Is Music Holding You Back, or Propelling You Forward?

Episode 10 of the podcast

Estimated reading time: 18 minutes

Note: This is Part 2 of “When I Used the Question As a Pickup Line.” Read that first. This story does have its own message, but much of the significance will otherwise be lost.

Michael and I had planned to have our first date while he was in town for the holiday.

However, since he was visiting family, time with them took precedence. In the end, he was unable to find time to himself before I had to leave for my next work trip.

So we started having phone calls—generally for hours at a time. I admired his depth, adored his sense of humor, and enjoyed discovering more interesting similarities and intriguing differences between us.

I told him how the impetus for the project had been my year-long music diet. (At the time, I was almost 3 months in, and was still having withdrawls.)

“So, how’s it work? If we’re together and a song that you already know starts playing on the radio, do you have to cover your ears?” he teased. “Do I need to change the station?”

“No, actually—that would be amazing! I can listen to familiar songs by happenstance, like over the radio, or in a movie or commercial. I can also listen to live performances or covers. It’s a way to make the music special again, you know? Nowadays, every song is available at anytime, but they become precious when you put limitations around them.”

“Yeah, for sure! Well, that’s cool. So, what are some songs you miss the most?”

“Oh man, I have a whole list!” I laughed and shared some of my most beloved tracks and artists, including the Beatles.

Now, most people do like the Beatles. A lot of people even love the Beatles. But me? I’m a fanatic about them. So I was pleased to discover that Michael was also a big fan of their music.

The conversation later evolved into what we were looking for in our romantic connections—and we were mutually excited by how well we aligned. It wasn’t just a spark, chemistry, and attraction. It was also common values, wants, needs, backgrounds, and timing. We both felt strong romantic potential.

Michael asked about my last relationship, and why it hadn’t worked out.

“Well, he was a pilot who was based on the opposite side of the country,” I started.

“At first, the distance wasn’t even an issue. We kept in touch so well between visits. Besides, when you’re in aviation, you accept that any relationship will have a distance component due to the nature of the work. I think the fact that both of us knew that made us work harder for it.”

“Gotcha. That makes sense,” he said.

“After a while, though, it got harder and harder to coordinate visits. He had a lot going on in his life, as well as kids to help raise. I could tell I was very low on the priority list, and eventually, it felt like there just wasn’t room for me. Towards the end, I felt very much overlooked and forgotten. It was hurtful. I couldn’t do it anymore.”

Michael understood how important it was to me that we stay in touch and prioritize each other—and it showed in his actions. We spoke every day, whether it was texting or phone calls, or exchanging our daily scores in Wordle.

He often sent pictures of his day to include me in his life. When I texted, he responded. When I called, he answered. (Isn’t it crazy that this is newsworthy?! Welcome to modern dating.) He consistently made time to connect with me and grow closer on a daily basis, even though we were several states apart.

Once, on a layover, he asked if I had time for a phone call. I told him I was laying down for bed and only had about 5 minutes. Regardless, he jumped at the opportunity—he called just to say hi and wish me a good night.

I treasured how he consistently made time for me. It made me feel valued, appreciated, and cared for.

After about a month, I was able to get a layover in Houston.

Michael planned brunch and an art museum for our first date, and picked me up at the hotel. When I stepped outside, I saw that handsome scruffy face smiling at me from the curb, waiting to open his passenger door.

We gave each other a hug, then climbed into the car and headed to breakfast. Michael reached over and held my hand.

After a few moments of chatting, I heard John Lennon singing on the stereo.

“It’s the Beatles! Oh my god!”

I excitedly interrupted our conversation to turn up the volume, and Michael chuckled. We both sang along to “Happiness is a Warm Gun,” and spoke about our mutual adoration for the band.

That song had just become a new happiness soundtrack for me.

We held hands on our way into the café, too, and sat down for breakfast. We shared stories about music and travel, and got deeper about some former relationships. It didn’t feel like a typical first date, because we’d already invested considerable time in each other. Less pressure, easier to find the conversation, and clearly connecting and mutually enjoying ourselves.

Afterward, I asked if he’d played the Wordle puzzle for the day. It was a cute little daily tradition to share our scores, but this time, we could do it in person—as a team. I moved to his side of the table and sat next to him so we could play it together.

It was exciting for both of us to be physically close for the first time—with someone we’d grown emotionally close to over the last month.

As we drove to the art museum, another familiar song came over the speakers. This time, it was “Do You Realize??” by the Flaming Lips.

“Hey, it’s your song!” I exclaimed.

“That’s right!” He said through a smile as he squeezed my hand.

We held hands a lot as we made our way through the exhibits. Occasionally, Michael would stand behind me and rub my shoulders and arms. Normally, I’m not so physically affectionate with someone on a first date, but I felt incredibly comfortable with him. Those interactions felt like the natural thing to do. It almost felt like we were already a couple.

