Some people revere Jean-Luc Godard, others obsess over finding subliminal messages in the films of Stanley Kubrick. Much as I love the work of these masters, the filmmaker whose work I tend to think the most about is John Hughes. From the iconic films he both wrote and directed (The Breakfast Club, Planes, Trains, and Automobiles) to those he wrote and produced (Home Alone) the movies Hughes helped create between 1984 and 1991 are all classics in my eyes. (Even I will admit that after that his work gets really iffy: 101 Dalmatians, anybody?) I grew up laughing at his films, and when I eventually found myself homesick for the Chicagoland area I knew growing up, I’d revisit the copies of his films that Istillwatch on a monthly basis. Eventually I’d come to the realization that while David Kamp rightfully called Hughes the “Sweet Bard of Youth” in his 2010 Vanity Fairpiece on the late director, I came to realize—thanks in large part to the distance between me and the place where I grew up—that Hughes was something even more; that he was to Chicago and its northern suburbs what Woody Allen was to Manhattan in the seventies and eighties. He made being from those bland suburbs seem more interesting than I recalled.

As all my friends know, if you engage me in a conversation about John Hughes, I’ll probably say, But his films are about so much more than just white suburban teenagers in the 1980s. And then I’ll talk your ear off about how he created stories about class conflict and rebelling against authority, and how, incidentally, many of his movies were shot in and around the Chicago suburbs where I grew up, from the Winnetka house Kevin McCallister protected from Joe Pesci and Daniel Stern, to the various houses in Evanston, Highland Park, and Skokie that you see throughout Sixteen Candles. I knew so many of these places and related so much to his work that I feel like I’m an authority on what I call “Hughes and the Hughesque”; so much so that, for five years, I was convinced it was my destiny to write the definitive book on the man and his work. And it was in those years that I probably learned more about myself than my subject, most notably the fact that fate’s plans for me did not include writing the biography of John Hughes.

A biography—a truly great biography—is a herculean task; it demands clear direction, intense research, and an ability to combine all the newspaper clips, interviews, and everything else you’ve read into something that captures the magnetism that drew you to the project in the first place. I ignored this aspect of the project. Thinking I was born to do this one important thing kept me from focusing on the hard work that getting that one thing done would require. I knew where I was going, but I hadn’t given much thought to how I was going to get there. My files bulged with magazine cutouts. I slogged through interview and drafts, but nothing really came together. I kept telling myself I was making progress, when, in fact, I was Don Quixote without a Sancho Panza, tilting at North Shore windmills that weren’t even there.

“You aren’t a movie critic. You didn’t know him personally,” one friend said after I revealed my plan over drinks, “and frankly, nobody even knows who you are.” I was, at this time, about to embark on a road trip to Pennsylvania to find the reclusive former model and actor, Michael Schoeffling, who played Jake Ryan in Sixteen Candles. “You’re wasting a lot of time and money you don’t have,” my friend concluded as he picked up the check.

I recognized these challenges, but initially I simply saw them as the obstacles between my destiny—the necessary hurdles on a hero’s journey. I started out undeterred and turned down freelance jobs in order to chase my dream, but as time marched on, my confidence began to erode. I failed to track down Schoeffling. Letters and e-mails I sent to even the most minor Hughes bit players went unanswered. After months, my notebooks were filled with only scribbles. I’d go to press junkets featuring people that acted in his films, but couldn’t get a minute of their time. I tried to question Ally Sheedy when she came into the coffee shop I was working in at the time but was told to get back to work. I even found myself standing next to Andrew McCarthy at an event, but I was too slow to introduce myself and he walked away before I could even open my mouth to speak. The thought of giving up slowly crept its way into my mind, no matter how hard I fought to ignore the impulse.

Then, one day an e-mail came from an old friend of a friend: “You’re trying to write a book about John Hughes? I can introduce you to him. When will you be in Chicago next?” I immediately replied that I’d find the next, cheapest plane ticket and be there as soon as humanly possible.

With hindsight, this was clearly a bad idea. By this time, I’d spent money flying out to Los Angeles to chase leads, wasted reams of paper printing even the most miniscule factoid, and even lost a part-time job because I went to an event in search of Matthew Broderick instead of showing up for my shift. Now here I was spending more money I didn’t have because somebody I hardly knew said they could introduce me to Hughes.

A few days before my trip to supposedly meet the director in Chicago, John Hughes suffered a fatal heart attack while visiting Manhattan. I was sitting on a couch just enjoying the day when I received a text message, possibly the coldest way to find out one of your heroes has died, informing me of the news that, not only had Hughes passed, but he was a few miles away from me in his last moments. I was devastated, not only because my favorite director had died so young but also because I’d never have the chance to ask him for his blessing. But I still took the flight to Chicago and met with the guy that had been planning to introduce me to Hughes. If my dream had come to an end with Hughes’s passing, I figured the city by the lake we both loved so much would be an appropriate place to mourn.

I showed up to the coffee shop wearing my Detroit Red Wings hat. I only recall this because as Chicagoans, Hughes and I shared a mutual love of the city’s rival hockey team, something his son wrote about for Grantland. After a few minutes of small talk with the friend of my friend, we started discuss what a bummer Hughes’s passing was. I said something like, It must have really sucked since you knew the guy. There was silence, then I remember a chuckle. “Oh, I didn’t actually know him,” he told me when we met up for coffee. “I just see him around town a lot, I think a few times at the grocery store. I figured we could track him down together.”

I returned to my Brooklyn apartment totally dejected, still with nothing to show, five years older. I didn’t write the ultimate John Hughes biography. And yet, this was not, in the end, time wasted. Like many of my generation, I was raised on feel-good mantras like “Do what you love and the money will follow,” but nobody ever emphasized the value of progress or self-awareness. Nobody ever taught me to look at my work and know when to give up the ghost. It was a lesson I needed to learn. It took me months to get over the fact that I wasn’t cut out for the job I had basically believed to be my divine right. But when I did, I became a more cautious writer. I focused not only on inspiration when beginning a new work, but also on logistics: Could I do this? How would I do this? And while my utter dedication is perhaps in some sense an admirable trait, one necessary to get anywhere in the world of constant rejection letters that is being a writer, it’s not just okay to give up on a dream; sometimes it is the best thing you can do, and unlike Jake Ryan surveying the ruins of his parents’ house after a wild party, saying, “What a disaster,” I can honestly say not writing theJohn Hughes biography stands as one of the most important life lessons I’ve ever received.