The Beginner’s Mind

Returning to the freedom of not knowing.

I haven’t been new at something in a long time.

Not really new. Not the kind of new where you don’t know the rules yet. Where you can’t tell if what you just made is good or terrible. Where you have to Google basic things that everyone around you seems to already understand.

I’ve led teams. I’ve been in rooms where people look to me for answers. I’ve run campaigns on every platform you can think of. And somewhere in the process of becoming the person who knows things, I forgot what it felt like to not know.

And then came Substack.

The thing about expertise

There’s a concept in Zen Buddhism called shoshin, beginner’s mind.

The idea is simple: when you’re a beginner, your mind is open. Full of possibilities. You don’t know what’s supposed to work, so you try things. You don’t know the “right” way, so you find your own way.

Photo by Matteo Paganelli on Unsplash

But when you’re an expert, your mind narrows. You know too much. You’ve seen too many patterns. You start optimizing before you’ve even started creating. You edit the idea before the idea has had a chance to become anything.

I’ve spent twenty years becoming an expert in advertising, content, social media and creative strategy. I know what works. I know the hooks, the formats, the posting times. I know which words trigger the algorithm and which ones don’t. I know how to build a carousel that gets saved and a video that gets shared and a post that looks vulnerable but is actually engineered.

And I think that expertise was slowly killing something in me.

What it feels like to not know

I started this Substack a few months ago. And the honest truth is I have no idea what I’m doing.

I don’t know the algorithm (Is there one?). I don’t know the growth hacks. I don’t understand why one post gets 200 views and the next gets 40, when they feel the same to me. I can’t tell which headlines work. I haven’t figured out the best time to publish. My subscriber count is small enough that I could invite them all to my house for dinner (in the backyard).

And here’s the part that surprises me: I love it.

Not in a performative way. Not in a “I’m so grateful for this journey” LinkedIn-caption way. I mean I actually, physically feel different when I sit down to write here versus when I open a content calendar at work.

The difference is that here, I don’t know the rules.

And because I don’t know the rules, I can’t optimize. And because I can’t optimize, I have to just... write. Think. Follow the thought wherever it goes. Trust that if I say something true, someone somewhere will feel it.

That’s terrifying. It’s also the most creatively alive I’ve felt in years.

The brands are coming

Now I see something is happening on Substack that I find both exciting and slightly alarming.

Brands are increasing their use of Substack newsletters to engage with their customers. American Eagle launched a subscription-based Substack newsletter called Off The Cuff . Hinge turned to Substack for its No Ordinary Love campaign, telling the stories of real-life couples who met on the platform, and even published the articles as a physical book. The RealReal created The RealGirl and is seeing high click-through rates on product links.

The share of newsletters run by brands hit 5.3% in 2025, up from 4.3% the year before.Services and consumer goods saw the biggest jump.

And here’s what’s interesting to me as someone who does this for a living: the VP of marketing at American Eagle said, “Not everything meaningful happens on a social feed anymore,” and described Substack as serving “a different purpose than traditional influencer marketing, with the goal of building credibility, trust and long-term brand building”

The brands are, of course, just discovering what writers on this platform already knew: the inbox is a more intimate space than the feed. The relationship is different. The attention is different. The trust is different.

But here’s what makes me nervous...

The optimization trap

I know what happens next. I’ve watched it happen on every platform I’ve ever worked on.

The brands arrive. The brands bring budgets. The budgets attract growth hackers. The growth hackers reverse-engineer what works. “What works” becomes a template. The template becomes a best practice. The best practice becomes the only practice. And slowly, imperceptibly, the platform that felt alive starts to feel like every other platform, a place where everyone is saying the same thing in the same way with the same hooks and the same formatting, because they all read the same article about what the algorithm rewards.

Sponsored newsletters are becoming common, not just sponsored sections, but entire issues underwritten by brands Creator-brand partnerships are blurring the line between editorial and advertising. Big-name creators like Dan Koe, Jay Clouse, and Justin Welsh joined Substack in 2025, bringing their audiences and their optimization playbooks with them.

One agency founder predicted that “Substack use will climb for brands at the start of the year, but only a few will still be using it regularly and successfully by summer 2026.”The ones who stick around? “The brands with a record of understanding content as a long-game.”

I think he’s right. And I think the reason has something to do with beginner’s mind.

Why the long game is a beginner’s game

Because for all the success stories, there are also the ones you don’t hear about. Which means the brands that will succeed on Substack are the ones willing to not be good at it yet. The ones who show up without a playbook. Who write something honest and sees what happens. Who resist the urge to optimize before they’ve found their voice.

The RealReal’s chief brand officer said their Substack “creates a space to celebrate and explore the collective enthusiasm of our community, enabling us to share our personality and point of view on an editorial platform largely free from algorithmic advertising.”

Largely free from algorithmic advertising. That’s the whole point. That’s why this space feels different. And the moment brands start treating it like another channel to optimize, that difference evaporates.

Walmart’s head of content noted that creators “are widening their aperture of where they build their communities beyond social” And the strategic shift is real: trust over traffic, owned distribution instead of rented reach.

But trust can’t be hacked. Trust is slow. It requires vulnerability and something that looks a lot like being a beginner, because beginners don’t perform. Beginners just do the thing and see what happens.

What I’m learning by not knowing

Ever since I stopped being the expert and started being the beginner, I write differently. Slower. More honestly. I don’t think about hooks. I think about what’s actually on my mind. And the writing that comes out is messier, less strategic, harder to categorize, which makes it feel more like mine than anything I’ve produced in years.

And when I write that way, I also notice something about getting reactions because when I write something true, I get replies. And the difference matters more than I can explain.

But I don’t want to belittle this platform:

Substack is evolving into something more than a Newsletter. It’s evolving into people’s home base. A place to publish, run a community, host podcasts, and build a business around your audience. The platform is growing fast and is likely about to enter a window of rapid growth There are smart tactical reasons to be here.

But the real reason I’m here is simpler than that. I’m here because it’s the only place left where I feel like a beginner. And being a beginner, after twenty years of being an expert, is the closest thing to creative freedom I’ve found.

A note for people like me

If you’re someone who has been doing your thing for a long time (leading teams, building brands, running departments, making content) and you feel that slow dulling that happens when you’ve gotten too good at something, I want to suggest something that sounds counterproductive.

Go be bad at something.

Not because it will help you grow (it will). Or as some kind of “personal brand play.” Just go find a space where you don’t know the rules and have to figure it out as you go.

For me, that space was Substack. For you, it might be something else entirely.

The point isn’t the platform. The point is the feeling. The openness. The not-knowing. The willingness to publish something and genuinely have no idea whether it’s any good.

That’s beginner’s mind. And it turns out it’s not a step backward. Or a step forward. It’s just the thing I’d been missing.

What’s something you used to be a beginner at that you miss? Or what’s something you’re a beginner at right now?

Tell me. I genuinely want to know.

—Ly