It was really hard to just pick one Rilo Kiley song to share in this series.

It would be hard to pinpoint even a single album to share, because all of them made a meaningful impact on me in high school and college.

One of my least favorite questions to answer is “what is your favorite [x]?”

It doesn’t even matter what X is. Color. Desert. TV show. Vacation spot.

I haven’t been able to answer this question in years because I instantly become paralyzed by the question’s parameters.

Favorite musical artist?! In what context?

My favorite artist to work out to is Eminem.

My favorite artist when working through depression is EKKSTACY.

My favorite artist when I’m hanging out with my kids is Bluey.

My favorite artist when I’m in the zone at work is Daft Punk.

But if you are asking me to have to pick a that felt the most constant in my life, part of nearly every day since high school?

For me, that’s Rilo Kiley.

More Adventurous was among the first CDs I bought online. I still have a 128kbps rip in my iTunes library. It has a little skip during A Man / Me / Then Jim which now feels weird to not hear when I listen to the album on iTunes or vinyl.

More Adventurous was the soundtrack to the road trip Rob and I took sophomore year of college to Iowa and Madison. We got lost using the iPhone 3Gs’s GPS technology, ending up in the town of University, Iowa instead of the University of Iowa. Portions of Foxes kept us laughing as we whipped the U-turn to head back in the right direction.

The Execution of All Things was a constant during my freshman year of college, a comforting soundtrack during a rather lonely and scary time in my life. The Good That Won’t Come Out puts me right back in the tattered light rail seat that carried me to my early morning lectures for a rather challenging math class. With Arms Outstretched was one of the first songs I learned on the guitar.

The self-titled EP ends with a song called Gravity, sung with a bit of a country twang. Rob and I imagined it being sung by an 1840s prospector. It would occasionally come on shuffle when we’d be carpooling back from a sales meeting in the early days.

Under the Blacklight disappointed me when it first came out. I bought it on release day after a Tuesday shift at Best Buy. I threw it on in the car and couldn’t believe how processed and over-produced it sounded. In hindsight, I rather enjoy Silver Lining, which is about the most accessible entry point I can recommend for the band.

I saw Rilo Kiley for the first time during the tour for that album. The songs from the album were way better live.

I saw Jenny Lewis again a couple months ago when she came into town. She didn’t play any Rilo Kiley songs, which feels right for her. Her solo stuff is pretty good, I really enjoy songs like She’s Not Me and Red Bull & Hennessy and Just One Of The Guys.

But I would love to hear those other songs live again someday with the whole gang.

The University of Minnesota’s Twin Cities campus is massive.

When I went there, I was told it was the third largest university in the country based off square footage.

The Minneapolis campus alone has an east bank and a west bank, connected by a bridge with a top that is for pedestrian use only.

I used to live in the Como neighborhood. It was a 30 minute walk from my house to the classes I had on the west bank. I could also take the 3, which made it more like a 5 minute bus ride.

My preferred method of transportation, which I would use up until the snow made it infeasible, was my bike.

When I moved down to campus for the first time, my dad wouldn’t let me bring my Specialized bike that he got for me in seventh grade.

Instead, he insisted on buying me a $99 Schwinn bike from Target. It weighed a ton and the brakes weren’t great, but it certainly got me from A to B.

I recently got rid of that bike, and it felt like getting rid of a car. In both cases, I usually get overcome with emotions such as grief from nostalgia, guilt from abandoning something I knew so intimately, and gratitude for being able to get so much life out of it.

One of the first times I put that bike to use was to attend a class on the west bank.

When I arrived at the beginning of the Washington Avenue Bridge, I was greeted by a spectacular view of the Minneapolis skyline.

The combination of that skyline, the breeze, and the views of the river below forced this song in my head.

I started singing it out loud, unable to place where I knew it from.

After having the same moment play out over the course of a semester, it finally dawned on me that I knew that song from hours of riding my bike in Pokémon.

Pure joy. That’s what this song reminds me of.

Even this evening, when I rode bikes with my family up to try the new ice cream shop in town, I got this song stuck in my head.

It truly is the perfect song for a bike trip.

My buddy Lucas (the same one who told me about POTUSA) is always sending me heavier stuff to listen to.

