The narrator of T.S. Eliot’s “The Love Song of J. Alfred Prufrock,” perhaps the greatest lament of the middle-aged man in all of Western literature, complains that he has “measured out my life with coffee spoons.” Chris Wilcha, the director of the new documentary Flipside, has measured his in abandoned hard drives. The movie, which had its world premiere at the Toronto International Film Festival this week, is a patchwork quilt of the documentaries Wilcha has begun and abandoned over the past 20 years, on subjects ranging from Ira Glass to the legendary jazz photographer Herman Leonard. But it’s also a chronicle of the success that bred that string of failures, and the attempt to reconcile what his life has become with what he thought he wanted it to be.

Wilcha is best known for The Target Shoots First, the autobiographical documentary he shot while working at the Columbia House music club—the one that used to reel in new members by offering 12 CDs for a penny—in the mid-1990s. As a self-proclaimed product of Generation X whose first job was working in a record store, Wilcha was deeply ambivalent about joining the ranks of the corporate conglomerates that the punk bands he played in and loved considered their mortal enemy. (Target has never been officially released on video, owing to its use of clips from the band that personified the tension between anti-corporate ethics and mainstream success: Nirvana.) But as he reflects in Flipside some 30 years later, he quickly discovered that “you can’t pay your rent by not selling out.” Hired into the marketing department at the age of 22 after graduating from New York University with a degree in philosophy, he found himself translating Gen X tastes for his older co-workers—one meeting involves determining whether the term “heavy metal” has become passé—while being given increasing authority over the writers and artists who create the company’s all-important catalogs. Even as he grows more adept at wielding his power over people many years his senior (in one painful exchange, a thirtysomething writer processes the humiliation of Wilcha kicking him out of a meeting), Wilcha grows increasingly convinced that he is on the wrong side of the managerial–creative divide. So it’s a little surprising to learn from Flipside that, after Target became a minor sensation and Wilcha won an Emmy for the TV version of This American Life, he has spent most of the past 15 years directing commercials. “I started the decade as a filmmaker,” he reflects. “Now I’m a salesman.”

The Target Shoots First is not only a generational document but a technological one, a product of the moment when collating video diaries of everyday life became accessible to anyone who could afford a video camera. (See also the first episode of Telemarketers, which is built around smeary standard-def footage of the drudgery and debauchery in a New Jersey call center.) Flipside, by contrast, emanates from an era when the standardizing of digital video collapses every moment into an eternal present. Unlike the ancient-seeming clips from the last millennium, the footage Wilcha shot of Leonard—whose iconic images of Dexter Gordon, Billie Holiday, and many others are instantly recognizable, even if he is not—almost 15 years ago isn’t noticeably distinct from the stuff he shot last year. The timelessness of digital video underlines Wilcha’s account of how, especially in the context of getting married and raising a family, a decade can go by in a flash, and suddenly your side hustle has turned into your main gig. But it might also contribute to the sense of permanence that has allowed so many of his projects to accumulate unfinished, the shelves filled with portable hard drives, the file drawers bulging with Hi8 tapes and CD-Rs. That footage might never decay, but the people captured on it do, as does the person they entrusted with telling their stories.

That might be why Wilcha frames Flipside around his relationship to his local record store, where as a teenager in the 1980s he often opted to get paid in music instead of cash. Flipside Records has certainly seen better days (as, from the looks of it, has its hometown of Pompton Lakes, New Jersey). The shoebox-shaped storefront is crammed floor to ceiling with worn LPs, with aisles barely wide enough to squeeze past another browser, and the days when owner Dan Dondiego could take on any kind of a staff seem to be long past. Wilcha’s abortive attempt to make a movie about his formative teenage haunt seems to weigh on the filmmaker particularly heavily, given how it might have helped revive the store’s ailing fortunes. And yet his attachment to it also seems to weigh him down. Like the closet in his childhood bedroom, filled with an indiscriminate mixture of heirlooms and random junk—a copy of Erik Barnouw’s history of documentary film sits beside a barf bag from his first airplane flight—Flipside’s bulging bins overflow with more history than one person could ever absorb, which begins to feel like more of a burden than a comfort. Judd Apatow, who first lured Wilcha to Los Angeles to shoot a making-of documentary about Funny People, says that he’d lose a piece of himself if he got rid of his concert T-shirts from the 1990s. But for Wilcha, pruning his archives, both filmic and personal, turns out to be just what he needs, a way of focusing on what he’s accomplished rather than what he left undone. Given that he’s got a stable family and a job that probably pays pretty well, it shouldn’t be that hard to count his blessings. Yet he has to let go of a particularly Gen X hangup, the idea that a person in their 50s should be held to a 20-year-old’s idea of the ideal life.