Afterwards, he drove us back to the hotel. We kicked off our shoes and laid across the bed, and I put on some background music as we chatted.

“Okay, I’m about to tell you something weird,” I said.

“Awesome, let’s hear it,” he chuckled. (I think he already understood that unusual thoughts and ideas would be a regular thing with me.)

“Well, several years ago, I noticed how anytime I played an album that I listened to a lot in high school or middle school, it would transport me back to that time. Suddenly, I could remember a lot more details about that chapter of my life. So, in early 2017, I started doing this intentionally, to build memories around music. Every time I feel like I’m in a new season or ‘chapter,’ I find a new album, and listen to it every day.”

“Hmm! That’s cool!”

As I started the music, I said, “This is my ‘chapter album’ for right now. It’s called With You In Spirit by Balance & Composure. They’re one of my favorite bands. Thankfully, this album came out right after I went on my music diet.” 

After a moment of reflection, I laughed: “God, I’m so weird.”

I was slightly embarrassed at suddenly being face-to-face with my eccentricity. Michael chuckled along with me, and then responded:

“Well, maybe… but I think it’s cool.”

I smiled at feeling understood and appreciated. Then, I leaned over and kissed him for the first time.

We kept in touch between dates, and continued to grow a little closer every day.

I could tell it made us both happy.

I came to Houston again about a week later. Even though art and music weren’t part of the second date, it was even better than the first.

We had scheduled our next date for a couple weeks later, but a few days prior, the plans fell through. Then, the same thing happened for the date after that—and the one after that. Each for different reasons, and all beyond our control.

The commitment to his kids as a single dad understandably took priority. But his workload, and other parts of his life, also started to demand more time than they had before. It was almost as though the universe was conspiring against us.

Even though our connection had required effort, it had never felt like work. We had navigated our obstacles very well. Now, they were bigger, and more difficult.

We had seemed to fit so easily into each other’s lives at first. But suddenly, I struggled to see where I could fit. I found myself frequently pondering one question:

“If I want this, and he wants this, why can’t we have it?”

Surely we could find a way to make this work, I thought.

We saw each other a few more times over the following months.

It wasn’t nearly as much time as I’d wanted together, but it was something.

Unfortunately, Michael’s workload and schedule became busier and less predictable by the week. The phone calls came less frequently. Then, the texts did, too. Soon, it seemed there wasn’t room for me in his life at all.

I started to feel the way I had often felt at the end of my previous relationship—unimportant.

I saw that Michael had too much going on to develop or maintain a relationship, no matter how much he wanted to. He simply didn’t have the capacity. But I struggled to admit that, and to accept it. I just wanted things to work.

I knew the additional demands on his time wouldn’t last forever; he was just in a busy season of life. Things were supposed to calm down again in a few months.

Besides, I understood relationships aren’t always easy. They require effort, and patience. Navigating challenges together is part of that—if not all of that. But… maybe it shouldn’t feel so challenging before the relationship even starts.

At some point, on a day that felt particularly lonely, I flipped to Michael’s entry in the book and gazed at it mournfully.

I thought back to that moment—the way we’d met, the excitement we shared… That was the energy I’d always wanted my love story to have. It had started the way I’d always wanted it to start.

I reminisced about our first date, and all the fun we’d had connecting through art and music. They’re two subjects I’m deeply passionate about, and I haven’t gotten to share those with many partners. I really appreciated getting to share them with Michael.

I thought back to our time at the museum, and I remembered the cute little game he had devised for us after we’d gone through all the exhibits.

“Okay, we’re gonna do something fun,” he said. “We have to figure out each other’s favorite pieces in the whole museum.”

“I love it!” I exclaimed.

“We can’t just say it, though. We have to lead each other to it.”

“Okay, gotcha. Do you wanna go first?”

He smiled and took my hand—and led me straight to my favorite artwork.

It was a hyper-realistic illustration by Tacita Dean, called Delfern Tondo, which appeared to be made with chalk or pastels. The canvas was enormous and circular, and black. No frame. The subject was a full moon partially obscured by clouds.

I found it captivating. It wasn’t just because of the beauty of the illustration, or the subject matter, or the unconventional way it was displayed. It was primarily because the drawing truly captured the mood and beauty of the moon in a way photographs never seem to do. And I appreciated having a way to enjoy it in broad daylight.

No wonder Michael knew it was my favorite piece. He had already heard me gushing over it.

But one thing I never told him was that it had also instantly reminded me of The Song. (The one my ex wrote about me, which inspired me to go on the year-long music diet that lead to starting the Happiness Soundtrack.)

