Six dresses and the search for one thing worth saying

Friday morning. Newsletter goes out Monday. I have nothing.

This week was brutal. No time to consume podcasts during my commute (because I work from home in sweatpants). No interesting studies jumping out at me. No clear insight forming. Just exhaustion, a toddler who thinks bathroom protocol is optional, and a closet full of dresses I'll never wear.

Wait. Why did I buy those?

First instinct: Write about retail therapy. Emotional shopping. How tired people buy things to feel better.

Great. Groundbreaking. Next I'll discover that water is wet.

Everyone knows this. It's not contrarian. It's just stating the obvious with a research citation slapped on top.

Also, the entire piece would center me and my poor impulse control. The dresses become the subject. That's not what The ONE Thing is. I'm the seasoning, not the meal (always wanting to use that saying).

Next.

Took me two days to realize I was asking the wrong question.

The question wasn't "why did I buy dresses I won't wear?"

It was "why does every piece of conventional wisdom say this is stupid, but it doesn't actually feel stupid?"

Started searching:

Found studies showing these purchases aren't failures of self-control. They're identity maintenance strategies. People buy symbols of the self they can't currently be as a way to keep that version alive.

The new parent with concert tickets they'll never use. The burned-out exec buying hiking gear. The PhD student stockpiling novels.

Not delusion. Survival.

Now we're getting somewhere.

Everyone expects you to shame this behavior.

"Be realistic! Live in the present! Stop wasting money on fantasy!"

What if that advice is actually dangerous?

What if killing all aspiration to match your current brutal reality is exactly how people lose themselves during hard phases and never find their way back?

Now we have something: A defense of behavior everyone feels guilty about. Backed by research. With actual stakes.

But.

First version was 80% my life. The toddler. The pregnancy. The sweatpants existence. Working from home. How I can't remember the last time I wore real pants.

Read it back. Sounded like a therapy session. Sad.

The insight was buried under personal circumstances that, while relatable to some, weren't universal enough. Not everyone is pregnant and potty training. But everyone has bought something for a version of themselves that doesn't currently exist.

Cut most of it. Kept the six dresses as one example among many. Personal detail as punctuation, not subject.

Overcorrected. Started explaining why people need to understand behavioral psychology better. How awareness changes everything. How we're all drowning in AI content and losing our humanity.

True. Also beside the point.

The piece started sounding like a TED talk (my BIG dream. But still). Lost all the edge. Became the exact kind of motivational garbage I'm trying not to be.

Cut the lecture. The insight should speak for itself.

Added a whole section about how this isn't permission to spend recklessly. How retail therapy is different. How there's a line between coping and compulsion.

Read it back. Sounded scared.

I'd made a contrarian argument then immediately hedged it. Basically told readers "here's why this behavior makes sense BUT ALSO don't do it too much okay?"

Pick a lane. Either defend the purchases or don't.

Cut the hedge. Added one parenthetical mid-piece: "I'm not saying spend yourself into a hole. Different problem, different psychology." Moved on.

The final version does four things:

Opens with the contradiction. "Be realistic" sounds responsible. It's also psychologically naive. Sets up tension immediately.

Makes it universal fast. Concert tickets, hiking gear, novels, dresses. You see yourself in at least one. The insight isn't about any specific purchase, it's about the pattern.

Commits to the contrarian position. Doesn't apologize. Doesn't hedge. Makes the case that killing aspiration isn't wisdom, it's surrender. Then trusts readers to decide what to do with that.

Ends with implication, not instruction. "Some are just proof you remember there used to be a version of you that wasn't this tired." Done. No over-explanation. No call to action. Let it land.

The personal detail (my six dresses) serves one purpose: proves I'm wrestling with this too, not lecturing from above. Then gets the hell out of the way.

Finding something worth saying isn't about having more ideas.

It's about:

Starting with genuine curiosity, not an agenda. I didn't set out to defend aspirational purchases. I set out to understand why mine didn't feel wrong despite conventional wisdom saying they were.

Finding research that explains the pattern. Not cherry-picking studies to support a predetermined point. Actually going looking for what's true.

Locating the contrarian angle. Where does conventional wisdom fail? What's the gap between what we're told and what's actually happening?

Trusting the insight to land without over-explaining. The urge to keep talking after you've made your point is strong. Resist it.

Getting your personal story out of the way. Use just enough to be human. Then shut up and let the research do the work.

The dresses aren't the story. The gap between aspiration and reality is the story.

My job isn't to tell you what to do with that information. It's to show you what's actually happening when you do it.

That's the difference between advice and insight.

I'll do this again. Find one thing. Chase down the research. Locate the contrarian angle. Try not to ruin it with too much of myself or too little edge.

Some weeks it'll work. Some weeks it won't.

That's the ONE thing process. And sometimes showing the process is as valuable as showing the result.

Who knew.

// Ann