Why do some people seem genuinely content with very little, while others feel restless even when life looks “successful” on paper? Economist and entrepreneur Nat Ware kept running into that question in a surprising place: Africa. He met people living with serious hardship who still showed a kind of calm happiness that didn’t match the story many of us tell ourselves about what it takes to feel okay.
Ware’s big idea is simple and uncomfortable: we’re often unhappy because our expectations run ahead of reality. Once you see that gap, you start noticing it everywhere, from travel and social media to money and parenting.
The moments that sparked Nat Ware’s happiness research
Ware opens with memories from several trips to Africa that stuck with him because they didn’t fit his assumptions about happiness and poverty.
He describes meeting:
- A one-legged taxi driver in Kenya
- Sonia, an orphan schoolgirl in Rwanda
- A disabled subsistence farmer in Mozambique
What shocked him was not their poverty. It was their happiness.
He’s careful to say not everyone was happy, but once people were above a basic subsistence level, he was struck by how many seemed genuinely content. That experience pushed him to take happiness seriously, both as an economist (it’s part of what he researches at Oxford) and as someone interested in social enterprise (because happiness is the ultimate social outcome).
He also points to a well-known policy idea from Bhutan: measuring national progress with happiness and well-being in mind, not only GDP. If you want background on that approach, the OECD’s overview of Bhutan’s Gross National Happiness (GNH) Index is a useful starting point.
A quick happiness quiz (and why it matters)
To show how often we misunderstand our own happiness, Ware runs the audience through a short multiple-choice quiz. It feels like a game, but it sets up his bigger point: we’re bad at predicting what will actually make us feel satisfied.
Question 1: The Olympic medal dilemma
You’re competing in the Olympics. What would you rather get?
- Second place
- Third place
- Second-to-last place
Many people choose second, because it sounds “better.” A surprising chunk even chooses second-to-last. Ware also jokes about results from monkeys, who pick options without understanding the emotional meaning we attach to them.
The punchline comes later: research suggests the happiest outcome isn’t what most people think.
Question 2: Lottery tomorrow vs. rising payments for life
Option A: You win $10 million tomorrow.
Option B: You get a small payment tomorrow, then payments that rise over your lifetime, totaling $8 million.
Ware’s audience leans toward the lifetime payments (Option B), while “the general population” tends to pick the big immediate payout (Option A). The monkeys split about 50-50, since there are two options.
Question 3: Salary choice, but relative to everyone else
You can choose your salary, but what others earn changes too:
- A: You earn $50,000, everyone else you know earns $50,000
- B: You earn $50,000, everyone else you know earns $60,000
- C: You earn $40,000, everyone else you know earns $30,000
Most people pick A. Almost nobody picks B. Only one person in the room picks C.
And that’s the point. The “right” answer for happiness is not always the highest number, it’s often the one that changes how you compare.
The reveal: what research says makes people happier
Ware then shares what the research suggests are the “correct” answers if the goal is contentment and satisfaction:
- Third place, not second (bronze medalists often feel relief, silver medalists often imagine gold and feel they “lost”).
- The lifetime payments (a path that keeps rising can feel better than one big spike).
- $40,000 when others earn $30,000 (relative position can matter more than absolute income).
The audience does okay, but Ware’s joke lands: in a couple of questions, the monkeys do better than humans. The humor is a setup for something more serious.
The paradox: richer than ever, but not happier
Ware points to a pattern many people recognize, even without charts:
- We’re wealthier than ever, but often feel less satisfied.
- We’re more prosperous, but more depressed.
- We have faster transportation, but also get faster at complaining.
- In many countries, there are now more suicides than homicides.
- Technology improves rapidly, but happiness doesn’t rise in step.
This is the tension at the heart of his talk: if money, speed, and convenience are improving, why doesn’t life feel better at the same rate?
The core idea: the expectation gap
Ware’s explanation is not that we have too much choice, or that people are only “reporting” depression more, or that it’s all family breakdown and politics. Those may matter, but he argues the most convincing driver is simpler.
We become unhappy when our expectations of reality exceed our experiences of reality.
He calls this mismatch the expectation gap. The larger the gap, the more disappointment we feel.
To make the idea practical, he splits the expectation gap into three types, based on how we form expectations:
- Expectations shaped by imagination
- Expectations shaped by other people
- Expectations shaped by our past
Gap 1: The imagination gap (when fantasy beats real life)
The imagination gap is what happens when your imagined version of life outruns what reality can deliver.
Why “choosing the best” can backfire
Ware makes an uncomfortable point: even rational decision-making can set us up for disappointment.
When you choose a product, a trip, or even a political leader, you usually pick the option you believe will be the best. That’s normal. But the act of choosing “the best” raises your expectations. Then reality arrives, imperfect and ordinary, and it often falls short.
The decision process that’s meant to maximize happiness can reduce it, because it loads the future with unrealistic hope.
How tech and media distort what feels “normal”
Ware argues technology makes this problem worse by making the unrealistic look real:
- Photos get enhanced.
- Imperfections get airbrushed out.
- Travel gets romanticized.
- Places and people get presented in their most flattering moment, from the best angle, in the best light.
He gives examples from travel and art, pointing out how famous sights can look magical online, then look crowded, messy, or underwhelming in real life. In contrast, some of the happiest travel moments come from what you didn’t plan, the thing you discover without a script.