This song in particular caught my attention right away, and it quickly became one of my favorite songs to rock out to. The rhythms are so complex that every subsequent listen is an opportunity to hear something new.

What makes me identify with music like this is the precision and order.

Plini, to me, is the epitome of coordination and process. The riffs are so intricate and detailed that it must require a ton of effort to ensure the musicians are playing the same piece.

Music like this is comforting to me because it feels like some order can be achieved even in the midst of complete chaos.

All this talk of precision gave me a realization: I’ve never been good at improvising with music. I don’t understand it.

If you want someone to sight read a piece and play it exactly as it’s written on page, I’m your man.

If you want to ask someone to solo in the key of G major, you’d be best sniffing elsewhere.

The best improv musicians I am aware from operate on a completely different plane than me. What they make doesn’t necessarily get pulled from their brains; rather, the music comes from their hearts.

That’s not to say that playing with precision is soulless. I take so much joy from being able to master a particularly challenging musical riff.

I just wish I could also get good at letting my heart take the lead from time to time.

I just met this girl a couple hours ago, and she’s clearly the coolest girl I’ve ever met.

One of the very first things she asked me after we met was if I wanted to see a magic trick.

She presents a deck of cards and asks me to pick a card.

Yes, she ultimately revealed my card.

Yes, it blew me away.

We start talking about Four Loko, which had recently been banned across the country. After doing a favor for a friend who paid me with a cardboard box filled with various malt liquors, I mentioned to her that I have some of the real stuff in my trunk.

I did have to warn her, though, that it was expired and had been sitting in the trunk for at least a couple days.

She didn’t care. We each grabbed one and slammed them.

After a couple more drinks, we decide to walk to Blarney’s, a bar that’s not too far from the Dinkytown home of our mutual friend whose sidewalk is now covered in shotgunned Four Loko runoff.

This was a random Thursday night in December. We both had stuff to do early the next morning. I had to film something for my internship. She needed to drive back to Wisconsin for a job interview.

But Blarney’s had exceptionally cheap Long Island Iced Teas.

And there was karaoke.

I don’t recall what she sang that night. I was too infatuated by her “who would win in an animal fight” discussion, of which you could tell she clearly had deeply considered these outcomes already.

I do remember trying to decide what I was going to sing. I was clearly confident, fueled by a potent combination of Four Loko, Long Islands, and love.

But I needed something I knew I could nail in front of a crowd.

So I chose I’m Gonna Be (500 Miles).

For this girl, for this moment, it just felt right.

I did end up making it to my shoot the next morning. I couldn’t get the eye liner off my face that the girl talked me into applying later that evening, so you can clearly see it in the B-roll footage that I acted in.

She slept through that job interview. She seemed to not mind it too much, though, since she ended up marrying me.

This reminds me, I really aught to sing it to her again sometime soon.

It’s just hard to find date night opportunities with your wife when you’ve got two rambunctious kids running around.

That, and the karaoke scene here south of the river is sus. Find me a place nearby where I can do Rap God without censorship, you cowards.

I used to take a trip to the north shore with my extended family every summer.

When we’d arrive, my dad would hand me and my siblings a bunch of cash when we arrived accompanied by some variation of this speech: “This is it for the weekend. Spend it wisely.”

One year, my dad performed this ritual in front of the gas station which shared a parking lot with our hotel.

We went in to pick out some snacks, and behind the counter, I saw a cassette tape with a familiar sounding name:

”The Presidents of the United States of America”

A few weeks prior to our trip, back when school was in session, I recalled standing at the bus stop and hearing my friend Lucas telling everyone all about this band.

He said his older brother was into them. They sang about things like cats and peaches, and they totally rocked.

I had looked up to Lucas since preschool. He was effortlessly charismatic. Absolutely hysterical, too. He has this infectious laugh, often deployed after he cracks a joke.

Since I had the recommendation of the coolest kid I knew floating around somewhere in my head ¹, I figured I could parcel out a fifth of my weekend allowance to give it a shot.

I immediately fell in love with the record. I listened to it endlessly for months.

None of the lyrics really made sense to me as a kid. Lyrics have never been something I’ve considered much when it comes to music.²

But as an adult, I get so much joy from rediscovering music from my youth and enjoying the artistry with a renewed perspective that comes with age.

It was tough to only pick one song from this album. So many memories are intertwined with these songs as their accompaniment.

