One Year In // The Charter
“I don’t know where this is leading me, but I like the direction I’m headed…” - Mel Robbins (via podcast)
One Year Down
Howdy everyone! Early January 2026 marked one year since I stood up keith.diy. I figured that was as good of an opportunity as any to take a break from the self-helpy essays I’ve been locked in on recently, and take stock on how this whole experiment has gone.
Consider this a brief detour from our standard programming to:
Share a few learnings and realizations I’ve had over the past year of keith.diy
Give a clearer sense of how I’m thinking about the site moving forward
Outline some initial changes you may start to see as a result
Before we jump in, I want to take a second to express my genuine gratitude and appreciation for any and every single person who’s read one of my essays or visited the site over the past year. I know we’ve all got 25 different things vying for our attention at any given time, so I truly appreciate anyone willing to carve out the time to engage with this stuff.
The fact that anyone clicked on one of my links this year means more than I expected. While this site is ultimately “for me,” the feedback and engagement I’ve gotten has put real wind in my sails and helped me stick with it. It would be ideal if every single thing I said resonated with every single one of you, but I know that’s never going to happen - as always, take what’s useful and feel free to leave the rest.
One last note - many of the quotes and concepts I allude to in today’s essay can be found in Kevin Kelly’s “101 Additional Advices” - if you don’t read everything below, I recommend at least giving this one a quick scroll. Tons of helpful nuggets in there.
OK - context out of the way, let’s discuss the past year.
Building in Public
Looking back, a lot of what I wrote this past year probably felt a little repetitive. Same themes, same questions, same general tone. Despite all the writing about intentionality, that itself wasn’t entirely intentional. I was basically just writing for myself, trying to work through a couple of things that felt unresolved, and this site became the place where I did that out loud.
At a surface level, the original motivation behind keith.diy was simple: I wanted to become a more “creative” person. That’s still true, but I now think that framing was incomplete. This site has ended up being less about creativity in the abstract and more about reshaping how I think about myself - as well as how I actually spend my time.
For most of my life, my identity has been fairly narrow. I spent years thinking of myself primarily as an athlete. Once I realized I wasn’t going to make the league (meaning the MLS 🙁), that identity shifted. Slowly, and largely unintentionally, I began defining myself more and more by my professional life: the industry, the company, the title. Somewhere along the way, a disproportionate amount of my sense of progress and self-worth became tied to those markers.
Over the past year, keith.diy has functioned as a way to loosen that grip.
More than anything, this site is becoming a tool for building a kind of self-actualization muscle - getting more comfortable taking initiative, committing to ideas, and generating momentum without anyone assigning me a task or holding a deadline over my head. Writing publicly was simply the most accessible place to start.
Doing that in public is a crucial piece of the equation. I don’t need massive exposure or validation - just enough visibility to create a bit of pressure. Enough that I can’t quietly abandon things, but not so much that fear or ego get in the way of starting.
Releasing essays, standing up the site, and even trying a few stand-up open mics all followed the same pattern: low-stakes creative efforts that forced me to commit to a specific output instead of lingering forever in the thinking-and-planning phase. (Read: procrastination.)
The through-line here isn’t actually writing or comedy. It’s action - incremental progress. Taking ideas that live in my head and making them real, even when the payoff is unclear. Sometimes those things land, sometimes they don’t*. The point is to keep moving.
I don’t know exactly where this is going. I do know that it feels like the right direction - and for now, that’s been enough to keep me going.
The next two sections dive deeper into the two ideas that sat at the top of my mind for most of the past year, and ultimately led to many of my essays circling similar ground:
How I think about status and professional trade-offs
Whether I’ve been too risk-averse throughout my 20s
If you’re tired of hearing me wax poetic on those topics, or you’re more interested in where this site is headed, feel free to skim ahead to the “Next Experiment” section further below.
On Feeling Behind
Leaning into a more creative, self-directed path has been energizing. It’s helped me flesh out my own thinking. But it’s also forced me to confront some very real trade-offs, and the insecurity that comes along with them.