Selection bias: when the highlight reel becomes the baseline
Ware also points to selection bias in what we see online. Algorithms tend to reward what gets the most likes, the most shares, the most engagement.
So you’re more likely to see:
- The best photo, not the typical photo
- The most impressive moment, not the normal moment
- The polished story, not the messy truth
Over time, the “top 1 percent” starts to feel average, and your expectations rise accordingly.
Persuasion: promises that inflate expectations
He adds another force: persuasion.
Politicians often win by promising fixes that won’t happen. Companies sell by talking up strengths and staying quiet about weaknesses. Ware gives a simple example: a company might highlight that its watches have never performed tasks so quickly, but it won’t brag that batteries have never run out so quickly (even if both are true in some sense).
Put tech, selection bias, and persuasion together, and the imagination gap grows. Our minds demand more than everyday life can provide.
Ware connects this to self-esteem too. Advertising, he notes, learned long ago that if you can make people dislike themselves, you can sell them something to “fix” it. When you’re constantly shown perfection, “normal” starts to feel like failure.
Gap 2: The interpersonal gap (when comparison sets the rules)
The interpersonal gap is about how expectations get shaped by the people around you.
Ware puts it plainly: we judge ourselves using local comparisons.
If you earn $50,000 in a poorer neighborhood, you might feel rich. If you earn $50,000 in a wealthy neighborhood, you might feel poor. If you get a small raise but everyone else gets a big raise, you may feel cheated, even though your income went up.
In this frame, happiness can feel like a zero-sum game. Your gain can sting someone else, and someone else’s gain can sting you.
Ware says this isn’t only about money. It also shows up in appearance. He mentions research suggesting people are happier when they’re around worse-looking people, because it changes how they think they’re being seen. It’s a blunt example, but it fits the point: we don’t evaluate ourselves in a vacuum.
The asymmetry problem: we look up more than we look around
Another issue is where we place our attention.
People tend to focus on the rich, the famous, and the beautiful, and ignore the rest of the distribution. That pulls expectations upward. It can make you feel less successful than you really are, because you’re comparing your real life to someone else’s edited highlight reel.
Ware connects this to the “hedonic treadmill” idea. If your standard of living rises but everyone else’s rises too, you may not feel better. You just reset what “normal” means.
Gap 3: The intertemporal gap (when the past becomes the benchmark)
The third expectation gap comes from time. Ware calls it the intertemporal gap.
You’re unhappy when your past reality feels better than your present reality.
He uses a simple example: two people can have the same average lifetime income, but the person whose income rises over time is usually happier than the person whose income falls over time. The difference is the direction.
He ties this to “anchoring,” the idea that we compare current life to a reference point. If life keeps improving, it feels like progress. If it declines, it feels like loss, even if the “average” looks fine on paper.
What this means for parenting
Ware applies the intertemporal gap to parenting in two ways.
First, when kids get everything early, it’s harder for them to experience a steady climb. The intention is loving, but the result can make later life feel like a downgrade.
Second, he warns about overhyping kids with constant messages that they’re extraordinary, that they can be anything, that they’ll be a president or prime minister, the next Mark Zuckerberg, or Beyoncé.
Confidence matters, but unrealistic expectations come with a cost. If someone grows up expecting greatness as a baseline, then a normal job, a failed business, or a routine life can feel like a personal defeat, even when it’s perfectly human.
How to close the gap (without pretending happiness is fluff)
Ware’s message isn’t “just lower your expectations.” It’s bigger than that. He argues we should take happiness and expectations seriously, not treat them like soft topics only meant for artists or “hippies.”
He frames this as a challenge for people who shape culture and incentives:
Win the imagination battle
- Push for more realistic representations of people, places, and products.
- Consider limits on digital enhancement in advertising, so expectations don’t get pushed into fantasy.
Win the interpersonal battle
- Prioritize income equality at the policy level.
- At the personal level, compete against yourself more than you compete against others.
Win the intertemporal battle
- Support kids and encourage them.
- Keep expectations grounded enough that life can still feel like progress.
Ware’s broader point is about aligning systems with what we know about human psychology. If expectations drive happiness, then media, policy, parenting, and business all play a role in shaping those expectations.
Why this changes how you think about “success”
Near the end, Ware circles back to the quiz. Those strange “correct” answers start to make sense once you see the expectation gap at work:
- A bronze medalist can feel happier than a silver medalist because the bronze medalist imagines fourth, while the silver medalist imagines first.
- A big lottery win often doesn’t create lasting happiness because the spike becomes the new baseline, not a steady climb.
- Earning less can feel better if it improves your relative position, because feelings are tied to comparison, not just totals.
We often make decisions based on absolute outcomes (more money, higher status, better options). But our emotions respond to relative outcomes (what you thought would happen, what others have, what you used to have).
Conclusion
Happiness doesn’t only depend on what happens to you, it depends on what you expected would happen. That’s the uncomfortable power of the expectation gap. When imagination, comparison, and nostalgia set the bar too high, real life can’t clear it.
A useful next step is to notice where your expectations come from, your feeds, your peers, or your own past. Once you see the source, it’s easier to spot when your mind is asking reality to do something it can’t.
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