I used to sing Peaches every night to my daughter. Both Lump and Weird Al’s Forrest Gump-inspired cover of Lump often get stuck in my head, my thoughts seamlessly bouncing between lyric versions.

I picked Dune Buggy because it’s the second song from this band that I regularly make my kids listen to.

We have a family playlist filled with songs that each person gets to select, and Dune Buggy is the first song of mine which appears in order.

We will often go through the playlist in that order when we are in the car.

At first, the kids groaned every time the first guitar lick came on.

These days, you’ll occasionally catch my daughter singing loudly along.

And come on, what’s not to love about a blind spider barreling around the sand in a spider-sized dune buggy?

It only takes 5 snare hits and 5 tom hits to instantly transport me back to the warehouse where you go crashing through the window in the very first level of Tony Hawk’s Pro Skater.

I spent so much time playing this game on the PlayStation. I wasn’t even particularly amazing at it. It was just fun to try and pull off the 900 again and again.

Recently, I learned that the N64 version of this game had to use abridged versions of all the songs on this soundtrack due to space limitations on the cartridges.

Amazing that we can now fit the entire contents of the Nintendo 64 library of games onto a 32GB SD card.¹

Ska is a genre of music I get embarrassed when I tell people I enjoy it. It is a genre for a specific brand of misfit. Think emo kids who aren’t overly emotional. Punk kids who aren’t anarchists.

I haven’t listened to much else by Goldfinger, but assumed that they would be playing this song toward the end of their set at When We Were Young.

Imagine my surprise when they called Tony Hawk onto stage before playing it.

Tony recalled the story of meeting the band and asking them to be part of the soundtrack. He said that he and Goldfinger grew up together and owe much of their success to their symbiotic relationship.

Then all of a sudden, the band starts playing the song, and Tony Hawk starts singing it!

There were several moments at When We Were Young where I would try to sing along to a song but couldn’t. I was overcome with emotion.

Seeing thousands of misfits singing this song in unison with the coolest misfit of them all on lead vocals? I couldn’t handle it.

Ska is fun. Ska is camp. Ska is dorky.

And I’m here for it.

As I climbed up on the table, the MRI technician handed me a laminated piece of paper and asked me what I want to listen to.

MRI machines are loud, so they provide you with a pair of headphones to wear while you lay as still as possible for around an hour.

It was six in the morning, early enough that I had to squint a bit to make out the SiriusXM channel listing.

My first instinct was to pick something that would make the technician laugh. I'm sure she was underpaid, overworked, and didn't want to be there any more than I did. The least I could do was try to get her to crack a smile.

I saw an EDM channel.

Perfect.

I ask her to throw that on.

I hear a chuckle through the low-quality speakers in the headphones. Mission accomplished.

As the test begins, my mind goes back to its default place of terrible thoughts. I am exhausted, I hate myself, I am a complete failure.

All of a sudden, I hear the following words:

I don't know who needs to hear this
We came here to get some healing
You can tell whoever's asking:
"Fuck, we're sad, but we're still dancing"

The swear word shocked me out of the funk for a moment.

The repetitive nature of EDM meant I got to keep hearing that chorus again and again.

After a few times, I hear another voice in my head:

"Sorry, can you please lay as still as possible?"

To this day, I've used this song as an anthem in the fight against my worst depressive thoughts.

It just sucks I can't really listen to it around the kiddos.

The algorithms¹ blessed me with this video last week, and I find myself coming back to it when I'm doing deep work.

I also am enjoying his Rammstein version, and I am eagerly looking forward to checking out the Linkin Park and Avenged Sevenfold ones soon.

If I could play the piano, this is absolutely the kind of stuff I would want to play.

I don't know if I'm one of the only weirdos that still uses Plex and listens to MP3s, but dammit, a carefully curated music collection of which I feel some ownership feels critically important to me.

I have started going back in and using the rating systems to rate entire albums.¹ Because this seems like a natural follow up question, I basically only give albums one of three ratings²:

• ★★★★☆ (4 stars): This is an important album to me, but I don't wanna hear it every day.
• ★★★★★ (5 stars): This album is everything right now.
• ★★★★⯨ (4.5 stars): Somewhere in between the two. It is either a 5 becoming a 4, or a 4 on its way to fivedom³.

