When Progress Stops Feeling Familiar

Before you read this week’s issue, I recommend going back to last week’s:“The End of the Year Is for Renegotiation.”

This piece assumes you did—or at least started—that work.

When something you wrote doesn’t let go

Each week when I sit down to write The Narrative Intel, I usually feel some sense of closure when I’m done. I’ve followed a thread. I’ve landed a point. I’ve said what I meant to say.

That didn’t happen last week.

The issue on renegotiation lingered -  not because the idea was unfamiliar, but because writing it surfaced something harder to ignore once I saw it on the page.

What caught me off guard wasn’t the idea of letting go. That part is familiar.

It was realizing how much of what I’m still carrying isn’t active work or explicit commitments at all, but behavior shaped by old agreements that quietly never expired.

I have a feeling this isn’t unique to me.

The lag between decisions and behavior

I’ve spent the last few days thinking about the agreements I’ve made with myself over the years — especially the ones tied to how I define success and what I believe I need to do to earn it.

What’s becoming clearer is that decisions change faster than behavior does.

You can decide that a certain definition of success no longer applies and still wake up the next morning operating as if it does. You can let go of an outcome intellectually and keep reinforcing it practically through habits, simply because your habits were built under a different set of rules.

That lag is uncomfortable. It feels like ambiguity. Like misalignment. Like you should be doing something — but you’re not entirely sure what.

For founders and CMOs especially, this is familiar territory. Strategy shifts faster than operating rhythm. The organization moves on paper; the functions and teams take longer to follow.

Habits that once signaled competence

Early in a career, urgency often is competence.

In support roles,  availability  isn’t optional. Interruptions aren’t distractions; they’re the job. . When something breaks, you respond. When the phone rings, you answer. Speed isn’t performative; it is required. 

That discipline matters. It builds trust. 

It served me well. It helped me earn responsibility, and eventually autonomy. 

The role changed a long time ago, but some of the habits didn’t.

Years later, the reflexes remain: checking messages  first thing in the morning, treating interruptions as inherently urgent, staying alert “just in case” something breaks - even when there’s no real reason to.

I haven’t done support work in over fifteen years. The agreement ended. The behavior didn’t. 

When progress stops feeling familiar

The question  isn’t whether these habits are “bad.” It’s whether they still mean what they used to mean. Under old measures of success, responsiveness was progress. Availability was progress. Speed was progress. Now, the measures are different. And that’s where things get strange.

Some days feel lighter. Quieter. Less urgent. Less reactive. And instead of reading that as progress, I notice myself questioning it. Am I doing enough? Am I being useful in the right way? Why doesn’t this feel as satisfying as it used to?

That discomfort isn’t failure. It’s unfamiliarity. 

I think it’s because progress under a new contract doesn’t register the same way—at least not yet.

Berkson’s Bits…

No predictions for 2026. Just some things worth understanding:

• GenAI: not how it works, but how you can work with it. It's a language (prompts) and a mindset.

• Simple → Complicated → Complex: effectiveness increases the further along this continuum you can operate..

• Authenticity and unique voice: when content can be manufactured at scale, novel is less valuable. Thoughtfulness matters more. 

What I'm Listening to…

New Year's Eve still brings to mind Dick Clark. Which leads to American Bandstand. Which leads to this.

Music is my love language. I've shared a lot of mine -- now I’m curious about yours.  I'd love to hear what YOU are listening to?. What are your favorites? What do I need to hear next?

Sitting in the space without rushing to fill it

The instinct, especially at the start of the year, is to resolve that discomfort quickly. To replace old habits. To define fresh metrics. To move on.

I’m resisting that impulse.

Instead, I’m paying attention to what shows up in the absence of the old signals. What kinds of days leave clarity instead of feeling drained. What kinds of work feel aligned, even if they don’t produce the familiar sense of momentum.

I suspect many of us carry these inherited behaviors longer than we need to, not because no one ever told us they no longer serve us, but because we never told ourselves.

If the end of the year was about renegotiating the contract, then this moment is about learning how to live inside the new one — without rushing to make it feel familiar.

That’s the work I’m sitting with..

Happy New Year!

Looking forward to continuing the conversation...

Alan