Write Freely
48th Edition - February 17th, 2025 - Monetization culture, third places, and ironic detachment
**A Note on Beyond Our Walls**
This space has always been a place of reflection for me—about navigating the complexities of education, school leadership, mental health, and personal growth through the lens of my own experiences. But as Beyond Our Walls (and the world) continues to evolve, I find myself drawn toward a broader, more aspirational approach.
This newsletter isn’t just about my own experiences—it’s about attempting to foster deeper conversations in order to build connections. I want this to be a place where we tackle with the bigger discussions, where we challenge ourselves to see the world from new perspectives, and where we find ways to bridge the gaps between us through shared humanity. The goal isn’t just to curate thoughts on education or leadership—it’s to create a space where you can see your own experiences reflected, where stories spark new ideas, and where we all leave each conversation with a little more perspective than when we arrived.
So, as I continue on this writing journey, I invite you to engage—to share your thoughts, your insights, and your own reflections. Because at the heart of all of this is connection, and I truly believe that’s where the most meaningful change begins. Thanks for being here!
I don’t remember the exact moment I hit “publish” on my first blog post, but I do remember how it felt—exciting, personal, and brand new. It was sometime in the early 2000s, likely my third or fourth year of college, when Blogger was one of the few platforms that made it easy to carve out your own little corner of the internet.
Back then, writing online was unpolished and unfiltered because there was nothing to compare it to. It was the unvarnished early days of online creation. No SEO strategies, no content calendars, no pressure to monetize because that wasn’t even a thing. Can you imagine? Just writing—because we had something to say, because we were figuring things out, because we wanted to connect. Or because we just wanted to make our friends laugh.
I wrote about whatever was on my mind—personal stories, books I was reading, snippets of conversations I’d had that made me think. It wasn’t about curating an image or growing an audience. It was just me, putting thoughts into the world. Also, nobody was really reading it, and that was absolutely fine. Actually it was probably lucky for me.
Then came video blogging. Before YouTube turned people into full-time creators, there was a small, passionate community of us, who had met at an online message board site, sharing videos on our personal blogs. It felt groundbreaking. I had a Sony camcorder that my wife had gotten me as a wedding present in the summer of 2005, a handful of blank digital video cassettes (see the image above), a chunky orange firewire cable used to speed up video transfer rates, and barebones access to Windows MovieMaker where I taught myself how to cut and edit clips of my daily life. I wasn’t trying to go viral—that concept thankfully didn’t even exist yet. I was just fascinated by the ability to document my world in a new way while meeting others interested in the same.
That sense of exploration led me to some incredible experiences—including the time I ended up on a movie set in Saratoga Springs, NY, where I was living at the time. A friend I had met through videoblogging worked in film production as a sound engineer and invited me to visit while she was on set. That’s how I found myself chatting with actor and all-around nice guy Tim Daly, watching him film a scene, and later recording a short QuickTime video clip of him telling me about a band he had been in as a kid that shared the same name as my blog at the time. It was one of those unexpected, serendipitous moments that happened simply because I had put myself out there in a space where connection came first.
How the Internet Shifted Writing from Expression to Product
The internet isn’t the same place it was back then. Social media, algorithms, and monetization models, discussed ad nauseum, have changed everything. Blogging used to be about expression, speaking your mind, or just being goofy. Now, it often feels like it’s about performance. Actually, YouTube first entered the fray in December of 2005. Coincidence? Happily, platforms like Substack appear to have brought back some of what I loved about early blogging—long-form writing, reader engagement, driving readers to other writers through recommendations, and, most importantly, meaningful conversation. But they’ve still made monetization the default goal.
And I have a strong feeling that even if you don’t set up paid subscriptions, there’s an underlying pressure: Should I be making money from this? Am I wasting my time if I don’t? Would people take me more seriously if I had a paid tier? Will they be annoyed if I ask to be paid?
I have had these exact conversations with myself a number of times on this three year Substack journey, and it’s very difficult to avoid. The signals are everywhere. Substack Notes, a relatively recent addition to the platform, is filled with posts about how to “optimize” your newsletter for revenue, how to convert free subscribers to paying ones, how to create “high-value” content.
Obviously I’m not saying this is all bad. Writers should absolutely be compensated for their work if that’s their goal. I’m not even going to say that I wouldn’t love to find a way to make writing my full time job. But lately, I’ve felt exhausted by the expectation that writing should always be tied to money. I like what I am building here without monetizing it. I have met some great people from all over the world, and it feels like there is so much opportunity for us to add some humanity back into the Internet.
Writing Shouldn’t Be Content First
I don’t want my words to feel like content, something to be packaged, optimized, and sold. I want them to feel like stories. The best writing—the kind that lingers, that makes people feel something—doesn’t come from a place of performance. It comes from a place of presence. I believe that writing, at its core, is about:
Observation – Paying attention to the world and capturing what we see.
Reflection– Processing our own experiences and making sense of them.
Connection – Finding common threads between our stories and others’.