In the melody that I only ever refer to as “The Song,” my ex was singing about finding himself awake in the middle of the night. How he couldn’t seem to stop thinking about me in those moments, and missing me. How he lost sleep over wishing he could go back and change pretty much everything about the way he had let things unfold.

They’re intense emotions to discover about someone who loved you—especially after going years without any closure.

And the video for this song features a full moon, partially obscured by clouds.

Imagine associating something as commonplace—and gorgeous—as the moon with someone who broke your heart. 

Before I heard that song, or watched the video, I had found the serenity of the moon absolutely breathtaking. I enjoyed the moments of peace that came from gazing at it. But now, every time I see a full moon, I can’t help but think of The Song—and all the perplexing emotions it stirs up within me.

That’s why I had to stop listening to it—but I couldn’t get away from the moon.

For a long time, the sight of it made me incredibly sad. Then, it made me angry. I wanted it back—without him attached to it. The artwork felt like a way I could do that. It also seemed to perfectly express the beauty I see in it.

That’s why I loved the drawing. I also appreciated forming a new association with the moon right there, with Michael.

That’s what I said in my smile, but I never said it in words. I didn’t think I should. I didn’t even know if I should feel any of those emotions. So Michael never knew.

I made several guesses as to his favorite piece, and I dragged him all over the museum to find it. At some point, it became comical to the both of us. Eventually, I gave up, upset that I couldn’t return the favor of making him feel seen.

He took my hand and lead me to a Magritte sculpture that we had both admired—the one of a man with a birdcage for a body.

“Oh yeah, of course,” I sighed.

We gazed at it together for a moment.

Its sad beauty was both intriguing and unsettling. The cage was open, and one bird was inside, peering out the door. Another bird was perched outside the door, as though he was showing the captive bird that it could leave at any time.

It was almost like the bird inside was afraid to abandon his sense of safety, even though the cage was also keeping him trapped.

“This is such an interesting piece,” I said. “What do you think it means?”

“I think it represents secrets,” said Michael. “The control they can have over us, how they can make us feel trapped, and how we sometimes feel the need to hold back parts of ourselves out of fear. But they could be the most beautiful parts.”

“Mm. I can totally see that,” I said as I nodded.

“What does it mean to you?” he asked.

I pondered for a moment, and finally shook my head as I replied, “I don’t know… Why is he still sitting inside? The door is open,” I wondered aloud. “It’s so sad. It’s like the bird outside is saying, ‘You can come out, you know. You have wings. You know how to fly. You don’t have to stay in there.’ But it’s never gonna leave. He’s always been there, and he always will be.”

Then, an unsettling thought jolted me out of this memory. I’d been staring at the journal the whole time, but suddenly, I actually saw it again.

I flipped through the pages from the very beginning, and saw the very first song in the whole project: “The Wishing Well,” by aKing.

It was my song.

I’m intimately familiar with the tune, and have memorized every last note—because I’ve played it thousands of times. The reason? It contains a memory of the man who wrote The Song. It’s the track that inspired my first year-long music diet, in 2019.

In our very first conversation, Michael had asked me about my song—and I had told him. But that’s not the one I told him about.

I don’t talk about that one. That’s the beautiful secret I keep from most of the world.

(I have written about it here, if you’d like to read it.)

It’s not that the song is lackluster. It’s that the memory attached to it is… twisted. Even though it is beautiful in some ways, the truth is, I’m ashamed of it.

My relationship with that person was intense and short-lived, and as I mentioned, it ended without closure. Because of that, I had long struggled to reconcile with reality. So for years on end, every time I ever played “The Wishing Well,” it was to replay the memory I associated with it.

Because that’s where I felt loved.

I played it over, and over, and over… because I found more happiness in that memory of him than I had in life without him.

Eventually, I became so addicted to it that I had to put it off limits for an entire year—along with everything else I’d ever heard before. That’s how I knew it was a pretty effective strategy, and that’s how I knew I could do it again, for Year 38.

And yet, I’d started this whole beautiful project by bringing that into the picture.

I shook my head in disgust and self-loathing at how pathetic I’d been all those years ago. Why was that the first happy memory that came to mind?

I flipped through the pages, and saw entry after entry of humanity at its finest—hundreds of people being vulnerable with me, a total stranger, sharing some of the happiest moments of their lives. Every entry proved that we all have this in common, even though every story is different. It’s so beautiful to me that it almost moves me to tears.

And I had started it all with the song from one of the ugliest chapters of my own life? The melody of a memory I’d grown addicted to?

How dare I defile this beautiful book with an embarrassing shadow of my miserable past. Was the memory behind the song even happy anymore?

The song has never changed, but my association has evolved tremendously. (That’s one reason I’m so fascinated by this concept of music and memory.)

