IN AUGUST 2007, I rode a bus for 17 hours from Toronto to Chicago to cover the Lollapalooza music festival. I was 18 and had just graduated high school, and that I was able to somehow convince my editor, not to mention my parents, that I was capable of independently making this cross-national trip to cover one of the world’s largest music festivals without a laptop, smartphone or any significant interviewing or journalistic experience seemed to me like the unwritten sequel to Almost Famous.

The publication I was writing for was Music Blend, a now-defunct offshoot of CinemaBlend, which seems to have since become one of the web’s leading resources for movie news and criticism with over six million unique hits per month.

This was definitely not the case in 2007. We did modestly well, and our success culminated in scoring, in our first few months, one talented writer (JP Gorman, where did you end up?) a press pass to Bonnaroo, in Tennessee.

Gorman, who was easily our best in my 18-year-old eyes, reported back in real-time throughout the weekend, writing daily summarizes and capitalizing on my teenage jealousy.

(This is only a little relevant, but my closest friends had recently flown down to the Coachella music festival, in California—a trip I didn’t join for any number of reasons, not the least of which being that I don’t remember being invited or having the money. Anyway, I was jealous of them, too.)

So it was in May that I looked up other major music festivals and discovered that Lollapalooza was a) not too far from Toronto and b) within workable dates that summer. I first emailed my capable editor, Lexi Feinberg, who quickly secured me a press pass—that initial shock and elation still ranks among the most significant highlights of my journalistic career, as any journalist’s first media access is. (It’s kind of like the professional equivalent of your first kiss: massive astonishment followed by massive deflation, once you realize how much more work there is to be done.)

But despite my ticket being a lock, my friends were mentally and financially spent from Coachella. I was alone, and my newfound sense of maturity had devolved into fear.

That initial shock and elation still ranks among the most significant highlights of my journalistic career, as any journalist’s first media access is. (It’s kind of like the professional equivalent of your first kiss: massive astonishment followed by massive deflation, once you realize how much more work there is to be done.)

So, raised in adolescence on and by the internet, I turned to the Lollapalooza message boards. As it happens there were dozens of people in just the same situation, some offering car rides, looking to fill extra seats or cheapen hotel costs. For some reason I didn’t fully register what a hostel was at that point in my life, and possibly my parents drew the line there anyway, insisting on a proper hotel.

The dude I found was named Ealon Gross. Ealon was in his early 20s, disturbingly pale with a face laden in baby fat. I remember Googling his name to find his MySpace, which told me he was in his early 20s, from St. Louis and an enormous Dave Matthews fan. (“I’ve seen them 27 times,” he’d later beam.) At the festival he wound up meeting his female friend whose name I remember starting with K, and whom I’m hesitant to call his girlfriend because the two of them shared this bizarre sub-dom friendship that always teetered on romance were it not painfully obvious that K wasn’t attracted to Ealon at all. He was also a pothead, which clashed somewhat with my never-wanting-to-smoke thing, and, of all the bands that performed that weekend (Daft Punk, Iggy Pop, Amy Winehouse, The Black Keys, Muse, My Morning Jacket, Interpol, Pearl Jam, Ben Harper; the list was exhaustively awesome), he was most excited to see Juliette and the Licks, Juliette Lewis’s short-lived pop-punk band.

We made an online agreement to split a hotel room 40 minutes away on the orange line of the L Train. I still remember very clearly riding in the late morning sunlight among the suburban Chicago businessmen, too wrapped up in the adrenaline of being in this foreign city to notice the length of the trip.

For a sheltered Jewish kid from suburban Toronto, Chicago was like Disney World. Its gorgeous above-ground train system seemed to me like something out of the 1950s; the abundance of coffee and doughnut shops, the ever-shadowing skyscrapers and the massive green oasis that is Grant Park, cultivated right in the heart of the city, screamed of being alive, of autonomy and individualism. No one could tell that I was an outsider, and so I lost myself in the crowd.