Wilcha lets it go, in part, by selling off his old records and tapes. (The CDs that Columbia House sold for fractions of a cent have gone back to being near-worthless.) But instead of condemning his once-precious possessions to molder on Flipside’s shelves, he sells them to a new, competing store, a spare, well-lit enclave where he’s surprised to find that his lowly cassettes have become prized artifacts for a new generation.

It’s the same discovery made by Hirayama (Koji Yakusho), the main character in Wim Wenders’ Perfect Days, a Japanese toilet cleaner who plays tapes of vintage rock in his van as he watches the Tokyo skyline slip by his windows. (The movie, which has been selected as Japan’s Oscar submission, will open later this year; Flipside is currently seeking distribution.) Hirayama’s fondness for reading Faulkner before he turns in at night suggests an inner life belied by his lowly occupation, but the movie doesn’t condescend to the toil of a physical laborer. He treats each public toilet he cleans with methodical care, using a mirror to check that even unseen corners are cleaned, and losing himself in the ritual of work. His life is solitary and orderly, but not empty. He savors the small pleasures, like the farewell wave from the lost child he guides back to his mother, or a woman’s laugh when he shows her how to work a transparent stall’s polarized doors. Wenders’ shots linger on what D.W. Griffith called “the wind in the trees,” the poetry of everyday life that movies can capture so well, even if they rarely bother to.

When Hirayama’s teenage niece unexpectedly comes to stay with him—we haven’t even suspected to that point that this taciturn man even has a family—he’s unsettled by the disturbance to his routine, and he bolts like a scared rabbit when she starts undressing for bed. But she marvels at the strange plastic rectangles he slips into his tape deck, even if he’s so out of touch that when she asks him if she can find the music on Spotify, he thinks it’s a store. A younger co-worker hips him to the fact that the cassettes are worth money, some upwards of $100 apiece. The movie never explains what might have triggered this vogue—Wenders himself says he’s mystified by it, although he enjoys watching his grandchildren get into listening to music offline—but there’s a hint in the tactile satisfaction of Hirayama’s daily routine. When he takes his niece to a favorite park, they both sit and point their devices toward the sky, but they’re facing in opposite directions: She’s using her cellphone to take a selfie; he’s using a film camera to take a picture of a tree. As Herman Leonard explains in Flipside, shooting on film forces you to pick a decisive moment rather than choose among a string of them, and to live with the result no matter what your intentions were. Like Chris Wilcha’s closet, Hirayama’s is also filled with boxes, each holding snapshots from a different month, but he goes back and culls them, tearing up the photos he’s not pleased with so what he’s left with is a chosen record, not a muddle of junk.

Cassettes, the writer Rob Sheffield said in the movie Cassette: A Documentary Mixtape, are “marked the way the human body is marked, by the space and time it passes through.” You can tell one that’s been played hundreds of times from one that’s never been out of its case just by holding it in your hands. The very imperfections that led earlier generations to shun tapes makes them attractive to a new one, for whom inconvenience and decay are like rare ingredients used to spice up a familiar dish. Chris Wilcha is haunted by the possibilities he never realized, and although Perfect Days never gives us more than a hint about Hirayama’s past, the tears that flood his eyes in one extraordinary close-up suggest he’s known both the joy and the pain that life has to offer. They’re marked by their survival, the distance between then and now, and the scars and the regrets are part of what makes them who they are. The longer they run, the less perfect they become, and the more uniquely themselves.