As 1939 gave way to 1940, retirement festivities for Straube elided with the usual toasts for his birthday. Blissfully isolated in Garmisch, he began the daunting project of responding to the outpouring of goodwill. “For your faithful remembrance receive my most heartfelt thanks,” he wrote in a note to his longtime friend Carl Boos, “and maintain this kindness for me also during those years in which I, far removed from singing and playing, will have to prove my existence like St. Francis in poverty.” Francis was hardly the go-to role model for someone who had wrangled as long over money and influence as Straube had done. But in another respect, the image well conveyed the watershed at which he found himself. Nearly a half century had passed since his apprenticeship with Reimann, and for the first time since then, he could ponder life from a vantage point emancipated from the relentless rhythm of church music. Already the previous July he had remarked to Hertha that in retirement, his new activity would be “above all not the sort of work that, cost what it may, has to be done over and over again within seven days!” Now he could afford to think in a longer arc, and he fell into philosophical flights of fancy about the vanity of human striving and the uncertainty of the future. “The separation from musical work has not been difficult for me,” he reflected that winter to his friend Otto Grüters, “since actually it was the same, year in and year out, and required the repeated engagement of all my energy and time. But was it worth it?” he asked. He continued candidly, replying to his own question: “The answer is doubtful for me. The separation from the boys has hit me harder, because the relationship to young people is liberating for an aging man, and that's profitable.” To Grüters's point that Straube had always achieved highly, he countered, “Ah, my dear, I was still young then and believed in myself, and I lived under the happy conceit that my work was worth something. Today I no longer possess the former, and I’m very skeptical of the latter.