At 3am last Wednesday, I caught myself in an internet consumption k-hole after clicking a link to a new song by Rodrigo Amarante, a Brazilian musician who was a member of the band Little Joy. The smooth timbre of his voice was so distinctive it immediately brought me back to 2008 when I listened to the Little Joy album obsessively.

Back then I was in my final year of university in Montreal, living in a primarily French-speaking neighbourhood with an Austrian roommate and feeling generally worldly and grown-up. To top it off, I was madly in love with an Australian guy I’d met on exchange in Melbourne, and we were trying to make it work, which I thought was mature.

I clicked link after link, listening to one song, then another, in a sort of YouTube-fuelled time warp. Little Joy was so emblematic of that year that I wondered whether it would be possible to boil other years down, extract their essence, solely based on the music I had listened to. That’s when I decided to try to make the playlist: one year, one defining song, from 2001 to now. The soundtrack to my post-pubescent life.

I say try, because I hadn’t made a playlist in ages, and I wasn’t sure that I could find a song for each year that would be able to transport me the way that listening to Little Joy did. Surprisingly, the first few years were easy. I knew that Is This It by The Strokes had to be on it, and John Mayer was deeply involved in the heady days of my early teens. The most recent years were also relatively simple to pin down, because I had listened to music almost non-stop in the lab while working on my PhD. All I had to do was conjure up the image of sitting at a microscope and I could picture myself looking at my phone and choosing to listen to Great Bloomers again, and again.

But what came in between was hazy. I sat and made notes about what had happened between 2003 and 2007, trying to decipher what had been important to me, who was important to me, what I had done. I finished high school, I’d been involved in theatre, I moved away from home for the first time. But none of those triggers seemed to work. I couldn’t remember who I was.

As I thought about it more, it started to make me squirm. I had a creeping suspicion that the reason I couldn’t remember was because I hadn’t really been myself. I had spent so much of that time imitating my peers, wanting to be liked, and trying desperately to eschew my deep-seated earnestness for the sort of detached elegance that I attributed to the girls in my class who never seemed to sweat in gym—the girls with shiny blonde hair who went to parties with older guys and always wore the perfect Roxy sweatshirt. So I started listening to music that I thought would lend me some of their coolness. I became a leading expert on Jack Johnson to try to get closer to a boy I liked. I dyed my hair blonde.

Then I went to university. I started wearing skinny jeans. I dated a boy in a band who told me I had to listen to The Smiths, and I did. I made lasagne. I made creative, brilliant friends. And, along the way, I started to grow up. When I listen to 1234 by Feist, I picture the first summer I spent doing research in Toronto, pounding the hot pavement downtown to get to the hospital, feeling excited to be working on a project that was so much bigger than myself.

One of the songs that still makes me happiest is Go Outside. I heard it for the first time on a music blog in 2010, and it quickly rose through the ranks and into my Top 25 Most Played. 2010 was a big year. I broke up with the Australian, chose a PhD project that I was passionate about, and started dating one of the kindest people I have ever known. When I played Go Outside for him for the first time, he couldn’t stop giggling. For him, it brought to mind the image of kids in a row boat, paddling in time. Every time the song played, we would both start pretending to row, and laugh hysterically.

My relationship with this playlist is complicated. Its mere existence makes me feel vulnerable, like I’ll be outed for having the wrong music in my life. So many of the songs make me cringe that I doubt I’ll ever be able to listen to it from start to finish.

But the process of making it gave me the chance to trace the path to where I am today. In spite of my best efforts, I’m still painfully earnest and no amount of mimicry can change that. Over time I’ve learned to embrace it. And now, I step to the beat of my own drum. Or row, as the case may be.