The _Path Between the Seas_ by David McCullough is really excellent. It starts with the French diplomat Ferdinand De Lesseps, specifically with the way his friendship with the king of Egypt enabled him to start the Suez canal project. It then details how he got the Isthmian Canal project off the ground and how, because he wasn’t an engineer, he became willfully blind to the realities in Panama. He made horrendously flawed plans (a sea-level canal through a mountain range, to be dug below the level of a massive river that flooded every year…), completely ignored all of the massive problems facing his company, and made press releases about how well everything was going right up until the day before the company was finally bankrupt. As a result, none of those huge problems got solved.
When the Americans finally stepped in 15 years later, they too made the mistake of appointing bureaucrats to run the project. The result was a shambles. Eventually President Roosevelt simply ignored Congress and appointed an individual to run the project. He was a railroad engineer named Stevens. Stevens was the first to realize that the real logistical problem to solve was not actually digging up the dirt, but disposing of it. The French had famously used steam shovels to dig the canal as fast as possible, just as they had in Suez. But once the dirt was loaded into train cars and carted away from the dig site, they used teams of men with shovels to empty them. Stevens calculated how fast the dirt would need to be loaded and unloaded, and set up a system of trains that could carry any quantity of dirt any distance, while loading as quickly as possible at the dig site and unloading it just as quickly at the dump site. Once he knew the numbers and had the system built, he could track exactly how quickly each train was unloaded and know which teams were working efficiently and which needed training to avoid falling behind.
Another good one by the same author is _The Wright Brothers_. It’s shorter and perhaps not as detailed as _The Path Between the Seas_ (but then it only took them 4 years while the canal needed 33), but it focuses on the actual tasks undertaken by the Wrights as they developed their first few airplanes. They first used gliders to test their wings and the control mechanisms. Then they built a wind tunnel to get accurate data about the lift and drag of a wing under specific circumstances. Then they built an engine lighter than any in use at the time. They designed their own propellers too, since nobody they talked to knew how to design one. Even for boats, the engineers who designed them just used heuristics and guesses and rules of thumb rather than any scientific processes in their work. The first few propeller shafts that they built turned out not to be strong enough and were destroyed. But they were methodical and driven, so they solved each problem one at a time until they had both a working airplane and a working knowledge of how to fly it.
Mastery by Robert Greene also mentions in a few pages this story about the Wright Brothers (they started from their expertise in bicycles, that’s how they got planes right) and it’s def a book the OP might be interested in.
I think it's deeper than bicycles. They never went to college or university (though their sister did), but they were extremely well read and researched everything they did. Their first business was a weekly newspaper and printing press. They built the press from scratch using scavenged materials, and they wrote most of the newspaper articles themselves. They sold advertising and set the type. When they went into bicycles they were again the entire staff. They sold to customers, repaired bicycles, and manufactured their own model of bicycle right in the back room of their shop. And now they were the ones making up advertising slogans and buying space in the papers.
They were raised with the understanding that they could learn anything, build anything, discover anything that they set their mind to. And once they had set their minds on flight it was only a matter of time.
When the Americans finally stepped in 15 years later, they too made the mistake of appointing bureaucrats to run the project. The result was a shambles. Eventually President Roosevelt simply ignored Congress and appointed an individual to run the project. He was a railroad engineer named Stevens. Stevens was the first to realize that the real logistical problem to solve was not actually digging up the dirt, but disposing of it. The French had famously used steam shovels to dig the canal as fast as possible, just as they had in Suez. But once the dirt was loaded into train cars and carted away from the dig site, they used teams of men with shovels to empty them. Stevens calculated how fast the dirt would need to be loaded and unloaded, and set up a system of trains that could carry any quantity of dirt any distance, while loading as quickly as possible at the dig site and unloading it just as quickly at the dump site. Once he knew the numbers and had the system built, he could track exactly how quickly each train was unloaded and know which teams were working efficiently and which needed training to avoid falling behind.
Another good one by the same author is _The Wright Brothers_. It’s shorter and perhaps not as detailed as _The Path Between the Seas_ (but then it only took them 4 years while the canal needed 33), but it focuses on the actual tasks undertaken by the Wrights as they developed their first few airplanes. They first used gliders to test their wings and the control mechanisms. Then they built a wind tunnel to get accurate data about the lift and drag of a wing under specific circumstances. Then they built an engine lighter than any in use at the time. They designed their own propellers too, since nobody they talked to knew how to design one. Even for boats, the engineers who designed them just used heuristics and guesses and rules of thumb rather than any scientific processes in their work. The first few propeller shafts that they built turned out not to be strong enough and were destroyed. But they were methodical and driven, so they solved each problem one at a time until they had both a working airplane and a working knowledge of how to fly it.