benefit enormously from the current system, you’re unlikely to start your revolution by dismantling the system that made you successful. Instead, you might fund a charity, launch a social enterprise, or invest in a purpose-driven company. Maybe you’ll even give a talk about resilience, or create an initiative to help people navigate the consequences of a problem that you benefit from. All useful? Yes. But in many cases, they shouldn’t have to exist at all. The world is so focused on treating the symptoms that it can forget to ask where the symptoms came from in the first place. We keep building institutions to solve problems that may never really be solved without changing the systems producing them.

The progress machine that doesn’t work for everyone

One of the book’s ideas is that society acts as a progress machine. Ideally, innovation, economic growth, and human ingenuity should produce increasingly better lives for increasingly more people. And by the look of it, it kind of does. But what happens when it is producing huge amounts of wealth and progress while a significant number of people aren’t sharing in it? The people with the most resources to change things and make a real difference are often also the people who have benefited most from the way things currently work. It doesn’t automatically make them bad people; they simply were able to use the system to their advantage. And quite possibly, some people might actually be really sincere about wanting to help the rest of the world to be and do better. But it does create a conflict of interest.

And Giridharadas thinks we’ve become very good at resolving that conflict psychologically, because now you can be one of the winners and see yourself as one of the people fixing the system and offering solutions. Think: philanthropy, the social enterprise, the impact fund, maybe a scholarship programme. You might see it as evidence that you’re part of the solution (and, to be honest, this is better than nothing), but the real question is whether you are trying to solve something while avoiding asking yourself what system has produced that problem and what your own relationship with that problem is.

The three ways of looking at elite generosity

Giridharadas lays out three possible ways of interpreting wealthy and powerful people trying to make the world better.

• The first is the generous interpretation: they’re truly trying to help. They know that the problems are huge, and they’re using the resources they have to do something useful about it. Most will say that it’s better than doing nothing.

• The second is the sceptical interpretation: they’re well-intentioned, but what they’re doing isn’t enough. Charity can relieve suffering without addressing the causes of suffering, and social entrepreneurship can solve a small part of a much bigger problem. This basically treats the symptoms, but nothing really changes.

• But then Giridharadas asks: what if some forms of elite-led social change actually help stabilise the system that created the problem? When the wealthy are doing good publicly, it becomes harder for people to question how they accumulated their wealth in the first place. You can technically give back without taking less, and you can help people affected by a system without being asked whether you’re helping maintain that system.

So one of the biggest ideas I took from the book was the distinction between doing good and changing the conditions that make the good necessary.

When “doing good” becomes a win-win

A huge part of the MarketWorld worldview is the idea of win-win. I have read about win-win situations in books numerous times (e.g., when it comes to negotiations) and believed it was a great idea. But in this book, the win-win is the assumption that business success and social progress can naturally reinforce each other. That companies can make money and improve society, that investors can earn returns and solve social problems, and that businesses can grow and improve workers’ lives. Most people want to believe that everybody can win, and sometimes everybody does win, and that’s why this idea is so appealing. BUT the truth is that sometimes it doesn’t work. Sometimes in order for someone to make more money, someone else needs to get less; sometimes protecting workers costs shareholders money (and they’re not happy); sometimes a regulation that benefits the public makes life harder for particular businesses (and they’re also really not happy!).

Sometimes redistributing power means the people currently holding the power have to give some of it up. And my guess is that nobody actually wants to do that.

What happens when business language takes over social change

Giridharadas argues that we’ve gradually replaced a language of power, rights and collective action with a language of business, innovation and individual action. Think about how we talk about changing the world now. We talk about scaling solutions, innovation, impact, entrepreneurs, stakeholders, social enterprise, investment, partnerships, thought leadership and measurable outcomes. These are not bad things, but the problem is that we’re not asking who made the rules, who has the power, who is excluded, who benefits and who suffers, what needs to change in law, what needs to be redistributed, etc. Well, we do a bit, but not nearly as much as we talk about the first list. The latter questions feel much messier, and most people would rather just ignore them if they don’t feel directly affected. And that’s partly Giridharadas’ point. When we turn every social problem into something that another new business, partnership, or innovation can “solve”, we stop questioning the system and stop discussing the deeper causes underneath the problems those innovations are meant to solve.

