On Winners & Losers

Andrew Roberts
4 min readJul 15, 2020


We’re indoctrinated to think of others as “winners” or “losers” from a young age

Whether you like it or not, you’re either a winner or a loser.

I wish I could say you had a significant choice in the matter, but you didn’t; it was mostly decided for you by a society that believes in a limited number of seats at the top.

The winners are those who are deemed worthy of the top, and who now get to pursue their own interests & leisure, knowing that — even if they’re not rich now — surely they will always be comfortable. They succeeded in school, learned the right lessons, and befriended enough people; so they have the network, career, and education to sustain themselves, forever.

One common misunderstanding about winners is that they “got lucky”, but this is only half true. Most winners (aside from the true trust-fund babies) genuinely have what it takes — they’re smart, competent, and sociable. The luck (if you care to call it that) is in being told that they’re special, and often from a young age.

I am one of the winners and, like all of us, there are two versions of my story.

In the first, I was a child of parents without college degrees. I was bright and talkative, but bullied into depression in middle school. Still, I worked hard, got great scholarships, and never asked for a dime from my parents. No one bought me a car, I was never given an allowance, and I was never given money for college. I moved out when I turned 18, and have never needed to go back for help. I earned my way.

In the second, I grew up in a large house, in a nice neighborhood, with lots of other well-to-do friends. I was treated to gifts on my birthdays and on Christmas, I was driven around town by my mother, and I was given all the books I could read. I went to schools filled with kids like me, whose parents could afford nice lunchboxes and school supplies. I could drive my parents’ car. I was always told I could do anything, and I said as much to my teachers and friends.

The system is built to support people like me. People who always had a safety net, but had to “work hard” for what they have. We can tell one half of the story or the other — but ultimately, it’s both. We’re both deserving and lucky. We’re both competent and systematically advantaged. It should come as no surprise, then, that these winning children grow into winning adults.

The real question is: Why do there have to be losers in the first place?

And while we’re at it, why are there so few winners? Why aren’t my poor immigrant classmates with me at the top — despite working even harder to learn the same middle-class English my parents spoke naturally? Those who had the same curiosity and desire to learn?

Who built the funnel to be this narrow?

The uncomfortable truth is that, to some extent, we all chose this — we are actively choosing it. An increase in the use of standards, grades, performance evaluations, and test-taking in schools; rigid one-size-fits-all curriculum; the idea that college is “mandatory” for finding a job; rampant individualism & desire to make one’s own way; social media with public comparisons of “likes” & “followers”…the list goes on.

We are obsessed with comparing, evaluating, and rank-ordering other humans to fit them neatly into pecking-order. Imagine thinking “oh, she’s not a good student” about your baby sister’s ability to walk. Imagine creating a test to see which baby is doing better at “socializing with humans” at age 1. Imagine telling your child that you will be directly testing their speaking & walking abilities against your neighbor’s child (6 months older) once a month. Horrifying? This is what we pay schools to do.

We are obsessed with manufacturing losers where there weren’t any to begin with. We live in arguably the wealthiest human society ever — where the vast majority of children are able to be safe, comfortable, and healthy — and yet only a tiny minority of children come out of this system “winners”, because we artificially tell the others that they have “lost”, as children. They learn their place from a young age, and they never recover.

This is worth repeating — we are born winners, and are taught, by the education system itself, to become losers.

So what do we do? Well, support non-evaluative education, for one. There’s nothing better you can do for your child’s self-esteem than enrolling them in a school without grades. We can also all internalize the notion of positive sum games. There simply don’t need to be winners and losers — in the game of life; we can all win.

Finally, if your child is failing in school, let them out! Free them from a punitive, vicious cycle of scorn, self-hatred, and depression. Give them love, kindness, and allow them to explore the world for themselves. Don’t allow people to tell anyone they’re a failure — and certainly don’t let them believe that about themselves.

We can make this world a better place for adults and children. But only if we commit to working together — to building a positive-sum, cooperative future out of the harsh winner-takes-all reality of the present.



Andrew Roberts