Writing Songs & Creative Constraint
I've been writing songs for about the last 27 years. That's a lot of years of writing words and setting them to music.
Most of those songs arrived the way good things tend to arrive: when I wasn't trying. A melody would surface during a drive. A phrase would catch in my mind on a trail. I'd sit down with the guitar and chord progressions would just... reveal themselves. Those moments felt effortless. Almost like I was discovering something that was already there, waiting.
But here's the thing about waiting for inspiration: it's great when it shows up. It's terrible when it doesn't.
I wanted to write more. Not just capture the songs that wandered into my consciousness, but sit down and actually create something when I had the time and space to do it. Sounds reasonable, right?
Except every time I tried, I'd end up staring at a blank page. Or playing the same progression over and over for an hour, waiting for something to happen. Or stalling out after a line or two. The harder I tried to make a song appear, the more it refused to cooperate.
A few weeks ago, I read Jeff Tweedy's book on songwriting. Given his prolific career, I was curious to pick up a technique or two that could make intentional writing feel less like pushing a boulder uphill.
One exercise stopped me: the "word ladder."
The instructions were almost annoyingly simple. Pick a topic. List some verbs in one column, some nouns in another. Then write something that connects them.
I picked "sales" as my topic. Don't ask me why. It was just on my mind.
Forty-five minutes later, I had a complete song. Words, melody, the whole thing. I recorded it in my kitchen so I wouldn't forget it.
Why It Actually Worked
Here's what normally happens when I sit down to write a song.
I face the blank page. This represents, theoretically, infinite possibilities. I could write about anything. Any style. Any structure. This sounds liberating. In reality, it's paralyzing.
Because each potential first line immediately triggers this internal editor: Is this interesting? Does it work? Should I try something different? Before I've written anything real, I'm already deep in revision mode, judging things that don't even exist yet.
The word ladder gave me something completely different. Not infinite possibility, but a constrained vocabulary and a forced starting point. I had a list of words that needed connecting. The task wasn't to create something from nothing. It was to find patterns among things that already existed.
This might seem like a minor distinction. It's not.
When you're finding connections rather than generating material from scratch, a different part of your brain takes over. The associative, pattern-seeking part. The part that notices relationships and makes unexpected leaps. That part can't really operate when the critical, evaluating part is running constant commentary.
With the word ladder, I was just following the words to see where they led. Not judging whether they were leading somewhere worthwhile.
There's something interesting here about how constraint can actually create more freedom. The word ladder made one thing harder: I couldn't use whatever words came naturally. But it made something else dramatically easier—I didn't have to generate everything from nothing, or evaluate every choice against infinite alternatives.
The constraint narrowed the space just enough that I could actually move through it.
What Came Out
Here's what emerged from forty-five minutes of connecting words about sales:
You believe in money / That's on par
Time is money / So let's hop in the car
A struggle for margin / A need for profit
The bonus is coming before the months soften
You could sell me a pen, that's in my hand
Or write a contract for a deal that won't land
So I'll sign my name on the dotted line
After you convinced me this will all be fine
Did you listen to the man?
Did you hear what he said?
We're gonna be rich soon
Or at least before we're dead
Here's your quota—they told us what to do
Tell a good story, generate revenue
Make a life worth living for the kids in your house
Turn rags to riches cause we're living hand to mouth
So show me the money, it's not just for fun
But lives only worth living if we've got income
I didn't plan to write about creativity getting commodified. I wasn't trying to explore the tension between making art and making a living. But "sales" as a topic pulled me straight into that territory.
Here's the thing though—this song isn't really about my life. I don't rely on songwriting for income. Consulting pays my bills. But the constraint pushed me into the perspective of someone who does depend on their creativity to survive. Someone for whom "make a life worth living for the kids in your house" isn't a metaphor.
What surprises me, looking at the handwritten word ladder now, is how the constraint forced language I would never have chosen on my own. "Struggle for margin." "Sign the dotted line." "Here's your quota." These aren't natural phrases in my songwriting. They came from following where the words wanted to go, into someone else's experience instead of just my own.
The exercise did something I didn't expect. It didn't just limit my options. It pushed me completely outside my own perspective, into linguistic and emotional territory I wouldn't have reached through pure self-expression.
Which is, when I think about it, what good constraints are supposed to do.
How We're Trained to Think
My consulting work has trained me to think in very specific ways. Optimize processes. Develop strategies. Measure outcomes. Track progress toward clearly defined objectives.
These skills are useful for certain kinds of work. They're also completely wrong for others, like songwriting.
But it's bigger than just my personal habits. The whole world of work has shifted away from making space for things that don't have clear outcomes. I have worked with executives who say they value creativity and exploration. And, I think they really mean it when they say it. But in practice? The pressure is always toward measurable results, clear objectives, and logical next steps.
And now there's this new thing happening. Leaders are starting to suggest that AI can handle creativity for us. Or at least be our "creative partner." The implication is that humans should focus on strategic thinking and let machines handle the messy, uncertain work of exploration.
This creates a weird situation. We get fewer opportunities to just ... wander. To follow something interesting without knowing where it leads. To spend time on work that might not produce anything useful. And when we do have free time, our minds have been so trained in goal-oriented thinking that we struggle to let go of needing everything to serve a purpose.
The word ladder worked because it created a structure that gave me permission to stop trying to make something "good" or "useful" or "strategic." I could just follow the words and see what happened.
It didn't unlock some magical creative power. It just made space for the part of my mind that likes to play with ideas without needing to justify why.
Where Else This Shows Up
I keep thinking about where else constraint creates better experiences than unlimited freedom.
In product design, we assume users want maximum flexibility and choice. More options mean more power, more control. But the research shows something different. Too many choices make people freeze up. They spend more time deliberating and feel worse about whatever they eventually decide. The best interfaces don't maximize options—they make the experience of using something feel natural, almost invisible.
In life decisions, the same thing happens. When you can move anywhere, do anything, be anyone, the freedom becomes overwhelming. Sometimes knowing what you won't do clarifies what you actually want.
The blank page is terrifying for the same reason unlimited possibility can feel paralyzing. When everything is possible, nothing is obvious.
A well-designed creative constraint trades some of that infinite possibility for the ability to actually move forward. But the constraint has to be the right kind. It needs to close off some paths while keeping others wide open.
The word ladder constrained my vocabulary and topic. But it left me completely free with melody, emotional tone, how I connected the words. That balance mattered. Too much constraint and you're just filling in blanks. Too little and you're back to staring at infinite possibility.
Sharing the Rough Draft
I didn't want to include my handwritten word ladder and the kitchen recording in this post. It makes me uncomfortable. They're rough drafts. The song needs more work. The recording quality is what you'd expect from someone playing into their phone.
I almost waited. Almost decided to polish everything up first, record it properly, and make it presentable.
But that impulse to wait for perfection completely misses the point of what happened here. The word ladder isn't about producing polished output. It's about accessing a creative process that doesn't require polish to function.
The rough stuff—the crossed-out words, the imperfect recording—that's actually the evidence. Evidence that creative breakthroughs usually look messy. That they come from experiments that sometimes work and often don't. That the word ladder worked for me this time with this topic doesn't mean it'll work next time. That uncertainty is part of the deal.
I write about a lot of different things here. Not everything needs to connect to everything else. Sometimes a song is just a song, and sharing how it came together is enough.
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