For a sheltered Jewish kid from suburban Toronto, Chicago was like Disney World. Its gorgeous above-ground train system seemed to me like something out of the 1950s; the abundance of coffee and doughnut shops, the ever-shadowing skyscrapers and the massive green oasis that is Grant Park, cultivated right in the heart of the city, screamed of being alive, of autonomy and individualism. No one could tell that I was an outsider, and so I lost myself in the crowd.

I entered the grounds with zealous professionalism, despite having interviewed only a band the entire weekend. The High Class Elite they were a New York-based glam-rock revival act that had formed shortly before and dissipated quickly after the festival itself.

I was excited, and after their morning slot on one of the festival’s smallest stages, I took them aside and asked them why they chose glam-rock. The lead singer, Franco V, stuttered, “Uh, well, I mean… that’s just, uh… you know… that’s… All my influences are… not all of them, but you know, where I’m at right now in life… I’m just feeling that the most.”

These guys had even less an idea of what they were doing than I did. I loved it.

I was “on assignment”, and therefore had no intention of drinking (even if I had been of legal US drinking age), but that didn’t stop my heart from racing when I discovered, later that day, that Budweiser had stocked cooler upon cooler of free beer in the press lounge area, loosely guarded by a single volunteer. I approached with so much trepidation that I must have looked underage, and distinctly remember the volunteer’s total disinterest as I helped myself to a bottle and quickly turned away, eyes wide, totally failing to suppress my grin of achievement.

Each night I returned to the hotel, unloaded my bags, reviewed my notes and photos, and wrote. I had no laptop, and the the hotel lobby’s dated PC didn’t have a word processor, so I would open up the Music Blend website and type my reports—ugly, clunky 2,000-word behemoths—straight into the system, sans spell-check or save button.

On the second night the computer froze and I lost everything halfway through. I went to bed at what seemed like the exhaustive hour of 1 a.m. that night, which now feels pathetic because every other journalist there probably went to bed no sooner than 4 a.m., after imbibing more and interviewing more and seeing more at the swanky club after-parties I didn’t even bother trying to sneak into.

On that second night, too, I returned so late to the hotel that Ealon had stayed up freaking out about my safety. Presumably out of some chemically-influenced desire to alleviate personal responsibility, he had called my mother in Toronto to tell her that, simply, he didn’t know where I was and he was going to bed.

Let me be clear: This is the worst possible thing to do to my mother. It still baffles me just to write it. It’s not like Ealon and I had spent any significant time together that weekend; we even left for Grant Park on different schedules, he at K’s behest and I with gusto way earlier. Any strong, independent and manly emotions I had developed were swiftly demolished by having to bring my mother down from her understandable hysteria about her teenage son’s well-being.

By Sunday night, I was ready jogging and worming through legions of stoned Pearl Jam fans to catch my 11 p.m. bus back to Toronto. I’d skipped my nightly report but assured Lexi that I would write at least three summaries later. My notebook was full and my camera batteries near death.

The only thing keeping me in Chicago was Ealon, who had wanted to bid me a proper goodbye, so I waited at the decided-upon water fountain for a half-hour, until 10:15, ultimately needing to borrow someone’s cell phone to ask him where he was.

“Oh, hey man. I’m at McDonald’s with K. Where are you?”

“I’m at the fountain. We were supposed to meet here a half-hour ago.”

“Oh, really?”

That, without a note of apology in his voice. I ran like hell to catch the bus. Ealon and I haven’t spoken since, though Facebook tells me he’s been a server at a St. Louis AMC since October 2012.

I can barely recall the ride home for all the exhaustion. There was a feeling of completion there, but also of certainty. Nothing seemed remarkable about any of this, certainly not as remarkable as anything that happened in Almost Famous. I was a man with a job.

The bus carried me through the night, back to Canada, back home. I went to work the next day.