The Playlist đźš—
Exactly a year ago, I was in the middle of a trip that I didn’t realize was going to change my life in certain ways. I had gotten a puppy in September 2024 & he was only six months old, so I was hesitant to leave him for the holidays. Instead, I thought it would be fun to bring him back home to Illinois.
I grew up with Bernese Mountain Dogs & my mom currently has one named Humphrey. Humphrey & I are buds. My mom got him after our other dog, Winston, passed away while I was in college. Winston was certainly my emotional support animal. My parents got him for me for my 10th birthday right before they got divorced. So being an only child, Winston went back & forth with me between my parents’ houses. When he passed away, it definitely hit me hard, so getting Humphrey was a light in the midst of losing Winston.
In between my junior & senior year of college, while I was at home for the summer, we got Humphrey so there was a lot of bonding time then. Then during my senior year, my mom had to travel for work for a chunk of time, so I insisted that Humphrey come to college with me for that month. Such a funny period of time… having this one-year-old Bernese Mountain Dog at college with me.
So, when I got Ferris, a Bernedoodle, I was like “he must meet Humphrey.” How do you get a Bernedoodle from SF to Chicago though? You drive. So the plan was that Ferris & I were going to do a bit of a cross-country road trip for the holidays. Make a real adventure out of it. I rented a car for the adventure & left on 12/19.
I was really looking forward to doing the road trip. I don’t have a car in SF, but I love driving, so when I get the opportunity, I enjoy it. When I was younger, my dad was also a road trip person, so every year for Spring Break we would drive from Chicago to Florida to visit my grandparents. In college, I continued the road trip adventure & would drive with my college friends to Florida for Spring Break. There was something special about the road trip process. The snacks. The conversation. The games. The music. Spend that much time in a car with people & you see a whole new side of them.
The plan on the way there was to do something that would break up the trip & make the adventure worth it. I like to ski, so I decided to stop for a night in Salt Lake City & ski up in the mountains at Snowbird. I was nervous about Ferris being in a hotel room, but he loved the hotel room life. I got him a little pop-up crate & a big bone to enjoy & we were set. So I got to Salt Lake City that night & in the morning, got right on the mountain, skied for a couple of hours, went back to Ferris & we were on the road again. It was perfect. Ferris also got to see snow for the first time.
Throughout the drive, I was listening to a variety of music & podcasts. It was a 36 hour drive each way so I needed to fill the time. On the second day, I started to hit some pretty flat areas. I knew I was back in the Midwest & that this was going to be the tougher part of the drive. I’ve driven I-80 plenty of times & know how painful parts of that drive can be. Now, this is not a dig at those places, but let’s be real… the actual drive is pretty monotonous.
I got pretty sleepy that second day & had to find someplace to stop to stay the night. I was in Nebraska & still pretty far from Omaha so I had no idea where I was going to stay. I found a place that was pet-friendly in North Platte, NE. Now, I had never heard of this place in my life. It was quite small, but it had a hotel that worked. This year, after I had already done the trip, I read On the Road by Jack Kerouac & in it, he talked about the Platte River in Nebraska & spending time in North Platte. I was like “no fucking shit… I actually know where North Platte is”.
“So we drove a hundred miles across Nebraska, following the winding Platte with its verdant fields.”
I got to the hotel & was pretty tired at that point. My plan was to check in, then unload the things I needed from the car & let Ferris out. This was my mistake. We got into the lobby of the hotel & the person behind the desk was so excited to see Ferris. Ferris was so excited to see him. So there Ferris is, just peeing all over the guy’s shoe & the lobby of the hotel. I never said it was going to be perfect traveling across the country with a six-month-old puppy.
Day 3, the last day of my drive there, I got up early & got out of North Platte. Now it was the homestretch. I just wanted to get home at this point. The people in my life were nervous about me doing this drive, which is fair enough, so I certainly had people tracking my location. When I got into Iowa, my friend Kevin texted me & was like “you better be stopping in Iowa City” (where we both went to college). I was like “shit, I should stop there.” So Ferris & I stopped on campus. I ate my lunch in the car. I let Ferris run around on the Pentacrest, where Humphrey had also run around while he was visiting me in college.
I also had a side quest on this trip. I was driving back to SF, which meant I could get special beer that’s only available in the Midwest & bring it back. Iowa City was the first stop for this — Big Grove. If you went to Iowa, you know what Big Grove is. It’s only made in the state. So I made a pit stop for some Big Grove beers.
Now, I would make the drive I’d done so many times before: Iowa City → Grayslake. Four more hours.
I got home & it actually wasn’t all that I thought it was going to be with Ferris & Humphrey meeting. Humphrey was 6 at that point, so he was not thrilled with me bringing home a doodle-fied mini-me of him. On Christmas morning, I think he wished his present was a one-way flight home for Ferris that day. Ferris was acting like the annoying younger brother who was following Humphrey everywhere. Even though Humphrey wasn’t thrilled, it was still quite funny & cute to see.
We celebrated Christmas in WI. My mom grew up in Madison, WI & my grandparents now live right outside of Madison. On the way up, I was able to make another pit stop for Midwest beers — this time it was New Glarus. Spotted Cow, of course. I stopped at a Woodman’s in Janesville, which is actually where the grocery store originated, & loaded up on Spotted Cow. A guy in the parking lot saw the CA plates on my rental car & was like “Are you loading up to go back home?” I told him yes & he responded with “I’m shocked you don’t have more.” Granted, I had at least three cases.