The “loyal opposition”

Giridharadas connects this to neoliberalism and the broader shift towards individual responsibility. The basic idea is that markets should have more freedom, the state should do less, and individuals should take more responsibility for their own lives. Fine. But what happened to the people who didn’t necessarily agree with that worldview? Giridharadas argues that parts of the political left gradually adopted some of the same tools and assumptions. Of course, they still cared about inequality and disadvantaged people, but at the same time, they increasingly tried to address those problems through capitalism rather than by challenging the system. So instead of asking how we can change the system, the question became how we can make the system produce better outcomes.

And, if I am being honest, that’s what made me question organisational design. The truth is that we can spend years helping an organisation become more efficient, more collaborative, more inclusive and more psychologically safe without ever asking whether the fundamental way the organisation is structured even makes sense.

The same goes for life design. Sometimes we spend years trying to adapt to the system we find ourselves in, without ever asking whether we should be in that system in the first place. If we can’t thrive where we are, we most likely need to understand why and then leave, so we can enter a new system that allows us to become who we want to become. Easy? Most of the time, it’s not. Necessary? I’d argue yes.

The thought-leader three-step

MarketWorld needs credible-sounding people to explain why everything is fine, or if not fine, then fixable through the right mindset. And here’s where thought leadership comes into play. :)

A thought leader is not a critic, because a real critic would identify what’s wrong and demand structural change. A thought leader is much more marketable than that. And much more useful for the wealthy and the powerful. A thought leader takes a serious problem, makes it feel manageable and personally empowering (this is important), and sends us home feeling inspired without threatening anyone. Giridharadas says the thought-leader formula has three moves.

First: focus on the victim, not the perpetrator. Talk about the person who got hurt, not the system that hurt them. And make it a human story. So instead of asking who or what caused something horrible, we’re asking how we can help the person who’s experiencing it. Let’s illustrate this: if someone is struggling because of a dysfunctional workplace, for example, we can teach them resilience, mindfulness, and how to manage stress, instead of looking into why the workplace is dysfunctional and how we can fix THAT.

Second: zoom in, not out. Now we take a structural problem (e.g., wage stagnation, racial inequality, healthcare) and make it an individual challenge that each person can work on themselves. For example, let’s say a person is struggling to cope with work demands. We teach them how to navigate their situation better, instead of tackling unrealistic expectations, workload, ineffective processes, or whatever else company-wide is causing it. It doesn’t mean we can’t look at individuals, because we can. But the problem is that if we only look at individual challenges, we ignore the larger, systemic problems that create those challenges.

Third: be constructively actionable. Give people steps they can take. And make it a listicle or a TED talk. It has to feel hopeful and doable. People want something they can do, and I’m the same. I don’t want to read a long article or watch a long talk, and then wonder what exactly that means for me. I want clear action points! And, in fact, I’m pretty sure I’ve created those listicles myself to make this easier for people. This is what you learn to do when you create content, when you learn marketing, and when you learn sales. Make it easy, simple, actionable. But Giridharadas points out the downside here too. If every serious idea has to end with five things you can do on Monday morning, we start favouring ideas that can be turned into neat individual actions. And systemic problems don’t always cooperate with that format. For example, things like lobbying for tax reform, organising politically, redistributing power, or changing the structure of an institution don’t translate well into a carousel called 5 things you can do today. That’s why the biggest, most complicated problems get ignored and eventually disappear: they are made smaller, easier to understand, personal, and easier to act on.

What happens to an idea when it enters the thought-leadership world

The truth is that real change is not a TED talk or a nice, engaging article. Real change is changing the law, organising citizens, and challenging the people in power directly, in the places where the power actually lives (in legislatures, courts, regulatory agencies, labour contracts). The language that MarketWorld has pushed out of the conversation is the language of power, justice, and rights. Now everything is framed in the neutral, inoffensive vocabulary of business: leverage, scale, impact, innovation, ecosystem. And when we describe a social problem in business language, we’re accepting that markets should lead and that solutions should be profitable.

“These elites believe and promote the idea that social change should be pursued principally through the free market and voluntary action, not public life and the law.”

There is some real pressure, it appears, on intellectuals to turn their ideas into commodities: bite-sized takeaways, Monday morning insights for the CEO, and quick action steps. Something written in a journal or in full paragraphs? Chances are it will be ignored, as it requires too much effort to read. So to enter this world is, in effect, to surrender: to let the winners define the terms of the conversation about what to do about the world they’ve helped create. But of course, it doesn’t mean that the people involved are bad. Most of them believe what they say. It’s structural, after all. The incentives are aligned in such a way that you can do a lot of publicly visible good while leaving the things that actually matter untouched.

