Midway through his second year as an engineering student at the University of Wisconsin in Madison, Charles Lindbergh decided to indulge a long-held curiosity. He was determined to learn how to fly a plane. His quest led him, on April 1, 1922, to Lincoln, Nebraska, the site of Ray Page's Flying School. Before so much as sitting in the cockpit, Lindbergh learned all he could about the mechanics of the plane he would be flying. Finally, on April 9, Lindbergh took to the sky for the first time. His first flight proved to be a transcendent experience: "...Trees become bushes; barns, toys; cows turn into rabbits as we climb. I lose all connection with the past. I live only in the moment in this strange, unmortal space, crowded with beauty, pierced with danger," he later recounted in "The Spirit of St. Louis." Unfortunately, Lindbergh's new-found enthusiasm for flight was not shared by his flight instructor, Ira Biffle. "Biff," as he was called, had been so shaken by the flying death of a good friend that he began to dislike flying. More and more frequently he concocted some excuse for not taking to the skies. Lindbergh grew frustrated; a flight instructor who doesn't like to fly was not the best teacher. Moreover, Biff Biffle was the only flight instructor at Ray Page's School. To make matters worse, the school's only training plane was being sold.

The man buying Ray Page's plane was Erold Bahl, a no-nonsense aviator determined to make flying a respectable profession. In 1922, aviation was still in its infancy and was regarded by most with a mixture of awe and suspicion. The practice of "barnstorming" had been devised to impress people with the skill of pilots and the sturdiness of planes. The name derived from the fact that these air shows took place in open rural fields. Barnstormers would fly over a region and drop leaflets down upon the locals announcing when the next air exhibition would take place. Daredevil stunts were promised, as were five-dollar plane rides. "Slim" Lindbergh was hired by Erold Bahl as an assistant. As a promotional stunt, Lindbergh volunteered to climb out onto the wing and wave to the crowds below. This practice was known as wing-walking. Lindbergh soon determined that in addition to wing-walking, he wanted to learn the then novel practice of parachute jumping. For years, he had been tormented by nightmares of falling from a great height. Parachuting, he was certain, would allow him to face down that fear. For instruction, he went to Charles Hardin, who, along with his wife Kathryn, designed and demonstrated parachutes. On his very first attempt, Lindbergh barely, but successfully, pulled off a "double-jump." This stunt involved wearing two parachutes, attached to each other. After the first chute opened it was cut off, allowing the jumper to free-fall. Then, the second chute would burst open just before the jumper slammed into the ground. The crowds loved it. Hardin taught Lindbergh all the finer points of parachuting, including how to land in almost any condition and avoid injury. It was a skill that would serve Lindbergh well throughout his life as an aviator.

Lindbergh's reputation on the barnstorming circuit grew when he teamed up with Harold J. "Shorty" Lynch in the summer of 1922. During a four-month tour of Colorado, Wyoming, Kansas, and Montana, Lindbergh did a little of everything: parachute jumping, wing-walking, and mechanics. Leaflets rained down on small towns and rural hamlets announcing that "Daredevil Lindbergh" was going to be in the area. Crowds were entranced as Lindbergh stood on a plane's wings as it did a loop-to-loop, or hung from its underside, seemingly, by his teeth alone. As the months wore on, however, Lindbergh decided he wanted to be the one flying the plane, not just performing the stunts. In April 1923, he purchased his first plane: a World War I surplus Curtiss JN-4D, or "Jenny." The fact that he had never flown a Jenny before, or soloed in any plane, for that matter, didn't dent his confidence.

The Jenny was considered a light and maneuverable plane. But it also had a reputation for being under-powered and slow. And, to make matters more interesting for the pilot, it had no brakes. To make up for the Jenny's shortcomings, Lindbergh was forced to develop exemplary piloting skills. As a stunt flyer, Lindbergh soon mastered the whole routine: barrelrolls, spins, and dives. His mother, Evangeline, accompanied him on a ten-day barnstorming tour, dropping leaflets out of the cockpit as Lindbergh buzzed the fields and towns below. Barnstorming, while exciting and glamorous, proved to be a difficult way to make a living. To make ends meet, Lindbergh was forced to take jobs as a flying instructor, handyman, and gas station attendant. By 1924, Lindbergh was looking for other ways to put his flying skills to use.