Here’s a prediction I’m confident will hold true for those buying tickets to see “Flipside”: Most will initially find the director and narrator, Chris Wilcha, to be an annoyance. Between the Woody Allen-like intonation and the poor-poor-privileged-me routine, you may want to return to the box office and demand a refund — but, really, you shouldn’t. Bear with Mr. Wilcha.

The film begins as a documentary about 87-year-old Herman Leonard, a photographer who apprenticed under Yousof Karsh and went on to make a name for himself as a portraitist of jazz musicians such as Nat King Cole, Louis Armstrong, and Miles Davis. Leonard is sharp, sanguine, and aware that his days are numbered; he is, in fact, dying. Then, Mr. Wilcha pulls the rug out from under us in order to complain.

And complain he does. Taking us back to 1993, Mr. Wilcha explains, “I’m part of a demographic blip called Gen X. Irony is our language … we resent corporations or advertisers to sell us anything. Our moral code is as simple as it is unattainable: we will never, ever sell out.” 

The voice-over runs atop a compendium of scenes from Mr. Wilcha’s youth — we see him inhaling helium and cutting himself while shaving — interspersed with period reportage. A spindly punk song sets the tone.

“The problem,” the 22-year old Mr. Wilcha realized in short order, “… is that you can’t pay your rent by not selling out.” Sacrificing his integrity, he gets a job at the Columbia House CD & Tape Club doing, of all things, marketing. Dad, who we see entering Mr. Wilcha’s office, beams with pride: He’s thrilled that his son is gainfully employed. But, then, the elder Wilcha made a name for himself in marketing as well. 

This doesn’t prevent Wilcha the younger from filming while on the job. A lot of goofing off takes place, and disgruntlement is the norm amongst his co-workers. Culling footage from his tenure at Columbia House, Mr. Wilcha came up with “The Target Shoots First” (2000), a documentary about office life that went on to receive more attention than the filmmaker could have imagined. That proverbial 15 minutes of fame? It’s real.

Otherwise, Mr. Wilcha fell in love, got married, had children, and decided to make a go of being a documentarian. When Judd Apatow — the writer, producer and director behind hits like “Anchorman: The Legend of Ron Burgundy” (2004), “The 40-Year-Old Virgin” (2005), and “Funny People” (2009) — came calling, Mr. Wilcha moved all and sundry from the East Coast to the land of milk and honey, California. 

And then … life happened. The “making of” feature commissioned by Mr. Apatow for “Funny People” had its premiere on Comedy Central and was summarily consigned to “Bonus Features” purgatory. In order to pay the bills, Mr. Wilcha began directing television commercials. What do you know? He proved a dab hand at it.

Still, the documentary bug didn’t leave him. He started a film about a young woman with writer’s block, stopped short, and then began a feature on Flipside Records & Tapes, a vintage music store at Pompton Lakes, New Jersey. Mr. Wilcha worked there as a teenager. The boss, Dan Dondiego, is bemused by his former employee’s efforts.

Then, bemusement turns to ire. Mr. Wilcha up and leaves the humble environs of Pompton Lakes to take off on another tangent: working for Ira Glass on the television version of his long-running PBS radio program, “This American Life.” After two seasons, Mr. Glass pulls the plug on the TV show and Mr. Wilcha is, again, working for corporate America. Gen X-ers, it seems, can’t catch a break.

Yet they can catch some insight. As the film pinballs through the byways of a freelancer’s life, Mr. Wilcha meets some interesting folks — including cult TV attraction Uncle Floyd and television writer and producer David Milch, creator of “NYPD Blue” and “Deadwood.” Mr. Apatow reappears, now gone gray, and bears the ire of Mr. Wilcha’s mother for stealing away her son. Mr. Wilcha bears the ire of his father, who wants him to clean out his closet already.

Then, we’re back to Herman Leonard, now dead, and Mr. Dondiego trying to make ends meet. We meet a former flame of Mr. Wilcha’s — they used to fool around at Flipside, as if the boss didn’t know about it — and Mr. Milch is in an assisted living facility, having been diagnosed with Alzheimer’s. What emerges, through all this back and forth and countless abandoned hard drives, is a coming-of-middle-age story, the realization that though not all hopes in life are realized, life itself can create its own rewards.

So, yeah, be annoyed with Mr. Wilcha’s navel-gazing up top. As the older and, dare one say, wiser filmmaker would likely be the first to tell you, he deserves it. “Flipside” takes a bundle of exasperations and finds within them a measure of acceptance and gratitude. Not a bad denouement for a demographic blip.