The McKinsey problem

Then there’s Sean Hinton, a former McKinsey consultant, who walks us through the firm’s way of solving problems, what the book calls the protocols. First you find the “business need”, then you frame the problem by setting its boundaries and breaking it into smaller parts, and you come up with a hypothesis really early on. Then you gather the data to prove it, present it in a crisp, convincing way, and finally implement and iterate. Hinton also learned to speak in lists of three, and never to “boil the ocean”, which basically means keeping the problem small enough that you don’t get overwhelmed by it.

And Giridharadas’ point is that this way of solving problems has become the way of solving problems. Not just in business, but in charity, education, health care, politics and the arts. We frame it, break it down, find the answer, etc. Even if we knew nothing about the problem a week ago. But consultants work for clients. And McKinsey consultants work for wealthy clients, who are doing quite nicely out of the way things are. So they can fix a process, or improve one organisation, but they’re never going to be paid to question the system that’s paying them. Hinton has a name for this: the “Trying-to-Solve-the-Problem-with-the-Tools-That-Caused-It issue”. Oh, and Giridharadas used to work at McKinsey himself. So he knows exactly how convincing it all is from the inside.

Aaaand this one stung a bit. I love mapping a system and finding the bottleneck and making a messy thing feel manageable. It’s basically my favourite thing to do. But this made me realise that making something manageable can also mean making it smaller than it really is. Some problems need to stay big for a while, so we can actually see what we’re dealing with before we start chopping them into neat little pieces.

The Sackler problem: do more good, or do less harm?

Next, Giridharadas describes something he calls the Aspen Consensus: the winners of our age get challenged to do more good, but nobody ever tells them to do less harm. One of his examples is the Sackler family. Their name was on museums and universities, they were celebrated as generous donors, and they also owned Purdue Pharma, the company behind OxyContin, which helped fuel the opioid crisis.

When someone gives away millions, we want to count it as proof they’re a good person. And the truth is that someone can do good in the world and still cause harm at the same time. But if we only ever celebrate the giving and never look at the harm, that’s a very convenient arrangement for the person doing both!

So, for example, you can:

• Launch a lovely wellbeing programme while the workplace culture is making people miserable.

• Donate to climate causes while running a business model that produces emissions it doesn’t need to.

• Run an inclusion initiative while your hiring and promotions keep reproducing the same inequality.

But doing something good doesn’t cancel out something harmful. Or at least it shouldn’t. Yet when we see someone do good, most of us stop paying attention to the harm they do.

Carnegie and the idea of the wealthy as trustees

Andrew Carnegie famously argued that wealthy people should act as trustees of their wealth and use it for the benefit of society. Sounds nice, doesn’t it? If you’ve accumulated enormous resources, it makes perfect sense that you should feel responsible for using some of them for other people’s benefit. BUT! Who really gets to decide what other people need? And what happens if the same system that created the enormous concentration of wealth is treated as basically legitimate, while inequality is viewed as just a temporary side effect? Some people get ahead, they get very wealthy, they give some of it back, and everyone wins.

But not so fast. This is where Darren Walker, the president of the Ford Foundation, comes in. Walker argues that inequality is built on much deeper conditions, such as ingrained prejudice, historical racial, gender and ethnic biases, and regressive tax policies, which together create the systems that allow inequality to grow. In other words, people aren’t just left behind because they failed to keep up with progress. Many are held back from the start because of who they are, where they live, or the political choices their society has made about how to treat them. So Walker asks wealthy people to look at themselves and ask whether the playing field they got rich on was actually level and fair, and whether the system compounds their advantages.

And this is where Giridharadas draws his big distinction between generosity and justice. Generosity is giving some of it back, whereas justice is asking why it was distributed this way in the first place, and how fair the game was that produced the winners.

There’s a similar question inside philanthropy itself

Another thing I found really interesting is how much the book pushes back on paternalism. Even when we’re truly trying to help, we can still slip into assuming we know what’s best for someone else. This is particularly obvious when wealthy institutions from powerful countries design programmes for people in poorer countries. So the people giving the money become the experts, the people receiving it become “beneficiaries”, and somehow the person with the least power ends up with the least say in a solution that’s supposedly for them.

Giridharadas’s alternative is democracy: when help comes through shared public institutions, the people receiving it aren’t just on the end of a transaction. They’re citizens, with a say.

Now, I feel that the same principle applies to org design, too. Who gets to design the system? If leadership decides what employees need without asking them, you get beautifully designed solutions to problems nobody actually has. For example, a wellbeing programme, maybe a new office, a values workshop, new tools and platforms, whatever. Leaders think these will make their people happier, while what people actually want is flexibility, fairness and psychological safety.

