2025 Reflection: Unlearning the Habits That Once Worked

On metrics, money, and learning to write without needing to convince

As the year comes to an end, I look back on the more than thirty essays I wrote this year and realize that the hardest part of becoming the writer I want to be hasn’t been learning new skills—but unlearning the habits my previous successes taught me.

This is my final week working on a client project I dedicated several years of my life to.

During that time, I helped build a podcast, write newsletters, launch books, grow communities, run workshops, sell conference tickets, assemble teams, and—inevitably—make money.

Speed. Performance metrics. Narratives. Volume. They weren’t just part of the work—they became embedded in my daily routine.

I’d wake up and, before even getting out of bed, reach for my phone. Refresh the dashboard. Check the numbers that mattered most that day. Sometimes it was ticket sales. Other times it was cost per lead or conversion rates on a new campaign.

At some point each week, I’d sit down with the Creative Director or the Copy Chief to plan our next move. We were always racing something: a presale, a launch, or the familiar “the client wanted this yesterday.”

We used to joke that we were building the plane while flying it. There was always momentum, always motion. And strangely, the more we did, the more there seemed left to do.

• “What if we try a new angle?”

• “What if we segment the message further?”

• “What if we add YouTube to the mix?”

Often, it felt like a game. New challenges every day. Levels to clear. Progress to unlock.

But when everything starts to feel like a game, you become so absorbed by the score that you forget why you started playing at all.

I still remember one of my first calls with this client, nearly eight years ago. I asked him, “Why share your knowledge with others in your industry? What are you actually trying to do?”

His answer is why I stayed as long as I did.

He said, “I got here by powering through. I know now there’s a better way. You don’t need to sacrifice your health or your relationships to succeed. But when I was starting out, I didn’t have anyone to look up to in this industry. I want to be that person now—so others don’t have to go through what I did.”

That story became a compass. I told it again and again while hiring the dozens of people who joined us in our mission. I returned to it in difficult moments. It made the work feel meaningful.

And I believe we did good work. The industry genuinely shifted after we began sharing his ideas.

But as we grew, I felt us being pulled deeper into the machinery of the internet business. Faster. Bigger. More efficient. Those pressures were rarely stated outright—but they governed everything. And somewhere along the way, I felt myself drifting from the original spark that made the work matter.

Write2Lead is my attempt to return to that earlier place. To carve out a small corner of the internet where better conversations are possible. Where curiosity isn’t replaced by numbers. Where people are invited to think, to exercise agency, and to build communities where money is a byproduct of care—not its justification.

To do that, I’m discovering I have far more to unlearn than I ever expected.

Unlearning the Need to Convince

My first essay was titled “Writing Without the Need to Convince.” In it, I tried to articulate a shift I was consciously making: moving away from persuasive writing and toward something more reflective. Less “do this, believe that,” and more “here’s something I noticed—this is the context it emerged from.”

That has been my intention.

In practice, the habit of persuasion still sneaks in. The other day, I caught myself starting a sentence with “Here’s the truth…” and stopped mid-thought. What am I doing? That’s not the language I want to use anymore. I know I’ll slip again. When I do, I hope you’ll forgive me—and understand where it comes from.

Another temptation is explaining things too early. There’s always the fear of losing readers if the point isn’t made obvious fast enough. We’re constantly told that attention spans are shrinking, that writing must deliver the payoff immediately, that anything requiring patience is a liability.

But I like to believe my readers are smarter than that. That they enjoy being challenged. I could flatten everything—spell it all out so no one ever has to pause or wrestle with a thought—but I find that kind of writing unbearably dull. Irony disappears along with personality. The text becomes efficient, clean, and lifeless.

So yes—some people may misunderstand my point. Some may not get it at all. That’s okay. I can live with that.

What I’ve also noticed is that I’ve grown increasingly impatient with writing that leaves no room for thought. Even when you read figures like Socrates or Freud, you encounter hesitation, doubt, unfinished ideas. They make it clear they’re grappling with uncertainty. So why does so much writing on the internet sound as though uncertainty has been edited out entirely?

When someone sounds too certain, my internal BS detector goes off immediately. And if that’s the standard I use when reading others, I feel obliged to apply it to myself.

All of this takes effort—even after more than thirty essays. But piece by piece, these choices help me unlearn the persuasive habits I relied on for years, and slowly move toward a kind of writing that invites reflection.

That, at least, is the direction I’m trying to walk in.

Unlearning the Chase for the Usual Metrics

I still refresh the dashboards more often than I’d like to admit—checking how many people subscribed, scanning open rates, noticing whenever an email dips below 30 percent and thinking, “I should have written a better title.”

It’s hard not to obsess over these numbers, especially early on, when they feel like the only indicators of whether a project is “working.”

But after a few months, I discovered a more meaningful metric—one that’s guided me ever since: resonance.

Resonance doesn’t show up on a graph.

It appears in the replies—the emails from readers who pause their day to think through a piece, then share their own perspective. Those exchanges hint at something dashboards can’t measure: the depth of connection you’ve created, the ideas you’ve stirred, the clarity you’ve sparked.

Socrates believed we are unreliable narrators of our own minds, and that dialogue forces our assumptions into the open. Conversation, for him, was a method of inquiry. Truth wasn’t transmitted by speaking at people, but approached through thinking with them.

That’s what resonance feels like—a shared search for something truer than what either person could reach alone.

And yet, as grounding as resonance is, there’s another metric I can’t fully ignore.

Money.

In the project I worked on for my client, money was the metric. It defined success, measured it, and ultimately rewarded it. And for the last two years, I delivered on that front consistently.

Now, in 2026, I’ll be dedicating myself to my own project full-time. I’m not worried about monetizing in the first five or six months—but the bills won’t pause just because I’m pursuing meaning. At some point, I’ll need a model that sustains the work.

What I don’t want is for money to become the compass.

I don’t want it steering me toward topics I don’t care about, or nudging me into offers I don’t feel compelled to create or deliver. I already have ideas for how to approach this—but what matters more than the specifics is the philosophy behind them: money should be a byproduct of the work, not its purpose.

And if I’m creating something I genuinely care about—something that truly supports others—then asking for a contribution doesn’t feel like a compromise. It feels appropriate.

Many creatives struggle here. Somewhere along the way, we absorbed the belief that getting paid contaminates the work—that suffering makes it pure. But there is nothing virtuous about this way of thinking. It isn’t noble. It isn’t rational. And it certainly isn’t healthy.

Still, knowing this doesn’t make us immune to the tension.

But like everything else I’m trying to unlearn, it begins with attention, demands consistent practice, and only softens with time.

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