The most rewarding and terrifying creative challenge you can set for yourself is creating a high volume of new, unique, high-quality content on a quickly rolling deadline. I know this because 15 years ago my friends and I created Cru Jones Society, a daily humor blog that featured at least one new long form piece each weekday, a weekly interactive prompt for readers to respond to that was curated into its own post, and an aggregated news roundup at the end of each week that was designed to be an easy way to outsource content generation, but in reality was the most time-consuming damn thing to write, ever. Also probably the most fun.

That’s why every weekday for the next 10 weeks I am posting a brand new long form essay on Jon of All Trades as part of my brand new series: JOAT 50 Song Countdown. If you’re reading this, you probably already know I like writing lists, I love music, and that I owe the vast majority of my professional success to my skills as a writer.

I have ranked and written about my 50 favorite songs of all-time. From Adele to Zac Brown Band, Patsy Cline to Plasma Canvas, Ludacris to Rise Against, this series offers a personal essay about the 50 songs that hit me the absolute hardest.

Full disclosure: I’m no music critic. I know fuck-all about music theory, so you can rest assured these essays are deeply personal, and any legitimate music criticism is incidental and accidental. Put another way: You don’t have to be a music expert either to enjoy these. Basically, if you like the way I write, my strong suspicion is that you’re going to enjoy these essays immensely. These essays are about me, first and foremost. Songs are a skeleton key to memory, and my favorite songs are almost always already linked to many of my favorite memories.

There’s a line in the movie High Fidelity where Rob (played by John Cusack) tells the audience that he and Barry (played by Jack Black) decided that “it doesn’t matter what you are like, what matters is what you like. Books, films, records, these things matter. Call me superficial. It’s the fuckin’ truth.”  For better or worse, our taste defines us.

So here I am. I have been a paid creative professional for more than 15 years, but I’ve been fighting burnout. I created an ambitious podcast format that didn’t go exactly as I hoped and I’m still reeling from it. I’m prosperous, but stagnant. I’m great at what I do, but bored. How to solve?

As I sit here writing this piece to launch this insane series, I have completed roughly 1/3 of the pieces that will comprise this series. Even now, with that runway, I feel intense fear of missing my deadlines and failing to meet the arbitrary goals I have set for myself. That might seem silly, but here’s the thing: I hope my shit matters enough that if I fail, you, dear reader, judge me for missing deadlines, if I do. Because I am intensely proud of what I’ve written so far, and think, hope, and expect that you’ll enjoy what I’ve written too.

I hope you enjoy following along with this project because I have found deep fulfillment writing it for you. Whether your feelings about any given song I love are good, bad, or indifferent, I hope you’ve found a new level of appreciation for the art in your own life. Leave me some feedback if you feel compelled to about any of these songs and please share with your friends on the socials. More than anything, this series is a tribute to the impossible miracle of artistic creation and the invisible connection it creates between strangers. We literally never know how our work touches others, which is the most beautiful reason to just create art for its own sake.

Come back Monday as I kick off this series with the first of 50 essays coming at you over the next 10 weeks. Hope you enjoy it!

Up first: The many ways being 17 feels.