English is full of expressions that make no sense without context and even less with it. "Pull yourself up by your bootstraps" is the best example I can think of. This expression isn't just literal nonsense—it's figurative nonsense.
You can't physically pull yourself up by your bootstraps. Go ahead: put on some boots, grab the straps, and try to pull yourself off the ground. You won't manage to "pull yourself up" in any meaningful sense because gravity is a thing. You can pull yourself up by a chair, a rock-climbing grip, or someone else's hand; you cannot pull yourself up by your bootstraps, or anything attached to your body. If you could, transportation infrastructure would look very, very different because humans would be capable of levitation.
Pulling yourself up requires relying on something—or someone—else. You need help, which makes "pull yourself up by your bootstraps" a nonsense expression on a literal level. But the idea the expression is now meant to point to—that a lone individual can succeed through their own work, with no help from anyone else—is also fiction.
You can't pull yourself up by your bootstraps, and thinking you can is fantasy.
The evolution of nonsense
The expression "pull yourself up by your bootstraps" was originally used to refer to a task that's impossible. It's believed to come from the German author Rudolf Erich Raspe, who wrote about a character who pulled himself out of a swamp by pulling his own hair.
It's a fun mental image, right? There's a certain cartoon logic to it, even if it sounds painful. That's probably why the phrase evolved to be about bootstraps, instead of hair, and stuck around for over a hundred years.
In the 19th century, the expression was mostly used to refer to impossible tasks. Here's an example from Bryant & Stratton's Counting House Book-Keeping in 1863:
The person competent to construct a system of philosophy on such a basis, would be able to show how a man might lift himself by his own boot-straps, or get rich by taking money from one pocket and putting it in the other.
People understood the expression "pulling yourself up by your bootstraps" to mean "attempting to do something absurd" until roughly the 1920s, at which point it started to evolve toward the current understanding: to do something without any outside help.
To be clear: I'm not saying that the current usage of the expression is "wrong." Idioms mean what they mean, regardless of the literal meaning. In the case of bootstraps, though, I think the physical impossibility is noteworthy.
Let's talk about Monopoly
There's an experiment involving the game Monopoly that I've thought about every month for the past ten years. In the experiment, which was conducted at the University of California Irvine, people just hung out and played Monopoly (which sounds pretty chill).
There was a twist, though: a coin toss meant roughly half the players started with twice as much money as the others. If you've played Monopoly, you know that having that much money basically ensures that you'll win, but the players didn't see it that way. The people with twice the cash, when asked, thought they won because of their amazing Monopoly skills.
"They don't talk about the flip of the coin," said Paul Piff, the researcher who conducted the experiment. "They talk about the things that they did. They talk about their acumen, they talk about their competencies, they talk about this decision or that decision."
It's human nature to take credit for positive outcomes, even if there's a lot of luck involved. This isn't to say that those players don't have skill—there's a good chance they made many Very Good Monopoly Decisions. But the best Monopoly player in the world would have a hard time winning against someone who starts with twice as much money as them.
That's where "pulling yourself up by your bootstraps" breaks down, to me. No one gets to where they are in life on their own—at least, not entirely. Everyone benefits from the resources they have—not only financial resources, like in the Monopoly game, but also the people around them.
Here's Piff, the Monopoly researcher, talking about exactly that:
I think across all people, it's universally true that there are things that you benefit from that you did not contribute to. There are things that you benefit from that you did not build; there are things that you benefit from that you did not make. You benefit from the roads that are built, from people that have helped you along the way, from the mentors that you accidentally found yourself in the same classroom with.
This isn't to say that hard work doesn't matter; it's just to say that it's not the only thing. No one pulls themselves up by their bootstraps. No one can.
I got this job at Zapier because a friend I made on Twitter thought I would be a good fit for it. I got the job before this one the same way. My friends helped me out, knowing that I'd do the same thing for them in a heartbeat. I've worked hard at every job I've ever had, but I've also been lucky to work with so many people who helped me become a better version of myself. The truth is that none of us does anything alone—and that we shouldn't expect anyone else to.
This isn't something you should feel guilty about, by the way. It's just something you should know. Hopefully, it will motivate you to help others.