The trip in total was a week back in the Midwest. I squeezed a lot into that period. Played basketball with my dad, spent Christmas in WI, did an annual family cookie-decorating tradition, saw my best friend’s family (who are like my second family), spent time at each of my parents’ places, went downtown Chicago. Made all the stops. Now it was time to head back to SF before New Year’s.
This time, I knew I had to spice things up for the drive. It was a holiday blackout period for my Ikon pass, so skiing was out of the cards. On the way there, I had noticed something while driving. I had interacted with people from so many different walks of life — at gas stations, rest stops, food stops, hotels. Across states & social classes. On the way back, I wanted to make the drive interactive. Is there one question I could ask every person to start a brief conversation & get some insight into who they are?
THEN IT CAME TO ME.
I was going to ask everyone what their favorite song was, either at the moment or of all time. Then I would make a playlist of the compiled list of songs.
I took a different route home since a snowstorm was hitting the Sierra Nevada. Instead of going through Wyoming, I went through Colorado. The journey back started. My first stop was for coffee off a random exit in Illinois. It was a Starbucks. It was ~5am & there were two girls working who were definitely in high school. They were the first people I asked: “What’s your favorite song? Either right now or of all-time.” They each needed a second but pulled out their phones & explored their Spotify playlists. One said Pink Matter by Frank Ocean & the other said jumpin’ by gio. The playlist had started.
By the end of the trip, the playlist was 2 hours & 11 minutes long. I knew maybe 30–40% of the songs, but a lot of them were new to me. There was only one person who didn’t want to participate & that’s because she said she only listened to audiobooks & not music.
Pass the Ax came from a woman in Nebraska. She told me I’d probably think they were insane because it was the song they played when they had a bad day & needed to jam in the car. Listen to it. You’ll get why she said that.
It Takes Two was from a dad in the hotel lobby in Boulder, CO. Balloon was from the worker, who was a student at the university, who checked me in at that hotel. En Mi Cuarto was from someone who worked at a grocery store in a misc. mountain town in CO. She said “I only like Spanish music” & was hesitant to give me the song… I was like “so I want to hear it.”
Simple was from someone working at a gas station in Nevada. This was on day 2 of the trip home, I had just gotten a speeding ticket & had then pulled in to fill up. I was NOT a happy camper at this point. A rock had hit the windshield of my rental car & cracked it slightly. Plus I had just gotten a speeding ticket… all within like 30 minutes. I did like the song after they gave me that one to add, so it cheered me up a bit.
Day 2, I ended up staying in Palm Springs. I didn’t HAVE to stay in Palm Springs. It was slightly out of the way… but I WANTED to stay in Palm Springs. I love that town & it was just part of the journey. It was a really long day, probably the toughest of the whole trip. But then I pulled off at exit 111, which was Palm Springs, & I just felt like a sigh of relief. My ritual those nights after I stopped driving was that Ferris & I would chill in the hotel room, I would have one celebratory local beer, a snack & pass out.
Day 3. Now it was just Palm Springs to SF. I just had to make it eight hours. Blondes (Have More Fun) came from a rest stop off the side of the road in CA & it had stunning views. I walked in & there was a woman who was about 70 sitting at the desk in the rest stop. You could just tell she was a spitfire. I told her about my playlist & asked her favorite song. She fucking loved it. She was feeling the pressure though… so she said “You go to the bathroom & when you come out, I’ll have my song.” I came out & was like “Where is my song?” & she hit me with this one.
Sympathy for the Devil came from this guy I ran into, in the parking lot of that same rest stop, with his wife.
You Can Do Magic came from someone on day 2 in Nevada. He could not find this song for the life of him. He had me looking at YouTube videos of different versions of this song because he didn’t remember the name. He was so charismatic about this song so I was along for the ride with him. I loved the dedication to it.
I made it through & I drove back over the Bay Bridge that last day. It was kind of a magical moment. I was like this is fucking sick that this is what I get to come back to. I never get sick of that view over the Bay Bridge. The full view of the city, Alcatraz, the Golden Gate Bridge.
Now, the last song My Sweet Lord came from the guy working at Hertz at SFO. The playlist was complete.
This trip was truly about the journey. It was a journey of exploring past parts of myself. It was 72 hours in a car with my own thoughts. It was getting to interact & converse with people across the West Coast & Midwest that I don’t usually do on a daily basis. Music was the backdrop to all of this. I was able to use music to go through the eras of my life. I was able to discover new music through real people.
Music is such a universal language. Everyone lit up when I asked them the question & most immediately pulled out their phones to try to find what they thought their favorite song was. I knew how I experienced music & how the people closest to me did but this validated how you could connect with complete strangers across the country with one simple topic. I’m not sure the moment it all clicked for me, but I was then flooded with ideas & possibilities of something that could help facilitate the conversation of “What’s your favorite song?”
With all of this being said, I’m not sure I would ever do that drive alone again. It really pushed me to my limits physically & mentally… but it was worth it. With a few days to spare in 2024, this trip completely changed the trajectory of where my 2025 was going to go.
