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You’re doing what you know to do. Putting in the effort, making the decisions, and trying to be patient. But somewhere between where you started and where you thought you’d be by now, you begin to wonder whether anything is actually happening.
Sometimes progress looks like an opportunity. Sometimes it looks suspiciously like something falling apart. And sometimes you can only recognize it much later, when you look back and see how the pieces connected.
These songs move through the questions, the waiting, and the occasional need to start again. There’s encouragement here, too — and a little room to turn it up when you’re ready.
The Architect — Kacey Musgraves (2024)
An apple is a surprisingly small place to begin asking enormous questions.
But that’s where Kacey Musgraves starts “The Architect”: with something ordinary enough to sit on your kitchen counter, yet complicated enough to make you wonder how any of this came to be. From there, the questions get bigger. Nature, chance, disaster, and eventually the design of a life.
Apparently, we’re going to need more than the customer-service number.
The acoustic setting suits those questions. In a World Cafe interview about Deeper Well, Musgraves explained that she wanted the album’s warm, organic instruments to reflect a more grounded place in her life. Here, that quiet sound leaves plenty of room for uncertainty.
A few times in my professional life, a change I’d prayed for arrived in a form I never would have chosen. A business we’d struggled to keep going came to an end. Later, a job I loved doing ended, too. Both brought uncertainty, but both also connected me to people and opportunities I needed.
Those experiences have taught me to trust that God gives us exactly what we need at just the right time. Sometimes we don’t know exactly what we need. Sometimes we don’t know when just the right time is. For me, it usually becomes clear only when I look back at everything that happened and see how it all worked out.
“The Architect” speaks to the part of me that believes there’s a design and would still appreciate a peek at the plans.
The song’s official video adds another layer. Between the apple and the snakes, I can’t help thinking of the Garden of Eden. Whether that’s what Kacey intended or not, those images bring a biblical connection to a song that never names God directly. And apparently, it resonated with more people than just me — “The Architect” won Best Country Song at the 2025 Grammys.
Backslide — Twenty One Pilots (2024)
“Backslide” brings us down from those enormous questions to a very familiar fear: what if you end up right back where you started?
Tyler Joseph’s delivery carries weariness, and the song’s repeated plea makes the struggle feel ongoing. There’s no comfortable distance between the person singing and the thing he’s afraid of.
That’s an important feeling to acknowledge in a playlist about progress. Sometimes you’re trying to hold onto ground you’ve already gained. An old habit returns. Your confidence wobbles. Something you thought you’d settled turns out to have a few more things to say.
Which is rude, frankly. You already had that conversation.
But the song also reaches toward help. Even in its uncertainty, there’s a willingness to admit that getting through this may require someone else.
The official video was directed by Joseph’s bandmate Josh Dun. Its ordinary errand becomes a much less ordinary journey, a fitting visual companion to the song’s sense of trying to keep moving while trouble keeps returning.
In the Meantime — Jess Ray (2025)
Jess Ray’s “In the Meantime” gives waiting some tenderness.
Her voice makes the song feel close, and its promise of a future beyond present trouble comes with an acknowledgment that we’re still living here, in the unfinished part.
It’s easy to put life on hold until something is settled. We’ll enjoy ourselves when the job works out. We’ll breathe easier when the answer comes. We’ll stop worrying once we know what happens next.
The trouble is that the meantime keeps filling up with actual days.
This song makes room for both hope and the ache of waiting. You can believe something better is ahead and still need comfort this afternoon.
The selected recording is from MATIN: Complete Edition (2025); the song originally appeared on Sentimental Creatures in 2015.
STILL — Crowder (2024)
There’s a particular kind of discouragement that comes from wondering why you’re still struggling with something you thought you’d be past by now. Crowder takes that feeling a step further: what if you’re letting God down, too?
And if you’re an overthinker like me, you can probably find plenty of evidence against yourself. Your thoughts can keep circling the same mistake long after there’s anything useful left to think about.
Interestingly, “STILL” began as a different kind of song. K-LOVE’s account of its creation explains that Crowder and co-writers Ben Glover and Jeff Sojka went into the session expecting to write something contemplative about being still and letting God work. As the lyrics developed, the emphasis shifted to the work God continues doing in us.
