How have astronomers and physicists responded to the challenge of getting “beyond the atmosphere” in the past century or so, and how did they go about making choices in how they did so? This case study examines a particularly poignant example of how an astronomer’s practice changed in the 1950s when that astronomer, Princeton theoretical astrophysicist Martin Schwarzschild, made a commitment to utilize newly improved balloon technology to answer a specific question arising from his own research agenda. Here we follow Schwarzschild’s efforts, which led initially to success, and then examine how, bolstered by his department Chairman, Lyman Spitzer, he built upon that success to generalize the new technology to try to provide a capability that might address a wider range of questions, and, aiding Spitzer’s plan, provide a stepping stone to an eventual Large Space Telescope. How he fared in making this decision reveals the challenges facing academic astronomers in the 1950s who attempted to send their telescopes aloft. It also reveals the complexities of taking on such projects, complexities that were unknown to the average mainstream astronomer.