While I had played “The Wishing Well” to relive an intoxicating memory, the reason I played The Song on repeat was even more destructive. It gave me a sense of closure and validation that I never got.

But the worst and most dangerous thing it gave me was hope.

It made me believe my ex wanted to revisit things someday. Every time I played The Song, it affirmed this belief more deeply. I soon found myself becoming addicted again—not just to The Song, but to possibility.

It wasn’t just the music that I kept on a loop. It was me. I had let myself live in an emotional loop in both songs.

I had used music as an emotional cage.

I am the bird stuck inside, and music is the cage I have surrounded myself with repeatedly. I wasted years of my life wilfully trapped beside an open door, refusing to either acknowledge or believe that I could fly away at anytime.

My musical cages had provided a sense of safety and peace that I couldn’t get from reality. But it was false—not to mention pathetic. When the story I was living didn’t go the way I wanted it to go, I would build myself a cage of only the happy and hopeful parts. I’d stay in there for as long as I could, to avoid reality.

And now I realized I was starting to do the same thing about Michael.

I was surrounding myself with our beautiful potential, and the alluring possibility that there would be room for me in his life again soon.

Maybe things would change, but I had to face the reality that there wasn’t room for me now. No one deserves to waste away in possibility. The real world has so much more to offer.

And if I was the bird trapped in willful ignorance, then Michael was the one perched out front, helping me see the cages I had built. Now that I saw them for what they were, I couldn’t let myself build another one.

For once in my life, flying away from my problems was actually the right thing to do.

I glanced again at all the entries. It occurred to me that I never would’ve had those interactions if I hadn’t flown away from my cages. Every single one of them had been a happy memory for me.

I had found so much real joy and peace through this project instead of the semblance that had come from playing those songs on repeat… or from playing those emotions on repeat.

I had discovered how beautiful the world is beyond the cage.

Flying away from it is scary, but the Happiness Soundtrack is proof that no matter what you lose, or how you lose it, you will find something through that loss. You’ll also grow from it in the process.

After reminiscing about several of those interactions, and the joy they’d given me, I finally forced myself to ask Michael the question I already knew the answer to.

“So, how much capacity do you feel you have for dating right now?” I asked over the phone.

“Very, very little,” he replied.

“Do you see that changing anytime soon?”

“No.”

I knew it would hurt to try and shrink myself down to fit in those small gaps. I knew I deserved more than gaps, and I knew he wanted to offer more than what he could give. I also knew how much it would hurt to let myself linger in the possibility of change.

I couldn’t grow in that cage. I could only grow from leaving it.

I admitted to Michael (and to myself) that we should stop trying to force something he didn’t have time for, just because we both wanted things to be different.

We officially stopped trying to force our romantic connection.

The next day, I went to the gym.

When I walked in, I saw the man who always smiles—the one who said his song was “Sail Into the Night” by Will Cookson, because it “got [him] through adulthood.” In that moment, that’s exactly what I needed help with, so I finally played the song for the first time.

I heard the soft piano playing a melody that was both uplifting and acknowledging of troubling times—like a hug from someone who loves you and understands that you’ve been struggling. It was followed shortly by opening lyrics that resonated with me deeply:

I know it’s a pain
when the stars let you down
and you’ve lost your way.

I immediately felt seen, and was ready for any message that followed.

The song goes on to say that even if you don’t have hope, it’ll be back someday. That venturing off into the void is a different kind of beauty. It’s okay to wander through uncertainty. You don’t always have to know where you’re going. Sometimes, you just need to trust that going is the right thing to do.

That music brought me a different kind of peace—one in accepting reality instead of reliving a memory, or lingering in possibility. And I never would’ve discovered that song if I hadn’t left my cage. It seemed like life had brought it to me when I needed it the most.

On my way out of the gym—which was the saddest workout ever—I thanked the man again for sharing his song. I said I had finally listened to it, and really appreciated the emotions it evoked.

For so long, I had let music hold me back. But now, it was helping me move forward. Instead of keeping me in a cage, it was reminding me that I still know how to fly.

Maybe Michael and I were never meant to have that relationship. Maybe it was only supposed to be potential. Maybe the reason he came into my life was to help me see the cages I had built—and maybe the Happiness Soundtrack is here to keep me from building anymore.

To everyone who has ever contributed to the journal, please know that it means more to me than you’ll ever understand. I am grateful from the depths of my heart.

I hope this story shows you that there’s a beautiful world beyond any cages you may have built, no matter how dark it may seem right now. There is a door, it’s always been open, and you already know how to fly.

Follow-up questions

What are some cages you’ve built around yourself? Have you ever built any with music?

How did you become aware of them? How did you find the courage to leave? How did things change once you escaped?

Feel free to share in the comments, but this is more for you to ponder and potentially journal about.