It’s not about tricks or tactics. It’s about the simple act of putting words down and seeing where they take you. And yet, so many of us feel the pressure to generate, optimize, and monetize to make sure our writing is “worth” something in a monetary sense. As a person this feels frustrating, but as an educator it feels more deeply concerning. How can we encourage the next generation of writers to take to the page as a space to find meaning and explore their own experiences if they only exist in a world where everything put out into the ether is only meaningful if you are getting paid for it. How do we convince them that the real value is in what it allows us to express, explore, and share?
Keeping Our Sidewalks Clean: Writing as a Small Act of Bravery
That’s why I keep coming back to a simple idea—one that applies not just to writing, but to how we engage with the world around us. I wrote recently about the idea of keeping your part of the sidewalk clean—doing what you can in your own small sphere of influence to contribute kindness, connection, and meaning to the world. Maybe writing, without the expectation of monetization, is one way we do that. Maybe writing for ourselves is a way of taking care of our own corner of the world, making sure our creative spaces remain authentic, honest, and free from external pressures. Maybe the simple act of writing without an agenda, without a strategy, and without a dollar sign attached is an act of quiet defiance against a culture that constantly tells us we have to produce to be valuable.
Write for Yourself
I can write because I love to write. Because I want to capture the world around me. Because putting thoughts into words just feels good.
And so can you. If you’ve been feeling overwhelmed by the pressure to turn your writing into something more, I invite you to step back and remember that the best writing isn’t created for algorithms. It’s created for us.
After all, I didn’t start writing online for money. I started because I had something to say, even if nobody really cared! And if you’re here, reading this, I bet you have something to say, too. So write. Share. Connect. And if that’s all your writing ever does? That’s more than enough.
Until next time, stay hydrated and take good care.
Tim
What I’m Thankful For
This week, I’m feeling especially grateful for my favorite local coffee shop—the kind of place where I somehow do my best thinking and writing. I’ve been on a third place kick lately, thinking about how important it is to have spaces outside of work and home where we can just exist, connect, and be part of something bigger than ourselves.
There’s just something about the low hum of conversation, the whir of the espresso machine, and the occasional clink of mugs that puts me in the right headspace. It’s like the perfect mix of background noise and movement—enough to keep my brain engaged but not distracted. Plus, there’s something comforting about being surrounded by people all doing their own thing—reading, working, catching up with friends—while I get lost in my own thoughts.
I love that these places exist. They remind me how much inspiration can come from simply stepping outside of our usual spaces and soaking in the energy around us. So if you have a coffee shop, a library, a park bench, or some other go-to spot where you feel at ease, I hope you get to spend some time there this week. It’s a good reminder that a little change of scenery can completely reset your mind.
What I’m Reading
There is so much beauty in the handwritten word. I’ve said this before - I worry that we are forsaking the recording of our time in history for a digital footprint that may or not exist in the future. Bring back the art of the handwritten letter, of the timeless piece of us that we give to others to be found by future generations so they can marvel, like we do when reading narratives of time gone by, at how we lived! It’s why I love Jillian Hess’s work focused on personal notes from days past, and why I was particularly drawn to her recent Valentine-adjacent post focused on different types of love beyond the romantic kind. We can learn so much by diving into the thoughts of those who lived before us.
This one got to me. Working in K-12 public education in the US means that the topics Catherine Shannon covers in her recent post, Everyone is numbing out, are constantly on my mind. I am deeply concerned about the world that we are leaving behind for the generations that are moving into adulthood, and I can see the ironic disinterest she describes all around me. Sometimes I even feel myself engaging in it. There is a hopelessness there that leads to armoring up, and there is no better armor than detachment. I suppose, as they say, the first step to solving a problem is recognizing there is one. Maybe, like all emotions, talking about our penchant for this modern day malaise is how we begin to combat it.
Looking for More Ways to Discover Meaningful Writing?
One of the joys of writing this newsletter is discovering incredible articles and perspectives that inspire deeper thought, like the pieces I’ve shared above. If you're looking to enrich your own reading life, here are two tools I personally use to find fresh, thought-provoking content:
The Sample: Think of this as your daily dose of serendipity. The Sample sends a curated newsletter recommendation directly to your inbox, tailored to your interests and reading habits. It’s how I’ve stumbled upon some of the most unique and impactful writing I’ve shared here. If you’re curious about discovering new voices and expanding your reading list, this is a fantastic place to start. (And yes, I use it myself!)
Refind: Where The Sample feels serendipitous, Refind is like having a personal researcher. Every day, it delivers tailored links based on my own preferences. I find a lot of the articles I include in this newsletter through Refind, from thought-provoking essays to emerging trends in education, leadership, and mental health. It's a great way to stay curious and informed.
And if you enjoy the work I do here on Beyond Our Walls and want an easy way to support it, you can now buy me a coffee, also known as writing fuel, at buymeacoffee.com/beyondourwalls or scan the QR code below. And if that’s not your thing (which is TOTALLY OK), simply click the heart at the bottom of the post and/or leave me a comment. I love knowing what you are taking away from my ramblings!
Enjoyed this read, I'm new to writing and I'm pulled to write in this later chapter of life. I want it for me, like therapy, I think. Never for $. I know stories matter, think I'll tell a few here . ☮️
Observation, reflection, connection. Yes to this kind of writing.