That gives the title a different meaning. Still struggling. Still learning. Still loved.
In his explanation of the song, Crowder says, “His grace doesn’t depend on us getting it right.” That’s a reassuring thought when you’ve been mentally reviewing everything you’ve gotten wrong.
The upbeat sound helps, too. There’s joy in remembering that, no matter how many times you fail, He’s still working on you.
Be Where Your Feet Are — Jason Mraz (2021)
Jason Mraz offers an instruction that sounds almost too obvious to need saying.
Until you realize your feet are in the kitchen, your mind is three weeks ahead, and you’ve been staring into the refrigerator without any particular interest in food.
“Be Where Your Feet Are” puts its reminder over an easy reggae rhythm. The
Released on the 2021 deluxe edition of Look for the Good, the song pairs its advice with playful images of movement, light, and feeling small. Its official video continues that sense of motion.
A distant goal can make today feel inadequate. But today is where you can actually do something. Finish the paragraph. Make the call. Or sit with someone you love without mentally conducting tomorrow’s business over their shoulder.
Flowers — Samantha Ebert (2024)
The flowers in Samantha Ebert’s song began with actual flowers.
In an interview about “Flowers,” Ebert explained that she became seriously ill in August 2023. She couldn’t attend her final year of college, lost the ability to drive, and spent months unable to get out of bed. Encouraging words from her family and get-well flowers beside her bed helped inspire the song.
That makes its image of flowers growing in the valley feel especially personal. She was writing from a place she hadn’t chosen.
I always tell people I have a black thumb instead of a green one, so despite the fact that I’m currently taking a landscaping class, I’m still probably not the person to consult about growing actual flowers. But the idea that something can grow in a difficult place? That speaks to me.
Ebert later described how she initially felt that illness had put her life on hold. Looking back, she saw that the same season had redirected her toward
Someone I met during one difficult professional chapter became the connection to the next. Later, the person who delivered the news that my job was ending introduced me to my current company about ten days afterward — a much better fit.
I’m grateful for how those circumstances worked out. I also remember how unsettling they were before I could see the connections.
If you’re still waiting, you may not have that perspective yet. “Flowers” gives us something to hold onto in the meantime: the possibility that this place has more life in it than we can currently see.
A little bouquet that never needs watering — a cheerful reminder that beautiful things can grow in unexpected ways.
Message to the World — Ballyhoo! (2020)
After the reflection in “Flowers,” Ballyhoo! opens a window.
The reggae-rock rhythm brings some movement, but “Message to the World” still belongs in the conversation we’ve been having. Its encouragement reaches outward, making room for other people in a story that can easily get trapped inside our own heads.
The song shares its name with the band’s album released in June 2020, during the early months of the COVID pandemic. That timing gives the idea of sending a message to the world a particular resonance. Most of us were having quite enough trouble figuring out what was happening in our own little corner of it.
When something is weighing on you, a change of rhythm can help. So can a conversation with someone whose company reminds you there’s more to your life than the situation you’re trying to resolve.
This song brings some of that company into the playlist.
Keep Your Head Up — Ben Howard (2011)
Ben Howard’s encouragement has some weather in it.
“Keep Your Head Up” moves through uneasiness before the refrain opens things up. The guitar and building rhythm give the reassurance somewhere to go; you can hear the song finding its feet.
Howard told American Songwriter that listeners often sent him notes about this song because they connected with its encouragement. In the same interview, he described sometimes putting an unfinished song aside and returning to it six months later. Even songs about keeping going can take their time getting there.
That’s a detail worth remembering when you’re frustrated with something unfinished. Leaving it alone for a while doesn’t necessarily mean you’ve given up. Sometimes you come back with something you didn’t have before.
And sometimes you just need encouragement from someone who isn’t asking for a progress report.
Keep Your Eyes Open — NEEDTOBREATHE (2011)
Bear Rinehart’s voice gives this encouragement some muscle.
“Keep Your Eyes Open” builds toward a chorus that feels meant to be sung with conviction, even if you have to borrow a little of the band’s conviction to get started. Its images of locked doors and gathering storms give the encouragement something to push against.
Waiting for a change and accepting one can be entirely different challenges. You can spend months hoping for an opportunity, then greet it with a detailed list of reasons you might not be ready.