We should just give the people who live inside the system more say over how it works, and make it better with them. Not decide it for them.

The conference model

Giridharadas also looks at the big global “let’s change the world” conferences, and he spends a big chunk of the book on Bill Clinton and the Clinton Global Initiative. The idea was to get people from business, philanthropy and government in a room, have them make public commitments to tackle big problems, and work on them together. And it sounds pretty awesome, but again, of course, that’s not all there is to it. Clinton spent his career in politics and government, and then ended up championing a model where change comes from companies, philanthropists and powerful individuals instead. The question shifted from “how do we build and fix public institutions?” to “how do we get rich and influential people to sort this out?”

Private actors can absolutely help, nobody is arguing that, but they’re not accountable to the public the way democratic institutions are. Just think about it: a company decides what it wants to do, a billionaire decides where to donate, a foundation picks which projects to fund, and a government, at least in principle, answers to the public and can make rules that apply to everyone. Very different kinds of power, and when we mix them up, we all get confused about who’s supposed to fix society.

And here’s what I think this book has to do with life design

The book is obviously about inequality, capitalism, philanthropy and political power, but I kept thinking about life design the whole way through, because there’s a version of the same problem that happens at the individual level, too! We can get obsessed with improving ourselves inside lives we’ve never really examined. Just think about it: we optimise our routines, build better habits, track our sleep and try to find our purpose. I’ve done all of these, and I’m sure most people have, too. But at some point I think it’s worth zooming out a bit and checking whether the problem is not that we’ve badly optimised ourselves, but that maybe we’re in the wrong environment, or maybe our job doesn’t fit how we naturally work best. And what if the version of success we’re chasing isn’t even ours? The more I learn about myself, the more I understand that I’ve spent years focusing on solving the wrong problems. And there is quite a big chance that the things we’re trying to “fix” about ourselves are actually a perfectly reasonable response to our circumstances.

And here’s what I think this book has to do with org design

Organisational design can very easily become a sophisticated way of making the existing machine run better. And, in a way, that’s kind of the plan. We clarify roles, redesign processes, improve onboarding and work on psychological safety, and all of that is useful. But there is a deeper question we need to ask, too: better for what, and for whom? If an organisation’s fundamental incentives are unhealthy, making it more efficient doesn’t necessarily make it better. It’s the Sackler problem again, just with org charts. You can build a beautifully designed system for producing outcomes nobody wants or cares about.

So now I think good organisational design needs two levels of thinking. The first is optimisation: how can this organisation work better? The second is examination: should it work this way at all? I’m really interested in designing organisations that are effective without losing their humanity, and I feel pretty clear on that, but I think “effective” needs a bit of interrogation too. Effective at what? For whom? At whose expense? And according to whose definition of success?

The hardest question in the book

So what does it take for people who benefit from a system to actually change it? Not just to make the symptoms slightly less painful, donate money, build a better product or create an initiative, but to actually give up some power, money, convenience or control when changing the system requires it.

This is where I think Giridharadas is being provocative on purpose, because we like the idea that everyone can win. It makes for a much nicer story. But the truth is that there is a conflict of interest. Sometimes changing a system means that someone who currently benefits from it gets less, and sometimes the people who are most comfortable inside a system are not the people best positioned to redesign it.

The bit I’m taking away

I don’t think the answer is “business is bad” or “rich people shouldn’t even try to help”. Businesses can do good, individuals can make meaningful changes, philanthropy can save lives, and good organisational design can improve people’s everyday experience of work. Sometimes the best way to change a system is to change something small inside it.

What I think the book gives me is a useful check before jumping straight into solution mode. Before asking “how do we make this better?”, ask: better for whom? Who benefits from things staying the same? Are we treating a symptom or changing a cause? Are we asking the people with the least power to adapt, or are we changing the environment around them? And are we trying to make the existing system more efficient when what it really needs is to be redesigned?

I think that’s probably the part I’ll carry with me, because this is why I think of life design and organisational design as the same problem at different zoom levels. We’re always designing systems. Sometimes the system is a life, sometimes it’s a team, sometimes it’s an organisation, and sometimes it’s a society. And the same temptation exists at every level: make the existing thing work better before stopping to ask whether it’s actually the thing we want.

Good design isn’t only about making a system work beautifully. Sometimes it’s about having the courage to ask whether the system itself is the thing that we need to redesign.