For most of my adult life, I’ve tried to optimize for a specific balance: doing work that’s at least somewhat interesting or beneficial, while still protecting time and energy for life outside of it. Even early on, when I was looking for my first job and had no real sense of what the corporate world would look like in practice, I can remember turning down interviews because I knew that if I got the offer, I wouldn’t be able to say no. I also knew those roles would require sacrificing just about every waking hour of my life just to keep up.
Over time, I’ve gotten close enough to see how a lot of the more traditionally “prestigious” paths tend to work. While I understand the appeal, I’ve never been compelled enough to make the sacrifices required to pursue them. The fancy name on a résumé or the status associated with a particular role has never felt worth trading away the other parts of my life. I want time with my wife, friends, and family. I like to exercise and play soccer. I can’t consistently operate on less than, like, seven hours of sleep. If you want traditional success, you’re usually going to have to sacrifice at least one of those. You’ll also probably have to get through case interviews, which, if we’re being honest, have never been my strong suit anyway.
As someone who’s fairly type A and has always taken pride in being a “high performer,” this approach created a minor identity crisis. It often felt like I was making an objectively stupid decision. Only in more recent years did I start encountering the now-popular idea of prioritizing direction over speed - a way of articulating something I’d felt intuitively, but struggled to justify when comparing myself to peers.
One line from Kevin Kelly has stuck with me as a useful reminder:
“The most common mistake we make is to do a great job on an unimportant task.”
In theory, ideas like this sound wise and grounded. In practice, they can feel pretty brutal. Choosing direction over speed often means watching others get very good at “playing the game” while you’re still trying to decide which game you even want to play. It means seeing people rack up impressive titles, promotions, and credentials while you’re still working through which path actually makes sense for you.
Through all the writing I’ve done over the past year, I’ve come to see this more clearly as the trade I’ve been making, whether I named it that way at the time or not. In practice, I’ve chosen sustainability over acceleration - prioritizing time, energy, and a fulfilling personal life over optimizing for the fastest possible climb up a corporate ladder.
And if we’re being honest, there’s likely some favorable storytelling going on here. I’m essentially positioning myself as the tortoise rather than the hare. I know how that story ends, and I’m choosing to believe it might hold true here as well - even if that belief is a little convenient.
Despite putting my finger on all of this, it doesn’t mean the insecurity disappears. It absolutely doesn’t. But over time, leaning more fully into creative work has helped recalibrate how I think about progress. I’ve become less fixated on whether I’m “behind” by traditional standards and more interested in whether I’m building a worldview and a set of skills that actually feel like my own.
To be clear, this isn’t a rejection of ambition. A raise would still be great. Career progression still matters to me. I’m just trying to be more intentional about which kinds of progress I’m optimizing for, and why. And candidly, the feedback and conversations that have come out of this site have felt more meaningful to me than any professional achievements to date**.
Getting Good at Starting
I spent a good chunk of my twenties reading essays and articles about how your twenties are the time to take risks. It’s the decade you’re supposed to commit to the grind, stay late at work, say yes to the difficult thing, and bet on yourself while the downside is still relatively constrained. No kids yet. Fewer obligations. Maximum flexibility. The message was consistent: this is the window.
As I approach 30, the cultural script would suggest that my risk-taking window is about to slam shut. Even if I know, rationally, that’s not actually how life works. This has led me to the same question numerous times over the past year: did I take enough risk in my twenties?
I’ve always been a fairly risk-averse person - it’s just who I am. I like stability. I like predictability. I like having a rough sense of how things are going to turn out. And while that disposition has helped me build a life I genuinely enjoy, it’s also forced me to confront the possibility that I’ve sometimes erred too far on the side of caution.
At the same time, I recognize that lingering on this backwards-looking question is just another version of dwelling on sunk costs. Which, after reading enough self-help, I know isn’t particularly useful. One line from Kevin Kelly has been a helpful reset for me here:
“Asking what-if about your past is a waste of time; asking what-if about your future is extremely productive.”
That quote helped reframe the problem. Instead of asking, “Did I take enough risk back then?” I’ve been trying to ask a more constructive question: How do I get more comfortable taking reasonable risks moving forward?
Said differently: how do I design situations that force me to grow, without blowing up a life I’m genuinely grateful for?
It’s no longer about answering whether I took enough risk in the past. It’s about creating small, contained situations where I force myself to take some now.