Doing this gives me the ability to create a smart playlist containing all of the albums with at least a 4.5 star rating.

This morning while getting ready, I uncharacteristically grabbed my iPad and used Plexamp to listen to that playlist on shuffle.

The first thing I noticed on the much larger screen was how awful the album artwork looked for many of my albums.

They looked quite pixelated and blurry. Some of them looked like scans where you could clearly see stickers and thin, diagonal white lines on the sides.

I decided this must be something I rectify tonight.

I've updated the artwork for maybe 50 albums so far, and I'm stunned at how much of a difference it makes to have nice looking album art.

I've had some of these albums for decades now. When I added artwork back in the mid 2000s, the best I could hope for in many cases was a 256x256px JPG that I could find on a message board.

At the same time, the past few weeks gave me several opportunities to pay attention to these albums in a way I never have before.⁴

For most of my life, I generally used music to distract me from my thoughts. I would occasionally listen to the lyrics and look up the meaning of a song, but those details were often secondary to the overall feeling of a track.

Something in the past couple of years changed that in me, though, and now I have been enjoying music on so many more levels. What was an artist going through when they made a song? What was the creative process like? What do these words mean to the artist?

The best system I found was to use the Plex web app on my laptop to select new album art, and then use the Plexamp iOS app to move from song to song, finding songs which had low res album art.

I noticed after a few changes that when I saved the album art on my laptop, it instantly reflected on my phone.

So of course, I started hovering over the "save" button on my laptop, then glanced down at my phone while clicking.

And what you'd see was a cool cross fade where the image got sharper. Cleaner. Fresher. Way more detailed. Way less pixelated.

It allowed me to be a bit of an ophthalmologist, covering one eye, flipping between two different lens strengths and asking whether I preferred option 1 or option 2.

Polishing up my music collection, cleaning up this blog... these were things I used to do for fun.

They were mindless activities. A chance to express myself without feeling any judgement.⁵ To feel accomplished and organized, a little slice of order within a chaotic life filled with incessant disorder.

I have been so busy for the past twelve years that I forgot what fun really looked like.

I thought fun was learning how to build a company. To understand what it takes to build successful and impactful software.

And in many ways, those things were fun. It is really cool to make computers do complex stuff, to build tech that makes people's lives better. It brings me so much joy.

But that's not the only thing that's fun in the world. And I might have done a bit better at relegating those pursuits to my professional life, and then figured out a way to pursue other joyful things outside of that.

It's weird coming back to my media library after essentially neglecting it for most of my adult life. It feels like opening a time capsule, but then jumping down into it and living amongst the decade old cruft.

But it feels good to clean it out and use it again. To treat it like my house instead of a history exhibit.

We come into this world craving the presence of others. But a few modern trends—a sprawling built environment, the decline of church, social mobility that moves people away from friends and family—spread us out as adults in a way that invites disconnection. Meanwhile, as an evolutionary hangover from a more dangerous world, we are exquisitely engineered to pay attention to spectacle and catastrophe. But screens have replaced a chunk of our physical-world experience with a digital simulacrum that has enough spectacle and catastrophe to capture hours of our greedy attention. These devices so absorb us that it’s very difficult to engage with them and be present with other people.

The sum result of these trends is that we are both pushed and pulled toward a level of aloneness for which we are dysevolved and emotionally unprepared. Sartre said hell is other people. Perhaps. But the alternative is worse.

Ironically, this article was shared to me by one of the few people I see IRL nearly every week.

Paul, Micah, Nick, and I get together every Monday night and make music. It’s often the highlight of my week.

We get dinner beforehand and talk about the day to day goings on of our lives. Then, we retreat to Paul’s multi-million dollar recording studio ¹ and just noodle around.

We don’t have a set agenda, no prescribed musical style. One of us just starts playing something, and the rest of us join in.

No matter how depressed, anxious, or frustrated I feel walking into Paul’s house, I never leave with those feelings. Getting to spend time with three smart, talented, and caring dudes always leaves me with a filled bucket.²

Find an activity that brings you joy and go do it with other people. And if you don’t know where to find those people, just ask someone. That’s what Paul did, and thanks to him, I’ve now got two new friends and a weekly outlet for building my guitar skills and expressing some creativity.³