Apparently, my enthusiasm sometimes requires a committee meeting.
This song feels like permission to adjourn the meeting and take a look. You don’t have to know everything that’s ahead to remain open to it.
O-o-h Child — The Five Stairsteps (1970)
Sometimes reassurance works best when it’s simple.
The voices in “O-o-h Child” pass the encouragement back and forth, and the arrangement keeps lifting it. What begins as a gentle reassurance gathers enough energy to make the possibility of easier days feel a little closer.
There’s no detailed explanation of how things will improve. No deadline, either, which the impatient part of me would admittedly appreciate.
But there’s comfort in hearing someone sound so sure when you aren’t feeling sure yourself. You don’t always need advice. Sometimes you need a familiar voice, a little kindness, and a few minutes when the future feels less daunting.
After “Keep Your Eyes Open” asks us to consider courage, this song lets us receive some comfort.
Be Still — The Killers (2012)
For a band called The Killers, this is a remarkably tender way to address someone.
Brandon Flowers sings over a restrained arrangement that gradually gains strength. There’s a protective quality to the song: encouragement to hold onto your heart and your sense of yourself while making your way through a world that can wear both down.
It sounds like something you might want to tell someone younger. Don’t let every disappointment change what you believe about yourself. There’s more ahead than you can see from here.
Then you realize you could probably stand to hear it yourself.
Crowder’s “STILL” reminded us that God continues working on us. This “Be Still” gives us a moment to gather ourselves and keep going. Together, they leave room for being unfinished without treating it as a failure.
Golden — HUNTR/X (2025)
A little restraint was lovely. Now we’re going to need the big chorus.
“Golden” gives the playlist its brightest lift, but there’s uncertainty beneath all that confidence. In KPop Demon Hunters, the song carries each singer’s struggle with identity and belonging — questions about who she’s meant to be, feeling misunderstood, or being the family’s black sheep.
Netflix’s account of its creation explains that the song began with a seven-page memo and went through numerous drafts while the team worked to make it serve both the characters and the
Even Kelly Clarkson had to work at this one. After performing “Golden” as her final Kellyoke, she told Seth Meyers how much practice it required and how difficult it was to find the right vocal placement. Watching the finished performance, you’d hardly know it.
If you ask me what’s on my bucket list, seeing Kelly Clarkson live would be close to, if not at, the top. So hearing her admit how much work went into “Golden” caught my attention. If even Kelly has to practice that hard, the rest of us can probably give ourselves a little grace.
That’s worth remembering when somebody else makes something difficult look easy. You’re seeing the performance, not all the practice.
As for me, I’ll be providing enthusiastic alto support from a sensible distance.
Worth Hearing
![KPop Demon Hunters (Soundtrack from the Netflix Film) [Amazon Exclusive Violet LP]](https://m.media-amazon.com/images/I/31Z1VUWrtsL._SL500_.jpg)
Bring that big “Golden” chorus home with the KPop Demon Hunters soundtrack on Amazon-exclusive violet vinyl.
Light — Michael Kiwanuka (2019)
“Light” gives us somewhere warm to land.
Michael Kiwanuka chose it to close his album KIWANUKA. In his Apple Music commentary, he explained that he wanted a dreamy, peaceful ending after the record’s larger journey. For him, light could mean the promise of what’s ahead or simply a lighter feeling in his heart.
You can hear that intention in the spacious sound. After the reach of “Golden,” this song lets the playlist settle without losing its warmth.
We began by asking about the design of everything. We’re leaving with something smaller to carry: a little hope, and perhaps a little less weight.
“Light” accompanies Nate looking through family photographs in Ted Lasso’s “International Break”, Season 3, Episode 10. He rediscovers his old violin, and later, after hearing him play, his father acknowledges how gifted he is. That feels fitting here. Sometimes looking back helps us understand something we’ve carried for years — and gives us a little room to move forward.
Looking back has helped me trust the parts of my life I can’t explain yet. I’ve seen circumstances that frightened me become connections I’m grateful for, although I certainly didn’t enjoy every minute of getting there.
Maybe you’re waiting for an answer, rebuilding after a change, or working toward something that’s taking longer than you expected. I hope these songs offer some company — a place for the questions, a little encouragement, and a reason to notice what might still be growing.