The Next Experiment: Selling One Thing
Writing these essays and trying my hand at stand-up has been awesome. I plan to keep messing around in both of those areas and continue building those habits, but they’re not the focus for this year. This year, my focus is on leaning into controlled risk-taking in a way that still fosters creativity, but starts to move a bit closer to entrepreneurship.
In the simplest terms possible: my goal for this year is to sell one singular product through this website.
I’m framing this goal narrowly on purpose. I’m not trying to start a company, build a brand, or turn this website into a side hustle. If I sell exactly one thing, I’ll consider it a success.
The real point is to force myself to work through the less glamorous parts of making something that resembles a business exist: building the infrastructure, deciding what to make, designing it, figuring out production, setting up payments, shipping it. All the unsexy, but necessary pieces of the puzzle.
It’s basically an exercise in building something from first principles - learning how the whole system works by being forced to deal with every part of it myself.
The first version of this needs to be as low friction, low upfront investment, and low downside as possible. Anything more complicated creates too many opportunities to overthink it, or talk myself out of starting altogether. In the immediate term, that almost certainly means I’ll be selling something print-on-demand. Think t-shirts, hoodies, stickers, things of that nature.
Practically speaking, you’ll likely start to see a few changes over the coming months:
The site structure will evolve. Instead of being so blog-centric, I’ll simplify the homepage and create clearer areas for writing, merch, and general overviews of what I’m working on.
Given the effort required to set up even a simple product operation, my writing cadence will likely slow down. Expect fewer essays this year.
Any products I release will likely touch on similar themes to the essays, possibly with short write-ups explaining the thinking behind them.
If you gave me your email to read essays, I’m not going to start blasting you with marketing emails. If I ever spin up a separate merch list, it’ll be built independently.
What Isn’t Changing
As I start to layer a more commercial angle into the site, I want to be clear about one thing: the core ethos isn’t changing. This has always been a quality-over-quantity experiment. Whether it’s an essay, a shirt, a piece of art, or something else entirely, the standard remains the same - everything here should feel intentional, thoughtful, and genuinely worth your time.
This approach is really a result of how exhausting the digital landscape has become. Between ads, sponsored posts, and constant attempts to sell something, it’s increasingly hard to just exist online without being marketed to. Social media isn’t really social anymore; it’s commercial media. This site isn’t going to become another piece of that noise. I’d much rather show up occasionally with something considered and interesting, even if that means showing up less often.
In that same spirit, I’m also interested in pulling this experiment in a more analog direction over time - things that foster real-world connection, like small pop-ups, in-person events, or projects that exist beyond a screen. I don’t have a fully formed vision for what that looks like yet, but it’s very much top of mind.
The Next Start
Longer term, my hope is that this self-actualization muscle eventually supports something more ambitious - likely somewhere in the realm of social entrepreneurship. I’m increasingly interested in the idea that business, at its best, can incentivize people to choose a product or service simply because it’s better, while any positive social impact emerges as a byproduct rather than being the pitch. I’m especially drawn to ideas around circular economies, but more broadly, I’m excited by the possibility of using markets and incentives as a force for good.
Selling a couple of t-shirts is obviously a long way from that. But learning how to design, produce, and ship anything feels like a prerequisite. It’s a concrete way to practice turning ideas into reality, rather than letting them live forever in my head.
Over time, I’ve come to realize that an ounce of application is worth a pound of knowledge. For a long stretch, I convinced myself that reading and thinking counted as progress. In reality, publishing my writing publicly was the first real experience I had of starting something. Selling one thing - anything - feels like the next step in that same direction.
As Kevin Kelly puts it:
“Many fail to finish, but many more fail to start. You can’t finish until you start, so get good at starting.”
This website was a start. Releasing my writing was a start. Trying stand-up was a start. Whatever this next experiment becomes is simply the next start.
In many ways, I think life is just about maximizing your shots on goal. Moving forward, I’m channeling my inner Monta Ellis - I may miss a thousand times, but I don’t plan to stop shooting.
Releasing this took a few weeks longer than I anticipated, so I should probably get to it.
*From my experience with comedy - things often do not land.
** Counterpoint: maybe I just need more impressive professional achievements?